View All Chicago IL Tudor Homes Listings

$549,900
4 Beds 3 Baths 12746019 MLS ACTIVE Status
Welcome to 3331 N Rutherford Ave - Classic Chicago Charm Meets Modern Flexibility in Schorsch Village! Steeped in timeless appeal, this Classic Brick Tudor Cape Cod offers an incredible footprint with Est. 2,916 total sq. ft. across three full levels of living space. Featuring a striking brick facade, pitched gables, and iconic stone accents, this home stands out with undeniable curb appeal on a pristine, tree-lined street. Inside, you'll find a thoughtful layout designed for both everyday living and grand entertaining. Highlights include beautiful hardwood flooring, soaring vaulted ceilings, skylights, and a dramatic open-to-below/loft view that fills the dining and living spaces with natural light. The main level offers comfortable living quarters, while the expansive 2nd-floor primary suite retreat boasts a bedroom, a dedicated walk-in closet, and a full private bath equipped with a deep soaking tub and separate shower. The fully finished basement adds massive extra living space-perfect for a family room, home office, or gym-alongside ample utility and storage areas. Step outside to enjoy a private, manicured backyard with a concrete patio, ideal for summer BBQs and outdoor relaxation. Nestled in Chicago's vibrant Dunning neighborhood on the Northwest Side, this home offers quiet, suburban-style neighborhood living with seamless urban convenience. Don't wait-homes with this much space and structural integrity in Dunning don't stay on the market long! Schedule your showing today.

3331 N Rutherford Avenue, Chicago

$530,000
5 Beds 3 Baths 12749606 MLS CONTINGENT Status
Beautiful Brick Multigenerational English Tudor in Sought-After Galewood! Welcome home to this charming and spacious brick English Tudor nestled in the highly desirable Galewood neighborhood of Chicago-a hidden pocket known for its beautiful homes, tree-lined streets, and exceptional location bordering Oak Park and Elmwood Park. Enjoy the best of city living with a neighborhood feel, including convenient access to downtown Oak Park, scenic Thatcher Avenue, and the beautiful trails of Thatcher Woods. This distinctive home offers 5 bedrooms, 2.5 bathrooms, and exceptional multigenerational living possibilities, with spacious living areas and kitchens on both the first and second floors. The first floor welcomes you into an elegant and light-filled living room featuring beautiful leaded stained-glass windows and hardwood floors. An arched opening leads to the separate formal dining room, creating a warm and inviting space for entertaining and family gatherings. Down the hallway are two comfortable bedrooms and an original, beautifully maintained full ceramic-tile bathroom. The spacious eat-in kitchen features Corian countertops, dishwasher, oven/range, garbage disposal, pantry, refrigerator, and microwave. Just beyond the kitchen is a flexible third bedroom or family room, along with a convenient mudroom leading to the expansive backyard and newer 3-car garage. The second floor offers an impressive and versatile living space, making this home ideal for extended family, multigenerational living, or guests. A separate front staircase leads to a large, bright living room with another beautiful leaded stained-glass window. A charming library or small home office sits just off the entryway. The second-floor living space also includes a large dining room, two generously sized bedrooms, a full bathroom, and a full eat-in kitchen. The expansive finished basement provides even more space to spread out, featuring a huge family room with high ceilings, a convenient half bath, and a laundry area with an additional small shower. A large, clean unfinished area offers tremendous potential for storage, a workshop, exercise room, or future customization. An exterior door provides direct access to the backyard. Additional features include newer central air, gas-forced-air heat, hardwood floors, and a newer 3-car garage. With its unique layout, timeless Tudor character, beautiful original details, and incredible potential for multigenerational living, this special Galewood home is ready for its next chapter. Come discover one of Chicago's best-kept neighborhood secrets-conveniently located steps to Oak Park, Elmwood Park, The Metra, Near O'Hare Airport,shopping, dining, transportation, and beautiful forest preserve trails. A rare opportunity to own a spacious, character-filled multigenerational home in the heart of sought-after Galewood!

1619 N Normandy Avenue, Chicago

$849,900
3 Beds 4 Baths 12640811 MLS ACTIVE Status
Welcome to 5801 N. Kenton Avenue, a rare opportunity to own a timeless residence in the heart of Sauganash, one of Chicago's most treasured historic neighborhoods. Designed by architect Frank Polito, this beautifully crafted 4-bedroom, 3.5-bath home offers approximately 2,800 square feet of living space on a spacious 7,400-square-foot corner lot. The home blends enduring craftsmanship with classic architectural charm, featuring original refinished hardwood floors throughout, elegant crown molding, beautiful built-ins, and a cozy wood-burning fireplace that creates a warm and inviting gathering space. The spacious floor plan offers exceptional flexibility for today's lifestyle while preserving the home's original character. A large sunroom fills the home with natural light and provides the perfect space to relax, entertain, or enjoy views of the backyard year-round. A full finished basement offers additional living and entertaining space, while the stately two-story masonry exterior with its distinctive mansard roof enhances the home's timeless curb appeal. Throughout, vintage details and quality craftsmanship reflect the rich history that makes Sauganash homes so highly sought after. Step outside to enjoy a fully fenced backyard designed for privacy and relaxation. The spacious back deck is perfect for outdoor dining, entertaining, or simply enjoying peaceful evenings, while the outdoor storage shed provides convenient space for lawn equipment, tools, and seasonal items. Situated on a desirable corner lot, the property offers added curb appeal, additional outdoor space, and endless opportunities to create your own dream backyard retreat. Located on a picturesque tree-lined street within the highly sought-after Sauganash Elementary School district, this home places you in the center of one of Chicago's most admired communities. Known for its distinctive Tudor, Colonial Revival, Georgian, English Cottage, and other classic architectural styles, Sauganash is celebrated for its mature trees, strong sense of community, and exceptional pride of ownership. Outdoor enthusiasts will appreciate being just moments from LaBagh Woods, Sauganash Park, the Sauganash Trail, and the North Branch Trail System, offering miles of scenic walking, running, and biking paths. With nearby parks, schools, neighborhood favorites, and convenient access to major roadways, Kenton offers the perfect balance of historic charm, natural beauty, and everyday convenience.

5801 N Kenton Avenue, Chicago

$1,040,000
3 Beds 4 Baths 12591451 MLS CLOSED Status
An unparalleled opportunity to own one of the North Side's most stunning, custom-designed Tudor homes. This masterpiece sits on a rare 45-foot lot, offering extraordinary character, meticulous maintenance, and original architectural details. The journey begins at the welcoming front porch, featuring stone pillars and a wrought iron arch, leading to an impressive heavy wood door. Ring Cameras at every entrance offer the homeowner added security. Inside, the formal entry boasts exquisite original plaster moldings and a gorgeous arched doorway. The expansive living room shines with coved ceilings, a custom stone fireplace, and abundant natural light from oversized windows. Designed for both intimate living and grand entertaining, the floor plan flows from the living room to a sun-drenched family room with brand new skylights and scenic views of the professionally landscaped grounds. The gourmet, fully renovated kitchen is a chef's dream, featuring custom-lit white cabinetry, sleek granite countertops, and high-end stainless steel appliances, including a built-in stove and oven. A cozy, custom-built breakfast nook offers tranquil backyard views. The upper level features three generous bedrooms, including a vast primary suite with double closets, and a third bedroom with a newly added marble bath including a Brand New LG washer/dryer combo for added convenience. The finished, high-ceilinged lower level is ideal for a home office, gym, or playroom featuring Brand New full sized Samsung Washer and Dryer. Set on an extra large lot, this property features a designer patio and a 2-car garage with Brand New EV Charger. This home is the perfect blend of vintage charm and modern luxury, featuring newer windows, updated 200-amp service, and BRAND NEW triple-zoned HVAC." Ask agent for the numerous upgrades list to this gorgeous home.

2821 W Greenleaf Avenue, Chicago

$365,000
4 Beds 2 Baths 12404748 MLS CLOSED Status
Multiple Offers Received! Charming Two-Story, 4bed/2bath brick Tudor-style home with HUGE dry basement! Nestled on a picturesque, tree-lined street surrounded by storybook homes, this move-in-ready gem blends classic charm with modern updates. The mainfloor features an open and inviting layout with a LARGE livingroom, dining room & kitchen, hardwood floors, and a wood-burning fireplace, along with two generously-sized bedrooms that can easily accommodate KING beds and a full bathroom. Upstairs, you'll find two more HUGE bedrooms with ample closet space and another full bathroom. This home also offers a spacious 2-car garage and a fully fenced yard, perfect for outdoor fun and entertaining! Recent updates include a new FTVN high-efficiency boiler and combo hot water heater (installed November 2024), a new sewer line from the house to the street, and a new sump pump (both installed August 2023). All interior plumbing has been rodded and cleared for worry-free clean-living! The roof is approximately 10 years old, and the tuck-pointing was done in 2020. A new deck and backyard fence were installed in 2022. Additional recent improvements include fresh paint throughout and new appliances. The huge basement with 8' ceiling height offers endless possibilities for customization. The location is also incredibly convenient, with nearby amenities such as Target, Aldi, Fresh Thyme Market, Walgreens, Planet Fitness, and Home Depot. It's just one block from North Avenue shops, restaurants and the CTA Bus #72, three blocks from the Metra station (providing EZ access to downtown Chicago), and close to two parks, as well as nearby Oak Park. Come see it this weekend!

1731 N Normandy Avenue, Chicago

$1,410,000
3 Beds 4 Baths 12285120 MLS CLOSED Status
Absolutely stunning 4-year new construction "Tudor Revival" on picturesque Dover St. in this historical Chicago Landmark District. This 3 bedroom/4 full bathroom home sits perched up on higher grade extra wide city lot with tree line views of the gorgeous homes on this block. Tastefully designed throughout, this home exudes a luxury feel, with traditional quality and character. Step inside the welcoming foyer and take notice of the glistening American Hickory hardwood flooring with sight lines straight through to the rear of the open concept layout. Upon entry you have a stunning formal dining room large enough to accommodate your full-size dining tables, buffets, or additional furnishings. Host your guests at the custom built dry bar on main level with beverage fridge, custom cabinetry, and quartz counters. The open concept kitchen features extra large island for entertaining with quartz countertops, in-island sink, and designer pendant lighting. Kitchen has ample storage with 42" white maple cabinetry and walk-in pantry with custom shelving. All stainless high end appliances. Huge family room off kitchen with fireplace is warm and inviting. Primary suite on second level is flooded with natural light from the back yard and features a walk in closet and primary en-suite bath with walk-in shower, soaking tub, double vanity, and heated floors. Secondary full bath off hallway and large laundry room with additional storage on second level. Lower level family room is cozy and warm with plush carpeting throughout. Great space to watch movies or games from a large sectional or have game night. Sitting area on lower level could easily be converted to a 4th bedroom with en-suite bath by simply adding a wall and entry door. Lower level full bath has shower and heated floors. Additional storage room in basement. The back yard of this home is an oasis in the city! Absolutely amazing covered back porch has a natural gas line for fireplace or grill. Stunning views of this plushly landscaped yard on the oversized city lot. Detached brick 3 Car garage with potential for a coach house unit!!! This home is a certified zero energy ready home. Energy Star certified LEED for Homes Gold Level. Solar panels with Enphase inverter, and EPA indoor airplus system. Just steps from the heart of Andersonville business district with amazing shops and restaurants, Uptown Entertainment District, The Riviera Theater, Aragon Ballroom, and Red line station. Close and easy access to Lakefront and Lake Shore Dr. This home is a show stopper. Schedule your showing today!

4730 N Dover Street, Chicago

$2,650,000
5 Beds 5 Baths 12064004 MLS CLOSED Status
Nestled in the exclusive and historic enclave of Castlewood Terrace sits this three-story Tudor Revival style home on a massive 90x114 wide lot. This 5BR, 3.2BA home has undergone an extensive renovation over the last four years, with every detail carefully crafted to ensure light, flow, and functionality were at the forefront. Built in 1909, Alexander Maltman, President of Aetna Bank, and his son, James, saw the opportunity to build lakefront estates, capitalizing on the growing entertainment district on Broadway Avenue. The Maltman's commissioned architect William Mann to design two Tudor style homes (this home and the one across the street), and the father-son duo built four homes total on the street, leaving an indelible mark on Castlewood Terrace. Natural light fills every square inch of the perfectly proportioned rooms, showcasing exquisite details crafted with the utmost precision. The first floor has a fluid layout-a captivating living room w/a wood-burning fireplace, adorned with a sleek custom-milled surround and bookcases. The naturally lit sitting room adjacent to the living room provides an ideal work-from-home environment, or space for large gatherings. The redesigned kitchen, semi-open to the living room, and open to the dining area, is a culinary haven with expansive counter space, professional-grade appliances, custom backsplash, handcrafted white oak cabinetry, and a contrasting handcrafted concrete island w/seating. Flowing seamlessly from the kitchen and dining room, the open and airy family room has new architect series Pella windows, custom wood paneling, a built-in media area, and a mudroom w/a discreet custom white oak closet. The family room extends to a two-tiered deck overlooking the pond and side yard. A tastefully updated powder room completes the main level. The upper level has three large bedrooms, including the expansive primary suite featuring a bespoke closet/dressing area, an additional walk-in closet, an office/sunroom, and a luxurious ensuite bath with a dual vanity and spa-like shower. Two additional bedrooms share access to the updated second full bath. The third floor is equipped with 2BRs, full bath, and ample closet space. This level offers many possibilities, such as a private primary suite, or guest/au pair suite, or office space. The modern aesthetic extends to the lower level, hosting a versatile play area with a preserved bar rumored to have once housed a speakeasy (in fact, when the sellers built the new garage, they found an underground tunnel believed to be part of a chain of speakeasies on the street)! Outdoors, the lushly landscaped fenced yard features a waterfall stone fountain, expansive grassy areas, and mature trees, creating a private suburban ambiance just moments away from downtown, Uptown, Andersonville, and Edgewater. The new 2-car Hardie board garage is equipped with custom storage, Pella architect series custom windows, and the option for an electric charging port. Adding to the allure of this home and location is the fact it is walking distance to the beaches along Lake Michigan, the Lake Front Trail, and one mile north of the Montrose Bird Sanctuary. Enjoy all the nightlife and entertainment Uptown has to offer, including concerts at the Riviera Theatre, Aragon Ballroom, and soon to be remodeled Uptown Theatre. Some of the best dining is within 2-4 blocks, including several restaurants in the Asia on Argyle corridor, Tweet, and Dib. Commuting downtown is simple: 146 (Gunnison & Marine, 1 block away) & 147 (Foster & Marine, 3 blocks away and runs express to Michigan Avenue) express buses, the Lawrence Red Line stop, or easy access to Lake Shore Drive!

905 W Castlewood Terrace, Chicago

$780,000
3 Beds 4 Baths 11909908 MLS CLOSED Status
Once in a lifetime opportunity to own one of the most beautiful custom designed homes on the north side This spectacular custom designed Tudor home is packed with incredible charm and original details like no other and sits on an extra wide 45 ft. Lot! Starting with the front porch with the stone pillars and wrought iron arch that leads to the original heavy wood front door, every detail of this house has been impeccably maintained. The formal entry foyer has original plaster moldings, a large closet with original doors and a beautiful arched doorway that leads to the family room. The grand extra-large living room is spectacular with original cove & plaster moldings, original stone fireplace, tons of extra-large windows and refinished hardwood floors. The dining room opens to both the living room and the family room and is the perfect size for a full dining room set and looks out on the incredibly landscaped side yard. The family room is full of sunlight from the huge windows and skylights and surrounded by green trees and landscaping. The completely rehabbed kitchen was custom designed with timeless finishes. The designer white cabinets are topped with upper glass cabinets that are custom lite, the gorgeous granite reflects the surrounding green that you see from every window, the stainless appliances are all high-end with custom fronts and include a drop-in stove top and built-in oven. Just off the kitchen is the most charming breakfast nook with built-in banquets and granite table offering views of the backyard. The gorgeous original staircase leads to the 3 large bedrooms and 2 baths on the second floor, each bedroom is large enough for a king size bed. The primary bedroom is huge and has 2 separate closets. The 2nd bedroom includes a walk-in closet, and the 3rd bedroom has a new attached marble bathroom with walk-in shower, granite counters and designer sink. The lower level is finished with high ceilings and perfect for extra bedrooms, extra office, playroom, workout room, etc. The yard for this home is truly spectacular. The 45 ft. Wide lot allows for tons of sunlight in and around the house, includes a designer patio and has been stunningly landscaped, it also allows room for an easy addition to the house. Other wonderful details include hardwood floor throughout, original sold core doors, new windows, custom lighting fixtures and window treatments including plantation shutters, arched doorways, dual heating and cooling systems, recess lighting, 200-amp service, tons of storage space and 2 car garage that can be expanded to a 3 car! Taxes $7783.74/yr. Chandelier in foyer and built-in office furniture excluded.

2821 W Greenleaf Avenue, Chicago

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Chicago, IL · Curated MLS Search

Tudor Homes in Chicago, IL

An editorially curated view of every active tudor homes listing in Chicago, IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings