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32792 - O6413831 - 2730 PRINCE JOHN RD, WINTER PARK, FL 32792 Just Added on 06/04/2026 12:21PM
$2,495 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Fantastic 4 Bed 2 Bath Winter Park Home with 2-car garage! Located in a highly desirable Winter Park area. Large living room/dining room combo, a large separate den area. The home has a large fenced-in backyard. Lawn care is included. Walking distance to the Cady Way Trail. *Bonus Amenity Included* -All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit building to help boost the resident’s credit score with timely rent payments, up to $1M Identity Theft Protection, HVAC air filter delivery (for applicable properties), move-in concierge service making utility connection and home service setup a breeze during your move-in, our best-in-class resident rewards program, on-demand pest control, and much more! More details upon application. Pet Friendly Home (with approval and a non-refundable pet fee).
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)Listing Agent: Mo Jabr (407-571-1441)
32789 - O6413279 - 300 CAROLINA AVE #301, WINTER PARK, FL 32789 Just Added on 06/04/2026 11:20AM
$739,000 | Condo | 2 beds | 2.0 baths | 1 car
Enjoy the best of living in this beautifully renovated well maintained 2-bedroom, 2-bath condominium located in the highly desirable gated Park West Condominiums. Perfectly positioned just steps from the renowned Park Avenue, this exceptional residence offers walking distance access to award-winning restaurants, charming boutiques, sidewalk cafés, and the popular weekly farmer’s market. This rare 3rd-floor corner unit which enhances privacy was completely remodeled in 2019 with quality upgrades throughout. The interior features are engineered wood flooring, updated tile, modern ceiling lighting, and a bright open-concept floor plan filled with natural light from expansive sliding glass doors leading to three private walk-out balconies. The redesigned kitchen in 2019 includes new cabinetry, countertops, a complete suite of kitchen appliances, including washer and dryer. Both bathrooms have also been tastefully renovated, creating a clean and contemporary feel throughout the home. Additional improvements include a brand-new HVAC system installed in July 2024, offering peace of mind and energy efficiency for years to come. Spacious bedrooms, generous storage, and seamless indoor-outdoor living make this condo ideal for both everyday living and entertaining. Park West residents enjoy beautifully maintained grounds along with community amenities including a sparkling swimming pool and tennis courts. The community is also conveniently located to Rollins College and Full Sail College. Whether you are searching for a full-time residence or seasonal retreat, this exceptional condo combines timeless Winter Park charm with modern updates and an unbeatable location.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: Kevin Mcclanahan (407-491-8509)
32792 - S5150136 - 4798 TANGERINE AVE #4798, WINTER PARK, FL 32792 Just Added on 06/04/2026 9:20AM
$185,000 | Condo | 2 beds | 2.0 baths
Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or entertaining. Enjoy an open living and dining area that flows seamlessly to a private screened porch with additional storage space, perfect for relaxing and enjoying the peaceful surroundings. The home offers generous room sizes, ample storage throughout, and a comfortable living environment within a quiet and established community. Residents enjoy access to community amenities including a sparkling swimming pool, fitness center, clubhouse/conference room, beautifully maintained grounds, and ample parking. HOA benefits may include exterior maintenance, landscaping, water, trash service, and roof maintenance, providing added convenience and value. Ideally situated in East Winter Park, this property offers exceptional access to everything Central Florida has to offer. Conveniently located just minutes from Full Sail University, the University of Central Florida (UCF), Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Enjoy nearby shopping, dining, entertainment, golf courses, parks, grocery stores, and everyday conveniences all within close proximity. Commuters will appreciate the easy access to major highways including SR-417 and SR-408, while Orlando International Airport is only a short drive away. Whether you are a first-time homebuyer, downsizing, investing, or searching for a centrally located primary residence, this home presents an outstanding opportunity to enjoy the Winter Park lifestyle in a peaceful and well-connected community.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)Listing Agent: Vincenza Di Cesare De Vieira, Pa (407-680-8118)
32789 - O6412857 - 230 E ROCKWOOD WAY, WINTER PARK, FL 32789 Just Added on 06/04/2026 8:28AM
$2,189,000 | Single Family Home | 5 beds | 4.0 baths | 2 gar
JUST LISTED! Located in the highly sought-after Winter Park Lake Sue area, this exceptional contemporary residence offers a rare opportunity to enjoy luxury living among some of the most architecturally significant and beautifully designed homes in Central Florida. Positioned within one of the region's most desirable neighborhoods, the property combines modern design, exceptional functionality, and an outstanding lifestyle location. From its prominent presence to its thoughtfully executed interior spaces, the home offers a seamless blend of modern esthetics and comfort. The open-concept floor plan is designed for both everyday living and entertaining, with expansive living areas that transition effortlessly into the covered outdoor living space, summer kitchen, resort-style pool, and heated spa. A highly desirable layout places both the luxurious primary suite and an additional bedroom/flex room on the main level, providing exceptional flexibility for guests, a home office, fitness space, or multi-purpose living. Upstairs, additional bedrooms and a large bonus room create ample space for family and entertaining. The private first-floor primary suite serves as a true retreat, featuring direct access to the outdoor living areas and a beautifully appointed spa-inspired bath. Throughout the home, quality finishes, extensive wood flooring, designer lighting, custom window treatments, and carefully curated details create an elevated living experience. The kitchen serves as the centerpiece of the home, featuring premium appliances, generous workspace, and a large entertaining island that connects seamlessly to the main gathering spaces. Perhaps most compelling is the location. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, the home enjoys convenient access to Park Avenue, Rollins College, East End Market, Winter Park Village, Downtown Winter Park, and Downtown Orlando. Residents enjoy the unique advantage of being positioned between the charm and sophistication of Winter Park and the energy of Orlando's most vibrant dining, cultural, and lifestyle destinations. Opportunities to secure a fantastic residence at this price point in the Winter Park Lake Sue area are increasingly rare. This is a unique opportunity to enjoy a wonderful lifestyle and home in one of Central Florida's most desirable neighborhoods.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)Listing Agent: Robert Kurzreiter Pa (407-476-4156)
32792 - O6409433 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 1 Day on yellowkey
$480,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.
Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)Listing Agent: Mostafa Boulhanna (407-536-1484)
32792 - O6405799 - 5530 S LAKE BURKETT LN, WINTER PARK, FL 32792 1 Day on yellowkey
$3,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
32789 - O6413554 - 311 E MORSE BLVD #6-12, WINTER PARK, FL 32789 1 Day on yellowkey
$275,000 | Condo | 1 beds | 1.0 baths
Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: Andrea Parra Chopite, Pa (407-515-0097)
32792 - O6413563 - 2918 ANTIQUE OAKS CIR #26, WINTER PARK, FL 32792 1 Day on yellowkey
$1,575 | Condo | 2 beds | 2.0 baths
This 2/2, 1,018 sq. ft. second story condo in Parkview Village features a living room & dining room combo! Screened in balcony, inside utility closet. This unit is close to community pool! Water/Sewer Included! Sorry, No Pets!! Application Fee: $50 / adult (18+) Full Credit/Skip/Eviction/Background check is done on all applicants. **Please have the following documents ready to attach as JPEG or PDF: Drivers License & Pay Stubs (3)**
Listing is courtesy of: PREMIER MANAGEMENT GROUP INC (407-370-4400)Listing Agent: Ken Warren (407-370-4400)
32792 - O6412306 - 2817 BRIGHT BIRD LN, WINTER PARK, FL 32792 1 Day on yellowkey
$2,800 | Townhouse | 3 beds | 2.5 baths | 1 gar
Welcome to Grayson Square in Winter Park. This beautifully maintained 3-bedroom, 2.5-bath townhome is located in one of the area’s newer gated communities and shows like new throughout. Exceptionally clean and well cared for, this home is truly move-in ready. The open-concept living and dining area offers a comfortable layout for both everyday living and entertaining. The covered lanai overlooks a peaceful pond, providing a relaxing outdoor space with a serene view. The kitchen features stainless steel appliances, quartz countertops, ample cabinetry, and generous storage. Upstairs, the spacious owner’s suite includes a walk-in closet and a private bathroom with dual sinks, quartz countertops, and a glass-enclosed shower. The second full bathroom includes a tub with shower combination. A washer and dryer are included for added convenience. Residents enjoy gated entry, a resort-style pool, and cabana amenities. Rent includes 1GB fiber-optic internet service along with 75 streaming cable and music channels. Conveniently located just minutes from Downtown Winter Park and Park Avenue, with easy access to SR 436, SR 434, and SR 417. Close to shopping, dining, and everyday essentials including Publix, Walmart, and Starbucks. Zoned for highly regarded Seminole County schools.HABLO ESPANOL.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)Listing Agent: Denise Del Castillo (321-960-3110)
32792 - S5151098 - 5503 ALBERT DR, WINTER PARK, FL 32792 1 Day on yellowkey
$405,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof (transferable documentation included). Features include updated flooring throughout (no carpet), fully fenced backyard, and 2-car garage. Zoned for desirable Seminole County schools (Eastbrook Elementary/Lake Howell High) with quick access to SR-436, shopping, and downtown Winter Park. Ideal for remote professionals, small families, or savvy buyers seeking low-maintenance ownership with room to work and grow. Quick closing available. Schedule today!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)Listing Agent: Fernando Perez De Armas (407-837-7144)
32789 - O6412954 - 1250 FORMOSA AVE, WINTER PARK, FL 32789 1 Day on yellowkey
$560,000 | Townhouse | 3 beds | 3.5 baths | 2 gar
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a private bedroom with its own walk in closet and ensuite—perfect for guests or a home office. On the second floor, enjoy open-concept living with a bright and airy great room featuring high ceilings, recessed lighting, and seamless access to an oversized balcony through sliding glass doors. The modern kitchen is a showstopper, complete with quartz countertops, stainless steel appliances, a walk-in pantry, white shaker cabinets and a large center island with breakfast bar seating. Upstairs, you'll find two additional bedrooms, including the spacious primary suite with a walk-in closet, double vanity, glass-enclosed shower, and built-in shelving. The third bedroom also includes its own ensuite for added privacy and comfort. Additional highlights include an oversized rear-entry 2-car garage, laundry room, ample storage, and low-maintenance living. Enjoy unbeatable proximity to I-4, Downtown Orlando, Dubsdread Golf Course, Rollins College, Park Avenue, and Winter Park Village—offering endless dining, shopping, and entertainment options. This modern gem offers the best of both worlds: a turnkey home in a central, vibrant location. Don’t miss your chance to own in one of Orlando’s most desirable areas!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Jeanine Louis, Llc (407-595-8634)
32792 - O6412797 - 5171 LAZY OAKS DR, WINTER PARK, FL 32792 3 Days on yellowkey
$2,250 | Condo | 2 beds | 2.5 baths | 1 gar
This Winter Park condo features two bedrooms and three bathrooms, with an attached garage for convenient parking. The entrance welcomes you with a charming foyer. At the heart of the spacious open great room is the kitchen—highlighted by custom cabinets, quartz countertops, and stainless-steel appliances, all thoughtfully arranged on the first floor. An oversized counter provides space for dining, and the combined dining and living area provide access through French doors to the enclosed rear porch. The living room is enhanced by a decorative built-in electric fireplace. Upstairs you'll find two bedrooms, each with en suite baths. The master bedroom stands out with custom closets, a large window that fills the space with natural light and raised ceilings that add dimension. Two-tone contrasting colors create a cozy and inviting atmosphere, and the master bath includes a double sink vanity, walk-in shower, and linen closet. The second bedroom also boasts raised ceilings, custom closets, and its own private bathroom. Lazy Oaks Condominium is a highly sought-after community in Winter Park, located off Old Howell Branch Road. Residents enjoy amenities such as monthly pest control, guest parking, curbside garbage collection, and private mailboxes.
Listing is courtesy of: PAINE-ANDERSON PROPERTIES, INC (407-695-7898)Listing Agent: Joyce Gary (407-782-3276)
32792 - O6412514 - 7577 DOCKSIDE ST, WINTER PARK, FL 32792 3 Days on yellowkey
$370,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
One or more photo(s) has been virtually staged. FABULOUS 3 bedroom 2 bath RENOVATED home with a 1 car garage located in a PRIME LOCATION!! Perfect for the first time homebuyer, investor or someone looking to downsize. The large family room benefits from natural lighting provided by the NEW WINDOWS installed(2024) throughout the ENTIRE house. The open kitchen overlooks the covered porch and large, FULLY FENCED backyard. The primary bedroom has LPV flooring with an UPDATED bathroom. NEWER carpets in the other two bedrooms. Second bath has a new toilet with a bidet, a tile bath/shower combo, and an updated vanity. NEW lighting, outlet and switch plate covers throughout. A NEW roof ridge vent was added for extra ventilation! NEW LANDSCAPING in the front. NEW DRAINFIELD (2026), water heater (2023), roof(2021). It is in Seminole County school district, 15 minutes to UCF, 5 minutes to shopping, and 10 minutes to the highway. HURRY, you don't want to miss this opportunity!!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)Listing Agent: Heather Pryor (321-303-5393)
32792 - V4949389 - 2054 EASTBROOK BLVD, WINTER PARK, FL 32792 3 Days on yellowkey
$500,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)Listing Agent: Melissa Stalzer (386-405-3457)
32789 - O6411141 - 649 N PARK AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$3,500,000 | Townhouse | 3 beds | 4.0 baths | 2 gar
Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)Listing Agent: Drew Henner (407-406-0662)
32792 - O6412363 - 508 DUNRAVEN DR, WINTER PARK, FL 32792 3 Days on yellowkey
$595,000 | Single Family Home | 3 beds | 2.0 baths | 2 car
Welcome to this stylishly renovated ranch-style pool home in Kenilworth Shores, a special Winter Park neighborhood known for its connected community, central location, and easy access to everything people love about Winter Park. This beautifully renovated 3-bedroom, 2-bath home sits on nearly a quarter-acre lot and offers the perfect blend of style, comfort, and outdoor living. Step inside and you'll immediately feel the warmth of the home. The renovated kitchen is truly the heart of the space, beautifully designed with stylish tile backsplash, stainless steel appliances, mission style cabinetry, bar seating, and an additional coffee or wine bar area that makes the space feel both functional and elevated. Open to the living room, the kitchen creates an easy flow for everyday living and entertaining. The home has been thoughtfully updated throughout with new flooring, plantation shutters, renovated bathrooms, and designer touches that give the home a fresh, modern feel while still keeping all the charm of a classic Winter Park ranch. A dining room along the back of the home offers views of the yard and access to the covered lanai and custom pergola overlooking the pool. This is truly a backyard retreat! The sparkling pool is surrounded by pavers, lush landscaping, bamboo for privacy, and a fully fenced yard. The covered lanai and custom pergola create the perfect setting for morning coffee, quiet evenings, or hosting friends by the pool. This is the kind of backyard that makes Florida living feel easy. A large storage area and laundry room provide extra space for bikes and yard tools just off the carport. The bedrooms are tucked together along the hall, with the primary bedroom positioned on the back of the home for privacy, with an additional bathroom featuring an updated vanity and shower and a door to the pool area. The additional bedrooms share the hall bathroom with stylish modern updates including all new tile, a frameless glass shower, vanity, and fixtures. The thoughtfully designed spaces feel modern while also remaining timeless and classic. Other notable additions over the years include a metal roof, irrigation on well, lush landscaping, and a refinished pool with tile surround. The 2-car carport provides plenty of covered parking for rainy days! Located in the City of Winter Park, this home offers incredible access to Park Avenue shopping and dining, Audubon Park with Michelin-star restaurants and local favorites, Sprouts Market, Lake Baldwin Dog Park, nearby parks, coffee shops, boutiques, and more. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High. Cady Way Park is nearby with a community pool, baseball fields, a playground, pickleball courts, and miles of recreational and bike trails. Style, location, privacy, sparkling pool! This Winter Park home checks all the boxes. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)Listing Agent: Kathryn Stelljes (407-982-7240)
32792 - O6411882 - 2242 KING JOHNS CT, WINTER PARK, FL 32792 3 Days on yellowkey
$2,395 | Single Family Home | 3 beds | 2.0 baths | 2 gar
This beautiful 3 bedroom, 2 bathroom home is located in the heart of Winter Woods in desirable Winter Park. This home offers a spacious split floor-plan with an open living/dining area. Features include tile throughout, a fenced-in backyard with patio area, 2 car garage, washer/dryer hookups, and is convenient to schools, recreational parks, restaurants, & the lovely downtown Winter Park. Please note the outdoor hot tub/spa does not work and will not convey. Pets under 50 lbs. Schedule a showing or submit an application online. All Real Property Management & Realty residents enjoy convenience and well-maintained homes, with our safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, and a 24/7 emergency maintenance response team. Please note the listed amenities may not be accurate.
Listing is courtesy of: REAL PROPERTY MANAGEMENT AND REALTY (407-897-3366)Listing Agent: Matthew Kirsch (407-897-3366)
32792 - TB8513990 - 1850 ASTER DR, WINTER PARK, FL 32792 3 Days on yellowkey
$500,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Welcome to the heart of Winter Park. This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming floor plan designed with both everyday living and entertaining in mind. The updated kitchen features stainless steel appliances, a spacious island, abundant cabinet storage, and seamless flow into the main living areas. A formal living area adds flexibility, offering the perfect space for a cozy sitting room, playroom, home office, or additional entertaining area. Natural light throughout the home creates a bright and airy atmosphere. Upstairs, you’ll find all four bedrooms and two full bathrooms, providing privacy and functionality for growing families. The screened-in porch overlooks a stunning backyard retreat complete with a sparkling pool, beautiful landscaping, and no rear neighbors for added privacy. Peaceful, quiet, and surrounded by nature and wildlife, this outdoor space makes it perfect for summer pool days, evening dinners outside, and making lifelong memories.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Brianna Lalumiere (727-641-3957)
32789 - O6412789 - 2006 CORNELL AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$338,000 | Single Family Home | 2 beds | 1.0 baths
Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its hardwood floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)Listing Agent: Stacia Stephenson (407-415-5700)
32789 - O6412745 - 1516 MILLER AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$1,549,900 | Single Family Home | 4 beds | 3.5 baths | 2 gar
New Construction!!! Escape the hassle of searching endlessly for your dream home in today's competitive market. Embrace the allure of new construction – Nestled in the vibrant Winter Park Grove neighborhood, this modern masterpiece awaits, promising a lifestyle of unparalleled comfort and convenience. Prime Location - Situated just minutes away from the bustling energy of Park Avenue this exceptional residence offers the ultimate in urban living. Explore local cafes, boutique shops, and entertainment venues with ease, all within walking or biking distance from your doorstep. Step inside to discover a world of contemporary elegance, where every detail has been meticulously crafted to perfection. The open floor plan seamlessly blends style and functionality, creating an inviting atmosphere that's perfect for both relaxation and entertainment. Boasting four spacious suites, including a lavish primary retreat on the main level, this home provides unparalleled comfort for you and your guests. Upstairs, two additional suites await, along with a versatile bonus room that can be transformed to suit your lifestyle – whether as a home office, gym, second living room, or fifth bedroom. Indulge your culinary passions in the gourmet kitchen, equipped with top-of-the-line Bosch appliances, including a 36" gas cooktop, built-in microwave, wall oven, French door refrigerator, and a wine fridge. With its sleek design and premium finishes, this kitchen is sure to inspire your inner chef. Step outside to your own private oasis, where a spacious lanai beckons you to unwind in style. Fire up the grill in the fully equipped outdoor kitchen, complete with a grill, sink, and refrigerator, and take a refreshing dip in the sparkling pool – the perfect setting for al fresco gatherings with family and friends. Pictures are of a previous model of the same plan- finishes and specifications are subject to change
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)Listing Agent: Kim Griffin (407-314-5033)
32789 - O6412754 - 840 W CANTON AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$675,000 | Single Family Home | 3 beds | 2.0 baths
Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the heart of Winter Park. Every detail has been updated, including new mechanical systems, electrical, plumbing, custom doors and windows, gutters, stucco finishes, fixtures, fresh landscaping, and new sod. Inside, you'll find an open-concept floor plan with professionally installed luxury vinyl plank flooring (2026) backed by a transferable 10-year warranty. The designer kitchen features butcher block countertops, a farmhouse sink, tile backsplash, and premium stainless steel appliances, including a ZLINE 36" six-burner gas range, ZLINE dishwasher, and KitchenAid refrigerator. A spacious bonus room with vaulted ceilings offers flexible living space for a home office, gym, media room, or playroom. The primary suite includes a spa-inspired bath with floor-to-ceiling porcelain tile, quartz vanity, touch-free LED mirror, and custom doors. Additional upgrades include copper plumbing already installed for a future tankless water heater. Step outside to a fully fenced backyard with gates on both sides and a private patio perfect for entertaining. Located just minutes from Winter Park Village, Park Avenue, Central Park, shopping, dining, entertainment, and Downtown Orlando, this low-maintenance Winter Park home offers exceptional rentability and walkability, and is situated in one of the area's most sought-after locations. Schedule your private showing today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)Listing Agent: Ken Pozek (407-813-2773)
32789 - O6412589 - 860 N DENNING DR, WINTER PARK, FL 32789 4 Days on yellowkey
$749,900 | Single Family Home | 3 beds | 2.5 baths
**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true new construction quality in an established neighborhood. Located steps from Winter Park Village, Park Avenue, Whole Foods, Starbucks, Publix, cinema, restaurants, and more. Arrive home to a grand 51' custom driveway flanked by mature Italian cypress trees, sculptural landscaping, and elegant iron railing — pulling directly to your covered front porch entry. No garage means no wasted space — just a clean, architectural arrival experience designed to impress. Inside, light-filled interiors with soaring 6" baseboards, full custom tile flooring, and an abundance of natural light create a gallery-like aesthetic that feels curated, not cookie-cutter. Custom liner windows in the dining room and primary suite flood the home with natural light while adding unmistakable architectural character. **The Kitchen:** - Designer floating shelves - Smart range and under-counter built-in microwave - Under-cabinet and island LED lighting - Decorative pendants and ambient lighting throughout **The Primary Suite:** A private retreat with ceiling-mounted rain shower and spa-like finishes designed to decompress after a walkable night out on Park Avenue. **Smart Home Ready:** - New AC system (inside and out) with smart thermostat - Tankless water heater and fully new plumbing - Smart lock entry - Google Nest doorbell with two-way audio - Smart soffit exterior lighting - Weather-monitored smart irrigation **Out Back:** A fully private PVC-fenced backyard sanctuary — spacious enough for pets, entertaining, and room to roam. A covered porcelain tile patio plus a separate fire pit slab make this an outdoor living extension you'll actually use year-round in the Florida lifestyle. Over 300 sq ft of additional space was added to accommodate two additional bathrooms, interior laundry, and a layout built for real life — including a new stacked washer and dryer. Properties combining true gut-renovation quality, luxury designer touches, smart technology, and this rare walkable Winter Park address don't last. Move-in ready — and built to last for decades.
Listing is courtesy of: OUTLET REALTY (407-353-5518)Listing Agent: Ladarrius Sanders (407-777-5919)
32789 - O6412619 - 747 MARYLAND AVE, WINTER PARK, FL 32789 4 Days on yellowkey
$2,500 | Single Family Home | 3 beds | 2.0 baths
Welcome to this charming 3-bedroom, 2-bathroom house located in the heart of Winter Park. This lovely home features a spacious back yard and patio perfect for enjoying the outdoors. The kitchen and bathrooms have been remodeled. It is a convenient 4 minute walk to Rollins College, and a 10 minute walk to local shops and restaurants on Park Avenue.
Listing is courtesy of: ALFANO PROPERTY MANAGEMENT (407-616-5343)Listing Agent: Rafael Pierluisi (407-221-2185)
32792 - O6405802 - 1944 NATALEN RD, WINTER PARK, FL 32792 4 Days on yellowkey
$519,000 | Single Family Home | 3 beds | 2.0 baths | 2 car
One or more photo(s) has been virtually staged. Located in the highly desirable Winter Park area, 1944 Natalen Rd offers the perfect balance of tranquility, convenience, and lifestyle. This property enjoys deeded access to serene Lake Berry while being just minutes from top-rated schools, the vibrant dining and boutique shopping of both Baldwin Park and downtown Winter Park, and everyday conveniences including nearby grocery stores and the renowned Winter Park Farmers’ Market. Residents will appreciate exceptional healthcare access with both AdventHealth Winter Park and the Orlando VA Medical Center at Lake Baldwin close by. Centrally located with easy access to UCF, Orlando International Airport, and Central Florida’s world-famous theme parks and attractions, this home provides an ideal combination of peaceful living and connectivity to everything Orlando has to offer.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)Listing Agent: Trevor Thomas (407-337-8738)
32789 - O6412456 - 503 KILSHORE LN, WINTER PARK, FL 32789 4 Days on yellowkey
$2,250 Increased | Single Family Home | 2 beds | 1.0 baths | 1 gar
LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout. Tile in the spacious open kitchen that opens into the living room, giving this home a wide-open layout. Enjoy, the peaceful, secluded feeling when lounging on the deck in the generous backyard during warm summer nights. Large, fenced backyard. Lake Killarney access for kayaking and canoeing.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)Listing Agent: Vincent Paige, Pa (407-256-8190)
32792 - TB8514256 - 652 SAINT JHONS #652, WINTER PARK, FL 32792 4 Days on yellowkey
$1,900 | Apartment | 2 beds | 2.0 baths
Don't miss this opportunity! Beautiful apartment located in Winter Park, one of the most convenient and desirable areas in the Orlando region. Conveniently located near Full Sail University, Rollins College, shopping centers, restaurants, entertainment, and major highways. Enjoy the comfort of a well-maintained community featuring a swimming pool and common areas for relaxation. This apartment offers an excellent combination of location, comfort, and quality of life. Pets are welcome, subject to size restrictions and approval. Properties in this area rent quickly, so schedule your showing before it's gone!
Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)Listing Agent: David Carballo (813-767-4897)
32792 - O6411994 - 2806 SUMMERFIELD RD, WINTER PARK, FL 32792 4 Days on yellowkey
$3,600 | Single Family Home | 4 beds | 2.0 baths | 2 gar
This spacious 4-bedroom, 2-bath home offers serene golf course views from your privately screened pool and patio. As you enter the home, you are welcomed by an open living area that flows seamlessly into the kitchen. The kitchen features a breakfast bar, high-end countertops, and large windows overlooking the enclosed patio and pool area. This outdoor space is perfect for relaxing or entertaining while enjoying scenic golf course views. The primary bedroom includes a spacious en suite bathroom with dual vanities and a tiled shower. Additional features include a two-car garage, with washer/dryer hook-ups. Conveniently located near the Crosby Wellness Center, Ward Park, Cady Way Trail, Park Avenue, Winter Park Village, and major roadways, this home offers easy access to shopping, dining, and entertainment. This property includes pool service and is approximately 2,779 total square feet (1,961 under air). Pets subject to owner approval. Schedule your showing today! All information is deemed reliable, but not guaranteed. Listing Brokerage does not discriminate on the basis of race, color, religion, national origin, sex, disability or familial status. All residents are enrolled in the Resident Benefits Package (RBP) for $50.00/month as additional rent, which includes renters insurance, credit building to help boost your credit score with timely rent payments, our best-in-class resident rewards program, $1M Identity Protection, move-in concierge service making utility connection and home service setup a breeze during your move-in, online resident portal for easy online rent payments & maintenance reporting, HVAC air filter delivery (for applicable properties), and much more! More details available upon application.
Listing is courtesy of: WILSON MANAGEMENT GROUP (407-896-1200)Listing Agent: Amy Spano (407-896-1200)
32789 - O6412258 - 2157 LAKE DR, WINTER PARK, FL 32789 6 Days on yellowkey
$689,000 Reduced | Single Family Home | 3 beds | 3.0 baths | 2 gar
Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake Killarney views, and a peaceful setting on a quiet private lakefront street. From the moment you enter, pride of ownership shines through, with custom built-ins throughout creating stylish and functional living spaces. The heart of the home is the updated kitchen and dining area, featuring high-end bamboo floors, stainless steel appliances, real wood custom cabinetry, and a large island overlooking a versatile flex space perfect for a formal living room, den, or office. The spacious great room is warm and inviting with a wood-burning fireplace and a dramatic wall of four French doors that fill the space with natural light. The elegant primary suite offers a walk-in closet and a spacious bath with dual vanities, a soaking tub, and separate shower. Step outside to a covered patio and expansive backyard with plenty of room to entertain, garden, or unwind. Just minutes from Park Avenue, premier shopping, dining, and Winter Park’s beloved parks and amenities, this is a rare opportunity to own a move-in-ready home in one of Central Florida’s most sought-after neighborhoods on .33 acres. Brand new roof and newer AC for total peace of mind. Schedule a private tour today.
Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)Listing Agent: Jacob Johnson (407-353-0106)
32789 - O6410174 - 338 BLUE HERON DR, WINTER PARK, FL 32789 6 Days on yellowkey
$865,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character and functionality in mind, this unique residence features abundant natural light, clean architectural lines, and a striking pass-through fireplace that creates the perfect ambiance between living spaces. Enjoy true Florida living with a private backyard pool, ideal for relaxing or entertaining year-round. The home also includes deeded access to a private dock and boat ramp, making boating on beautiful Lake Killarney just steps from your door. Perfectly positioned for convenience and lifestyle, this property is just a 6-minute drive to the upscale shopping and dining of Park Avenue, only 10 minutes from Downtown Orlando and Camping World Stadium, and approximately 35 minutes from Walt Disney World. Whether you're seeking a stylish primary residence or a one-of-a-kind Central Florida retreat, this home delivers the perfect blend of location, design, and lifestyle. Call to schedule your showing today!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)Listing Agent: Samuel Kingsford (407-808-6633)
32792 - O6410294 - 2808 BRIGHT BIRD LN, WINTER PARK, FL 32792 6 Days on yellowkey
$399,000 | Townhouse | 3 beds | 2.5 baths | 1 gar
Impeccable 2-story townhome, newly built in 2024 and located in Grayson Square, a Gated Luxury Townhouse Community in enchanting Winter Park, with modern, sophisticated architecture and landscaping. The interior features the high-end Lux Fresh package, complemented by owner upgrades including light dimmers, ceiling fans, and a custom kitchen island. The chef’s kitchen is equipped with new stainless-steel appliances and expansive white stone countertops. Alabaster cabinetry with ceramic tile plus smooth stone counters adds a touch of elegance throughout. Shaw LVP floors on the main level and 2nd level bathrooms. Owner's suite with an oversized walk-in closet and a dual-sink ensuite. Spacious second and third bedrooms. 9' ceilings throughout. The first floor features a stunning open-concept living area with vinyl wood-plank flooring. Laundry closet on 2nd level. Kohler raised commodes on the 2nd level. Private patio area surrounded by lush greenery. Attached garage with 2 extra off-street parking spaces. The home includes a Ring doorbell and a rear security camera. Eeros internet modem and Extender for boosted device connectivity. includes a resort-style pool oasis with a cabana, with a view of the community lake. Competitive HOA fees cover roof replacement, Spectrum internet and TV, and general property upkeep. Situated in a manicured community with a sparkling pool, this home is close to fine dining, shopping, and entertainment, with easy access to downtown Orlando and local theme parks. It is highly rated for its proximity to quality Seminole County public schools and its convenience to daily necessities like Publix and Starbucks, as well as the shopping and dining of Park Avenue.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)Listing Agent: Sean Flatley (609-208-8204)
32789 - O6412140 - 1404 BORDER DR, WINTER PARK, FL 32789 7 Days on yellowkey
$1,200,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.
Listing is courtesy of: THE AGENCY FL (407-335-4119)Listing Agent: Brian Hyser (407-951-2472)
32792 - O6412139 - 1320 GLADIOLAS DR, WINTER PARK, FL 32792 7 Days on yellowkey
$485,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!
Listing is courtesy of: OPTIMA REAL ESTATE (407-366-4500)Listing Agent: Deborah Morgan (407-314-8610)
32789 - O6410979 - 2261 MULBRY DRIVE, WINTER PARK, FL 32789 7 Days on yellowkey
$1,995,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Welcome to this extraordinary, better-than-new residence in the heart of Winter Park, a thoughtfully designed and impeccably upgraded custom, one-owner home built in 2020 that effortlessly blends timeless elegance with today’s most sought-after luxury features. Situated on a wonderfully deep, private lot with no HOA, this remarkable two-story home was crafted for elevated everyday living, unforgettable entertaining and seamless indoor-outdoor enjoyment. Offering 3,696 square feet, the flexible floor plan features four bedrooms, three full baths, a loft and a bonus room with a coffee/cocktail bar adjacent to accommodate a variety of lifestyles. The expansive first-floor primary suite is a true retreat, featuring a spa-inspired bath with heated floors, a soothing tub, an oversized walk-in shower and two large walk-in closets. The downstairs office with an en suite bath can easily function as a private guest suite or fourth bedroom. Quality craftsmanship shines throughout with detailed ceilings, engineered oak hardwood flooring, crown molding and baseboards, designer doors and hardware and plantation shutters throughout, creating a sophisticated yet inviting atmosphere. A rare combination of warmth and sophistication, this home beautifully balances luxury and functionality for modern living. The exceptional chef’s kitchen features a 60-inch Wolf gas range with a large griddle and double ovens, an expansive center island, a Sub-Zero refrigerator, a dining area and an adjacent butler’s pantry with an additional dishwasher and sink and a laundry room. Spacious gathering areas flow effortlessly into the spectacular outdoor retreat, complete with a covered lanai with remote screens, summer kitchen, outdoor fireplace, sparkling saltwater pool, separate heated spa and incredible privacy. Additional highlights include a Sonos sound system, high-definition security cameras, natural gas, a full-house generator, a separate air-conditioned workshop and a two-car garage. This exceptional Winter Park home offers the rare opportunity to enjoy newer construction elevated far beyond builder standards. Check out the 3D walk through tour! Call today to schedule your private showing.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)Listing Agent: Jo Ann Lamar (321-231-0052)
32792 - O6411958 - 2676 BARBADOS DR, WINTER PARK, FL 32792 7 Days on yellowkey
$340,000 | Townhouse | 3 beds | 2.0 baths
Welcome to this beautifully maintained 3-bedroom, 2-bathroom corner-unit townhome located in the heart of Winter Park. Offering 1,743 square feet of thoughtfully designed living space, this home combines comfort, style, and an unbeatable location just minutes from shopping, dining, parks, and top-rated schools. The desirable corner-unit placement provides added privacy, extra natural light, and a spacious feel throughout. Inside, you’ll find luxury vinyl plank flooring flowing seamlessly throughout the home and a stunning vaulted ceiling that creates an airy, open atmosphere in the living room. The beautifully updated kitchen is truly the centerpiece of the home, featuring gorgeous wood countertops, ample cabinet space, and an open-concept layout perfect for entertaining family and friends. Step outside to the rear screened-in patio and enjoy peaceful pond views in your own private outdoor retreat. Whether you’re sipping your morning coffee or unwinding after a long day, this tranquil space offers the perfect setting to relax and enjoy Florida living year-round. This exceptional Winter Park townhome is a rare opportunity you won’t want to miss.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)Listing Agent: Joseph Sipp (407-820-7016)
32789 - O6411306 - 640 N PARK AVE #5, WINTER PARK, FL 32789 7 Days on yellowkey
$3,200 | Condo | 1 beds | 1.0 baths | 1 gar
One or more photo(s) has been virtually staged. Welcome to Park Aire, a small iconic condo community located on Park Avenue by the WP9 golf course. 1st floor unit with oversized window views of the golf course and Casa Feliz. This one bedroom unit has an updated kitchen and bath. Amenities include a covered parking space, swimming pool, social room, a guest room for rent, open air patios on the third floor, under building covered parking spot and laundry in building garage and 2nd floor. You are close by for shopping and dining along Park Ave area.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)Listing Agent: Andy Holland (407-948-7172)
32792 - O6411325 - 610 ELLENDALE DR, WINTER PARK, FL 32792 7 Days on yellowkey
$399,000 | Single Family Home | 4 beds | 3.0 baths | 1 car
Under contract-accepting backup offers. Discover timeless charm and modern comfort in this beautifully maintained 4-bedroom, 3-bath home built in 1957, located in one of the most highly desirable areas of Winter Park. Nestled along picturesque, tree-lined streets, this property offers the perfect blend of classic character and thoughtful updates. Step inside to find a recently remodeled kitchen featuring top-of-the-line appliances, ideal for both everyday living and entertaining. The spacious layout provides generous living areas and comfortable bedrooms, making the home perfect for families or anyone seeking extra space. Major updates provide peace of mind, including a newer AC system, roof replaced in 2010, and updated plumbing. Outside,the private backyard retreat is designed for relaxation and gatherings, complete with a cozy fire pit and a versatile accessory unit—perfect for guests, a home office, or rental potential. Located within an excellent school district and just minutes from popular restaurants, boutiques, andshopping, this home offers the best of Winter Park living—charming neighborhood appeal with convenient access to everything you need. A rare opportunity to own a classic home in one of Central Florida’s most sought-after communities.
Listing is courtesy of: 4 ACRE REALTY LLC (407-963-7850)Listing Agent: Amy Fouraker (407-963-7850)
32789 - O6411706 - 1571 WOODLAND AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$6,000,000 | Single Family Home | 5 beds | 7.0 baths | 3 gar
Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blending refined luxury with modern comfort. Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stacked crown moldings, custom ironwork, designer lighting, and extensive millwork throughout. The gourmet kitchen is thoughtfully appointed with Viking and GE Monogram appliances, custom Busby cabinetry, an oversized island, and a butler’s pantry. It also includes multiple filtered water and ice zones designed for effortless entertaining. The spacious primary suite offers a true retreat with spa-inspired marble finishes, an oversized walk-in shower, a jetted soaking tub, and exceptional custom closet space. Additional features include a private elevator, Control4 automation, integrated audio/video/security systems, five HVAC systems, a central vacuum system, and a Generac whole-home generator. A fully finished and expansive basement level serves as a unique and exceptional extension of the home’s living and entertaining space. Designed for both relaxation and recreation, it features a game and arcade room, a full beverage center with a dishwasher, microwave, and Scotsman ice machine, a fitness area with a sauna and steam room, an additional laundry room, a creative storage center, and a private 4K theater with seating for multiple guests. Outdoors, resort-style living awaits with a saltwater pool and spa, a summer kitchen with a custom copper hood, an electric gated entry, landscape lighting, lush cascading bougainvillea, and ten mature magnolia trees creating exceptional beauty and privacy. The property also features a dog run with artificial turf. Three ventless gas fireplaces, including one on the private covered porch, add warmth and ambiance throughout the home. This home also features a whole-house water softener system. Top-rated A+ public schools are within a short walk or bike ride. Nearby highly regarded private schools include Park Maitland School, The Christ School, The First Academy, Trinity Preparatory School, Lake Highland Preparatory School, and Bishop Moore Catholic High School. Perfectly positioned within walking distance of the boutiques and dining of Park Avenue, and just minutes from the Winter Park Golf Course, Rollins College, and Advent Health Winter Park, this is a rare opportunity to own an exceptional custom estate in one of Central Florida’s most sought-after communities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)Listing Agent: Vonda Fields (321-438-6906)
32792 - O6411912 - 1761 GLADIOLAS DR, WINTER PARK, FL 32792 7 Days on yellowkey
$375,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
INVESTOR SPECIAL! Priced to sell and loaded with potential, this 4-bedroom, 2.5-bath home in Winter Park offers an excellent opportunity for investors, renovators, or buyers looking to add their personal touch. Situated on a spacious corner lot in the established Garden Lake Estates community, the property features 1,656 square feet of living space, a two-car garage, and a covered patio. The home is being sold AS-IS and is ready for updates, making it an ideal fix-and-flip, rental investment, or value-add opportunity. Conveniently located near shopping, dining, major roadways, and Seminole County schools. Priced below market. Don't miss this chance to unlock the potential of a well-located property in one of Central Florida's most desirable areas.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)Listing Agent: Mauricio Gomez (407-272-7277)
32792 - O6411608 - 200 SAINT ANDREWS BLVD #704, WINTER PARK, FL 32792 7 Days on yellowkey
$164,999 | Condo | 1 beds | 1.0 baths
Excellent opportunity in the heart of Central Florida! Welcome to this charming 1-bedroom, 1-full-bath condominium located in the desirable Four Seasons Condominiums of Winter Park. Step inside to a spacious living area that flows seamlessly into the dining and kitchen spaces, creating a comfortable and functional layout perfect for everyday living or entertaining. The primary bedroom features a large walk-in closet, offering comfort and convenience. Relax and enjoy the view from the oversized private balcony just off the living room. Ideally situated just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, shopping, and dining, this location truly offers convenience at every turn. Enjoy being only minutes from the renowned Park Avenue, local museums, and everything Winter Park has to offer. Four Seasons Condominiums is a beautifully maintained 20-acre community within the Winter Park city limits and located in a highly sought-after school district. Residents enjoy an array of amenities including three swimming pools, tennis courts, shuffleboard courts, laundry facilities, and a clubhouse with a library. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo is a must-see!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Veronica Figueroa (407-519-3980)
32792 - O6404011 - 2803 BANCHORY RD, WINTER PARK, FL 32792 7 Days on yellowkey
$495,000 | Single Family Home | 4 beds | 2.0 baths | 2 car
Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One of the bedrooms has been converted into a large closet and dressing room, offering generous storage while still allowing the option to easily convert the space back into a traditional fourth bedroom if desired. The backyard extends the home outdoors with a patio and cobblestone brick area that is well suited for entertaining, outdoor dining, or quiet evenings at home. Set within the established Winter Park Pines community, the home offers sidewalks for excellent walkability, with Cady Way Trail just steps from your door for morning runs, bike rides, and everything in between. Nearby, Cady Way Park adds even more to the neighborhood lifestyle with its pool, tennis and pickleball courts, playground, and beach volleyball, while Park Avenue offers boutique shopping and exceptional dining just minutes away. UCF, Rollins College, and Full Sail University are all within easy reach, along with AdventHealth Winter Park and Orlando International Airport. Zoned for top-rated Winter Park schools, this home combines comfort, convenience, and the everyday appeal that continues to make Winter Park Pines one of Winter Park’s most established neighborhoods.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Melissa Johnson (407-681-4393)
32789 - O6411654 - 1119 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$4,995 Reduced | Townhouse | 4 beds | 3.0 baths | 1 gar
Welcome home to this beautifully updated Cherokee Park townhome, where modern elegance meets comfort in the heart of highly desirable Winter Park. Perfectly situated near some of the area’s best dining, shopping, and entertainment, this home offers both luxury and convenience in one exceptional location. Step inside to a bright and airy open-concept living space featuring wood-style flooring, soaring vaulted ceilings, and a sleek modern fireplace that creates a warm yet contemporary focal point. Large windows throughout flood the home with natural light, including a stunning arched window overlooking lush greenery for a peaceful and inviting atmosphere. The thoughtfully updated kitchen and bathrooms feature clean contemporary finishes, stone countertops, designer lighting, and premium frameless glass showers. Fresh interiors, updated fixtures, and organized closet shelving make this home completely move-in ready with both style and functionality in mind. Upstairs, spacious bedrooms offer comfort and privacy with abundant natural light and spa-inspired bathrooms designed for relaxation. Step outside to your own private backyard retreat featuring low-maintenance luxury landscaping, pristine white stone accents, and premium artificial turf that keeps the outdoor space vibrant year-round. The fully fenced yard is perfect for relaxing evenings, entertaining guests, or enjoying peaceful mornings outdoors. Located just minutes from the renowned shops and restaurants of Park Avenue, residents will enjoy easy access to boutique shopping, fine dining, local cafés, and everyday conveniences including Trader Joe's. You’re also close to scenic parks, Lake Virginia, and Rollins College, making this location ideal for those seeking an active and connected lifestyle. Zoned for highly rated Winter Park schools and professionally managed by Atrium Management, this home offers the perfect combination of style, location, and convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)Listing Agent: Raquel Elliott (407-921-3772)
32789 - O6411722 - 1077 MINNESOTA AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$1,395,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Location. Design. Lifestyle. Newly built in 2025 by Nautilus Homes and lightly lived in, this exceptional custom residence offers the perfect blend of modern construction, elevated design, and an unbeatable Winter Park location. Ideally positioned between Orlando Avenue and Orange Avenue, just moments from Park Avenue, Mead Botanical Garden, acclaimed dining, boutique shopping, and cultural attractions, this is a rare opportunity to enjoy the very best of Winter Park living. Framed by mature landscaping and featuring dual front porch seating areas, the home encompasses over 3,000 square feet of thoughtfully designed living space and more than 4,000 square feet under roof, with four bedrooms, four full baths, and a dedicated first-floor office. More than $100,000 in post-construction enhancements further elevate the home's style, functionality, and everyday comfort. Inside, wide-plank Crème Brûlée hardwood flooring flows throughout, creating a warm and sophisticated backdrop. Custom closet systems in every bedroom, plantation shutters, and designer Arhaus lighting add a refined touch throughout the home. The spacious great room is anchored by a custom-built entertainment wall featuring a sleek vapor fireplace and integrated LED accent lighting, creating a striking focal point for both relaxing and entertaining. The chef’s kitchen seamlessly combines beauty and function with ceiling-height custom cabinetry, a handcrafted wood range hood, premium finishes, and an elegant butler’s pantry accented by designer Kit Kat tile. A built-in wine and coffee bar enhances the home's entertaining appeal while providing everyday convenience. Designed for flexibility and privacy, the floor plan offers a first-floor guest suite and office, while three additional en-suite bedrooms are located upstairs. The luxurious primary suite serves as a private retreat, featuring a spa-inspired bath with a soaking tub, oversized nine-foot walk-in shower, dual shower systems, frameless glass enclosure, and linear drain detailing. Outdoor spaces have been thoughtfully curated for effortless living. Professional landscaping, mature trees, full gutter systems, artificial turf, and decorative rock accents create a private, low-maintenance backyard sanctuary. The oversized 24' x 22' garage is equally impressive, featuring custom cabinetry, a dedicated tool wall, overhead storage systems, and Shark Coating epoxy flooring. Zoned for highly regarded Audubon Park K-8 and Winter Park High School, and located just minutes from Park Avenue and Winter Park’s vibrant dining and entertainment district, this move-in-ready residence delivers luxury, convenience, and timeless design in one of Central Florida’s most sought-after neighborhoods. This property may be under audio/visual surveillance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)Listing Agent: Frank Benevento (407-492-5153)
32792 - O6411633 - 946 ENCLAVE PL, WINTER PARK, FL 32792 8 Days on yellowkey
$2,175,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Pre-Construction. To be built. Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a private, residential setting while remaining connected to the area’s finest dining, shopping, and cultural amenities just minutes away in downtown Winter Park.. With a limited collection of custom homes, this community delivers an elevated lifestyle defined by architecture, walkability, and enduring charm. This custom single-family home is thoughtfully designed with exceptional craftsmanship and upscale finishes throughout. Each residence features high-performance, low-E double-pane windows, 8-foot solid core interior doors, and tankless gas water heaters for modern efficiency and comfort. Homes are appointed with premium Wolf and Sub-Zero appliances, designer-selected finishes, and a curated palette of colors and materials. These homes have it all; summer kitchens well equipped with fridge and grill and a sparkling pool. Spacious layouts, refined detailing, and quality construction create an elevated yet livable environment, all set within a beautifully landscaped and private setting. There is still time for the Buyer to personalize design selections and explore certain home plan modifications. Upgrade options are also available, including the opportunity to add a detached cabana and/or guest house, subject to builder pricing, lot compatibility, and community guidelines. Please inquire for additional details and available customization options.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)Listing Agent: Matthew Burks (407-257-5347)
32792 - O6410963 - 950 ENCLAVE PL, WINTER PARK, FL 32792 8 Days on yellowkey
$2,125,000 | Single Family Home | 5 beds | 4.5 baths | 2 gar
Pre-Construction. To be built. Discover refined modern living in The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 custom residences by FG Schaub Custom Homes. Tucked beneath mature oak canopies and surrounded by lush natural beauty, this intimate neighborhood offers a rare blend of privacy, walkability, and timeless architectural design. Ideally located just moments from Phelps Park, the YMCA, exceptional dining, boutique shopping, and the cultural attractions of downtown Winter Park, The Enclave delivers an elevated lifestyle in one of Central Florida’s most sought-after locations. This striking custom residence showcases contemporary architecture with clean lines, dramatic windows, and exceptional curb appeal. Thoughtfully designed for both everyday living and upscale entertaining, the home features expansive open-concept spaces, soaring ceilings, and seamless indoor-outdoor flow. Every detail reflects superior craftsmanship and designer-selected finishes curated to create a timeless yet modern aesthetic. Luxury appointments include premium Wolf and Sub-Zero appliances, high-performance low-E double-pane windows, 8-foot solid-core interior doors, and tankless gas water heaters for comfort and efficiency. Spacious living areas are complemented by a resort-style outdoor experience featuring a sparkling pool and a fully equipped summer kitchen, ideal for year-round entertaining. Beautifully landscaped grounds and quality construction create a private retreat while remaining connected to the very best of Winter Park living. Buyers still have the opportunity to personalize select finishes and explore certain floor plan modifications. Optional upgrades may include a detached cabana and/or guest house, subject to lot compatibility, community guidelines, and additional pricing. A rare opportunity to build a truly custom luxury home within one of Winter Park’s most exclusive new communities.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)Listing Agent: Laura Earl (443-994-9441)
32792 - S5150790 - 2529 WINDWARD WAY, WINTER PARK, FL 32792 8 Days on yellowkey
$299,000 | Townhouse | 3 beds | 2.0 baths
Welcome Home in the heart of Winter Park! Fantastic single-level townhouse fully remodeled with 3 bedrooms and 2 bathrooms, featuring beautiful cathedral ceilings upon entry and modern upgrades throughout. This move-in ready property offers a brand-new 2026 roof, freshly painted interior and exterior, a beautifully renovated kitchen, and fully updated bathrooms with elegant quartz countertops. Featuring a newer A/C system and new water heater, this home provides extra peace of mind for the new owners. Situated on a spacious corner lot, this home is perfect for families seeking comfort, style, and convenience. Enjoy your own private fenced backyard, ideal for relaxing, entertaining, or pets. The community offers a low HOA with fantastic amenities including a swimming pool, tennis courts, and playground. Conveniently located just 8 miles from UCF with quick access to shopping, dining, entertainment, and major highways. A perfect blend of location, lifestyle, and value!
Listing is courtesy of: MY Q REALTY, LLC (407-289-7608)Listing Agent: Myriam Quintero (407-289-7608)
32792 - O6411550 - 942 ENCLAVE PL, WINTER PARK, FL 32792 8 Days on yellowkey
$2,195,000 | Single Family Home | 5 beds | 5.0 baths | 2 gar
32792 - O6411247 - 7517 LAUREL SPRINGS DR, WINTER PARK, FL 32792 8 Days on yellowkey
$399,990 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. *MULTIPLE OFFERS! FINAL AND BEST OFFERS BY 10 PM 06/01/26* Welcome home to this beautifully maintained 3-bedroom, 2-bath *POOL* home in desirable Winter Park! Offering 1,678 square feet of single-story living, this home features an open floor plan with a spacious kitchen/family room combination. The open kitchen features 36” oak cabinetry, upgraded SS appliances, a garden window, and a kitchen island overlooking the dinette and family room. You’ll find laminate and tile flooring throughout the home, updated bedroom light fixtures (2026), and a converted 2-car garage offering flexible bonus space if you desire. Owners can escape to their primary suite with a walk-in closet, en-suite bathroom, and private French doors leading out to the HEATED SALTWATER POOL. Step outside to your own private backyard featuring an oversized covered patio with screened-in pool and a built-in spa, plenty of yard space to enjoy, a backyard shed for additional storage, a swing set, and a playhouse perfect for outdoor fun. With NO HOA, you’ll have the freedom to truly make this space your own! Major updates provide peace of mind, including a NEW water heater (2026), electrical panel replacement (2023), salinator replacement (2023), pool heater replacement (2024), roof (2019), and AC (2025). Conveniently located near shopping, dining, parks, and top-rated Seminole County schools, this move-in-ready home is the perfect blend of comfort, functionality, and Florida living!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)Listing Agent: Jadel Patterson, Llc (407-922-5936)
32789 - O6406823 - 723 SYMONDS AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$2,000,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer finishes, and contemporary ambiance that immediately sets the tone for the home. Beyond the entry, the main living spaces unfold into an open-concept kitchen, dining, and living area designed for both everyday comfort and elevated entertaining. The chef’s kitchen is beautifully appointed with custom cabinetry, a Wolf stove, Bosch dishwasher, a premium side-by-side True Residential refrigerator and wine column combination, and a separate under-island beverage refrigerator designed for effortless entertaining. Expansive PGT sliding doors connect the interior spaces seamlessly to the lanai and outdoor retreat, while the Klipsch 5.1 surround sound system, electric fireplace, Anderson windows, ceiling fans, and integrated Elon smart-home system enhance the experience throughout the home. The outdoor living area was designed as a private modern zen-inspired escape, featuring a fully air-conditioned and heated lanai with cedar-lined ceilings, rolled screens, and direct access to the serene backyard retreat complete with a four-person sauna. Thoughtfully integrated technology and upgrades include Jellyfish lighting, Nest cameras, power-over-Ethernet shades, leak protection system, water filtration systems including Aqua Sauna Water Filter and Kohler Connect Water Minder, as well as two separate AC units serving each floor independently. The first floor also offers a private guest suite, ideal for visitors or multigenerational living. Upstairs, the second level features a spacious laundry room, two additional en-suite bedrooms, and an impressive primary suite designed as a true retreat. The luxurious primary bathroom showcases a standing shower with digital water controls, dual sinks with custom storage cabinetry, and an expansive custom walk-in closet. Additional highlights throughout the home include engineered wood flooring, electric blinds, and refined designer details at every turn. Crowning the residence is a spacious third-floor bonus area offering endless flexibility for a media room, fitness studio, office, or additional lounge space, all fully air-conditioned for year-round comfort. Combining exceptional craftsmanship, advanced smart-home functionality, and an unbeatable Winter Park location with exceptional proximity to both Park Avenue and Winter Park Village, this extraordinary residence places premier dining, boutique shopping, cafés, entertainment, and everyday conveniences just moments from home while delivering a truly elevated lifestyle experience.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)Listing Agent: Nick Mckee (407-913-0171)
32789 - O6411443 - 184 SANDLEWOOD TRL #2, WINTER PARK, FL 32789 9 Days on yellowkey
$2,000 | Condo | 2 beds | 2.5 baths
Welcome to Sandlewood Trail Condo.
Listing is courtesy of: NOELKE REALTY (407-607-7166)Listing Agent: Tom Noelke (407-607-7166)
32789 - O6409323 - 2418 EUSTON RD, WINTER PARK, FL 32789 9 Days on yellowkey
$749,000 Reduced | Single Family Home | 3 beds | 2.5 baths | 1 gar
Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the highly sought-after Winter Park 32789 zip code, just moments from scenic Lake Killarney. Situated on an oversized 0.27-acre lot with no HOA, this exceptional property offers endless possibilities, including ample space to add a pool, guest house/ADU, or create the custom outdoor living space of your dreams. Full of charm and warmth, the home features bright and spacious living areas designed for both everyday comfort and entertaining, highlighted by a cozy wood-burning fireplace. The recently renovated kitchen showcases updated cabinetry, new countertops, newer appliances, and stylish tile flooring throughout the entire first floor. The kitchen flows seamlessly into the breakfast area overlooking the expansive fenced backyard, creating the perfect indoor-outdoor lifestyle. Upstairs, you’ll find wood flooring throughout the staircase and second floor, along with three light-filled bedrooms, two full bathrooms, and a versatile flex space ideal for a home office, playroom, or study area. Additional upgrades include a renovated downstairs half bath, updated secondary bathroom, professionally cleaned and sanitized AC ducts, new ceiling fans in all bedrooms, a newly installed garage door, a new garage roof, new irrigation system and a main roof replacement completed in 2018. Relax on the inviting front porch swing and enjoy peaceful lake breezes with your morning coffee or evening glass of wine. Ideally located near Park Avenue, Winter Park Village, premier dining, shopping, entertainment, and major highways with easy access to Downtown Winter Park and Orlando. Move-in ready and filled with modern updates, timeless character, and unbeatable potential, this property also presents an incredible opportunity to live in while your custom dream home is being built.
Listing is courtesy of: TOLARIS REALTY GROUP LLC (407-322-5253)Listing Agent: Rick Bavec (561-389-2070)