Winnetka Heights Homes For Sale

Newest Winnetka Heights Listings

Nestled along a beautiful, tree-lined street in the coveted Winnetka Heights Historic District, this stunning Craftsman home was thoughtfully restored in 2018, blending historic character with modern comforts. A welcoming covered front porch sets the tone, offering an inviting place to enjoy a glass of wine, visit with neighbors, or take part in the neighborhood’s social traditions. Step inside to discover a grand entryway, soaring ceilings, abundant natural light, and beautifully preserved architectural details. Rich woodwork, decorative ceiling beams, built-in benches, and sliding French doors add warmth and character throughout. The spacious formal dining room, complete with a cozy fireplace, flows into the inviting living room, creating wonderful spaces for everyday living and entertaining. The updated kitchen is designed to inspire, featuring a commercial-grade range, generous cabinetry and counter space, and an oversized pantry. A first-floor guest bedroom with an ensuite bath provides privacy for visitors, while a full-size laundry room adds convenience. Upstairs, two additional bedrooms share a hall bathroom, while the exceptional primary suite offers a retreat rarely found in historic homes. The oversized bedroom features a sitting area, spacious ensuite bath with soaking tub and separate shower, and generous walk-in closet. Outside, the private backyard offers multiple spaces to relax and entertain, including a deck, patio with pergola, and grassy lawn. An electric gate provides secure off-street parking. Beyond the home itself, Winnetka Heights is known for its historic architecture, tree-lined streets, and welcoming, socially connected community with lots of events put on by the Winnetka Heights Neighborhood Association. Just minutes from Kevin Sloan Park & the vibrant Bishop Arts District, with its eclectic restaurants, boutiques, coffee shops, & entertainment, this location offers the best of historic neighborhood living with modern urban conveniences.

121 S Montclair Ave, Dallas

$960,000

4 Beds ⋅ 3 Baths ⋅ 21405512 MLS

Come for the historic character. Stay for the space galore. Winnetka Heights Prairie style FourSquare offers spaciousness with carefully preserved details and sensitive updates that maximize storage & function. This property comes complete with a recently built ADU that complements the warmth of this historic home adding flexible space well suited for today’s lifestyles. A full front porch welcomes visitors into a large foyer that opens to light-filled formals. Glass-paneled sets of pocket and French doors define the transitions from Foyer to Living to Dining. Original picture rail molding remains intact. An ornate fireplace framed by built-in window seats anchors the living room. The eat-in kitchen features built-in bench seating, excellent storage, to-the-ceiling Shaker-style cabinetry and an induction range with double ovens. The second living area offers multipurpose possibilities. Imagine home office use or a movie room, playroom for toddlers or overnight space for guests. All four of the upstairs bedrooms have large windows & abundant natural light. A 284 SqFt screened porch overlooking the backyard was added in 2023. Its Saltillo tile floor, herringbone pattern, and pale blue beadboard ceiling are a delight. The ADU, designed by local historic preservation architect Alicia Quintans, includes upstairs guest quarters with a full bath and conditioned space below for a workshop, storage or creative projects. The exterior of the main dwelling has undergone extensive restoration. See SDN attachment for more improvement details. Class IV impact-resistant roof + foam insulation (2020); refinished pine floors & fresh paint throughout (2026); dedicated laundry area (2023); Zoysia sod & north-side fencing (2026). Zoned for Rosemont Schools. Just a short stroll to the Kessler School and Kevin Sloan Park. The WHNA is an active and vibrant support group dedicated to preserving the district as an enduring symbol of early 20th century life in Dallas.

111 S Rosemont Ave, Dallas

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 21392762 MLS

Some homes captivate with their beauty. Others draw you in with their story. This remarkable 1915 American Foursquare does both. Set on an oversized 75' × 150' lot in the heart of the Winnetka Heights Historic District, this magazine and home tour featured residence is celebrated for its rare blend of historic character and thoughtful stewardship. A full front porch welcomes you inside, where gracious formals bathed in natural light showcase rich maple millwork, original pocket doors, a tapered collonade from foyer to living plus built-in window seats and bookcases. The updated kitchen designed by Orchid Interiors features custom cabinetry, Carrera marble countertops, a large island, breakfast banquette, exposed brick, and a butler’s pantry. Upstairs, the spacious primary suite includes an ensuite bath, walk-in closet and private sitting room. Two additional bedrooms offer flexibility for family or guests. Framed by mature trees, one of Winnetka Heights’ largest lots includes an oversized detached, drive-through garage, with overhead doors on both the driveway and alley sides, a pergola-covered deck. The expansive lawn and established gardens create an inviting outdoor retreat. Space remains for a future swimming pool as well as added space above the garage. Roof with 10yr warranty (2017), beverage cooler (2018), attic insulation (2018), professional landscaping (2019), front and rear sprinkler installed (2019), cedar privacy fencing (2021), electric gate to alley (2021), exterior lighting added front and back (2021), refrigerator, downstairs HVAC (2022), microwave and cooktop (2024), whole house water filtration system (2024), dishwasher (2026), heat&air mini-split primary bath (2026). See Summary of Improvements for more details. Walk to the new Kevin Sloan Park, the Kessler Theater (deemed the best listening room in Dallas!), popular Cenzo's Pizza and Deli and all the shops and eateries along W Davis. Only 1 mile to all the fun in vibrant Bishop Arts!

105 S Winnetka Ave, Dallas

$474,999

3 Beds ⋅ 3 Baths ⋅ 21378357 MLS

Finish this house out the way you'd like it. Owner has already worked this through the city to get this craftsman style home into its new layout, with a new back built out for a third bedroom, bathroom and utility room. The roof is new from the interior roof structure to the 30-year shingles, foundation has been leveled and warrantied, rough plumbing, updated gas lines, rough electrical, HVAC Ductwork and furnace, spray foam in walls, exterior siding. This home needs your style placed in it to finish it out. All this with a plan & permits finished and green tagged. Lastly with an opportunity to take advantage of the City of Dallas Historic Tax Exemption Program. Enough Talkin' Let's Get Walkin'!

311 N Clinton Ave, Dallas

$489,999

3 Beds ⋅ 2 Baths ⋅ 21383017 MLS

Some homes make you choose between character and convenience. This one rather politely declines. Set beneath mature trees in the Winnetka Heights Historic District, this fully renovated three-bedroom, two-bath Craftsman makes a strong first impression with deep navy siding, crisp white trim, natural wood front doors, and a wide covered porch overlooking neighborhood green space. Inside, original hardwood floors bring warmth from room to room, complemented by oversized windows, substantial millwork, and an abundance of natural light. The floor plan feels open without losing the architectural character that gives the home its sense of place. The primary suite is a standout. Multiple windows keep the bedroom bright and airy, while French doors open to a beautifully renovated bath with a double vanity, fluted wood cabinetry, brass-framed mirrors, warm statement lighting, and a glass-enclosed walk-in shower wrapped in rich green tile. The second full bath has character of its own, with a granite-topped vanity and marble-tiled tub and shower surround. The updated kitchen is designed for both gathering and everyday life, with a generous island, plenty of cabinetry and workspace, and a dedicated pantry. Toward the back of the home, a sun-filled dining area is wrapped in windows and opens directly to the deck, creating an easy connection between indoors and out. Other updates include new HVAC and insulation. Out back, mature trees create a wonderfully shaded setting with a deck, fenced lawn, stone pathways, and a detached two-car garage. It feels private, established, and ready for long dinners outside or an unhurried Saturday morning. With Bishop Arts just minutes away and the Kevin W. Sloan Park close at hand, this home offers the character you come to Winnetka Heights for, with the thoughtful updates and everyday functionality that make staying awhile especially appealing.

418 S Willomet Ave, Dallas

$774,900

4 Beds ⋅ 3 Baths ⋅ 21304680 MLS

Back on the market and ready for its next chapter! This 1920s Winnetka Heights gem was extensively renovated in 2015. A 4-bedroom, 3-bath prairie-style home starts with an inviting front porch that overlooks a tree-lined street, while inside you'll find wood floors, two living areas, two dining spaces, custom cabinetry, large pantry and Carrera marble countertops. The kitchen opens to a second living area featuring a custom wet bar and easy access to the backyard, creating additional space for everyday living and entertaining. The functional two-story layout provides separation between living and private spaces. The private primary suite includes a walk-in closet, double vanities, a dedicated vanity area, and a soaking tub. Three additional bedrooms and two full baths provide space for family, guests, or work-from-home needs. Conveniently located near the Bishop Arts District, neighborhood parks, local dining, and entertainment.

209 S Windomere Ave, Dallas

$599,000

3 Beds ⋅ 3 Baths ⋅ 21224014 MLS

VERY MOTIVATED SELLER! BELOW DCAD APPRAISED VALUE! Enjoy the thoughtfully renovated and preserved vintage charm of this storybook airplane bungalow in historic Winnetka Heights. This is the most charming of Winnetka Heights! 3 Bedrooms. 2 full and 1 half bath...which is hard to find. Versatile second living space can be a fourth bedroom, office, library, or playroom! Even a separate sizable utility room with folding table! Freshly painted inside and outside. Refreshed landscaping. Downstairs primary ensuite with huge bath and walk-in closet. High ceilings on both floors. Original wood flooring (no carpets). Current baths. Flexible floor plan. Foodie kitchen. Windows, windows, and more windows! Plus a large front porch and expansive back yard with a party deck and a special brick patio area for the firepit. And, Rosemont Elementary!! Fantastic location! This neighborhood just feels good. A short jaunt to Bishop Arts, TYPO, charming Davis Street, local restaurants and hangouts. A short drive to downtown Dallas, the design district, medical district, and even the North Dallas Tollway. Totally turnkey. Even the refrigerator, washer and dryer are included! Move in today and have a party tonight!

214 S Montclair Ave, Dallas

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Listings provided by North Texas Real Estate Information Systems (NTREIS). Listing data has been deemed reliable but is not guaranteed to be accurate by the MLS.

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Winnetka Heights – Dallas' Most Iconic Historic District

Originally marketed as “Dallas’ Ideal Suburb” in 1911, Winnetka Heights stands today as one of the city’s most beautifully preserved and celebrated historic neighborhoods. Designated as both a City of Dallas Historic District and listed on the National Register of Historic Places, it remains a testament to early 20th-century suburban design, architectural craftsmanship, and community resilience.

Prestigious Beginnings and Prairie Grandeur

What is now Winnetka Heights began in 1890 as part of the Midway Addition to Oak Cliff. By 1908, the area was reimagined and replatted into a 50-block residential development by a group of prominent businessmen. Their goal: to create a prestigious, upscale suburb close to the city, yet removed from its congestion.

Development quickly gained momentum. Prairie-style homes, many built for Dallas' wealthy elite, lined the tree-shaded avenues, and the architecture reflected the opulence and attention to detail of the era. These homes were constructed using the finest materials and featured distinctive exteriors, broad porches, and richly crafted interiors. Over time, additional lots were filled with smaller Arts and Crafts-style bungalows, offering architectural harmony across various home sizes.

While only a few of the original developers' residences remain today, their legacy lives on through the neighborhood’s enduring historic character and thoughtful planning.

Decline, Rediscovery, and Preservation

Like many urban neighborhoods, Winnetka Heights experienced a period of decline after World War II. As housing demand surged, many of the large single-family homes were subdivided into apartments. By the 1960s, the neighborhood faced urban blight, and many of its historic properties had fallen into disrepair.

The turning point came when a new generation of homeowners, drawn to the area’s architectural charm, affordability, and urban proximity, began restoring its aging homes. Their grassroots efforts led to the creation of the Winnetka Heights Neighborhood Association, which pushed for protective zoning and formal historic recognition.

In 1981, Winnetka Heights became the first neighborhood in Oak Cliff to be designated a Dallas Historic District, paving the way for long-term preservation and revitalization.

A Vibrant Historic Community

Today, Winnetka Heights is celebrated not only for its architectural integrity but also for its strong sense of community. Ongoing neighborhood projects have included park and street beautification, historic lighting installation, sidewalk restoration, code enforcement, and crime prevention initiatives. The annual Holiday Home Tour draws visitors from across the region and showcases the neighborhood’s rich character and vibrant spirit.

Through decades of care and commitment, Winnetka Heights has transformed into a living example of early 20th-century neighborhood design—one that continues to thrive while honoring its past.