Browse All Winans Second Add Properties for Sale

Timeless character. Completely reimagined. Nestled in the most picturesque and enchanting pocket of Oklahoma City, this historic Heritage Hills residence captures the timeless charm that make this neighborhood one of the most beloved places to call home. The home’s location offers effortless access to local favorites like Harvey Bakery, Commonplace Books, Midtown, Paseo and other nearby amenities that make this area so coveted. Thoughtfully restored, the 4-bedroom, 2.5-bath home includes a dedicated office, a wonderfully versatile 1,000+ sq ft basement, and a rare, fully updated 1-bed, 1-bath studio attached to the two-car garage; perfect for guests. Nearly every surface has been renewed with extraordinary intention, blending old-world charm with modern luxury. The redesigned layout flows effortlessly through sunlit rooms adorned with restored original hardwood floors, original chandeliers, designer lighting, and Morris & Co. wallpaper that add warmth and heritage charm at every turn. The completely rebuilt kitchen feels straight from a design magazine, featuring a wet bar, premium appliances including a Bertazzoni range, and custom white oak cabinetry with thoughtful built-ins that elevate beauty, maximize storage, and enhance functionality. All-new electrical, majority updated plumbing, updated ductwork, Smart Nest thermostats, underground electrical service, Ring cameras, and 220V outlets provide peace of mind and modern convenience, while the detached studio offers its own WiFi-enabled mini split and a gas line prepared for a future outdoor kitchen or firepit. Expansive new wood decks invite you to enjoy the backyard beneath the canopy of mature trees, creating the perfect backdrop for morning coffee, lively gatherings, or quiet evenings. An extraordinary opportunity to own a lovingly restored piece of Heritage Hills history.

321 NW 20th Street, Oklahoma City

$805,000

4 Beds ⋅ 3 Baths ⋅ 1230026 MLS

Built in 1918, this warm and inviting Craftsman bungalow blends historic architectural character with generous modern living spaces. Nestled beneath old-growth sycamores planted as part of the original neighborhood plat, the home welcomes you with a gracious covered front porch—truly made for greeting neighbors and enjoying the daily rhythm of the community. Inside, an informal entry highlights the classic saddle-back staircase with a prairie-style balustrade, illuminated by a charming 30-pane piano window. The formal living room features large front-facing windows and a striking original fireplace framed by 16-pane upper windows. Both the fireplace and stair rail showcase beautifully preserved serpentine tiger oak, a distinctive hallmark of the era. A formal dining room extends beyond. At the rear of the home, a quasi-open kitchen connects to a substantial 463-square-foot addition, which includes a powder bath and a bright, comfortable second living area. Custom floor-to-ceiling built-ins and large doors overlooking the backyard make this an ideal gathering space. Outside, a spacious raised deck allows for ample room to entertain, beyond which is a well-maintained and developed backyard. Upstairs, four generous bedrooms are served by two large bathrooms. The oversized primary suite offers two closets, a sitting area, and an en-suite bath. The southeast bedroom is paired with an attached study, with both rooms enhanced by custom interior louvered shutters and multiple original 12-over-1 wood windows. Two additional bedrooms and a shared hall bath complete the upper level. In total, the home offers more than 2,700 square feet of living space. Located in nationally recognized Heritage Hills, the home enjoys immediate access to Downtown, Midtown, Uptown, and Automobile Alley. The neighborhood features an active association, beautiful parks and green spaces, pedestrian-friendly sidewalks, the beloved Overholser Mansion, and abundant character and charm.

217 NW 20th Street, Oklahoma City

$489,000

3 Beds ⋅ 3 Baths ⋅ 1226158 MLS

Architectural charm meets everyday livability in this beautifully preserved Dutch Colonial in Historic Mesta Park. Original hardwood floors, abundant natural light and a fireplace framed by built-ins anchor the main living area creating a warm, timeless setting. The dining room transitions effortlessly into an updated kitchen appointed with granite countertops, stainless steel appliances and classic cabinetry that honors the home’s character while delivering modern function. A versatile study or sunroom, lined with French doors to the backyard, offers flexibility for a home office, creative space or quiet retreat. The main level also features a spacious laundry room with custom cabinetry, built-in bench seating and a convenient half bath. Upstairs, the primary suite is a calm, private escape with crown molding, soft finishes and a sliding barn door leading to a walk-in closet. The ensuite bath is thoughtfully updated with a walk-in shower and contemporary tile. Two additional bedrooms share a well-appointed hall bath with dual sinks and updated finishes. Outdoor living is equally compelling with an expansive wood-beam pergola complete with string lighting, ceiling fans and a fireplace ideal for year-round entertaining. Mature landscaping, raised garden beds and a hammock area create a relaxed backyard setting. A two-car detached garage (sold as-is) and unfinished basement provide additional storage. Positioned just blocks from Perle Mesta Park and the Uptown 23rd District, this home delivers the best of Oklahoma City’s historic lifestyle - distinct architecture, meaningful updates and exceptional walkability.

216 NW 22nd Street, Oklahoma City

$429,000

3 Beds ⋅ 3 Baths ⋅ 1223023 MLS

Freshly painted downstairs interior! Classic 3-bed, 3-bath home in the heart of Mesta Park! Fully renovated in 2016 with updates to electrical, plumbing, and foundation, plus a freshly painted exterior. Inside you'll love the gorgeous hardwood floors, tall ceilings, and louvered shutters throughout.The chef's kitchen steals the show with European stove and fridge, shaker cabinets, apron-front sink. and an oversized pantry with drop zone. Each bedroom has a dedicated bath, with two bedrooms on the first level- an incredible find in this historic neighborhood. A standout home!

321 NW 22nd Street, Oklahoma City

$869,000

4 Beds ⋅ 4 Baths ⋅ 1193228 MLS

Nestled on a tree-lined boulevard in Historic Heritage Hills, this 1919 bungalow has been fully reimagined for modern living while preserving its timeless charm. Taken down to the studs in 2020 - including the garage, the renovation included restored original windows, new roof, electrical, plumbing, HVAC and sewer lines. The thoughtfully designed floor plan offers two bedrooms downstairs, each with ensuite baths, plus two bedrooms upstairs. The living room is anchored by a painted masonry fireplace with custom built-ins and abundant natural light, flowing seamlessly into the dining room and kitchen. The dining room is stylish and functional with designer lighting and direct access to the sunroom. The kitchen is a chef’s dream with custom cabinetry in a green-and-wood palette, quartzite counters, artisan backsplash, stainless appliances and a Bertazzoni gas range and oven. A large island with seating completes the space. The primary suite is located on the first floor, with French doors opening to the deck. The ensuite bath offers a spa-like retreat with a large walk-in shower featuring dual showerheads and a rainfall fixture, plus a custom double vanity with stone counters. A generous walk-in closet with built-ins completes the suite. The backyard has a spacious deck for entertaining, mature trees providing shade and privacy and a landscaped lawn with pathways leading to the detached two-car garage. A whole-house Generac generator ensures peace of mind, while the garage includes an EV charger, conduit for future solar and upgraded power. Additional upgrades include storm windows and doors, custom window shades, smart thermostats and switches (including the streetlight) and a SimpliSafe security system. Tech-forward features such as a whole-house Cat5 network, fiber internet and WiFi extending to the garage elevate everyday living. A rare opportunity to own a fully modernized historic home, just blocks from Uptown and Midtown dining, shopping and entertainment.

201 NW 20th Street, Oklahoma City

$621,670

4 Beds ⋅ 3 Baths ⋅ 1171509 MLS

Heritage Hills craftsman stunner restored in modern classic style! This recently completely remodeled home features top-of-the-line finishes including new paint throughout, 48" Thermodor gas range with grill & double oven, large island & wine chiller, farm sink, leathered finish granite, subway tile backsplash and so much more! The amazing master suite offers a large bedroom and a beautiful shower & soaking tub. The two additional downstairs bedrooms offer ample room and share a spacious hall bath. The upstairs boast a room that could be a second master bedroom, study or playroom with an additional full bathroom. Need storage? Head downstairs to the large basement that stays dry in even the wettest months. Step outside to the backyard oasis that boasts an electric gate, huge deck and a detached two car garage. Don't wait, schedule your private showing today!

220 NW 21st Street, Oklahoma City

$620,000

3 Beds ⋅ 3 Baths ⋅ 1166198 MLS

Historic Heritage Hills, Craftsman inspired home, with a large front porch! Open concept floor plan with an abundance of natural light and beautiful hardwood floors! Original fireplaces and built-ins, half bath, remodeled kitchen, utility/mud room and large dining leading to a spacious outdoor patio. Second floor has a suite with a remodeled bath and large walk-in closet. There are two additional bedrooms and a second full bath upstairs. Walking distance to Uptown 23rd Street district, Paseo, and Midtown.

316 NW 21st Street, Oklahoma City

$300,000

3 Beds ⋅ 2 Baths ⋅ 1139964 MLS

Located in the iconic Heritage Hills neighborhood, this bungalow is full of character and potential. Just blocks away from the vibrant Midtown and Uptown Districts and the picturesque, tree-lined Robinson Blvd, this single-story home offers an opportunity to restore its former glory with modern updates. The home features 3 bedrooms, 1.5 baths, and a basement, offering plenty of space to reimagine and customize to your needs.

217 NW 21st Street, Oklahoma City

$657,000

3 Beds ⋅ 3 Baths ⋅ 1139344 MLS

Heritage Hills Happy! This modernized historic home beautifully combines original 1920s charm with today’s favorite finishes and conveniences. Gorgeous wood trim and floors throughout, paired with a recently renovated kitchen and bathrooms. The flexible living spaces cater to both entertaining and everyday needs. You’ll fall in love with the updated kitchen, featuring white subway tile, quartz counters, stainless steel appliances, a spacious pantry, and a built-in eating area with custom banquette seating. Additional basement storage is conveniently located off the kitchen. The primary suite stands out with a painted brick fireplace, generous closet, full-sized laundry area, and a luxurious hotel-inspired bath. Enjoy a clawfoot tub, waterfall quartz vanity with double sinks, white subway tile walk-in shower. The secondary bedrooms are spacious with ample storage and are adjacent to a renovated bathroom. The backyard offers a cozy cottage feel reminiscent of the East Coast, with a lush lawn and landscaping surrounding a renovated garage apartment. This space includes a bedroom, kitchen, full bath, and laundry, perfect for guests, a home office, or rental income. Living in Heritage Hills means becoming part of a community. Neighbors decorate for every season, gather on front porches, and celebrate holidays at the local park. Enjoy nearby restaurants, shopping, and the charm of historic downtown. Total Square Footage: Main house - 2,364 SF, Apartment - 362 SF, Total ='s 2,726 SF (plus an additional 259 SF of storage space next to apartment.)

309 NW 21st Street, Oklahoma City

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