View All Woodlawn Chicago IL Greystone Homes Listings

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

$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

$410,000

6 Beds ⋅ 2 Baths ⋅ 12663098 MLS ⋅ CLOSED Status

Stunning Greystone two-flat in SIZZLING hot Woodlawn! This is an exceptional opportunity in one of Chicago's fastest-growing neighborhoods. This classic multi-unit property offers two spacious 3-bedroom residences with soaring ceilings, original woodwork, and beautiful vintage details, including decorative fireplaces and charming built-ins that showcase timeless character. The partially finished basement already includes a bathroom and offers incredible potential-create a garden unit, duplex down, or reimagine the entire property as a grand single-family home. The options here are truly endless, so bring your vision, your creativity, and your contractor. Ideal for a 203K loan and surrounded by exciting new development. The location is unbeatable-minutes from the Obama Presidential Library, Griffin Museum of Science and Industry, University of Chicago, beaches, golf courses, parks, top-rated schools, and a vibrant dining scene. Schedule your showing today and explore the possibilities. Property is being sold **AS-IS**.

6418 S Drexel Avenue, Chicago

$727,500

8 Beds ⋅ 3 Baths ⋅ 12464172 MLS ⋅ CLOSED Status

$15,000 seller credit and a low interest rate! A Greystone rebuilt with permits in vibrant Woodlawn. This 2023 gut-rehab blends historic elegance with modern upgrades. Potential rental income of up to $6,000/month. With the seller's credits you can reduce your mortgage payment to around $4,000, offering up to a potential $2,000 in monthly profit. The property features tall ceilings, hardwood floors, and condo-quality finishes like quartz countertops, shaker cabinets, and stainless steel appliances. Each unit has in-unit laundry and oversized decks. The first-floor includes a 2 bed/1 bath setup and is duplexed down with $60K in structural basement enhancements, providing future living space potential. Updates include new electrical, plumbing, main water line, main sewer line, and a 2-car garage. Located steps from the 63rd Green Line, near the University of Chicago, and close to the Obama Presidential Center, Hyde Park, and the lakefront. A unique opportunity to own a turnkey multi-unit in one of Chicago's most dynamic neighborhoods.

6347 S Drexel Avenue, Chicago

$330,000

4 Beds ⋅ 3 Baths ⋅ 12327400 MLS ⋅ CLOSED Status

Spacious Greystone rowhouse with garage in Woodlawn in need of a little TLC and cosmetic updates. First floor offers large living area with original pier mirror, separate dining room with built in cabinets, an updated kitchen (2019) and a powder room. Second floor features 4 bedrooms and two updated baths, but is in need of new flooring. Lots of south facing windows, large unfinished basement with decent headroom and exterior access. Roof is 5 years old, boiler less than 10, hot water tank replaced in 2023, electrical panel upgraded to 200 amps in 2019 and home is partially rewired. Laundry in the basement, deep garage off alley. Come and make this your dream home in a vibrant area close to the Chicago to lake front, Jackson Park, the Obama center and the University of Chicago. Welcome!

6523 S Woodlawn Avenue, Chicago

$600,000

3 Beds ⋅ 4 Baths ⋅ 12304613 MLS ⋅ CLOSED Status

Discover the charm of Woodlawn in this impeccably renovated Classic Greystone, where timeless architectural details are thoughtfully integrated with sophisticated, contemporary finishes and luxurious features. The open-concept design creates a seamless flow throughout the space, blending old-world character with modern elegance in perfect harmony. Tucked away on a peaceful, tree-lined street in the heart of Woodlawn, this flawlessly renovated 4-bedroom, 3.1-bathroom Greystone home exudes timeless charm featuring sleek recessed LED lighting, graceful up-lighting, and steel balusters that highlight its original architectural splendor while incorporating the best of modern design. The chef's kitchen is a perfect example, with white shaker cabinets, stainless steel appliances, spacious pantry and a large island, seamlessly merging style and function. The luxurious primary suite provides a private sanctuary with a Juliet balcony, a walk-in closet, and a spa-like bathroom. This indulgent retreat features Carrera marble, twin vanities, a freestanding soaking tub, separate shower boasting a rain showerhead and body sprays, creating an atmosphere of relaxation and luxury. Every element is thoughtfully designed to offer an unparalleled experience of comfort and sophistication. The fully finished lower level is a true extension of the home, offering an additional bedroom and full bathroom, along with a theater room, wet bar, and ample storage. At its heart lies a versatile recreation room, thoughtfully designed to adapt to your lifestyle. With spaciousness and refined design, it serves as the perfect setting for both relaxation and social gatherings, adding an extra layer of functionality and luxury to this remarkable home. Step out the back door to a spacious rear deck, a private backyard, and a two-car garage with additional storage, all securely enclosed by a wrought iron fence. This residence is a perfect fusion of elevated design and everyday comfort, offering a lifestyle of unparalleled style and grace. Ideally located near the University of Chicago, the Obama Presidential Center, Jackson Park, the Museum of Science and Industry, Lake Michigan, Lake Shore Drive, the Metra, and Hyde Park shopping, this home boasts an exceptional location that seamlessly blends cultural, recreational, transportation conveniences and more!!

6418 S Greenwood Avenue, Chicago

$673,000

3 Beds ⋅ 4 Baths ⋅ 12159836 MLS ⋅ CLOSED Status

Exquisite gut rehab Single Family Greystone in Woodlawn with 3+1 bedrooms, 3.5 baths w/high end finishes. Property features open floorplan w/formal dining area, staircase with custom stair case w/wrought, hardwood floors, exposed brick, fireplace, custom light fixtures, custom heating register vents restored from original home, ceiling fans & high ceilings throughout. Whole house filtration system, Whole house vacuum system, new 90% high efficiency furnace, new a/c, new 90% tankless water heater, built-in humidifer and new roof, new windows & new poured concrete. All new plumbing & sewer lines. Kitchen cabinets were designed & built by a luxury custom cabinet maker extra deep w/hidden storage & self closures, double oven, 6 burner stove, Breakfast bar w/pendants & overhang for barstools, cabinets on both sides & built-in wine/beverage refrigerator, Quartz counters, farm sink, custom backsplash, all SS appliances (refrig has ice/water). Porch off kitchen for entertaining. Ensuite Master w/marble bath, tub & private deck. All Baths feature stone/marble shower surround & heated floors w/custom in-lays, frameless showers w/European massage sprayers & floating vanities. High end camera system w/7" touchscreens & intercoms on every level in all rooms. Full finished basement w/exterior access, 7'9 foot ceiling height, wine cellar, entertainment area/recreation rm, bedroom, full marble bath & laundry room. 1 secured gated exterior pkng spot w/remote gate. Property is fully gated. Enjoy all Woodlawn has to offer - New Obama Library, Museum of Science & Industry, Jackson Park Golf Course, The Marina, Charter School, University of Chicago, Robust Coffee shop, near transportation & more!!

6448 S Greenwood Avenue, Chicago

$540,000

3 Beds ⋅ 4 Baths ⋅ 12141049 MLS ⋅ CLOSED Status

One of Woodlawn's Finest Greystone emphasizes its high-end finishes and modern amenities. It highlights key features like abundant natural lighting flows over beautiful hardwood floors, and custom design elements, such as coffered ceilings, crown molding, and LED lighting. The kitchen is very elegant with a waterfall island, Bosch stainless steel appliances, and soft-close cabinets. The family room connects to an outdoor deck and backyard, ideal for entertaining. The master suite offers luxury with a walk-in closet and a spa-style marble bathroom, which includes heated floors and a separate shower with multiple showerheads. The basement is fully finished with plush carpeting, a large recreational room, a laundry area with Samsung appliances, and a spacious bedroom with an additional bathroom. Practical upgrades include new windows, roof, 2 sump pump's, and insulation. This home's location is convenient to the University of Chicago, public transportation, and the future Obama Presidential Center, making it an attractive option for those looking for both luxury and accessibility in the area. Schedule your viewing today!

6513 S Woodlawn Avenue, Chicago

$630,000

6 Beds ⋅ 4 Baths ⋅ 12098256 MLS ⋅ CLOSED Status

East Woodlawn has not seen a Classic Greystone 2 Flat Remodeled to this condition in years. This fully renovated 2 Unit property has amazing touches from top to bottom. Each unit features 3beds & 2 Full Bathrooms with a huge open concept on from the living room, flowing thru the dining room into the kitchen. Each Unit features custom coffered ceiling designs with full modern touches throughout. New Roof, Updated Plumbing, updated electrical, new furnaces, new AC units, new back porch, and a new garage to house those vehicles. New Hardwood floors with quartz counter tops along with soft close cabinets and highend appliances to top it off! Walk to the University of Chicago, Jog to the Lake or Bike to the New Obama Center!!! As you can tell, this is an amazing location for this East Woodlawn 2flat. The basement is connected to the first floor for the optional duplex so you can finish it or you can seal off that entrance and create a 3rd unit because it has another entrance and exit in addition to the 7 foot ceilings! You will not be disappointed with this purchase!!! This is also a Great Airbnb option considering how close it is to all Chicago has to offer!!! Schedule your private showing today and don't miss out on this HOT WOODLAWN 2Flat!!!

6361 S Greenwood Avenue, Chicago

$350,000

3 Beds ⋅ 2 Baths ⋅ 11994999 MLS ⋅ CLOSED Status

Step into the elegance of the Maximalist lifestyle. Imagine having your Oppenheimer inspired martini on the settee in the parlor. This Greystone is perfect for the home buyer casting aside all the current neutrals in favor of a more elegant lifestyle. Upstairs boasts three bedrooms, and a bathroom that was formerly a bedroom. Your laundry room washer and dryer are upstairs as well (formerly the upstairs bathroom). The main level consists of the formal and informal parlor, dining room, kitchen and a half bath. You have a full walk out basement with a plumbed out bathroom and laundry ready for your ideas! Parking potential for one car off street parking. Home warranty included. Not one to sleep on.

6446 S Greenwood Avenue, Chicago

$565,000

9 Beds ⋅ 7 Baths ⋅ 11863534 MLS ⋅ CLOSED Status

Historic 3 story Greystone 4 unit building in heart of the Woodlawn neighborhood! This building boasts beautiful marble foyer, original trim and gorgeous stairways that are full of character. The three above grade units are empty and ready for new tenants, with market rents $1400-$1800! Live in one unit and have the other units pay your mortgage! The back decks are almost brand new with concrete patio. The electrical services have also been updated. Copper pipes throughout. Schedule your showing today!

6352 S Ingleside Avenue, Chicago

$620,000

10 Beds ⋅ 4 Baths ⋅ 11812552 MLS ⋅ CLOSED Status

Newly updated cash flowing 3 unit greystone in one of the most desired and fastest growing communities on the south side of Chicago, East Woodlawn! Situated on Greenwood avenue just a couple blocks from the University of Chicago and minutes away from the Obama Center. All units are occupied and features a spacious layout, hardwood floors throughout, updated bathrooms and kitchens with individual heating and cooling! 1st floor is duplexed to a finished basement with two means of egress for a potential 4th unit. Detached Two car garage for convenient parking or additional storage. This one won't last. Bring your buyers, offers and schedule a showing today!

6402 S Greenwood Avenue, Chicago

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