Location: Winter Park
Do Not Show Listings
721 DUNBAR ST, WINTER PARK, FL 32789
$399,99943 Days on yellowkey MLS ID: O6405338
1 Days Off yellowkey (back on 5/13/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1018 Built: 1950 Tax: $5,267 (2025)Community: Carver TownSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,267
Elementary School: Lakemont Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Welcome to 721 Dunbar St in Winter Park, a 2-bedroom, 2-bath home with a simple layout and plenty of potential. This property offers a comfortable starting point for everyday living and a great opportunity for buyers who want a home they can make their own over time. Inside, the home offers practical living spaces and a layout that works well for daily routines. The two-bedroom, two-bath setup adds flexibility for guests, a home office, or changing needs. The home has a solid foundation for updates, giving the next owner the chance to improve and personalize the space to match their style and preferences. Outside, the property gives you room to enjoy the yard and think about future possibilities. Whether you want to refresh the outdoor space, add your own touches, or simply enjoy the home as it is, there is a lot of opportunity here. Located in Winter Park, the home is close to shopping, dining, parks, and major roads, while still being in an established residential area. The neighborhood adds to the appeal with its convenient location and access to everything that makes Winter Park a popular place to live.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
311 SCOTTSDALE SQ #311, WINTER PARK, FL 32792
$109,900238 Days on yellowkey MLS ID: O6355536
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 785 Built: 1974Monthly Fee: $2,097 Tax: $1,271 (2024)Community: Winter Park Woods CondoCondo
Taxes:$1,271
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned for highly rated schools in Florida, which helps with both property value and long-term rental demand. The location is a major plus. This condo sits in the heart of Winter Park / Winter Park Pines / Goldenrod area, close to Full Sail University, UCF, AdventHealth, Orlando International Airport, and main highways for easy commuting. You’re just minutes from shopping, grocery stores, restaurants, gyms, parks, and Winter Park’s retail corridors. You also have quick access to downtown Winter Park, Orlando, and major job centers, which keeps rental demand very strong in this area.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Omar Rodriguez (321-442-2001)
432 W SWOOPE AVE, WINTER PARK, FL 32789
$695,000150 Days on yellowkey MLS ID: O6375719
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2317 Built: 2014Monthly Fee: $463 Tax: $9,138 (2025)Community: Swoope ParkTownhouse
Taxes:$9,138
Remarks: A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Thomas Bonner (407-401-3748)
40 PALMER AVE, WINTER PARK, FL 32789
$6,950,000131 Days on yellowkey MLS ID: O6380444
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 5905 Built: 2026 Tax: $12,774 (2024)Community: Robert Dhu Macdonald ParkSpa: YesSingle Family
Taxes:$12,774
Remarks: Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what luxury living looks like in the heart of Winter Park. The exterior architecture is refined yet commanding, with classical influences interpreted through a modern lens, setting the tone for the exceptional level of design and finishes found inside. One of the most remarkable features, and an offering rarely found in Winter Park, is the underground four-car garage. Designed to discreetly accommodate an impressive vehicle collection, the garage is complemented by a striking spiral staircase that rises from the basement through the main living level and continues to the second floor. The family room is nothing short of breathtaking, featuring bespoke millwork with integrated shelving, soft architectural lighting, and a dramatic fireplace wrapped entirely in marble. The kitchen is a culinary showpiece designed for those who expect nothing less than perfection. Calcutta marble countertops cascade across the space, paired with stunning custom cabinetry, and a professional-grade Thermador appliance suite. A dedicated dirty kitchen allows for discreet preparation, while an expansive walk-in pantry ensures effortless hosting and immaculate presentation. The primary bedroom wing features a spa-inspired bathroom finished in rich marble, featuring dual vanities, a freestanding soaking tub and an enormous walk-in closet with a separate washer and dryer. Upstairs, a dedicated laundry room and a spacious secondary living area provide flexibility for family living, guests, or relaxation. The lower level extends the home’s versatility, offering a workshop, dedicated holiday and seasonal storage, and seamless elevator access to the main level of the home. Outdoor living is equally impressive. A large covered exterior lanai with a pool bath and full summer kitchen creates a seamless indoor-outdoor lifestyle, ideal for entertaining year-round. The backyard is truly resort-inspired, featuring a large swimming pool, sunken fire pit, and spa, all set within a private, beautifully secluded outdoor setting. What ultimately sets 40 Palmer apart is not just its design or finishes, but its unmatched combination of luxury and location. Just minutes from Park Ave shopping and restaurants, moments from the famous Winter Park Golf Course, yet privately tucked away, this home offers a lifestyle that is both vibrant and exclusive. A truly rare opportunity to own a part of the exceptional standard of living delivered by Vimaro Homes.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
1745 INDIANA AVE #J, WINTER PARK, FL 32789
$524,00047 Days on yellowkey MLS ID: O6402920
1 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1616 Built: 2008Monthly Fee: $464 Tax: $6,444 (2025)Community: La Casas De IndianaCondo
Taxes:$6,444
Elementary School: Killarney Elem
High School: Edgewater High
Middle School: College Park Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Well-maintained townhome in Winter Park, ideally located near Park Avenue’s shops, restaurants, and everyday conveniences. The home features a bright, open floor plan with new luxury vinyl plank flooring throughout the main level. The kitchen has been updated with white cabinetry and newer appliances, offering a functional layout that flows seamlessly into the living and dining areas—well-suited for both daily living and entertaining. Upstairs, the bedrooms provide comfortable space with a practical and efficient layout. The primary bedroom includes an ensuite bathroom and a walk-in closet with built-in storage. The HOA covers roof, exterior maintenance, and landscaping, offering a low-maintenance ownership experience. Enjoy a fenced and enclosed back patio, creating a private outdoor setting ideal for entertaining, dining, or relaxing. In addition, the rear alley access offers a tucked-away, low-traffic environment with added flexibility and privacy. Additional features include a two-car garage and a central location with convenient access to major roadways, shopping, and dining.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Tala Nijmeh (901-417-3534)
541 W CANTON AVE, WINTER PARK, FL 32789
$2,800,00091 Days on yellowkey MLS ID: O6389829
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3553 Built: 2024 Tax: $4,692 (2024)Community: Winter ParkSingle Family
Taxes:$4,692
Remarks: Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood entry door, to its charming striped awnings and the flicker of gas lanterns, every detail of the exterior is carefully curated. Classic marble-paved patios frame the home, and a courtyard-style pool with fountain and sandblasted marble decking invites quiet relaxation or festive gatherings. Inside, soaring ceilings, beautiful hardwood floors and immersive color-drenched rooms create an inviting space that is luxurious but unpretentious, bold yet serene. The stunning staircase features a custom wrought-iron railing with an antique finish, offering a striking architectural focal point. The chef’s kitchen, a culinary sanctuary and social hub, is complete with graphite La Cornue range and pot filler, Monogram paneled refrigerator, custom plaster hood, quartzite countertops and backsplash, and grand center island that opens to a gathering room with a gas fireplace. This more relaxed living area flows effortlessly through French doors to the pool and patios, creating an ideal indoor-outdoor lifestyle. A butler’s pantry with a second refrigerator, cabinetry and prep space adds functionality, while the formal dining room, living room, and bar area with sink and built-in beverage cooler are ideal for entertaining. A beautiful downstairs powder bath features designer wallpaper, elegant sconces and custom cabinetry. The upstairs primary suite offers spa-like serenity, including a wet room complete with soaking tub framed by a picture window. Three additional bedrooms include one with an en-suite bath, while the other two share a hallway-accessible bath with double vanity and walk-in tiled shower. This masterpiece set in the heart of Winter Park, thoughtfully surrounded by lush landscaping and carefully placed privacy screens, offers polish and presence in an ideal location.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Bianca Khoury (407-797-1121)
141 W LAKE SUE AVE, WINTER PARK, FL 32789
$4,200,00043 Days on yellowkey MLS ID: O6406437
Bed: 5 Bath: 6.0 Gar: 4 Liv Area Sq Ft: 5500 Built: 2027 Tax: $11,049 (2025)Community: Virginia HeightsSpa: YesSingle Family
Taxes:$11,049
Remarks: Pre-Construction. To be built. A Generational Opportunity in the Heart of Winter Park Presenting an exceptionally rare opportunity to build a fully custom luxury estate on one of Winter Park’s most extraordinary homesites. Situated on an expansive 1/2-acre corner lot, an offering virtually unheard of in this coveted location, this property represents the pinnacle of luxury new construction potential. Scheduled for Summer 2027 completion, this bespoke residence offers the flexibility to bring the current architectural concept to life, collaborate with the builder to tailor the design, or create an entirely custom vision with your own architect and design team. The proposed architectural concept showcases an impressive modern estate designed for elevated living and grand-scale entertaining, featuring a dramatic double-height foyer, soaring two-story great room, expansive walls of glass that flood the interiors with natural light, a highly desirable 4-car garage, oversized bedroom suites, and thoughtfully curated indoor-outdoor living spaces throughout. Designed to deliver a true resort-style experience, the outdoor living concept includes a saltwater pool and spa, covered lanai, summer kitchen, and expansive entertaining areas ideal for year-round Florida living. Further elevating this offering is deeded access to Lake Sue, providing an exclusive lifestyle opportunity rarely available in this location. Enjoy the best of both privacy and recreation while being moments from everything Winter Park is known for. Perfectly positioned just minutes from renowned Park Avenue, residents enjoy immediate access to premier fine dining, luxury boutiques, private clubs, and cultural attractions, all while being zoned for top-rated schools. Oversized parcels of this caliber with deeded lake access are exceptionally scarce, making this a true legacy acquisition, an opportunity to create a one-of-one estate in one of Central Florida’s most sought-after neighborhoods. Luxury, land, lake access, and limitless potential—this is Winter Park living at its absolute finest.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
408 HOLT AVE, WINTER PARK, FL 32789
$745,00043 Days on yellowkey MLS ID: O6405857
Bed: 2 Bath: 0.0 Liv Area Sq Ft: 1440 Built: 1942 Tax: $5,765 (2025)Community: Trotters RepSpa: NoApartment
Taxes:$5,765
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Remarks: Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia. The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick street in one of Winter Park’s most walkable and desirable neighborhoods. The asset is being delivered with strong in-place cash flow. Current rents provide additional value-add potential, with at least one unit currently operating below market rental rates, creating an opportunity for future income growth and increased returns. The block construction property has undergone significant capital improvements, including updated electrical panels (2019), new hot water heater (2019), new windows (2017), and a new roof (2015). Two of the three units were completely renovated in 2019, offering updated interiors while maintaining the charm and character of the surrounding neighborhood. The front unit includes washer/dryer hookups, while the middle and rear units share a common exterior-access washer/dryer area. Utilities are currently included in the rent and have been factored into annual operating expenses. This is a rare opportunity to acquire a stabilized multifamily asset with strong rental demand driven by proximity to Rollins College, downtown Park Avenue, dining, shopping, and employment centers throughout Winter Park.
Listing is courtesy of: THE REAL ESTATE PRINCIPLE, INC (407-739-7209)
Listing Agent: Brian Opre (407-739-7209)
1405 MILLER AVE, WINTER PARK, FL 32789
$899,000110 Days on yellowkey MLS ID: O6386405
0 Days Off yellowkey (back on 5/8/2026)
REDUCED by $51,000 (5.4%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1884 Built: 2023Monthly Fee: $200 Tax: $8,200 (2025)Community: H Vanwies SubTownhouse
Taxes:$8,200
Remarks: Under contract-accepting backup offers. Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes. Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet, the home features a desirable first-floor primary suite and elevated design details, including Level 4 drywall, engineered oak floors, Bosch appliances, LED mirrors, and a Lutron Caséta lighting and Triathlon shade system. A Calacatta Gold porcelain slab electric fireplace serves as a striking focal point in the living room. The open-concept floor plan is both functional and inviting, filled with natural light and offering views of a private paved patio and fenced backyard—ideal for relaxing or entertaining. Enjoy a low-maintenance, lock-and-leave lifestyle within an intimate four-unit community tucked along a picturesque, tree-lined brick street. Additional highlights include a private two-car garage with EV charging port, guest parking, and close proximity to premier dining, shopping, and daily conveniences, including Publix and AdventHealth. A rare opportunity to own a design-forward residence in an exceptional location.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Rikhil Amin (407-792-8069)
5454 BRACKEN COURT, WINTER PARK, FL 32792
$199,00044 Days on yellowkey MLS ID: O6401099
0 Days Off yellowkey (back on 5/7/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1332 Built: 1984Monthly Fee: $110 Tax: $728 (2024)Community: Fernbrook TrailsTownhouse
Taxes:$728
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Middle School: Tuskawilla Middle
Remarks: Charming two-story townhouse in Winter Park offering great potential for the right buyer! This 3-bedroom, 2-bath home features a cozy fireplace, a spacious layout, and a back porch overlooking a large, fenced backyard—perfect for outdoor enjoyment. The property does need some TLC, making it an excellent opportunity for investors or buyers looking to add their personal touch. Conveniently located near shopping, dining, parks, and major roadways, this home combines location with opportunity.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mark Ramey (407-496-1766)
1660 PALMER AVE, WINTER PARK, FL 32789
$4,950,000485 Days on yellowkey MLS ID: O6282425
3 Days Off yellowkey (back on 5/7/2026)
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 6406 Built: 2024 Tax: $6,144 (2024)Community: Comstock ParkSpa: YesSingle Family
Taxes:$6,144
Remarks: Under contract-accepting backup offers. New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator, that offers nearly 770 square feet of multi-use space. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...
Listing Agent: Mick Night (407-629-4446)
2500 LEE RD #202, WINTER PARK, FL 32789
$224,999499 Days on yellowkey MLS ID: O6277579
REDUCED by $10,000 (4.3%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 956 Built: 1969Monthly Fee: $432 Tax: $2,327 (2025)Community: Lakeside Manor Condominium Association, Inc.Condo
Taxes:$2,327
Remarks: One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool & Clubhouse overlooking Lake Killarney. You will love Paddle Boarding, Kayaking and Boating just steps from your door. Beautifully updated 2-bedroom, 2-bathroom condo located on the shores of Lake Killarney in highly desirable Winter Park. This immaculate home offers tranquil lakeside living and unbeatable convenience, minutes from Trader Joe’s, Park Avenue, Rollins College, and Downtown Orlando. The condo is upgraded throughout with New AC & Water Heater, New Interior Paint, New Lighting, New Ceiling Fans & Window Blinds, Updated Door Hardware, Primary Bathroom Renovation featuring new tile, modern vanity, and LED mirror, Upgraded Exterior Doors & Windows. Open-concept kitchen with wood cabinetry, granite countertops, a built-in wine rack, and breakfast bar, flows into the spacious living area and private balcony. Enjoy two private patio spaces front and rear, overlooking the courtyard, perfect for relaxing and entertaining. With only one neighbor to the side and one below, this unit offers enhanced privacy. Split-Bedroom Design, Two large bedrooms, each with walk-in closets. Primary suite includes a private exterior entrance and a fully renovated bathroom with walk-in shower. Second bathroom includes a tub/shower combo and tile flooring. Enhance your life living minutes from Park Avenue (shopping, dining, events), Rollins College (3 miles), Winter Park Village, I4 for easy commuting, Downtown Orlando, Orlando International Airport, Disney, and Universal (20–30 mins). Low HOA Includes Water & Trash, Cable & Internet, Lake Access & Dock, Pool & Clubhouse, and Designated Parking.
Listing is courtesy of: THE ANDERSON GROUP & CO PL (407-960-5657)
Listing Agent: Alison Maltby (407-325-1483)
1809 HAMMERLIN AVE, WINTER PARK, FL 32789
$549,000157 Days on yellowkey MLS ID: O6373616
REDUCED by $36,000 (6.2%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1818 Built: 2006 Tax: $5,826 (2024)Community: Terazzo Del Sol Condo Assn IncCondo
Taxes:$5,826
Remarks: Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is effortless in the expansive kitchen featuring granite countertops, premium wood cabinetry, stainless steel appliances, and a generously sized pantry. A half bathroom and utility closet complete the ground floor, where ceilings soar to a height of 9'3". Ascend to the upper level to discover the luxurious master bedroom suite, boasting French doors leading to a balcony, a spacious walk-in closet, and a lavish ensuite bath featuring dual sinks, a glass-enclosed shower, and a relaxing garden tub. Two additional bedrooms await upstairs, both sharing access to a covered porch perfect for savoring your morning coffee. The second full bathroom and laundry closet round out the upstairs layout, with one of the bedrooms boasting its own walk-in closet. New 2026 Updates to include New Roof Feb 2026, Carpet, New main DBL pane windows, complete interior paint, light fixtures/fans. You will appreciate the convenience of an attached 2-car garage designed for SUVs, two covered entries, adorned with mature trees. Solid build quality utilizing concrete block construction on both floors. Located just a short stroll from the vibrant East End Market and various shopping, this residence also offers easy access to upscale Park Avenue, Rollins College, Baldwin Park, Florida Hospital, and the serene beauty of Leu Gardens. Zoned for Audubon and Winter Park HS, this home truly has it all!
Listing is courtesy of: NICOLE-HUDSON REALTY CORP (407-491-5488)
Listing Agent: Edward Rice, Jr (407-353-0331)
1630 LASBURY AVE, WINTER PARK, FL 32789
$2,750,00049 Days on yellowkey MLS ID: O6404300
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4917 Built: 2003 Tax: $14,204 (2025)Community: Comstock ParkSpa: YesSingle Family
Taxes:$14,204
Remarks: The seller has just completed a full renovation. Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features generous common areas, including a large family room, a formal living room, a separate dining room, a kitchen with an adjacent breakfast room, a dedicated home office, a loft-style office or playroom, and a cozy home theater located above the garage. The kitchen, primary bedroom, and both the family and living rooms provide stunning views of the pool and backyard. The three-car garage offers ample space for large vehicles. Beyond the pool, you’ll find a charming gazebo and a fully equipped outdoor kitchen. Built with block and stucco construction and topped with a durable tile roof designed to last up to 100 years, this home boasts incredible durability and aesthetic appeal. Combining the feel of new construction with a rare, expansive lot in a well-established neighborhood, it provides privacy, mature landscaping, and modern elegance all in one.
Listing is courtesy of: COMPASS FLORIDA, LLC (305-851-2820)
Listing Agent: Teresa Chris Harralson (404-229-8737)
770 W WEBSTER AVE, WINTER PARK, FL 32789
$725,000352 Days on yellowkey MLS ID: O6323574
1 Days Off yellowkey (back on 4/11/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1967 Tax: $4,856 (2024)Community: Capens AddSingle Family
Taxes:$4,856
Remarks: Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining and entertainment. Don’t miss this unique opportunity! PROPERTY SOLD AS-IS. VALUE IS IN THE LAND. NO REPAIRS.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Lisa Gould (407-721-7612)
517 ROUGHBEARD RD, WINTER PARK, FL 32792
$565,00067 Days on yellowkey MLS ID: O6399029
1 Days Off yellowkey (back on 5/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1873 Built: 1971 Tax: $4,323 (2025)Community: Winter Park Pines Unit 17Single Family
Taxes:$4,323
Elementary School: Aloma Elem
Middle School: Glenridge Middle
Remarks: Under contract-accepting backup offers. Welcome home to the Winter Park Pines where the trees line the streets and the mailman delivers to your door. This beautifully maintained 3-bedroom, 2-bathroom home offering 1,873 square feet of comfortable living in the highly desirable and serene Winter Park Pines community. This light-filled residence features a thoughtfully designed split floor plan with high ceilings, fresh interior paint (2026), skylights, and laminate and tile flooring throughout, creating a bright and inviting atmosphere from the moment you enter. The open living and dining areas are anchored by a charming wood-burning brick fireplace, while crown molding, ceiling fans, and French doors add both style and functionality throughout the home. The well-appointed kitchen includes white and gray cabinetry, stainless steel appliances, and a convenient pantry closet, perfect for both everyday living and entertaining. It flows seamlessly into the main living areas, making it easy to gather with family and friends. The spacious primary suite offers a private retreat, thoughtfully separated from the secondary bedrooms, and features a walk-in closet with custom built-ins, ceiling fan, and French doors leading to the expansive and shaded backyard. The renovated en-suite bathroom showcases double vanities and a beautifully tiled shower with frameless glass enclosure. The secondary bedrooms are well-sized and versatile, with easy access to the renovated hall bathroom featuring a granite double vanity, navy cabinetry, and direct access to the backyard, ideal for indoor-outdoor living. Step outside to enjoy a fully fenced, landscaped backyard situated on a generous .22-acre lot. The expansive patio with terracotta tile flooring provides the perfect space for outdoor dining, entertaining, or simply relaxing in a private setting. Additional highlights include a two-car garage and a Ring home security and surveillance system for added peace of mind. Located just minutes from top-rated Winter Park schools, the Cady Way Trail, Winter Park Pines Golf Course, Advent Health Winter Park campus, Crosby Wellness Center and a variety of shopping and dining options, this home offers both tranquility and convenience. Residents also enjoy access to nearby community amenities including a pool, playground, beach volley ball courts and tennis/pickleball courts. With close proximity to major roadways, downtown Winter Park, and Orlando International Airport, this property truly combines comfort, location, and lifestyle. Don’t miss the opportunity to make this exceptional home yours in one of Winter Park’s most sought-after neighborhoods. Roof 2020, HVAC 2022, Plumbing 2014, Water Heater 2021.
Listing Agent: Amy Turner (407-803-3885)
Lot #21 KAROLINA AVE, WINTER PARK, FL 32789
$944,89099 Days on yellowkey MLS ID: O6387812
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2662 Built: 2025 Tax: $2,207 (2024)Community: Karolina On KillarneySingle Family
Taxes:$2,207
Remarks: Pre-Construction. To be built. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and intentional design create a home that feels both elevated and livable. What makes this opportunity truly unique: this is the last remaining homesite within a curated collection of three custom builds—each thoughtfully designed with its own architectural identity, yet unified in creating a refined, cohesive streetscape. The other two homes are already underway, making this your only chance to secure a position in this limited offering. Located just 6 minutes from Park Avenue, you’re moments from Winter Park’s best—boutique shopping, award-winning dining, and everyday conveniences—while also being close to top-rated hospitals and major thoroughfares. Offered as a custom build, this home allows you to tailor finishes, selections, and details to match your vision. Pricing reflects the base build, with upgrade options available to create a fully personalized end product. With new construction opportunities in 32789 at this price point becoming increasingly scarce, offerings like this are few and far between—especially with the ability to fully customize your home from the ground up.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Vinny Lay (407-756-4255)
2774 BRIGHT BIRD LN, WINTER PARK, FL 32792
$465,000547 Days on yellowkey MLS ID: O6266098
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1907 Built: 2024Monthly Fee: $375 Tax: $1,009 (2023)Community: Grayson SquareTownhouse
Taxes:$1,009
Tax Year: 2023
Remarks: Motivated seller! Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same time! Schedule a tour today!
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Priscila Triska (321-354-5459)
5331 OAK CT, WINTER PARK, FL 32792
$460,000339 Days on yellowkey MLS ID: S5130868
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1263 Built: 1976 Tax: $2,311 (2024)Community: Wrenwood Heights Unit 2Spa: NoSingle Family
Taxes:$2,311
Remarks: Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Nataliya Voroshylo Hylton (407-284-7247)
1131 WILDMEADOW RUN, WINTER PARK, FL 32792
$825,00088 Days on yellowkey MLS ID: O6392218
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2589 Built: 2020Monthly Fee: $165 Tax: $5,312 (2024)Community: Meadows At Hawks CrestSingle Family
Taxes:$5,312
Middle School: Sanford Middle
Remarks: Winter Park - Located in the gated community of Hawks Crest, this 4-bedroom, 3.5-bath home offers 2,589 square feet of well-designed living space on a premium pond-view lot. Built in 2020, the home features a downstairs primary suite, open-concept living area, and a versatile upstairs loft. Additional highlights include a tile roof, modern finishes, a screened-in patio for outdoor living, and access to community amenities. This home combines location, layout, and value in a beautiful Winter Park gated communities.
Listing is courtesy of: BECK REALTY LLC (407-256-6369)
Listing Agent: Joann Beck (407-256-6369)
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