View All Chicago IL Greystone Homes Listings

8 Beds ⋅ 6 Baths ⋅ 12756234 MLS ⋅ NEW Status

Fully renovated three-unit Greystone in North Lawndale! Excellent opportunity for owner occupant or house hacking/investment. Property offers new mechanical, electrical, and plumbing system, new roof, Modern kitchens with white shaker cabinets and quartz countertops, Updated bathrooms and Separate utilities for each unit. First floor offers 2 bedrooms and 2 bathrooms and second and third floor has 3 bedrooms and 2 bathrooms. Basement is preapproved for an ADU, offering the potential to create a fourth unit or can be duplexed with the first floor for additional living space. Two car brick garage. Convenient access to public transportation, major roadways, neighborhood amenities, and downtown Chicago. Area experiencing continued investment and redevelopment, Strong rental income potential.

1505 S Spaulding Avenue, Chicago

$325,000

3 Beds ⋅ 3 Baths ⋅ 12756214 MLS ⋅ NEW Status

Stop the car!!! This elegant greystone is built to last and ready for you to move into, featuring hardwood floors 5 bedrooms and 2.5 baths for your family needs. Home also features a FULL inlaw space in the finished basement ready for a growing family. outside features a spacious deck great for entertaining plus a gazebo on the patio and a 2 car garage. Gas forced air heat and central air for those warm nights...Pool table stays, don't pass this one by. easy to show. All appliances listed stays !!!

514 W 66Th Street, Chicago

$460,000

7 Beds ⋅ 3 Baths ⋅ 12756203 MLS ⋅ NEW Status

Beautifully maintained Greystone multi-unit property offering 7 bedrooms, 3 bathrooms, and 2 kitchens. This spacious building features a 2-car garage and a roof that was replaced just 2 years ago. A great opportunity for investors or owner-occupants seeking a well-cared-for property with plenty of space and timeless character.

2114 S Trumbull Avenue, Chicago

$749,900

4 Beds ⋅ 4 Baths ⋅ 12755067 MLS ⋅ NEW Status

Welcome to this stately Greystone row house in Chicago's architecturally rich and historic Hyde Park-Kenwood District. Offering an impressive 3,378 sq/ft across three stories, this timeless 4 bed, 3.1 bath residence presents a rare opportunity for inspired design or adaptive reuse. Many original architectural details remain including coffered ceilings, custom windows and millwork and original hardwood flooring, all reflecting the home's classic craftmanship. A full basement provides excellent potential for additional finished living space. Ideally located within walking distance to shopping and restaurants, parks, Kenwood Academy, the Metra, the University of Chicago and the lakefront, this property combines historic charm with everyday convenience. Formerly operated as an early learning center, the building is equipped with commercial grade fire protection, opening the door to alternative uses such as a day care, group home, or sober living house (buyer to verify permitted uses). A truly unique offering in one of Chicago's most distinguished neighborhoods. This property may be eligible for up to $25,000 in forgivable down payment assistance. Please check under the additional info tab for details on Wintrust's current DPA program specific to Cook County.

5114 S Dorchester Avenue, Chicago

$399,998

3 Beds ⋅ 2 Baths ⋅ 12729152 MLS ⋅ NEW Status

Classic greystone character, generous room sizes, and thoughtful renovations come together in this approximately 1,800-square-foot, 3-bedroom, 2-bath second-floor condo. Hardwood floors flow through the main living areas, including a bright living room with bay windows, recessed lighting, and a fireplace, as well as a separate dining area framed by graceful arched openings. Renovated within the past five years, the kitchen features abundant white shaker cabinetry, marble-look quartz countertops, an oversized waterfall island with seating, a farmhouse sink, subway tile backsplash, stainless steel appliances, and a family-sized double-door refrigerator. The expansive primary suite offers plenty of room to unwind and connects to a beautifully renovated bath with marble-look porcelain tile, a freestanding tub, separate shower with rainfall showerhead and niche, and a double vanity with quartz countertops. A 200-square-foot rear deck extends the living space outdoors. In-unit laundry, central HVAC, and included exterior parking complete the home, all conveniently located near the University of Chicago and Metra transportation.

4512 S Greenwood Avenue Unit #3, Chicago

$499,900

7 Beds ⋅ 3 Baths ⋅ 12753194 MLS ⋅ NEW Status

LOCATION. GOOD NEIGHBORS. POTENTIAL. IT ALL MATTERS! Rare Chicago Greystone on a quiet block with working neighbors, featuring a unique side DRIVEWAY, garage, fenced yard, central A/C, and a finished basement with in-law arrangement and 2 separate exits. Rehabbed in 2020 with convenient first-floor in-unit laundry. Just steps from Ogden Ave and exciting new development coming soon, and only minutes from the West Loop and Downtown Chicago. Strong income potential with rents currently below market-THE MATH DOESN'T LIE! Have your agent run the numbers for you! This is a rare opportunity to own in a location with room for growth, strong rental potential, and incredible upside. Don't miss this one!

1944 S Springfield Avenue, Chicago

$2,150,000

12673900 MLS ⋅ NEW Status

Once in a Generation, The Crown Jewel of Oakland set on a botanical campus spanning 70 feet of frontage. If you seek the best, if you have exquisite taste, if you want a one of a kind with an elevator that opens directly into most apartments with grand terraces, you have arrived. Located in an exclusive community alongside million dollar homes & within 1/4 block of Mandrake Park, 5 minute walk to the lakefront at the very north end of Drexel Blvd, with its idyllic fountain & cul-de-sac is a magical whimsical storybook setting offering 5 Massive full-floor units ultra-luxurious 3-4 Bed/2-3 Bath residences set in a made for TV boutique, elegant, Gothic Greystone. Be inspired by the grand, formal lobby with inlaid stone floors, intricate woodwork, stunning modern art, a crystal cut chandelier & super "mod" LED wall sconces. The elevator opens directly into most residences' private foyer, which leads to a massive great room, with soaring ceilings & 7' tall window bays that capture phenomenal sun soaked south & west vistas up & down lush & forested Drexel Boulevard. Gorgeous plank hardwood floors, which contrast with sleek 7" crown & baseboard moldings, 8' tall solid core doors, polished chrome door handles & accessories, a custom designed & built fireplace with glass, stone & quartz mantel + gorgeous lighting with Decora switches & dimmers. Adjacent to the great room, cook, entertain & eat in a true & REAL gourmet kitchen with 1 1/4" thick quartz countertops, a massive work island with bar stool seating, state-of-the-art stainless appliances, a multi burner stove, tunnel exhaust hood, dishwasher, 36" refrigerator with ice & water dispensers, built-in microwave drawer & brilliant porcelain full height backsplashes. Other features include strategically placed cable & electric for flat screen televisions, Hi Efficiency HVAC, high tech LED lighting & many other features. Gracious jaw dropping primary bedroom suite with an infusion of natural light from tall south facing windows, enormous walk-in closet is ready to house a large wardrobe, with custom double hanging SS organizers some which include 20 lineal feet of hanging & 55 lineal feet of shelves. Resort Luxury spa bathroom with heated porcelain tile heated floors, steam shower, quartz bench, a custom designed floor to ceiling glass wall & door system, a rain shower, handheld shower & separate body washes, 6' air bath, a wall mounted floating double bowl vanity & two large mirrored medicine cabinets. Numerous oversized rear terraces offer respite to enjoy cocktails, read a book or have breakfast through dinner, private & spacious with sweeping downtown views. Full Laundry Center complete with full size washer & dryer, countertops & cabinetry cabinets. Enjoy fully curated exotic botanical gardens fully with specimen trees & bushes, many grafted, from around the world, including Japan, various countries in Eastern Europe, Canada & the USA ( all irrigated controlled by app) topped off with 9 car garage (2 of 9 Tandem). Fully stabilized with exceptional longer term tenants, this stunning, unique, trophy property offers a rare hybrid opportunity pairing investment with legacy. Full financials, floorplans, survey, and extensive pictures available. Actual Annual Income $213,045/NOI $141,525 / 6.5CAP Pre Approved buyers only. 48-72 hours' notice to show M-F (no weekend showings)

3967 S Drexel Boulevard, Chicago

$3,750,000

5 Beds ⋅ 5 Baths ⋅ 12750844 MLS ⋅ NEW Status

A rare and seamless blend of architectural history and sophisticated modern living. Situated on one of the neighborhood's most desirable blocks, this spectacular 5,500 square foot, 5-6 bedroom, 4.5 bathroom greystone has been meticulously renovated for a comfortable contemporary lifestyle while honoring its classic Gold Coast character. The handsome three-story stone exterior is capped by an ornate, original copper pediment and roof cresting - welcoming one to the home's many well-preserved historic details. Inside, the expansive front living room offers an inviting layout with space for multiple seating arrangements, a stately fireplace, and a bright and large view, framing mature trees and beautiful Gold Coast architecture. The dining room features the second of the home's three original fireplaces and easily accommodates large family gatherings and dinner parties. The leaded-glass pocket doors provide an elegant partition between the dining room and the home's kitchen. Bathed in morning light, the expansive chef's kitchen is a triumph of thoughtful design and high-end utility. A thick slab of deeply veined white marble tops the oversized central island, which features comfortable counter seating beneath pendant lighting. The culinary suite is anchored by a 48" Wolf range with dual ovens, a Sub-Zero refrigerator, a Bosch dishwasher, and a dedicated wine and beverage fridge. A large bay window, built-in banquette seating, and custom storage cleverly tucked under the rear staircase ensure this magnificent space is as functional as it is beautiful. Stepping out onto the rear terrace reveals a curated private escape. A custom pergola provides shade, while integrated infrared heaters extend the space's use into the cooler months. Designed for effortless entertaining, this exceptional outdoor sanctuary features dedicated areas for grilling and alfresco dining, alongside a full outdoor living room where a fire table provides an inviting focal point for evening gatherings. Back inside, the grand main staircase provides a masterclass in late 19th-century craftsmanship. Rich hardwood handrails and treads contrast with the crisp white wainscoting and expertly carved newel posts. Cleverly concealing a discreet main-floor powder room, the staircase rises past a stunning original stained-glass window to the home's upper levels. Occupying the entire front portion of the home's second level, the primary suite has a deep-set picture window with leafy street views and two closets. The ensuite primary bathroom features beautiful tilework, an oversized, spa-quality shower, separate soaking tub, and double sinks. A second ensuite bedroom with a balcony and a multi-use family room are also located on this level. The home's third floor thoughtfully accommodates three additional, generously sized bedrooms. The front bedroom with cathedral ceilings and a library wall is accessed by a pass-through 14x10ft bonus room, which can be easily tailored to your lifestyle and needs. Completing this level, the two remaining bedrooms share a classic Jack-and-Jill bathroom. The lower level is home to a large family room, a temperature-controlled glass wine room, a dedicated home gym (bedroom six) with modern bath and shower, and a rear mudroom with laundry. A two-car tandem garage completes the home. 1437 N. Dearborn is a truly exceptional and inviting home not often found in the neighborhood. This is a rare opportunity; located two blocks from Lake Michigan and Lincoln Park, in close proximity to beaches, top-rated schools, seasonal farmers' markets, world-class shopping, and fine dining.

1437 N Dearborn Street, Chicago

$365,000

6 Beds ⋅ 2 Baths ⋅ 12753109 MLS ⋅ NEW Status

Rarely Available Greystone 2-Flat! This Gem has the original wood work thru-out along with gorgeous hardwood flooring. The built-in on the first level adds character that blends with the remodeled upgrades perfectly. All units feature remodeled kitchen and baths with stainless steel appliances, dishwasher and granite countertops with ceramic style modern flooring and new vinyl windows (2022)Newer roof with silver coating. Seperate heat in all units. First floor has 3 bedrooms and Second floor has 3 bedrooms. Partially finished basement with laundry and storage. Detached 2 Car Garage and conveniently located near transportation and the Obama Presidential Library.

6525 S Vernon Avenue, Chicago

$1,199,000

5 Beds ⋅ 6 Baths ⋅ 12752105 MLS ⋅ ACTIVE Status

Welcome to this exceptional Greystone vintage 3-unit building offering 5 bedrooms, 5 full bathrooms, and 1 half bathroom, perfectly blending classic Chicago charm with modern comfort. Featuring beautiful landscaping, a fenced backyard, and thoughtfully designed living spaces, this remarkable property presents an outstanding opportunity for both homeowners and investors. A stunning hardwood staircase welcomes you through the main entrance, providing access to both the first- and second-floor units. Let's begin with the second-floor residence. As you enter, you're greeted by a bright and spacious living room, highlighted by a beautiful English skylight lantern above the foyer and oversized windows that fill the home with abundant natural light. Located just off the living room, the primary suite offers a private retreat with a separate sitting area, generous closet space, direct access to a private balcony, and large windows that create a warm and inviting atmosphere. On the opposite side of the living room, the second bedroom features a walk-in closet and ample living space. The unit includes two full bathrooms-one with a luxurious walk-in steam shower and the other with a relaxing soaking tub. Conveniently located between the bedrooms, the dedicated laundry room adds everyday comfort and functionality. Toward the rear of the home, the open-concept family room and kitchen create the perfect gathering space, centered around a cozy fireplace with both gas and wood-burning options. The kitchen is beautifully appointed with stainless steel appliances, a large center island with breakfast bar seating, pantry storage, and expansive windows that surround the space with exceptional natural light. The first-floor unit mirrors the upper-level layout, offering incredible flexibility for multi-generational living or rental income. It features its own fully equipped kitchen, two full bathrooms, a dedicated laundry room, and an added layer of security with alarm sensors installed on every window. From the rear staircase, you'll find access to the basement studio unit. Before entering the studio, you'll pass a spacious recreation room, utility area, and a separate laundry room dedicated exclusively to the lower-level residence. Inside the studio, you'll find a thoughtfully designed living space featuring a full kitchen with stainless steel appliances, a microwave, air fryer, and range hood. The studio also includes one full bathroom, one half bathroom, and generous closet space, creating a comfortable and functional living arrangement that's perfect for guests, extended family, or rental income. The rear staircase also provides convenient access to the rooftop, the first-floor unit, and the second-floor residence, making movement throughout the building both practical and efficient. Designed with long-term comfort and peace of mind, the property is equipped with multiple tankless water heaters, multiple zoned furnaces, multiple sump pumps, and a comprehensive security system, showcasing the exceptional care and quality invested throughout the home. Step outside to enjoy the beautifully landscaped, fenced backyard featuring a brick paver patio, mature landscaping, and multiple outdoor seating areas-an ideal setting for entertaining family and friends or simply relaxing outdoors. Conveniently located near public transportation, bus routes, restaurants, grocery stores, shopping, and everyday conveniences, this exceptional Greystone offers the perfect combination of timeless Chicago architecture, modern functionality, and outstanding investment potential. Don't miss this rare opportunity to own a versatile, meticulously maintained multi-unit property that seamlessly blends historic character, modern upgrades, and exceptional income potential-all in one of Chicago's most desirable neighborhoods.

4448 N Tripp Avenue, Chicago

$895,000

3 Beds ⋅ 4 Baths ⋅ 12742136 MLS ⋅ ACTIVE Status

Set on historic Washington Park Court in the heart of Bronzeville, 4917 S Washington Park Ct is a commanding 4-bedroom, 3.5-bath Greystone within the Washington Park Court Landmark District. The home has been fully updated and thoughtfully redesigned, preserving the character and presence of the original Greystone while creating a comfortable modern interior. Original hardwood floors remain on the top level, complemented by a beautifully designed luxury primary bath, an oversized working pantry, and generous living spaces throughout. Outside, a rooftop deck above the garage provides additional space for entertaining and relaxing. With its substantial Greystone facade, historic surroundings, and beautiful updates, 4917 Washington Park Ct offers the rare combination of landmark Chicago architecture in a modern home.

4917 S Washington Park Court, Chicago

$350,000

5 Beds ⋅ 2 Baths ⋅ 12749441 MLS ⋅ ACTIVE Status

Greystone architecture and original details give this early 1900s two-flat a character that's distinctly Chicago. Projecting bays, tall windows, hardwood floors and original millwork bring warmth and architectural interest throughout two well laid out residences. The first-floor unit offers 2 bedrooms and 1 bath with separate living and dining rooms, an updated kitchen with granite countertops and stainless steel appliances, in-unit laundry hookup, and a primary bedroom with walk-in closet. Upstairs, the 3-bedroom, 1-bath residence features an expansive living and dining space, updated kitchen and bath, hardwood floors, and in-unit laundry hookup. A full unfinished basement offers additional storage and utility, while generous outdoor space and parking for up to four vehicles are valuable additions. With two distinct residences, the property lends itself equally well to owner-occupancy or a fully income-producing investment. Located near Garfield Park, just east of the Conservatory, with convenient access to public transportation and downtown, this is an opportunity to own an architecturally rich piece of Chicago in a prime location. This property can be purchased as a package with nearby buildings 5315 W Monroe (MLS#12748904); 3344 W Fulton (MLS#12748759) or purchased separately. MULTIPLE OFFERS RECEIVED - Highest & best Due by Tuesday 9/8 at 2PM

4319 W Jackson Boulevard, Chicago

$525,000

2 Beds ⋅ 2 Baths ⋅ 12687306 MLS ⋅ CLOSED Status

Sun-filled condo in a stately 3-story Greystone on quiet, leafy one-way street. Very well-maintained boutique 8-unit building in a prime Lakeview location with parking included. Easy walk to the lakefront path, Red Line, Whole Foods, Wrigley, and Southport Corridor. Split two-bedroom layout with spacious rooms, separate living and dining areas, high ceilings, and oak hardwood floors throughout. An open side lot to the north, oversized windows, and high ceilings provide abundant natural light and warmth making this bright and cheerful condo feel like home. Filled with period detail, including an original built-in hutch and beautifully preserved trim throughout. Additional features include central air and heat, double-hung thermal-pane windows, in-unit laundry, spacious private rear deck, and a private walk-in storage room in the basement, perfect for bikes and seasonal items. The kitchen offers granite countertops and newer stainless-steel appliances, including a refrigerator (2024), microwave (2024), dishwasher (2025), and disposal (2024). Washer and dryer replaced in 2023. Low HOA of just $296/month in an immaculate, well-run association. Major updates include a new central air system (2026) and furnace (2021). Available to move-in after 8/31.

3826 N Fremont Street Unit #2N, Chicago

$1,198,988

8 Beds ⋅ 4 Baths ⋅ 12749117 MLS ⋅ ACTIVE Status

This beautiful, rare, and meticulously maintained vintage greystone is a fantastic, solid investment opportunity and an investor's dream! An ideal turnkey operation, it features two 3BR rentals plus a fully-furnished, top-rated, 2BR Airbnb, allowing several options for the buyer: enjoy income from the popular Airbnb and the fully-rented units; reside in a unit (or two) and reduce your mortgage payments through value-added rentals; or transform the entire building into your single family dream home! This spacious and sun-drenched beauty retains its vintage charm with 10' ceilings, hardwood floors, huge double hung windows, built-ins, and some original moldings. The main level 3BR, 1 bath features a wood burning fireplace with built-in mantel and bookshelves, full kitchen, in-unit W/D hookup, and window blinds. The second level 3BR, 1.5 bath was fully rehabbed in late 2019 with all new kitchen and baths, refinished floors, new in-unit W/D, built-out closets, new light fixtures, new wood blinds, new HVAC. The open plan, inviting 2BR, 1 bath, garden-level Airbnb (since July, 2018) with private entrance is fully furnished and has all the extra amenities guests expect, making it a top-rated (4.9/5) destination with Superhost designation. First and second level units open onto private decks with newly-rebuilt and sealed back stairs, including easy access to the roof via pull-down stairs on the second level deck, plus 15' x 8' secured storage area under the stairs. The Airbnb opens out the private back door to a storage area featuring full-size washer and dryer, then into the huge, secure and private backyard. Enjoy a green, urban oasis with mature landscaping, two large patios, and path leading to the masonry 2.5 car garage with extra storage space above (or retain the current garage renter for the extra income). The new roof (7/2019) is fitted with 9.0 kW Roof Mount Solar PV Array solar panels, offsetting utility costs. The location is the icing on the cake! Just steps from the University of Chicago law school and the Renee Grossman Residential Commons, and a stone's throw from the Green Line and Jewel-Osco, this property offers community, connectivity, and convenience. Only 3/4 mile from Jackson Park, the transformative Obama Presidential Center, and the vibrant lakefront, this location offers investment stability and exciting growth potential. Schedule your private showing now!

6109 S Greenwood Avenue, Chicago

$335,000

8 Beds ⋅ 2 Baths ⋅ 12742625 MLS ⋅ ACTIVE Status

Exceptional investment or house-hacking opportunity situated on a picturesque, tree-lined residential street in Chicago. This striking, legal two-unit brick Greystone offers two expansive residences, each featuring four bedrooms and one full bathroom, providing the space and flexibility. Each unit boasts a well-appointed kitchen with granite countertops and abundant cabinet storage, along with a full bathroom featuring a bathtub and exhaust fan for added comfort and convenience. Unit 2 has been beautifully refreshed with new flooring throughout, fresh paint, modern LED lighting, and brand-new stainless steel appliances, making it completely move-in ready. A full unfinished basement presents exciting value-add potential for a future duplex-down or possible third unit. Convenient access to public transportation and the expressway makes commuting throughout the city easy, while the nearby 71th Street and 75th Street commercial corridors offer a variety of shopping, dining, and everyday conveniences. Whether you are expanding your investment portfolio or looking to live in one unit while generating rental income from the other, this impressive Greystone offers outstanding space, versatility, and long-term potential.

6947 S Wabash Avenue, Chicago

$825,000

2 Beds ⋅ 2 Baths ⋅ 12731612 MLS ⋅ ACTIVE Status

Vintage lovers rejoice! Incredible opportunity to live in a 1894 Greystone on tree lined Dearborn with ultra-low assessments ($250!) including outdoor parking. This lovely 2 bedroom/2 bath home with woodburning fireplace, 10" ceilings, wood flooring and lovely library/den/guest rm, has been recently updated including a new huge, bright, eat-in kitchen any cook would envy with a long wall of windows. Stylish primary bedroom will easily accommodate a king-sized bed, sitting area, plus 2 roomy closets. Ensuite luxury bath is simply gorgeous. 2nd bedroom currently features built in bunk beds and bespoke floor to ceiling storage cabinetry. Your spacious living and dining room will easily accommodate various seating arrangements as you enjoy the beautiful tree top views of Dearborn. Please note this is a 3rd floor walk-up but it's worth the climb! Parking is not covered. Seller has replaced 8 of the 10 windows within last 2.5 years. HVAC replaced within last 8 yrs. Extra storage outside of unit.

1329 N Dearborn Street Unit #3, Chicago

$849,500

12744974 MLS ⋅ CONTINGENT Status

Pride of ownership! Immaculately constructed and fully rebuilt in 2017, this stunning 6-unit multi-family Greystone offers exceptional modern living and investment potential. Two of the six units are spacious duplexes located on the first floor of a deep lot, and all units are finished to a condo-grade standard. Extensive renovations completed in 2017 include a new roof, energy-efficient windows, professional tuckpointing, updated concrete work, new HVAC systems, plumbing, electrical, and beautiful hardwood flooring throughout. Each unit features custom-designed kitchens and bathrooms, a wood-framed back deck with durable steel screen doors, and soundproofing between floors for enhanced privacy. The lower levels boast elegant ceramic tile flooring, and every unit has its own utilities conveniently located on the same floor. All units are currently rented, offering immediate income for investors. This property boasts an extraordinary High cap rate-an exceptional return that is rarely seen in today's market. There is significant upside potential as current rents are well below market value, with at least $200 per unit of additional rental income easily achievable. For more information or to schedule a viewing, please call today.

1448 S Hamlin Avenue, Chicago

$825,000

3 Beds ⋅ 3 Baths ⋅ 12745319 MLS ⋅ ACTIVE Status

Beautiful duplex down, three bedroom condo in a historic East Lakeview Greystone. This spacious 2,300 square foot home offers three bedrooms and three full baths. The home's large front living room features a bright south facing bay window, wood burning fireplace, and an original hand carved colonnade that is sure to spark conversation. The central dining room complements the modern kitchen, which features a stainless steel appliance package and a large granite island with barstool seating for two. The generously sized primary suite includes an ensuite double vanity bathroom and a deep walk-in closet. Also on this level are a laundry room with a full-sized washer and dryer, and bedroom two which has direct access to the full guest bathroom. Downstairs, an expansive lower-level family room features a second fireplace (gas) and handsome built-in cabinetry. A third bedroom, a storage area, and a full third bathroom complete the lower level. Outside, a quiet front patio provides a seasonal escape. One oversized exterior parking space is included. An extremely walkable location, this home is within steps of public transportation, grocery stores and the best dining and shopping Lakeview has to offer. Nettelhorst Elementary.

734 W Briar Place Unit #1, Chicago

$589,900

10 Beds ⋅ 4 Baths ⋅ 12742351 MLS ⋅ ACTIVE Status

Classic Gothic Greystone 3-flat nestled on a deep lot with a rear garage in sought-after Washington Park. Each spacious unit offers approximately 1,500 square feet of living space. The building was reportedly gutted to the studs in 1996, with updates including oak floors, windows, electrical, plumbing, bathrooms, and kitchens. Separate electric, gas, and hot water provide added convenience for each unit. The full basement is unfinished and offers future potential. The main-level unit is available for owner occupancy. Ideally located on the LFA line and within walking distance of the train, with easy access to the University of Chicago, Chicago campus hospitals, Hyde Park, and the Obama Presidential Center. Easy to show. Pre-approved buyers only. This opportunity won't last!

Chicago

$1,295,000

10 Beds ⋅ 4 Baths ⋅ 12741174 MLS ⋅ ACTIVE Status

Excellent investment opportunity in the heart of Andersonville! This handsome three-unit greystone offers an impressive 10-bedroom, 4-bathroom configuration with spacious apartments with individual HVAC systems and strong rental income. Unit 1 is a generous duplex-down featuring four bedrooms, two full baths, and a separate family room, while Units 2 and 3 each offer three bedrooms and one bath. Additional highlights include private rear decks, common laundry, and a two-car garage. Ideally located near the restaurants, shops, cafes, and neighborhood amenities along Clark Street, with convenient access to public transportation and the lakefront. A substantial, income-producing property in one of Chicago's most desirable neighborhoods-schedule your showing today!

1319 W Foster Avenue, Chicago

$400,000

12 Beds ⋅ 3 Baths ⋅ 12742498 MLS ⋅ ACTIVE Status

Turnkey investor opportunity! This oversized, fully brick two-unit Greystone is a true turn-key multi-family cash cow, boasting 12 bedrooms across three levels. Perfect for a buy-and-hold investor seeking maximum rental yields or a house-hack scenario where tenant rents cover the mortgage. Unit 1: Expansive layout featuring 4 spacious bedrooms, 1 full bath, formal living and dining rooms, and pristine hardwood floors throughout. Unit 2: Massive top-floor layout with 5 bedrooms, 1 full bath, separate living and dining spaces, and optimized square footage for high rental income. Additionally, there is a finished basement featuring 3 bedrooms, 1 full bath, modern recessed lighting, high ceilings, thorough insulation, full code-compliant plumbing/electrical, and 2 egress exits. New tear-off roof (2020); furnaces and hot water heaters (2016); updated plumbing & electrical (2016); and a fully secure perimeter with a steel fence (2016). Fully cemented rear pad providing low-maintenance, secure off-street parking for 3 to 4 vehicles.

4312 W Adams Street, Chicago

$430,000

5 Beds ⋅ 3 Baths ⋅ 12742024 MLS ⋅ ACTIVE Status

Completely renovated and move-in ready, this stunning Greystone 2-flat offers an exceptional opportunity for both investors and owner-occupants! Beautifully updated throughout, this turnkey property features one tenant-occupied unit, providing immediate rental income, while the other unit offers flexibility for an owner-occupant or additional rental income. The spacious first-floor unit is a duplex-down featuring 3 bedrooms and 2 full bathrooms, offering generous living space and a functional layout ideal for larger households. The second-floor unit features 2 bedrooms and 1 bathroom with abundant natural light and modern finishes. Both units have been recently rehabbed, providing a fresh, contemporary feel throughout. Additional highlights include laundry hookups in the basement, a large concrete parking pad in the rear, and ample off-street parking for added convenience. Ideally located near schools, parks, public transportation, shopping, and major expressways, this property is an excellent opportunity to generate rental income, owner-occupy, or expand your investment portfolio with a turnkey multi-unit building. Schedule your private showing today!

4024 W Arthington Street, Chicago

$1,430,000

4 Beds ⋅ 4 Baths ⋅ 12741737 MLS ⋅ ACTIVE Status

Rare find! Gorgeous and enchanting Greystone on historic Alta Vista Terrace! One of only four three-story homes on this magical block: "Street of 40 Doors". Home has attached garage, beautiful front garden and 3 outdoor spaces/decks. Vintage detail preserved throughout, mixed with tasteful updates, combine modern amenities without taking away from the true character of this historic gem. Main level includes bright living room, separate formal dining room with wood burning fireplace, large kitchen with Viking/Bosch appliances, breakfast nook, powder room, and direct access to cozy terrace with built in custom Lion grill. Three bedrooms, an office, full bath, and access to a large deck adorn the second floor. Spacious master suite encompasses the top level. 2 skylights bring in abundant sunlight. Huge, professionally designed walk-in closet, large master Carrara marble bathroom with radiant heated floors, separate shower, clawfoot tub, and sauna. Library with additional fireplace, wet bar and access to top deck complete this third floor suite. Lower level boasts a family room with beautiful original stone wall, large laundry room, a second powder room, garage and abundance of storage. Dual zoned heating and air, newer tear off roof. A truly stunning home! Agent Owned

3823 N Alta Vista Terrace, Chicago

$2,849,000

5 Beds ⋅ 5 Baths ⋅ 12741954 MLS ⋅ ACTIVE Status

Nestled in leafy East Lakeview is this iconic 5 BR/4.1 BA Chicago Greystone on a massive 35' x 167.5' lot, with over 6,800 sq. ft. of finished living space. This home is essentially new construction inside of a vintage envelope. During its extensive 2016 gut renovation, no detail was overlooked, nor expense spared. Thoughtfulness, craftsmanship and innovation were at the fore. New Marvin windows were custom made to look like the originals, and all doors, staircases and wood trim were custom built to fit the style of the home, while adding a contemporary feel. The exterior facade and masonry was diligently maintained for authenticity. Stepping through the front door, the charming foyer leads to a grand staircase. Opening to a bright and airy south-facing formal living and dining room, the space is perfect for large scale entertaining and watching the seasons change from every window. The main living spaces flow beautifully into the chef's kitchen, which features custom cabinetry, quartz countertops, Wolf and Sub-Zero stainless steel appliances, two dishwashers, an island with bar seating, and a butler's pantry with a Sub-Zero wine refrigerator and beverage drawers. The back half of the main level is designed for fun and relaxation. Curl up with a movie or good book by the originally preserved fireplace, read the morning news in the dining area surrounded by windows, or host a competitive game night with plenty of room to spread out. The attached 2.5 car garage is easily spacious enough to store a third car; above it, with direct access from the living spaces, is an 800Sq.Ft. rooftop deck, perfect for large gatherings or a cozy retreat. Upstairs are 4BR's and 3BA's, with lots of natural light coming from the large windows and two skylights. The huge primary bedroom suite includes an oversized walk-in closet, with expansive custom cabinetry, a laundry hook-up, and a chute to the main laundry room. The en suite primary bathroom is spa quality, with large marble slabs, heated floors, dual vanity, walk-in shower and a full tub. Two other bedrooms are large and well designed with generous closets/storage, and the bathrooms have beautiful stone and tile, with heated floors. Currently the 4th bedroom is used as a stunning library and office with an original oak mantel and fireplace. Downstairs the entire lower level was dug down to add two feet of ceiling height and create additional comfortable living space, with stunning porcelain tile floors and radiant floor heat throughout. A large, open family/recreation room measures 54' feet long, has a surround- sound TV viewing space, and a future wet bar area (plumbing and power is already installed). The lower level has one additional bedroom and one full bath, and the adjacent rec room is large enough to easily add a 6th bedroom or an au paire/guest suite. This location is the best of lakefront living! Steps to the Lake Shore Drive pedestrian underpass to the lakefront path, Sydney Marovitz Golf Course, tennis courts, Belmont and Montrose Harbors, Starbucks on the next corner, and so much more. Multiple restaurants and neighborhood staples nearby such PR Italian Bistro, El Mariachi, Good Times BrewPub, and The Bake House, plus endless options down Broadway. Whole Foods, Jewel-Osco, Target and the soon-to-arrive Trader Joes are all within a four block walk or drive. Public transit is easy with the CTA Sheridan Red Line Station 3 blocks away, and the Broadway, Lake Shore Drive Express, Sheridan and Irving Park bus lines all within one block. Commuting downtown is easy and convenient via Lake Shore Drive at the end of the street. Plenty of school options nearby such as Bernard Zell Anshe Emet, Greeley Elementary, Disney Magnet School, or a straight shot down Lake Shore Drive to Latin School, Francis Parker and the Lab Schools.

652 W Sheridan Road, Chicago

$350,000

5 Beds ⋅ 2 Baths ⋅ 12738750 MLS ⋅ ACTIVE Status

Welcome to 1431 S. Christiana Avenue, a classic Chicago Greystone two-flat that offers an exceptional turn-key opportunity for savvy investors or owner-occupants looking for live-in rental income with strong upside. Beautifully presented with timeless stone masonry and a secure fenced perimeter, this property features bright, versatile living spaces highlighted by beautiful hardwood floors, light neutral tones, and classic arched pass-throughs. The main residential layout offers expansive, light-filled living rooms and dedicated dining areas, seamless eat-in kitchens equipped with extensive cabinet storage and gas ranges, functional full baths, and comfortable bedrooms alongside flexible bonus rooms ideal for home offices. Beyond the upper living quarters, the home presents incredible equity potential with a massive unfinished basement ready for duplexing down or future expansion, plus a low-maintenance back yard complete with a private concrete parking pad and easy access to local transit and Downtown Chicago.

1431 S Christiana Avenue, Chicago

$750,000

2 Beds ⋅ 2 Baths ⋅ 12737182 MLS ⋅ CONTINGENT Status

Beautiful extra-wide Greystone inside of magical Wrigleyville. One of the largest footprints in the area - over 1800sq/ft. Unique design and flooded with light. Owner-occupied required. Giant cook's kitchen, super-sized deck, LOW assessment. Building well-maintained. Unit well-maintained. An incredible city pad for Chicago Lovers. Sure to be one of the hottest properties on the market.

3810 N Fremont Street Unit #2B, Chicago

$799,000

9 Beds ⋅ 6 Baths ⋅ 12738119 MLS ⋅ PENDING Status

Bronzeville Exceptionally Striking, Classic Iconic Chicago, 3 unit 3 Story 1890's Greystone set on oversized lot size 25 by 161 with 2 car garage. Mammoth Floorplan, Multiple Bays, Expansive footprints , offer (3) 3 bedroom 2 baths, separate GFA/CA, washer dryer in units, hardwood floors, high ceilings, fireplaces, significant mill work and built ins, full basements with opportunity for further expansion. Hyper Convenient 1/4 block to green line, minutes to Lakefront, Kenwood/Hyde Park, U of C Campus and much more. Perfect for owner occupant, investor or 1031 Candidate. Fully Stabilized with meat on the bone. Income $78,900/GRM Can also purchased as package with 4734

4736 S Prairie Avenue, Chicago

$1,275,000

8 Beds ⋅ 3 Baths ⋅ 12737803 MLS ⋅ CONTINGENT Status

Set on one of Roscoe Village's beautiful tree-lined streets, this extraordinary and rarely available greystone is anything but typical. With a distinctive layout, oversized lot, detached greystone garage, finished studio space, and an abundance of original architectural character, this property offers a level of flexibility that is incredibly hard to find. Located in the highly sought-after Audubon School District, it is an exceptional opportunity for a single family home, owner-occupant investor, or multi-generational household. Owned and lovingly maintained by the same owner for more than 20 years, the main residence encompasses the first and second floors. Each floor features 3 bedrooms, 1 bathroom, a formal living room, formal dining room, and a beautiful custom wood-burning fireplace. Original details throughout the home include rich oak millwork, hardwood flooring, stained-glass accents, oversized windows, and spacious rooms that showcase the scale and craftsmanship of a bygone era. The kitchen was thoughtfully renovated in 2016 and features custom cabinetry, stone countertops, stainless steel appliances, and a large center island that creates an inviting gathering space. The bathroom was updated in 2021, providing a fresh complement to the home's classic architectural details. The garden apartment adds another layer of flexibility and potential. Currently configured as a 2-bedroom, 1-bath residence, it includes a full kitchen, comfortable living space, and excellent storage. The apartment was previously used as a 3-bedroom layout, offering additional possibilities for future use. One of the property's most unusual features is the detached greystone garage. Above the garage, a finished loft currently serves as a fitness studio and is already plumbed for a bathroom. Whether envisioned as a private office, art or creative studio, gym, workshop, guest space, or future finished living area, this bonus space provides tremendous potential. The property also includes a separate carport and an oversized yard with plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying the space. The home's substantial construction is further highlighted by approximately 12-inch-thick limestone walls, reflecting the quality, permanence, and craftsmanship characteristic of Chicago's historic architecture. And the location is hard to beat! Just two blocks south of the popular Roscoe Street corridor, you'll be close to neighborhood restaurants, cafes, parks, boutique shopping, and everyday conveniences, while still enjoying the peaceful residential atmosphere of this sought-after pocket of Roscoe Village. Properties with this combination of architectural character, scale, outdoor space, additional living space, and flexibility rarely come to market. A truly special opportunity to own a distinctive piece of Roscoe Village with the potential to adapt to a variety of lifestyles and investment strategies.

3248 N Oakley Avenue, Chicago

$899,000

9 Beds ⋅ 6 Baths ⋅ 12736649 MLS ⋅ ACTIVE Status

Discover timeless Chicago architecture in this stately three-unit greystone located in the heart of Bronzeville. Showcasing the distinctive Romanesque style-one of Chicago's most recognized architectural traditions-this classic building blends historic character with modern convenience. Each spacious residence features 3 bedrooms, 2 full bathrooms, and a separate formal dining room offering generous living space ideal for both everyday living and entertaining. The thoughtfully designed interiors include hardwood floors, soaring ceilings, in-unit laundry, and abundant natural light. Spacious kitchens are appointed with granite countertops, ample cabinetry, and room for a breakfast table or casual dining. Each unit is separately metered and equipped with its own furnace and water heater, providing convenience, efficiency, and simplified property management. The first and second-floor units are occupied by long-term tenants, providing immediate, stable rental income. The third-floor unit is currently vacant, presenting an ideal opportunity for an owner-occupant to move right in while benefiting from rental income, or for an investor to lease the unit and maximize the property's income potential. Step outside to enjoy brand-new rear porches, providing each unit with a private outdoor deck. The property also features gated parking with one dedicated parking space for each unit, offering added convenience for residents. The full basement provides additional value with the potential to create an additional dwelling unit or expand the property's existing living space. Situated on a picturesque tree-lined street, this exceptional investment or owner-occupant opportunity is just minutes from public transportation, neighborhood parks and green spaces, and the vibrant dining, shopping, and cultural attractions of nearby Hyde Park and South Loop. Whether you're looking to expand your investment portfolio or own a piece of Chicago's architectural heritage, this exceptional Bronzeville greystone offers the perfect blend of historic character and modern amenities. Enjoy stable rental income or sell later as individual condos. An outstanding opportunity for both investors and owner-occupants.

4408 S Michigan Avenue, Chicago

$650,000

12736126 MLS ⋅ ACTIVE Status

Turnkey vintage Greystone with six spacious 2-bed/1-bath apartments - a rare income package for the investor who wants cash flow now with the ability for further upside later. Originally built in the early 1900s and previously taken down to the brick in a full gut rehab in 2014, this classic 3-story masonry building leaves little to be desired. Two apartments have been tastefully renovated with brand-new kitchens, baths, appliances, and other upgrades totaling roughly $50K in recent capital improvements. New tear-off roof approximately 7 years old, complete masonry overhaul approximately 9 years ago, and new water service. All units are separately metered for gas and electric to keep expenses lean. Desirable floor plans, all featuring in-unit laundry, individual mechanicals, and utilities. Stabilized income in its current condition could easily generate an extra $1k/mo. The fenced rear yard offers potential to add off-street parking and create a new revenue stream. Great access to the CTA Green Line, Metra, and Chicago bus with Garfield Park, Humboldt Park, and the historic boulevard system right around the corner. Bring your investors - this one checks the boxes.

736 N Spaulding Avenue, Chicago

$364,999

8 Beds ⋅ 2 Baths ⋅ 12735939 MLS ⋅ CONTINGENT Status

Step into a classic 1898 Chicago Greystone, ideally situated in the evolving North Lawndale neighborhood just west of Douglas Park, between Roosevelt and Douglas Blvd. This area is seeing exciting revitalization-Inside, both units offer a layout with formal living room and dining room, hardwood floors. The first-floor unit features 4 Bedrooms and is currently rented month to month. Upstairs, the second unit has 4 Bedrooms and is currently rented on a fixed lease. Recent updates include new hot water tanks for both units and individual forced-air heating systems, offering convenience and independence for each space. The unfinished basement opens the door to future possibilities-whether you envision a duplex-down for added living space or a separate finished area for additional rental income. 2 parking spots on the back parking pad, new fence was recently installed. A new roof was installed 2 years ago. With both front and rear access, the potential here is easy to imagine. A location that keeps you connected-close to CTA lines, I-290, the Illinois Medical District, UIC, Pilsen, the West Loop, and downtown. A property with character, flexibility, and upside in a neighborhood on the rise-come take a look and see how it fits your vision.

1418 S Saint Louis Avenue, Chicago

$725,000

10 Beds ⋅ 5 Baths ⋅ 12734515 MLS ⋅ CONTINGENT Status

Fully Renovated Greystone in a rapidly appreciating neighborhood offering immediate income and long-term upside. This turnkey multi-unit property generates over $5,000 per month from two occupied units, while the vacant garden unit creates an ideal owner-occupant or value-add opportunity. Situated on desirable Sacramento Boulevard near historic Douglas Park, the building features renovated units with hardwood floors, updated kitchens and baths, in-unit laundry, and modern finishes throughout. A 2-car garage adds convenience and additional rental appeal. The vacant garden unit offers 3 bedrooms and 1 bathroom. The second-floor 3 bed / 2 bath unit rents for $2,300 per month, and the top-floor 4 bed / 2 bath unit generates $2,750 per month. A rare opportunity to own a fully renovated, income-producing Greystone in a high-growth Chicago neighborhood. Live in one unit or lease all three while benefiting from strong cash flow, equity growth, and continued area revitalization.

1130 S Sacramento Boulevard, Chicago

$425,000

6 Beds ⋅ 2 Baths ⋅ 12733768 MLS ⋅ CONTINGENT Status

Exceptional opportunity to own this beautifully updated 2-unit greystone just a short distance from the Obama presidential library. This quiet block offers a glimpse into the neighborhood's promising future. Upon arrival, you will be amazed by the supreme curb appeal! This meticulously renovated two-flat building exudes a captivating blend of contemporary elegance and classic charm. Every detail has been thoughtfully curated to offer ultimate modern comfort and style, making this property a true standout in its class. Both units are condo style luxury units with soaring high ceilings, tastefully designed new hardwood floors throughout, spa style custom bathrooms, and beautiful accent walls. With an open floor plan, each unit features a brand new chef's kitchen with luxurious white European cabinets, stunning quartz countertops, custom hardware, with a new stainless steel appliance package per unit. The exterior provides ultimate security and privacy including an exterior wrought iron fence and a brand new two-car garage. All major components including plumbing, electrical, HVAC, windows and roofing have been completed with approved ARCHITECTURAL PLANS AND CITY OF CHICAGO PERMITS. Live in one unit while renting the other. This property offers exceptional value and versatility. Conveniently located near schools, parks, public transportation, shopping, and major expressways, this is an opportunity you won't want to miss.Schedule your private showing today and secure your $20,000 Cook County equity fund buyer grant.

5742 S Morgan Street, Chicago

$640,000

2 Beds ⋅ 2 Baths ⋅ 12729172 MLS ⋅ ACTIVE Status

82 E Elm is a hidden gem, tucked inside a Gold Coast Greystone building on one of the most desirable tree-lined streets. This beautifully maintained 2-bedroom, 1.5-bath residence offers the perfect blend of vintage character and everyday practicality. The low assessments provide value without sacrificing location or lifestyle. The fully renovated kitchen, outfit with custom wood cabinetry and high end appliances, further merges modern functionality with charm. The spacious primary suite has it's own fireplace and access to a private patio. The second bedroom offers the perfect guest room or office space. Additional highlights for convenience include in-unit laundry, half bath, extra storage, and shared rooftop deck to unwind above the city. Just steps from Oak Street Beach, the lakefront, Rush Street dining, and Michigan Avenue shopping, this is perfect for full time or in-town residents. Schedule your showing today!

82 E Elm Street Unit #1, Chicago

$549,000

6 Beds ⋅ 2 Baths ⋅ 12726268 MLS ⋅ CONTINGENT Status

Calling all house hackers and investors! Welcome to this thoughtfully reinmagined historic greystone multi family building in West Garfield Park. Each unit has 3 generously sized bedrooms, a full bathroom redone with modern finishes and tilework, luxury vinyl flooring, separate living and dining rooms, brand new kitchen with shaker cabinetry, quartz countertops, beautifully tiled backsplash and new stainless steel appliances to finish the look. Fully renovated basement features an in-law suite with additional bedrooms, full bathroom, perfect for extended family or guests. Each unit has been equipped with individual washer/dryer hookups, separate tankless hot water heaters, new heating and cooling systems, and each units have their own separate utilities. A brand new back porch leads to a minimal maintenance back yard and a 2 car detached garage off the alley. Seller has thought of everything you could need. Nothing to do but move in and start renting! Call & schedule your showing today!

4330 W Wilcox Street, Chicago

$585,000

12 Beds ⋅ 4 Baths ⋅ 12731019 MLS ⋅ ACTIVE Status

We just installed a brand new roof and re-built the parapet! Turnkey 4-unit brick greystone, fully gutted and rebuilt in 2020, offering four spacious 3-bedroom /1-bath units (12 bedrooms total) plus a finished walkout garden level and two exterior parking spaces. Steps from Douglass Park and the Pink Line, and minutes to the Illinois Medical District, the West Loop, and I-290 - a location drawing steady renter demand and sustained investor interest along the revitalizing Ogden corridor. Each unit was rebuilt with modern kitchens, updated baths, and separate mechanicals, positioning the building for immediate lease-up at current market rents. Comparable renovated 3-bedroom units in North Lawndale are leasing in the $1,500-$1,800 range, giving a new owner a clear path to strong, stabilized cash flow with value-add upside on any below-market unit. Tax advantage: The 2025 assessment was successfully appealed at the Cook County Board of Review, reducing the assessed value from 50,400 to 40,174 - roughly a 20 pct reduction and an estimated annual savings of about $2,000. Post-appeal real estate taxes are projected in the ~$7,600-$8,100 range, materially lowering carrying costs and directly improving NOI for an income-focused buyer. Ideal for an investor seeking stabilized West Side cash flow or an owner-occupant house-hacker. As a 4-unit, the building qualifies for the Fannie Mae 5 pct-down owner-occupant program (2-4 units), which - unlike FHA - does not require the property to pass the self-sufficiency (net rental income) test, widening the buyer pool. Financing eligibility subject to buyer qualification. Offering memorandum with rent roll and expense detail available on request.

1307 S Kedzie Avenue, Chicago

$525,000

2 Beds ⋅ 2 Baths ⋅ 12723934 MLS ⋅ CONTINGENT Status

Stunning vintage 2 bed + den, 2 bath condo on a beautiful tree-lined street in the heart of East Lakeview. Move right in to this pristine top floor condo located in a stately historic Greystone building. Newer gourmet kitchen with granite counters and stainless steel appliances, newer windows, in-unit laundry, central HVAC, hardwood floors throughout, newly updated hall bath, high ceilings, and several skylights to allow for abundant natural light. Large layout with 2 bedrooms plus a den that is currently being used as the third bedroom. Brick fireplace is strictly decorative and is being sold as-is. Enormous storage in the basement. Located a half block from the cafes, shops, restaurants, and nightlife on North Halsted Street, three blocks from the CTA Belmont Red/Brown/Purple Lines station, and in the heart of everything East Lakeview has to offer!

833 W Buckingham Place Unit #3, Chicago

$520,000

3 Beds ⋅ 2 Baths ⋅ 12720695 MLS ⋅ CONTINGENT Status

Timeless vintage architecture meets refined modern living in this exceptional top-floor residence, nestled on a picturesque tree-lined street just a half block from the lake. Set within an intimate six-unit greystone dating to the early 1900s, this sun-drenched home showcases the craftsmanship vintage enthusiasts cherish, including original millwork, cove moldings, soaring 10-foot ceilings, five-panel wood doors, decorative mantels, coffered dining room ceilings, custom radiator covers, original honeycomb tile, a classic clawfoot tub, and two fireplaces. Offering exceptional flexibility, the expansive 3-bedroom, 2-bath floor plan can easily accommodate a fourth bedroom, home office, or additional living space. Modern updates include SpacePak central air (2021), Bosch in-unit laundry, radiant heat, private storage, and a covered deck perfect for outdoor entertaining. A garage parking space is included. Located in a meticulously maintained, 100% owner-occupied building with a strong association (no rentals permitted), this rare residence offers the perfect blend of historic elegance and contemporary comfort just moments from the lakefront, beaches, neighborhood dining, and all that Uptown has to offer-including the highly anticipated Trader Joe's coming soon. Cat-friendly building. Welcome home!

823 W Lakeside Place Unit #3E, Chicago

$274,900

9 Beds ⋅ 3 Baths ⋅ 12728907 MLS ⋅ PENDING Status

Don't miss this spacious and well-maintained Greystone featuring two generous units plus a finished basement. Each unit offers a full dining room, eat-in kitchen, and separate utilities-providing privacy and convenience for all occupants. First Floor: Beautiful hardwood floors throughout, 3 comfortable bedrooms, and inviting living and dining spaces. Enjoy outdoor relaxation on the rear deck. Second Floor: Carpeted with 4 well-sized bedrooms-ideal for larger families or tenants seeking extra space. Tenants are responsible for their own electric and gas. The property includes a gated backyard and ample street parking. Great opportunity for owner-occupants or investors looking for space, functionality, and charm! This property may qualify for up to a $15,000 Home Buyer Grant through the Chicago Neighborhood Recovery Program.

6522 S Peoria Street, Chicago

$109,900

7 Beds ⋅ 2 Baths ⋅ 12728094 MLS ⋅ CONTINGENT Status

Greystone 2 flat ready for your rehab ideas. Lots of renovations nearby. One 4 bedroom and one 3 bedroom unit. Full basement. Room for a garage. Take advantage of all of the appreciation in the area. Sold as is. No survey provided.

6550 S Union Avenue, Chicago

$725,000

2 Beds ⋅ 2 Baths ⋅ 12722439 MLS ⋅ CLOSED Status

Nestled on a picturesque, tree-lined street in the heart of East Lakeview, this beautifully updated top-floor residence occupies the entire upper level of an intimate Greystone three-flat. Offering an extra-wide layout with 2 beds and 2 baths, the home is filled with natural light and thoughtfully designed for comfortable everyday living and effortless entertaining. A private skylit entry opens to an expansive living and dining area featuring soaring ceilings, oversized windows, rich hardwood floors, elegant millwork and a beautifully restored fireplace. Tastefully renovated in 2023, the kitchen offers granite countertops, hardware and fixtures by Rejuvenation, custom cabinetry, plus new GE range/oven and Bosch dishwasher (2022) with direct access to a private rear deck, perfect for outdoor dining and relaxing. The spacious primary suite features a generous walk-in closet with dressing area and a luxurious skylit marble bath with double vanity. A well-appointed second bedroom and full marble bath provide excellent flexibility for guests or a home office. Recent improvements include a new furnace (2026), hot water heater (2021), tuckpointing of the front facade (2025), a rebuilt common rear deck (2020), rear stair and deck repairs (2026) and a roof and skylight inspection (2026). Additional highlights include in-unit laundry, an oversized garage parking space with dedicated storage, and an unbeatable East Lakeview location just moments from the lakefront, Whole Foods, neighborhood restaurants, Wrigley Field, parks, shopping and convenient public transportation - this exceptional home offers the perfect balance of quiet residential living and vibrant city convenience.

3614 N Fremont Street Unit #3, Chicago

$375,000

8 Beds ⋅ 2 Baths ⋅ 12639070 MLS ⋅ PENDING Status

Historic jumbo Chicago Greystone in West Garfield Park, recently operating at a 9.5-10 percent cap rate. This spacious 2-unit property is zoned RT-4 and eligible for the City of Chicago's ADU Program, offering strong current income, a vacant unit ready for immediate market-rate rental, and compelling value-add potential for investors looking to increase long-term returns. The first-floor unit features 3 bedrooms and 1 bathroom. The second-floor unit features 5 bedrooms and 1 bathroom. All bedrooms are generous in size, and both units offer huge living rooms, large dining rooms, and expansive enclosed rear porches. Both units went through extensive cosmetic renovations in 2024, including new bathrooms, lighting, flooring, paint, and stainless steel stove and refrigerator appliances. Unit 1 received copper plumbing and electrical updates, as well as a new furnace and water heater in 2024. Unit 2 received copper plumbing, electrical updates, and a furnace replacement in 2021, along with a new water heater in 2023. Additional improvements include a new basement furnace in 2024, several new windows in 2024, roof maintenance and repairs in 2024, and a new sump pump installed in March 2026. Unit 1 is currently rented to a CHA tenant for $1,600/month, with 89% paid by CHA. Unit 2 is currently vacant and ready for immediate market-rate rental. It was recently rented for $2,519/month through CHA, and the seller has active interest from new CHA tenants at $2,850/month. Tenants pay heat, gas, and electric. With much of the framework already in place, the basement provides a unique opportunity to further maximize the property's long-term income potential. The basement offers 8-foot ceilings, three separate entrance/exit points, and is currently framed out as a spacious 1-bedroom unit. Prior kitchen plumbing locations are visible, and the bathroom area is framed out with prior drain locations visible for a sink, toilet, and shower. The layout also allows for separate access to storage, mechanicals, and a future laundry area. The rear of the property includes a concrete parking pad inside a fully fenced yard. This is a solid investment opportunity with size, character, recent updates, existing rental income, separate utilities, and room to add future value.

4225 W Jackson Boulevard, Chicago

$749,995

7 Beds ⋅ 5 Baths ⋅ 12720697 MLS ⋅ PENDING Status

Stunning Greystone in East Rogers Park! Legal 2-flat with a finished lower level apartment. Fully rehabbed in 2016, the property boasts updated kitchens and bathrooms throughout. Units 1 and 2 offer hardwood floors, spacious formal dining rooms, family rooms, dens, and primary suites with en-suite baths. The modern kitchens are equipped with granite countertops, stainless steel appliances, and quality finishes. The lower-level unit includes 2 bedrooms, 1 bath, and an open-concept living, dining, and kitchen area. Additional highlights include a coin-operated laundry facility, gas forced-air heating, central air conditioning, and two outdoor parking spaces. An excellent nearly turnkey investment or great owner occupier!

7065 N Wolcott Avenue, Chicago

$775,000

3 Beds ⋅ 3 Baths ⋅ 12722002 MLS ⋅ CLOSED Status

Vintage Chicago, done exactly right. Welcome to your new home, 636 W Grace #1W, is a meticulously historic Greystone duplex which seamlessly blends timeless vintage charm with upscale modern finishes. South facing bay windows pour sunlight across the living room, anchored by a gorgeous hand-carved mantle with a gas fireplace that steals the show at every gathering. The second bedroom doubles as a knockout TV room with space for a king bed and deep sink-in couches. The open-concept kitchen and dining area serves up stainless steel appliances, granite countertops, custom cabinetry and a large island with storage on both sides. Pantry/laundry area has ample space for all your staples, towels and more. The generous primary suite impresses with walk-in closets and a separate office for today's live/work lifestyle. Two upstairs bathrooms feature designer-selected natural stone and high-end porcelain tile, along with Kohler fixtures. Gorgeous hand carved oak bannister takes you to a lower level with a large entertaining area with a 2nd wood burning fireplace. Generous 3rd bedroom with huge closet and private bathroom with shower. Plus two large walk-in closets on the lower level- one is ready to become your own private sauna room with beautiful cedar walls. Additional highlights include French doors, hardwood flooring, LED recessed lighting, custom window treatments. Leased parking space conveniently located right across the street in covered garage. Building amenities include a large shared rooftop deck with grill and beautifully landscaped backyard patio with two grills-perfect for parties. A large private storage room is included. Unbeatable East Lakeview location just steps to the Lakefront path and beaches, express transit, Whole Foods, neighborhood dining ,shopping, fitness, spas & more. Stunning condo is thoughtfully updated throughout, offering effortless move-in convenience in this rarely available, south-facing exquisite Greystone.

636 W Grace Street Unit #1W, Chicago

$799,000

9 Beds ⋅ 6 Baths ⋅ 12711183 MLS ⋅ PENDING Status

Unicorn Alert. Majestic without straining for it, 3-unit Greystone sequestered on a classic, iconic, intact storybook streetscape just off King Drive in the Heart of Bronzeville. The kind of block a location scout stumbles onto, and a neighborhood never stops being proud of. Three expansive 3-bedroom, 2-bath residences, each with a separate formal dining room. Significant documented capital improvements across sixteen years of single ownership delivering a turnkey opportunity for an investor or owner-occupant. Gated entry, professionally landscaped with irrigation system in place. Endless appointments, Premium millwork, crown molding, picture rail, trim and rich hardwood floors throughout. Gourmet kitchens, Granite & Quartz Countertops with stainless appliances. Washer and dryer, separate central air and gas forced air, individual hot water tanks in each unit. Closet organizers, window treatments, designer lighting throughout. Guest and Primary baths feature oversized and double vanities, tub/shower, built-in medicine cabinets and extensive stone and marble. Rear decks and oversized patio bookmarked by a two-car garage. Continuous exterior program including full structure power washing, tuckpointing and masonry restoration completed in 2026. Dual divided full unfinished basement separates private storage from building mechanicals at the rear, with the front section served by its own dedicated entry and exit offering expandable space for a workshop, office or additional dwelling unit. RM-5 zoning offers a clear path for an ADU; Zoning Certificate delivered as 3 Dwelling Units. This is a high value opportunity, Exceptional location, Hyper Convenient, walking distance to green line, minutes to lakefront, South Loop, U of C, Hyde Park, and much more. Current income $83,868. 48 hours' notice required for all showings. See broker's private remarks.

438 E 45Th Place, Chicago

$700,000

12 Beds ⋅ 4 Baths ⋅ 12723147 MLS ⋅ ACTIVE Status

Versatile greystone building in the heart of Little Village offering excellent investment or owner-user potential. Originally configured as a 4-unit residential property, select units have been converted to professional law offices over the years while retaining the flexibility to easily convert back to residential use. Solid masonry construction with spacious layouts, high ceilings, and classic character throughout. Large attic on top of the building that could be converted into additional living space. Ideal for continued office use or conversion back to multi-family residential. Prime South California Avenue location with strong rental demand in the surrounding neighborhood. Don't miss this rare opportunity to own a flexible, income-producing property with multiple use options.

2536 S California Street, Chicago

$269,900

3 Beds ⋅ 2 Baths ⋅ 12709087 MLS ⋅ CONTINGENT Status

Experience timeless sophistication in this 3 bedroom | 2 bath restored historic greystone. Welcome to Woodlawn, a neighborhood redefining Chicago's South Side where classic Chicago architecture meets refined contemporary design. Thoughtfully renovated in 2017 with high-end finishes and a level of exceptional craftsmanship that remains as relevant today as the day it was completed. An elevated foyer welcomes you with soaring high ceilings, dramatic coffered detailing, drenched with natural light, this open-concept is the perfect blend of sophistication & modern design. Richly appointed hardwood floors, solid-core 8-foot doors, custom window treatments throughout. The chef-inspired kitchen was designed for everyday living featuring custom cabinetry, granite counter tops, pot filler, premium stone back splash, and designer fixtures that elevate every culinary experience. The primary suite with walk-in closet is a retreat complemented by luxurious spa-style soaker tub perfect for relaxation after a long day. With newly installed unit laundry, water heater and parking this condo showcase is PHENOMENAL. Why settle for builder-grade when you can own the best value in today's market and a lifestyle you'll love. Access to the Obama Presidential Center, the University of Chicago, Jackson Park, local coffee shops, the lakefront, and the exciting redevelopment fueling the community's continued growth. This is not the South Side you remember. It is a community rich in history, investment, culture, and opportunity.

6409 S Maryland Avenue Unit #3, Chicago

$674,500

3 Beds ⋅ 4 Baths ⋅ 12721995 MLS ⋅ ACTIVE Status

Come home to this charming, Kenwood Greystone located on quiet, historic block. Featuring 4 bedrooms, 3 1/2 baths, gorgeous, dark stained, hardwood flooring on main level, premium, wood laminate flooring upstairs, modern kitchen and full, finished, lower level. Chef inspired kitchen with 42" custom cabinets, SS appliances and granite countertops. Primary bedroom with ample closets, en-suite bath that features dual vanities, jacuzzi tub, and separate, oversized shower. Dual zone HVAC system, contemporary feature wall with a built-in electric heater and decorative flame effect in living room, finished basement has custom, epoxy flooring and wet bar area complete with custom cabinetry and beverage refrigerator in the family room for entertaining family and friends. Near parks, the lakefront, bike trails, Lake Shore Drive and minutes from Hyde Park and Downtown. Pack your bags and move right in! Pre-qualified buyers only.

4420 S Berkeley Avenue, Chicago

$425,000

7 Beds ⋅ 2 Baths ⋅ 12721049 MLS ⋅ ACTIVE Status

RED HOT Englewood 2 flat! Greystone remodeled recently with quartz countertops, 42 inch white cabinets, washer/dryer in unit, Newer roof, Newer parking pad in rear. Unfinished basement waiting to be improved to living space but 2nd floor is a 4 bedroom tenant, 1st floor is 3 bedroom with tenant. 1st floor has central air. Basement could be duplexed down for more living space also has ingress and egress. Do not disturb tenants. Showing thru appts.

5406 S May Street, Chicago

$1,315,000

10 Beds ⋅ 7 Baths ⋅ 12711910 MLS ⋅ PENDING Status

Exceptional opportunity to own a piece of Chicago's architectural history in the heart of Lakeview! This stunning turn of the century Greystone sits on a rare, extra-wide 37.5' lot, featuring a lush private side yard and a 3-car garage that adds additional income potential. Located in the Burley school district, this multi-unit provides the potential to be a high yield legacy asset. Physical layout spans four functional levels, a raised garden, main level second floor & two additional upper levels. Perfect for an owner-occupant looking to "house hack," This building offers an oversized owner's unit starting on the third floor landing with a skylight. In addition there are three high-demand rental units to cover your mortgage. Three of the units offer two bathrooms. Step inside to find high ceilings, original millwork, and vintage character including original built-in hutches & hardwood floors throughout. Modern mechanicals provide peace of mind: individual gas furnaces, central air for all units, and updated electrical service include 4 tenant plus one common meter. The property also features a full 9 basement' with storage lockers (6x8) and coin-operated laundry facilities. Proximity to Ashland Avenue and the neighborhood "Jewel" mall provides tenants with unmatched convenience and transit access.

1628 W Nelson Avenue, Chicago

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