Location: Winter Park
Keyword(s): Glenridge Middle
Keyword(s) Middle School: Glenridge Middle
Do Not Show Listings
2681 FITZHUGH RD, WINTER PARK, FL 32792
$750,00064 Days on yellowkey MLS ID: O6383699
0 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 1966 Tax: $5,903 (2024)Community: Winter Park Pines Merrie OaksSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,903
Elementary School: Aloma Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Rebecca Bininger Junod (407-230-3650)
1841 HARLAND PARK DR, WINTER PARK, FL 32789
$1,895,000116 Days on yellowkey MLS ID: O6369653
0 Days Off yellowkey (back on 4/11/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3470 Built: 2014Monthly Fee: $262 Tax: $21,031 (2024)Community: Windsong-Knowles PlaceSingle Family
Taxes:$21,031
Elementary School: Brookshire Elem
Remarks: Price reduction. Motivated seller! Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added privacy. The formal dining room features a pass-through to the Butler's Pantry, which leads into a chef's oasis—Wolf stainless steel appliances for the serious chef, and solid surface countertops. The gourmet kitchen opens up to the family room. This home is a Great floor plan for entertaining friends and family. Eat in nook is located off the kitchen for dinners together. The primary suite is located on the first floor with a spa-like ensuite. Double vanity, extra-large shower, large bathtub for when a relaxing bath is just what you need after a long day. Upstairs, you will find a bonus room, as well as the remaining bedrooms. off the bonus room is a bedroom and a full bathroom, great for guests. The other two bedrooms and bathroom are located on the opposite side of the upstairs to create a split floor plan. Large backyard for enjoying the Florida weather. New EV charger in garage, new A/C unit. Home includes surround sound. This home features numerous upgrades, too many to list. Windsong community offers a resort-style pool with lake views, a playground, lake for fishing. Close to restaurants, schools, and shopping.
Listing is courtesy of: SELECTIVE REALTY GROUP LLC (407-627-1727)
Listing Agent: Shanon Luiz (407-247-2241)
639 FRIAR RD, WINTER PARK, FL 32792
$795,00022 Days on yellowkey MLS ID: O6395715
1 Days Off yellowkey (back on 4/20/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1950 Built: 1967 Tax: $3,415 (2025)Community: Winter Park PinesSingle Family
Taxes:$3,415
Tax Year: 2025
Remarks: Welcome to 639 Friar Road, ideally situated on a quiet street in the highly desirable Winter Park Pines neighborhood. This extensively updated residence offers the character of a classic 1960s home with the quality and feel of a 2026 renovation. Major improvements include a new roof, new HVAC system with new ductwork, new panel box, and thoughtfully curated high-end kitchen, bath, and lighting design elements. Original terrazzo flooring has been meticulously restored and polished throughout, preserving the home’s timeless appeal. Featuring four bedrooms, three full baths, the home offers a functional open-concept layout with a desirable split floor plan. Two primary suites, each with private en-suite baths, provide flexibility for multi-generational living or guest accommodations. The property showcases strong curb appeal and continues to impress outdoors with a spacious backyard and an oversized lanai designed for entertaining. Zoned for highly rated Winter Park schools, this home delivers an exceptional blend of style, comfort, and indoor-outdoor living in one of Winter Park’s most established neighborhoods.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Dianne Moore (407-494-7575)
744 CORNWALL RD, WINTER PARK, FL 32792
$695,000266 Days on yellowkey MLS ID: O6332168
REDUCED by $20,000 (2.8%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1968 Built: 1968 Tax: $5,359 (2024)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$5,359
Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!
Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)
Listing Agent: Tammy Cuddy (407-608-9593)
418 GILBERT RD, WINTER PARK, FL 32792
$740,00029 Days on yellowkey MLS ID: O6385950
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1964 Tax: $9,094 (2025)Community: Winter Park Pines Ut 5Single Family
Taxes:$9,094
Remarks: Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!
Listing is courtesy of: SOTERA LIVING (407-725-9660)
Listing Agent: Lianna Dangelo (321-446-3509)
2330 COLDSTREAM DR, WINTER PARK, FL 32792
$650,00032 Days on yellowkey MLS ID: O6384436
0 Days Off yellowkey (back on 4/15/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1750 Built: 1958 Tax: $6,951 (2024)Community: Brookshire HeightsSingle Family
Taxes:$6,951
Remarks: Completely renovated and move-in ready! This beautifully updated home has been fully remodeled with attention to detail and quality finishes throughout. Recent upgrades include brand-new flooring, modern appliances, fresh interior and exterior paint, and a new A/C system, offering comfort and peace of mind for years to come. The home is in excellent condition. Truly feels like new construction without the new construction price. Perfect for first-time homebuyers looking for a turnkey property or investors seeking a strong rental opportunity in a desirable location. Conveniently located near shopping, dining, major roadways, and top-rated schools. Don’t miss this opportunity to own a fully updated home in a fantastic area!
Listing is courtesy of: DTB FLORIDA REALTY, INC. (786-543-8296)
Listing Agent: Marta Faustino (786-543-8296)
240 N PHELPS AVE, WINTER PARK, FL 32789
$2,279,00046 Days on yellowkey MLS ID: O6389035
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2889 Built: 2026 Tax: $6,605 (2025)Community: Sylvan HeightsSpa: NoSingle Family
Taxes:$6,605
Remarks: Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a custom paneled feature wall with a sleek built-in electric fireplace, creating a striking focal point for the space. The gourmet kitchen is designed for both everyday living and entertaining, highlighted by a large center island with seating, European slab cabinetry, premium hardware, designer countertops, and high-end appliances. Ample storage and a clean modern aesthetic make this kitchen as functional as it is beautiful. Tucked beneath the staircase is a custom wine storage feature, adding a unique luxury detail. The first floor also includes a private guest suite with its own en suite bathroom, perfect for visitors or multi-generational living. A dedicated home office provides a quiet workspace, while the main-floor laundry room adds convenience. Outside, a professionally designed outdoor kitchen extends the living space and creates the perfect setting for year-round entertaining under the Florida sky. Upstairs, the luxurious primary suite serves as a private retreat. The spacious walk-in closet features a fully custom organization system, while the spa-inspired primary bathroom includes a dual-sink vanity, elegant freestanding soaking tub, and oversized walk-in shower with premium tile work. Three additional bedrooms complete the second floor. Two share a beautifully appointed Jack-and-Jill bathroom, while the fourth bedroom features its own private en suite bath, offering flexibility for guests or family members. Located at 240 N. Phelps Avenue, this home places you just minutes from Winter Park’s iconic Park Avenue — a vibrant destination known for its boutique shopping, award-winning restaurants, art galleries, and charming sidewalk cafés. Residents enjoy access to top-rated schools, including Winter Park High School, as well as renowned cultural destinations such as the Morse Museum of American Art and the Polasek Museum. Outdoor lovers will appreciate nearby Central Park, Mead Garden, and the scenic Winter Park Chain of Lakes. Conveniently located near I-4, SR-417, downtown Orlando, Lake Nona Medical City, UCF, and Orlando International Airport, this home offers the perfect balance of luxury, convenience, and the timeless charm that makes Winter Park one of Central Florida’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: GOLDEN GROUP REALTY LLC (407-990-5905)
Listing Agent: Milena Fernandes (407-990-5905)
3172 CROWN JEWEL CT, WINTER PARK, FL 32792
$339,9009 Days on yellowkey MLS ID: O6397498
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1406 Built: 2019Monthly Fee: $146 Tax: $4,977 (2025)Community: Coronado TwnhmsTownhouse
Taxes:$4,977
Elementary School: Cheney Elem
Remarks: Under contract-accepting backup offers. Get ready to fall in love with this stunning, move-in-ready townhome in the highly desirable Coronado Community—located in a top-rated school district! Built in 2019, this beautifully designed 3-bedroom, 2.5-bath home is packed with modern style, from its eye-catching stone exterior to its one-car garage and spacious paver driveway. Step inside and be wowed by the bright, open floor plan—perfect for entertaining or simply enjoying everyday living. The main level features sleek tile throughout, a generous storage closet, and a gorgeous kitchen complete with solid wood cabinets, granite countertops, stainless steel appliances (including a BRAND-NEW microwave), and plenty of space to cook and gather. Open the sliding glass doors and relax on your private lanai—your own little escape! A convenient half bath completes the first floor. Upstairs, the spacious primary suite is your personal retreat, featuring high ceilings, a ceiling fan, a walk-in closet, and a beautifully updated bathroom with dual sinks, granite counters, and a tiled shower. Two additional bedrooms—each with high ceilings and fans—share a stylish, modern bath. This home has been meticulously maintained and thoughtfully upgraded with NEW features including a microwave, Samsung washer & dryer, updated cabinet hardware, modern lighting, upgraded faucets and showerheads, a glass shower door in the primary bath, a Nest thermostat, and fresh paint throughout. Location? It doesn’t get better than this! With quick access to 436, 417, 408, Hwy 50, and Alafaya Trail, you’re just minutes from UCF, Valencia College, Waterford Lakes, and the charm of downtown Winter Park.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Kate Sprinkle (407-492-6232)
3312 HEARTWOOD AVE, WINTER PARK, FL 32792
$465,000188 Days on yellowkey MLS ID: O6352582
1 Days Off yellowkey (back on 4/13/2026)
REDUCED by $19,000 (3.9%) on 04/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 1983 Tax: $2,183 (2025)Community: Bel-Aire PinesSpa: NoSingle Family
Taxes:$2,183
Remarks: One or more photo(s) has been virtually staged. A family home with a private entrance to a large In-Law suite upstairs and private entrance to spacious downstairs living. The downstairs has three (3) bedrooms and two (2) baths on a split floor plan with plenty of room to entertain. This home is move-in ready and recently had a new roof installed which comes with a five (5) year warranty which covers all repairs and is transferrable. All systems in this home have been lovingly maintained for the next owner. No repairs needed. The yard is completely fenced in for safety and has flower beds already installed if gardening is your thing, along with a storage shed and irrigation system for the front yard. Come take a look! PLEASE SHUT OFF LIGHTS AND FANS WHEN SHOWING IS COMPLETE and END SHOWING IN SENTRILOCK.
Listing is courtesy of: MID-STATE PROPERTIES PSL LLC (561-843-9537)
Listing Agent: Stacy Morano (561-843-9537)
2454 BROOKSHIRE AVE, WINTER PARK, FL 32792
$1,399,00057 Days on yellowkey MLS ID: O6384924
Bed: 4 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2509 Built: 2023 Tax: $11,586 (2024)Community: Brookshire Heights 1St AddSingle Family
Taxes:$11,586
Remarks: One or more photo(s) has been virtually staged. Welcome to this aesthetic custom luxury home in an unbeatable Winter Park location.From the moment you arrive, the custom landscaping and automated lighting make a statement, day or night.At the center of the home, the chef's kitchen is both a showpiece and a performance space. A commanding 48-inch Z-Line gas range with 8 Italian-made brass burners anchors the room, complemented by Café luxury appliances, a stainless steel refrigerator, quartz countertops, and custom cabinetry. The walk-in pantry with floating shelves and under-shelf lighting adds both beauty and function. An indoor wine bar with built-in cabinetry and wine refrigerator enhances the entertaining experience, while an upstairs beverage station keeps every level equally equipped.The primary suite is a full spa experience. The glass enclosed shower features a rain head, body jets, and handheld fixtures. A soaking tub, dual vanities with quartz counters, and a generously proportioned walk-in closet complete the retreat. Imported aged brass designer light fixtures are included in the sale. Philips Hue smart lighting synchronizes every indoor and outdoor light in one app, and a smart security camera system with fingerprint keypad entry completes the tech package. The outdoor living experience rivals the interior. A covered lanai with a fully equipped summer kitchen, including a built-in grill, dedicated refrigerator, and generous prep space, flows into a landscaped courtyard designed with an Italian villa, Mediterranean feel. As evening falls, intentional landscape lighting transforms the grounds into an intimate setting perfect for al fresco dinners, fireside gatherings, or projecting the big game under the stars. Walk to pickleball courts, athletic fields, and a premier wellness facility. Park Avenue's celebrated boutiques and dining are just minutes away. New construction of this caliber is increasingly rare in Winter Park. Schedule your private showing today. The furniture and décor, curated by a professional design team, are negotiable, making it possible to move in with the full look already in place.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Norma Gonsalves (407-451-9533)
200 SAINT ANDREWS BLVD #705, WINTER PARK, FL 32792
$180,00056 Days on yellowkey MLS ID: O6386469
1 Days Off yellowkey (back on 4/14/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 727 Built: 1970 Tax: $2,018 (2024)Community: Four Seasons CondoCondo
Taxes:$2,018
Remarks: Under contract-accepting backup offers. This isn’t your average condo. It’s professionally updated with large rooms and more closet space than you’ll know what to do with. There’s even a washer and dryer right in the unit (no more laundry runs!), newer appliances, and parking right outside your door. On a scale from 1 to 10, this place is easily a TWENTY! Seriously, no expense was spared to make it super comfortable. You’ll love the bright living room that opens into a dining area and cozy kitchen that has been remodel and replace for today's lifestyle. There’s no carpeting flooring anywhere, making clean up easy! They even thought of the little things and replaced the following items: doors, bigger baseboards, oversize crown molding, shiplap ceilings, fancier trim work on doors, locks and knobs, updated electrical outlets and switches, brand new vanity cabinet in the bathroom, toilet and all around newer light fixtures—it’s all been done for you. The full-size washer/dryer is cleverly tucked away in the primary closet for convenience. The location? Perfect! At Four Seasons you’re just minutes from Winter Park shops and restaurants—and downtown Orlando is just a short trip away when you want some excitement. If you’re looking for comfort AND style in an unbeatable location—this is it!
Listing is courtesy of: WINTER PARK REAL ESTATE CO LLC (407-405-6612)
Listing Agent: Jonathan Lacko (407-405-6612)
1000 S SEMORAN BLVD #805, WINTER PARK, FL 32792
$174,70034 Days on yellowkey MLS ID: O6392099
REDUCED by $5,000 (2.8%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1003 Built: 1969Monthly Fee: $355 Tax: $1,111 (2025)Community: Golfside Villas CondoCondo
Taxes:$1,111
Elementary School: None
Remarks: Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy access to shopping, dining, and major roadways. One of the few units in the community featuring a screened patio AND an in-unit washer and dryer, providing added convenience and everyday ease. Low HOA fees make this an excellent opportunity for both homeowners and investors alike. Whether you're looking for a primary residence or an income-producing property, this condo stands out with its upgrades, location, and unique features. NEW ROOF April 2026! Call today to schedule your private showing.
Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)
Listing Agent: Carrie Sue Shawfield (407-963-7749)
633 BALMORAL RD, WINTER PARK, FL 32789
$1,795,000186 Days on yellowkey MLS ID: O6353491
3 Days Off yellowkey (back on 3/24/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2674 Built: 1968 Tax: $10,321 (2024)Community: Kenilworth Shores Sec 06Single Family
Taxes:$10,321
Remarks: Under contract-accepting backup offers. An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area’s private and pristine ski lakes with no public boat ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-a-half-bath, single-story residence with a covered boat dock, ideal for enjoying lake life immediately or while planning a future custom build. The northeast-facing front provides the ideal orientation to capture breathtaking sunsets across the water each evening. Whether you choose to renovate the home or build a new architectural masterpiece, this offering presents the ultimate canvas for creating a generational lakefront retreat. Within minutes of downtown Winter Park, Park Avenue and A-rated public schools, this property combines the best of convenience, serenity and luxury lakefront living. A special opportunity to bring your vision to life on one of Winter Park’s desired private lakes.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
1210 FAIRWAY DR, WINTER PARK, FL 32792
$549,00011 Days on yellowkey MLS ID: O6398533
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1979 Tax: $7,265 (2025)Community: Golfside Sec 3Spa: NoSingle Family
Taxes:$7,265
Remarks: Welcome home to this beautiful single-story Pool home in the Golfside community of Winter Park. Offering 3 bedrooms, 2 bathrooms, and 1,737 square feet of living space, this home features a spacious and inviting layout designed for both everyday living and entertaining. Upon entry, you are welcomed into the living room, while an adjacent dining room combination provides additional flexible gathering space. The family room offers French door access to the covered rear patio, creating a seamless indoor-outdoor flow to the expansive backyard, perfect for hosting family and friends.The kitchen opens to the main living areas and is equipped with stainless appliances, stone countertops, and ample cabinet space. A hallway just off the family room leads to all three bedrooms and two full bathrooms, including a spacious primary suite with an ensuite bath. Additional features include engineered wood throughout the main living areas, extra storage closets, an interior laundry room, and a 2-car garage.Ideally located near Winter Pines Golf Club, this home also offers convenient access to I-4 and SR-417, making it easy to reach shopping, dining, entertainment, downtown Orlando, the airport, area attractions, and the beaches.
Listing is courtesy of: CENTRAL FLORIDA PRIME REAL ESTATE LLC (407-404-4041)
Listing Agent: Albin Hubscher (407-404-4041)
1636 ELIZABETHS WALK, WINTER PARK, FL 32789
$2,195,00021 Days on yellowkey MLS ID: O6395638
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3412 Built: 2016Monthly Fee: $268 Tax: $25,133 (2025)Community: Windsong Elizabeths Walk 43/81Spa: YesSingle Family
Taxes:$25,133
Remarks: Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend the living space outdoors to a beautifully designed lanai, complete with a gas-heated pool and a fully equipped summer kitchen featuring a grill, sink, beverage refrigerator and additional seating area. The main level also includes a well-appointed guest suite with a private bath, offering comfort and privacy for visitors, along with a dedicated office or study space. Upstairs, a spacious bonus room provides flexibility for a media room, playroom or lounge, while two additional bedrooms accompany the expansive primary suite. The primary retreat is designed for relaxation, showcasing dual walk-in closets and a luxurious bath with a freestanding soaking tub, oversized shower and separate vanities. High-end finishes are showcased throughout, including travertine flooring across the main living areas and rich wood floors that continue through the bedrooms, staircase, upper hallway and bonus room. As a resident of Windsong, you’ll enjoy access to exceptional community amenities, including resort-style pools, a splash pad, playground and access to the scenic Winter Park Chain of Lakes, creating a lifestyle that is both vibrant and serene in one of Central Florida’s most desirable settings.
3054 BLUEBROOK DR, WINTER PARK, FL 32792
$427,50012 Days on yellowkey MLS ID: O6398450
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1939 Built: 1973 Tax: $6,422 (2025)Community: Laurel SpgsSingle Family
Taxes:$6,422
Remarks: "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And there is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one to sell quickly.
Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)
Listing Agent: Eugene Weatherspoon (407-878-4468)
2919 BOWER RD, WINTER PARK, FL 32792
$779,00036 Days on yellowkey MLS ID: O6391025
3 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2325 Built: 1971 Tax: $9,857 (2025)Community: Winter Park PinesSingle Family
Taxes:$9,857
Remarks: Beautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of Winter Park! This move-in ready home offers a bright, open layout with multiple living spaces, perfect for both everyday living and entertaining. The upgraded kitchen features stainless steel appliances, granite countertops, breakfast bar, custom cabinetry, and a farmhouse-style undermount sink, all opening to a spacious dining area with a stunning exposed brick fireplace. A newly enclosed and fully air-conditioned back room (converted from the former porch) offers exceptional flex space—perfect for a bonus room, playroom, or additional living area. Designed to maximize Florida living, this space features an expansive sliding glass door that seamlessly blends indoor and outdoor living, while a separate dedicated HVAC system ensures optimal comfort year-round. The primary suite includes a walk-in closet, dressing area, and en suite bath with dual-sink granite vanity and step-in shower. Just off the primary bedroom is a newly added office/nursery space, perfect for working from home or a private retreat. Split floor plan with two additional generously sized bedrooms and a full bath for added privacy. Enjoy Florida living outdoors with a spacious patio, sparkling pool, and large backyard featuring brand-new sod—perfect for entertaining or relaxing. Additional upgrades include fresh paint and a high-end seamless metal roof. Prime location just minutes to Cady Way Park, shopping, dining, and zoned for top-rated schools. Don’t miss this one—schedule your showing today!
Listing Agent: Nick Mckee (407-913-0171)
3021 AARON BURR AVE #3, WINTER PARK, FL 32792
$140,00012 Days on yellowkey MLS ID: S5147382
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1090 Built: 1974Monthly Fee: $479 Tax: $1,992 (2025)Community: ColoniesCondo
Taxes:$1,992
Remarks: Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Daiana Garcia Medrano (321-315-4686)
676 DUNBLANE DR, WINTER PARK, FL 32792
$750,000140 Days on yellowkey MLS ID: O6365557
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 1962 Tax: $5,584 (2024)Community: Kenilworth Shores Sec 04Single Family
Taxes:$5,584
Remarks: This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as a home office, creative studio, workout space or playroom — all with tranquil views of the pool and backyard. The property features a beautifully landscaped, fully fenced yard and a private pool area, perfect for entertaining, relaxing, or enjoying the Florida lifestyle. Originally updated in 2012, the home benefits from a well-balanced and comfortable floorplan, complemented by key mechanical upgrades including a newer HVAC system and roof, and a brand-new water heater installed in 2024. With these major updates already completed, the property is truly move-in ready — offering peace of mind and lasting value. Don’t miss your opportunity to own a beautifully maintained home in a location that continues to deliver on both lifestyle and convenience. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, the location also offers close proximity to top institutions and amenities, including Rollins College (2.3 miles), Full Sail University (2.4 miles), AdventHealth Winter Park (0.9 miles), and the VA Medical Center (1.3 miles). Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, all within a short drive, offering walking paths, open green space, and recreational opportunities. ASSUMABLE VA LOAN at 2.25% Interest Incredible opportunity to assume the seller’s VA mortgage at just 2.25% interest. Just minutes from the vibrant centers of Baldwin Park and Park Avenue, this property provides convenient access to an array of restaurants, boutique shops, cafés, and year-round events. 676 Dunblane Drive is a rare opportunity to own a well-located, move-in-ready home in one of Winter Park’s most established and sought-after neighborhoods. Book your private showing TODAY!
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Emma Kaplan (407-942-7542)
520 FITZWALTER DR, WINTER PARK, FL 32792
$1,000,00051 Days on yellowkey MLS ID: O6380171
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2111 Built: 2022 Tax: $10,205 (2024)Community: Brookshire Heights 1St AddSingle Family
Taxes:$10,205
Remarks: Under contract-accepting backup offers. Welcome to a rare gem in one of Winter Park’s most sought-after neighborhoods, Brookshire Heights—where trees line the street and the mailman still delivers right to your front door. Perfectly positioned with the scenic and wooded Cady Way Trail in your backyard, this custom-built 2022 residence offers over 2,100 square feet of thoughtfully designed single-story living, where refined style meets everyday ease. A desirable open-concept floor plan showcases three bedrooms and two bathrooms, enhanced by wood-look plank tile flooring, soaring ceilings and doorways, crown molding, and recessed lighting throughout. Expansive sliding glass doors with electric retractable blinds and transom windows flood the home with natural light, creating a seamless connection to the covered, screened lanai—perfect for effortless indoor-outdoor living and sophisticated entertaining. The beautifully appointed kitchen is both striking and functional, featuring crisp white shaker cabinetry complemented by a contrasting gray island with seating for four, all topped with sleek white quartz countertops. A dedicated wine and beverage bar with a built-in refrigerator adds an elevated touch, while stainless steel appliances and a spacious pantry ensure everyday convenience. Bathed in natural light, the dining area offers an inviting and elegant setting for both intimate gatherings and larger-scale entertaining, with expansive windows that bring the outdoors in. The primary suite serves as a serene retreat, complete with private lanai access for a tranquil indoor-outdoor connection. A generously sized custom closet provides ample storage, while the spa-inspired bathroom features a timeless clawfoot soaking tub, honeycomb tile flooring, an expansive walk-in shower, and a dual quartz vanity—creating a luxurious, resort-style experience. Two additional bedrooms offer flexibility for guests, family, or workspace, including one with stylish built-in shelving. A beautifully finished hall bath reflects the same elevated design and attention to detail found throughout the home. Designed with functionality in mind, the well-appointed laundry room features built-in cabinetry and a hanging bar, provides convenient access to both the primary suite and main living areas. A spacious 2.5 car garage allows plenty of room for storage, a golf cart or other toys. Ideally located, this residence offers convenient access to premier institutions including University of Central Florida, Rollins College, and Full Sail University. Enjoy nearby recreation at Winter Park Pines Golf Club and Cady Way Park, featuring a pool, playground, tennis and pickleball courts, and beach volleyball. Spend weekends boating from Dinky Dock Park onto the renowned Winter Park Chain of Lakes, or explore the charm of Park Avenue with its boutique shopping and fine dining. Everyday convenience is enhanced with close proximity to AdventHealth Winter Park and the Crosby Wellness Center, along with easy access to Orlando International Airport. Zoned for top-rated schools including Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, this exceptional property seamlessly blends lifestyle, location, and lasting value. Roof - 2022, HVAC - 2022, Electrical - 2022, Plumbing - 2022, Water Heater - 2022
Listing Agent: Amy Turner (407-803-3885)
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