Multiple Cities, Zip Codes, Addresses, Streets, Neighborhoods, MLS IDs
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Ex.Miami OR Coral Springs OR Boca Raton 33319 OR 33321 OR 33467
Please click on one of the below schools to see properties that are marked as being nearby those schools in the MLS.
Winter Park High - O6415941 - 1421 CHAPMAN CIR, WINTER PARK, FL 32789 1 Day on yellowkey
$1,550,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.
Listing is courtesy of: KELLY PRICE & COMPANY LLC
Winter Park High - O6413910 - 121 E FAWSETT RD, WINTER PARK, FL 32789 1 Day on yellowkey
$3,490,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Under Construction. Brand new construction by LUIH Homes, ideally situated on a charming brick street in one of Winter Park’s most desirable locations. Thoughtfully designed with over-the-top quality, exceptional functionality, and timeless style, this five-bedroom, five-and-one-half-bath residence offers an outstanding floor plan for both everyday living and entertaining. Elegant double entry doors open to a welcoming foyer and a light-filled interior featuring beautiful wood flooring throughout the main living areas and all bedrooms on both levels. The open-concept design seamlessly connects the spacious living room, dining area, and chef’s kitchen, creating a warm and inviting atmosphere. Expansive windows and sliding glass doors flood the home with natural light while providing picturesque views of the covered lanai, pool, and backyard. The kitchen is beautifully appointed with premium Thermador appliances, including a six-burner gas range with oven, built-in oven and microwave, and a Zephyr under-counter wine refrigerator. Custom cabinetry, generous workspace, and a large walk-in pantry make this kitchen as functional as it is stylish. The first floor also features a private guest suite complete with a walk-in closet and ensuite bath, as well as a dedicated office positioned toward the front of the home with views of the front entrance and driveway. Outdoor living is equally impressive. The expansive 40-by-14-foot covered lanai overlooks the approximately 40-by-15-foot pool and offers a fully equipped summer kitchen with abundant space for lounging, dining, and entertaining year-round. Upstairs, the luxurious primary suite serves as a private retreat featuring a spa-inspired bath, oversized custom walk-in closet, and access to a covered balcony. Three additional bedroom suites, each with a private bath, provide comfortable accommodations for family and guests. A spacious family/media room and secondary laundry room complete the second level. Enjoy an exceptional Winter Park lifestyle just minutes from the renowned shopping and dining destinations of Park Avenue, Hannibal Square, and Winter Park Village. Zoned for highly sought-after Audubon K-8 and Winter Park High School, this outstanding location also offers convenient access to major hospitals, downtown Orlando, Orlando Executive Airport, Orlando International Airport, and major roadways for easy commuting throughout Central Florida.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY
Lake Howell High - O6409708 - 3443 ALLSTON LN, WINTER PARK, FL 32792 1 Day on yellowkey
$299,999 | Townhouse | 3 beds | 2.0 baths | 1 gar
3-bedroom, 2-bath SINGLE-story block townhome with garage located in an excellent school district! Recent improvements include a BRAND-NEW ROOF (2025), BRAND-NEW HVAC SYSTEM (June 2026), and BRAND-NEW WATER HEATER (June 2026), all still under warranty! Plus fresh interior paint throughout (June 2026) and new flooring in the rear bedroom (no carpet in the home). With the big-ticket items already completed, this home offers exceptional peace of mind and truly worry-free ownership. The spacious floor plan features soaring living room ceilings, generously sized bedrooms, and a screened rear patio with ceiling fan and lighting, perfect for relaxing or entertaining—all on one level with no interior stairs. Two of the bedrooms feature sliding glass doors providing direct access to the backyard and abundant natural light. In addition to the screened patio, you’ll enjoy a large open patio area ready to become your own private outdoor retreat for grilling, gardening, or entertaining. Enjoy a super low HOA of just $65 per month, which includes access to a community pool just a short walk away, as well as a serene lake with a covered dock and gazebo perfect for relaxing, fishing, or socializing with neighbors. Ideally located near Downtown Winter Park, Park Avenue, Rollins College, Full Sail University, UCF, and Valencia College, with easy access to SR-436 and endless shopping, dining, and entertainment options just minutes away. This home is a true gem offering excellent schools, recent upgrades, a prime location, low HOA fees, and a warm, welcoming atmosphere. Whether you’re a first-time homebuyer, downsizing, or seeking a fantastic investment opportunity, this property checks all the boxes. Don’t miss your opportunity to make it yours!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS
Winter Park High - O6415611 - 1220 WOODMERE DR, WINTER PARK, FL 32789 1 Day on yellowkey
$1,700,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Welcome to 1220 Woodmere Drive, where timeless elegance and modern luxury come together in one of Winter Park’s most coveted neighborhoods. This exceptional 4-bedroom, 3.5-bath residence offers 2,815 square feet of thoughtfully designed living space, blending classic charm with today’s most desirable comforts. The spacious first-floor primary suite serves as a private retreat, complete with dual walk-in closets and a spa-inspired bath designed for relaxation. Rich solid hardwood floors flow throughout the main downstairs living areas, creating warmth and sophistication at every turn. Upstairs, a smart split-bedroom layout provides three additional bedrooms and two full baths, offering privacy and flexibility for family and guests alike. A detached two-car garage adds even more versatility, featuring an expansive bonus room above—perfect as a home office, fitness studio, creative space, or hobby room. Ideally positioned on one of Winter Park’s most sought-after streets, this home places you just moments from the Winter Park Racquet Club, the scenic Chain of Lakes, and the vibrant shops and dining of downtown Winter Park. With top-rated public schools nearby and an unbeatable location, this is a rare opportunity to enjoy the very best of Winter Park living. 1220 Woodmere Drive isn't just a home—it's a lifestyle.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
Lake Howell High - O6416235 - 2304 INAGUA WAY #2304, WINTER PARK, FL 32792 1 Day on yellowkey
$1,750 | Condo | 2 beds | 1.0 baths
Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the established community of Winward Square with access to a community pool and tennis courts, this home offers both convenience and comfort. Don't miss out on this opportunity to live in Seminole County in this lovely property. Sorry Pets are not permitted. *Washer and dryer are in as/is condition and for tenant convenience only *Tenant is required to carry Renters Insurance If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. *RESIDENTS BENEFIT PACKAGE* Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application
Listing is courtesy of: CT HOMES REALTY CORPORATION
Lake Howell High - O6415961 - 5894 SHALE CT, WINTER PARK, FL 32792 1 Day on yellowkey
$315,000 | Half Duplex | 2 beds | 2.0 baths | 1 gar
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Talk about location, location, location! Welcome to this beautifully updated and well-maintained 2-bedroom, 2-bathroom, 1-car garage home in Winter Park, perfectly situated in the charming Aloma Park community. Just about 1 mile from the 417 Greenway, this home offers easy access throughout Orlando, while also being walking distance to the Cross Seminole Trail and Cady Way Trailhead—perfect for biking, running, rollerblading, or simply enjoying an active lifestyle. Inside, this move-in-ready home feels bright, warm, and inviting with sandy-toned wood-look tile and laminate flooring that lighten the entire space. The kitchen has been beautifully updated with granite countertops, soft-close cabinets, stainless steel appliances, a new microwave, and ample storage. The popcorn ceilings in the main living areas have been removed and replaced with a clean knockdown finish, giving the home a fresh and updated feel. The bathroom updates are a major highlight: one bathroom has been fully renovated with a walk-in shower, while the second bathroom features a new countertop, new cabinetry, and soft-close cabinets. Additional updates include a 2021 roof, HVAC system from 2016, new water heater, washer and dryer, energy-efficient double-pane windows, energy-efficient French doors, LED fixtures, and solar tubes that fill the home with natural light. There is also attic space for convenient extra storage. The primary suite offers a bonus sunroom/flex space that is insulated and equipped with plexiglass sliders and a mini-split unit hook-up, making it perfect for a home office, greenhouse, playroom, sitting room, or creative space. French doors with built-in blinds lead out to the screened lanai, creating an easy indoor-outdoor flow. Outside, enjoy a beautifully landscaped, fully fenced backyard with a utility shed that has its own breaker—perfect for storage, hobbies, or the handy person in the house. The pavers in the front courtyard and back patio add even more charm and function to the exterior spaces. Aloma Park is a small, quaint Winter Park community with only two cul-de-sac streets, 42 duplex homes, and no through traffic. Residents enjoy access to a community pool, tennis courts, basketball courts, and a clubhouse available to rent for gatherings. Zoned for excellent A-rated Winter Park schools and conveniently located near UCF, Full Sail University, Rollins College, downtown Winter Park, Oviedo, shopping, dining, and major roadways, this home offers the perfect blend of comfort, convenience, and affordability. Hurry to see this Winter Park gem — there’s nothing to do here but bring your furniture!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS
Lake Howell High - C7527235 - 1535 LAWNDALE CIR, WINTER PARK, FL 32792 2 Days on yellowkey
$450,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.
Listing is courtesy of: SOVEREIGN REAL ESTATE GROUP
Winter Park High - O6415216 - 350 CAROLINA AVE #407, WINTER PARK, FL 32789 2 Days on yellowkey
$2,895 | Condo | 2 beds | 2.0 baths | 1 gar
Experience maintenance-free living in this spacious 2-bedroom, 2-bath condominium offering 1,529 square feet in the gated Park West community in the heart of Winter Park. Located on the top floor, this spacious residence features vaulted ceilings, hardwood flooring, quartz countertops, stainless steel appliances, walk-in closets, a soaking tub, a stacking washer and dryer, and charming Juliet balconies. Residents enjoy exceptional amenities, including a community pool, tennis courts, clubhouse, and an assigned garage parking space. Water service is included in the rent. Park West is across the street from the weekly Winter Park Farmers' Market, and one block from Park Avenue; you'll have easy access to boutique shopping, highly renowned restaurants, the SunRail station, and everything that downtown Winter Park offers. Cats will be considered on a case by case basis with a non-refundable pet fee and monthly pet rent. Prospective tenants are subject to the Park West Condominium Association approval process and associated application fee.
Listing is courtesy of: FLORIDA ONE REAL ESTATE LLC
Winter Park High - S5150999 - 3045 AARON BURR AVE #12D, WINTER PARK, FL 32792 2 Days on yellowkey
$1,650 | Condo | 2 beds | 2.0 baths
Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access to everything Orlando. Featuring new flooring and a clean, fresh interior, it is ideal for any lifestyle.
Listing is courtesy of: LPT REALTY, LLC
Winter Park High - O6415981 - 1265 ARLINGTON PL, WINTER PARK, FL 32789 2 Days on yellowkey
$879,000 | Townhouse | 3 beds | 3.5 baths | 1 gar
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!
Edgewater High - O6415985 - 1521 CAVENDISH RD, WINTER PARK, FL 32789 2 Days on yellowkey
$470,000 | Single Family Home | 2 beds | 1.0 baths | 1 car
Virtually Staged. Located in the heart of Orwin Manor, one of Winter Park’s most beloved historic neighborhoods, 1521 Cavendish Road is a beautifully renovated 2-bedroom, 1-bath home offering 1,042 square feet of thoughtfully updated living space. Positioned between Winter Park, College Park, and Downtown Orlando, residents enjoy convenient access to AdventHealth, Loch Haven Park, the Orlando Museum of Art, Orlando Science Center, Park Avenue, Ivanhoe Village, and some of the area's most celebrated dining, shopping, and cultural destinations. Surrounded by mature landscaping, manicured hedges, colorful garden beds, and stately palms, the home's curb appeal reflects the character and pride of ownership found throughout the neighborhood. French front doors open to a spacious foyer that leads into a bright family and dining room combination, where new pine laminate flooring, crown molding, plantation shutters, and updated lighting blend historic character with modern comfort. The renovated kitchen features shaker cabinetry, Silestone countertops, stainless steel appliances, abundant storage, and natural light. Both bedrooms have been thoughtfully updated with new flooring, LED recessed lighting, ceiling fans, and plantation shutters, while the recently renovated bathroom pairs basketweave tile flooring, subway tile, quartz countertops, and classic finishes that honor the home's original style. Outside, the large backyard has been transformed into a private retreat featuring a composite deck, new fencing, mature palms, raised garden beds, steel-edged landscaping, and a paver walkway. Thoughtfully updated while preserving its architectural charm, this home offers a rare opportunity to enjoy historic character in a neighborhood that continues to benefit from the growth, investment, and enduring appeal of Winter Park and Downtown Orlando. Schedule your private tour today.
Listing is courtesy of: STOCKWORTH REALTY GROUP
Winter Park High - O6415360 - 240 N PHELPS AVE, WINTER PARK, FL 32789 2 Days on yellowkey
$2,250,000 | Single Family Home | 5 beds | 4.5 baths | 2 gar
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK
Winter Park High - O6415814 - 418 R GILBERT RD, WINTER PARK, FL 32792 2 Days on yellowkey
$4,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools.
Listing is courtesy of: SOTERA LIVING
Edgewater High - O6415537 - 685 OVERSPIN DR, WINTER PARK, FL 32789 3 Days on yellowkey
$629,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Super Location! Close to Urban Bike trail, Winter Park Village, Dubsdread Golf Course, Advent Health. This home was custom built with large white wood window casing, formal dining room with plenty of natural light, 10 foot ceilings, crown molding, 8 ft doors, upgraded tile, 3 sets of French Doors open to back and so much more. Gas fireplace in the family room with high-top bar seating in the kitchen also featuring upgraded granite countertops, stainless steel appliances including a gas range, and plenty of storage space with 42 cabinets. Oversized laundry room with extra storage space. Downstairs also features a spacious half bath with a new countertop.All 3 bedrooms are Upstairs. Bathrooms all have new Quartz counters from recent renovations. All bedrooms come with large closets. 2nd and 3rd bedrooms are connected with "Jack and Jill' bathroom with 2 separate sinks. Master Bathroom has large walk-in shower and separate Jetted Tub.Long driveway provides access to detached oversized garage in the back. Wrought iron fencing in backyard adds to a wonderfully landscaped yard.Nearby is Rollins College, the Charles Hosmer Morse Museum of American Art, Mead Botanical Garden, Albin Polasek Museum and Sculpture Gardens, the Enzian Theater, and so much more.Winter Park is also home to over 70 parks, all home to various events, festivals and celebrations throughout the year.A quick ride to almost anywhere in central Florida, minutes to Downtown Orlando, Winter Park Village, College Park, and Park Ave, 20 min to Disney World, and plenty of shopping and award-winning restaurants just minutes away! Pictures taken January 2024
Listing is courtesy of: HOMEVEST REALTY
Winter Park High - O6414890 - 231 CHELTON CIR, WINTER PARK, FL 32789 3 Days on yellowkey
$4,950,000 | Single Family Home | 4 beds | 6.0 baths | 3 gar
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
Edgewater High - O6415735 - 151 N ORLANDO AVE #238, WINTER PARK, FL 32789 3 Days on yellowkey
$2,750 | Condo | 2 beds | 1.0 baths
Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.
Listing is courtesy of: COLONIALTOWN REALTY
Winter Park High - O6414677 - 528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792 3 Days on yellowkey
$535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Edgewater High - O6415098 - 1473 BERKSHIRE AVE, WINTER PARK, FL 32789 3 Days on yellowkey
$1,429,000 | Single Family Home | 5 beds | 4.0 baths | 2 gar
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features 10-foot ceilings, 8-foot doors, luxury vinyl plank flooring throughout, and an expansive great room with an electric fireplace. The gourmet kitchen is designed to impress with quartz countertops, custom cabinetry, stainless steel appliances, a large center island, and abundant storage. A unique under-stair wine cellar adds character and sophistication, while a first-floor guest suite provides privacy and flexibility. Upstairs, the spacious primary suite overlooks the backyard and pool area and includes a spa-inspired bathroom with dual vanities, a soaking tub, walk-in shower, and generous walk-in closet. Three additional bedrooms comfortable accommodations, including a Jack-and-Jill layout and a private In-suite bedroom. A conveniently located upstairs laundry room completes the second level. Step outside to your private outdoor retreat featuring a beautifully landscaped backyard, sparkling in-ground pool, covered lanai, and summer kitchen with built-in grill—perfect for entertaining year-round. Ideally located just minutes from Winter Park’s renowned shopping, dining, parks, and cultural attractions, this exceptional home offers the rare opportunity to enjoy the benefits of brand-new construction in one of Central Florida’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: KARDOSH REALTY
Winter Park High - O6414862 - 2032 KIMBRACE PL, WINTER PARK, FL 32792 4 Days on yellowkey
$2,188,888 | Single Family Home | 5 beds | 4.0 baths | 2 gar
A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF | Saltwater Pool & Spa | Smart Home | Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled within one of Winter Park's most desirable neighborhoods and just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. Thoughtfully designed with a Zen-inspired aesthetic, the home seamlessly blends clean architectural lines with warm natural elements to create a living experience that feels refined and restorative. From the moment you arrive, an atmosphere of calm surrounds you, offering a peaceful escape while remaining moments from everything Winter Park has. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A stunning semi-floating steel staircase with solid whiteoak treads serves as a dramatic architectural focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining and everyday luxury. A sleek Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, striking marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, expansive dual-entry shower wrapped in marble, semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-caliber outdoor living experience evokes the serenity of a luxury Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Located nearby highly regarded Winter Park schools and less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, this is a sanctuary. A place to unwind, recharge, and experience the very best of Winter Park living.
Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO
Winter Park High - O6415084 - 2715 PRINCE JOHN RD, WINTER PARK, FL 32792 5 Days on yellowkey
$519,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
GREAT HOME & GREAT VALUE — add your TLC and DIY and you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All dimensions must be independently verified by the buyer.
Listing is courtesy of: VIA PROPERTIES LLC
Winter Park High - O6414770 - 525 S LAKEMONT AVE, WINTER PARK, FL 32792 5 Days on yellowkey
$2,199,900 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Featuring 4 spacious bedrooms and 4 beautifully appointed bathrooms, this masterpiece showcases custom cabinetry and closets throughout, ensuring every space is both functional and refined. The chef’s kitchen is a true showpiece, complete with a coffee bar, walk-in pantry with customized shelving and designer lighting, and seamless flow into the open-concept living and dining areas. A wine room adds sophistication and convenience for the entertainer at heart. Upstairs, enjoy a spacious loft area with a wet bar, perfect for hosting guests or creating an additional entertainment lounge. Step outside to your private outdoor oasis, featuring a heated pool, fireplace, outdoor kitchen, and surround sound system—designed for year-round entertaining and relaxation. This home is pre-wired for security cameras and enhanced by custom landscaping and lighting, offering beauty and privacy from day to night. Located in highly sought-after Winter Park, Florida, near world-class dining, shopping, and top-rated schools. Contact us today for a private showing!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III
Lake Howell High - O6412855 - 3641 OAK VISTA LN, WINTER PARK, FL 32792 5 Days on yellowkey
$475,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home. Have your morning coffee or afternoon cocktails sitting out back on the porch enjoying the birds. This large, fenced 120 x 80-foot yard provides plenty of room for little ones and pets to play, gardening, or simply unwinding. for comfortable Florida living! Perfectly situated in a desirable, close-in location and zoned for award-winning Seminole County schools, this remodeled, one-story home offers the ideal setting for all family households. Step inside and discover an inviting split floor plan featuring 3 spacious bedrooms and 2 modern bathrooms. The formal living and dining rooms create an elegant atmosphere for entertaining, while the stunning remodeled kitchen is light and bright, complete with contemporary finishes and new appliances. Relax in the cozy family room, where a charming brick wood-burning fireplace adds warmth and ambiance on cool evenings. You do have formal areas that have a multitude of options for space where YOU Need it. Once you get to the kitchen you will be amazed with the sleek white brand new cabinets with trendy quart counters and a gorgeous back splash. WOW! You can enjoy yourself while you are at the sink and watch whatever is going on in the backyard. No expense spared with banks of drawers too. Additional highlights include a 2-car garage, newer windows for energy efficiency, and NO HOA—giving you the freedom to truly make this home your own. Bring your camper, toys because you have loads of room in the backyard to work on multiple projects. Roof and A/C are 2021 adding to peace of mind with your insurance 4 point inspection. Garage is even 24x21. With ample parking, an amazing outdoor space, and proximity to top-rated schools, shopping, dining, and major highways, 3641 Oak Vista Lane delivers the ultimate Florida lifestyle for your family inside the home and outside. You deserve your own Backyard paradise. Don’t miss the opportunity to make this move-in ready Winter Park gem your forever home. Seminole County schools complete the package. Schedule your private tour today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO
Edgewater High - O6411927 - 2500 LEE RD #220, WINTER PARK, FL 32789 5 Days on yellowkey
$199,900 | Condo | 2 beds | 1.0 baths
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.
Winter Park High - S5151458 - 738 S PENNSYLVANIA AVE, WINTER PARK, FL 32789 5 Days on yellowkey
$735,000 | Single Family Home | 3 beds | 2.0 baths | 1 gar
Under contract-accepting backup offers. Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.
Listing is courtesy of: COMPASS FLORIDA LLC
Winter Park High - O6414744 - 648 W SWOOPE AVE, WINTER PARK, FL 32789 5 Days on yellowkey
$2,700 | Single Family Home | 3 beds | 1.0 baths
FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open floorplan. Living/Dining room combo. Designer light fixtures. Fenced backyard. Located within walking distance to Park Avenue, Hannibal Square, the Winter Park Village, Rollins College and more. No smoking. Pets will be considered with an additional, non-refundable pet deposit. Move-in ready and available for occupancy July 1, 2025. Background and Credit Check required. $50 application fee. First month's rent + $3,000 security deposit. Tenant must carry renter's insurance. Lawn care and pest control included. Owner will consider pets.
Lake Howell High - O6412441 - 1511 GLADIOLAS DR, WINTER PARK, FL 32792 5 Days on yellowkey
$470,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. Welcome to this beautifully updated 4 bedroom, 2 bathroom pool home in the heart of Winter Park, where modern upgrades, comfortable living spaces, and exceptional outdoor amenities come together to create the perfect place to call home. Thoughtfully renovated and move in ready, this home offers the ideal blend of style, functionality, and Florida living. The heart of the home is the stunning kitchen, completely remodeled in 2024 with approximately $60,000 in improvements. Featuring white shaker cabinetry, quartz countertops, stainless steel appliances, a spacious center island, and abundant storage, this space was designed for both everyday living and entertaining. Luxury vinyl plank (LVP) flooring installed in 2024 flows throughout the home, complementing the open layout, vaulted ceilings, and abundant natural light. The spacious primary suite provides a relaxing retreat, while three additional bedrooms offer flexibility for family, guests, a home office, or hobbies. Recent improvements continue throughout the home, including a beautifully renovated guest bathroom completed in 2025, a custom closet system added in 2024, and a roof replaced in 2021, giving buyers added confidence and peace of mind. Step outside and discover your own private backyard oasis. The screened lanai overlooks a sparkling pool, expansive patio area, fire pit, and outdoor kitchen, creating the perfect setting for weekend gatherings, summer cookouts, or relaxing evenings at home. The irrigation system operates from a private well, helping maintain the lush landscaping while keeping water costs down. Located in an established Winter Park neighborhood known for its excellent schools and convenient access to shopping, dining, parks, and major roadways, this home offers easy access to everything Central Florida has to offer. With extensive updates, a desirable floor plan, and incredible indoor and outdoor living spaces, 1511 Gladiolas Drive presents a rare opportunity to own a truly move in ready home in one of Winter Park's most desirable locations. Schedule your private showing today!
Winter Park High - O6407648 - 1221 RICHMOND RD, WINTER PARK, FL 32789 5 Days on yellowkey
$4,995,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Owner/Agent - Properties of this caliber are exceptionally rare in Winter Park — in a neighborhood defined by its walkability to Park Avenue, top-rated schools, and exclusive deeded access to the Winter Park Chain of Lakes. While new construction continues to emerge throughout Winter Park, few can approach the level of intention, artistry and personal investment found here. Named best custom home in the entire Southeast, this grand award-winning residence was conceived and executed by Master Custom Homebuilder Chris Salhab of Valdara Custom Homes as his own family home. Every element of this home reflects a standard of craftsmanship and care that is immediately felt upon entry and discovered anew in every room. The open-concept floor plan flows effortlessly between interior and exterior living spaces, where a summer kitchen, covered entertaining areas and a signature rain curtain that doubles as an outdoor movie screen create an experience unlike anything else on the market. Intelligent design, smart home integration and refined finishes complete a residence that is as functional as it is extraordinary. Offered with the added benefit of premium lease income through early 2027, this is a rare chance to secure one of Winter Park's finest homes as both a trophy asset and an immediate income-producing investment. Private showings by appointment only.
Listing is courtesy of: LA ROSA REALTY HORIZONS LLC
Winter Park High - O6414626 - 1137 SOUTH PENNSYLVANIA AVE, WINTER PARK, FL 32789 6 Days on yellowkey
$2,995 Reduced | Single Family Home | 3 beds | 2.0 baths | 1 gar
Location!! Walking distance to Rollins campus and to downtown Winter Park. Beautiful 3-bedroom 2-bathroom home. Recently renovated kitchen and freshly painted. Nearby schools include Audubon Park elementary, Glenridge Middle School, and Winter Park education center school. This house is in the perfect location, close to great restaurants and within walking distance to Winter Park farmer's market.
Listing is courtesy of: COLDWELL BANKER REALTY
Winter Park High - O6412134 - 413 W MORSE BLVD, WINTER PARK, FL 32789 7 Days on yellowkey
$2,695,000 | Townhouse | 3 beds | 3.5 baths | 2 gar
LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!
Winter Park High - O6412851 - 2974 CHANTILLY AVE, WINTER PARK, FL 32789 7 Days on yellowkey
$550,000 | Single Family Home | 3 beds | 2.0 baths
Virtually Staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, septic/drainfield improvements, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!
Winter Park High - O6414263 - 1724 PINE AVE, WINTER PARK, FL 32789 8 Days on yellowkey
$3,095,000 | Single Family Home | 3 beds | 4.0 baths | 4 gar
Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits. Expansive walls of glass and disappearing sliders flood the interiors with natural light while creating a seamless connection between indoor and outdoor living spaces, all while maintaining a remarkable sense of privacy. Designed for both everyday living and effortless entertaining, the open-concept floor plan showcases a spectacular custom entertainment bar featuring a stunning stone countertop, handcrafted cabinetry, an ice maker, a wine tower and a beverage cooler. The great room, dining area and kitchen flow together in one expansive space, framed by pocketing glass doors on both sides that open completely to the front courtyard and the rear lanai, pool and backyard beyond. The chef’s kitchen is a true centerpiece, outfitted with an impressive suite of Wi-Fi-enabled Thermador appliances, including a six-burner gas range with a steam oven and warming drawer and an integrated refrigerator with freezer drawers and additional refrigerated storage drawers. Thoughtfully designed for both functionality and style, the kitchen also features an appliance garage, a dedicated coffee bar, custom cabinetry and a large pass-through window that pockets into the wall, providing convenient service access to the covered lanai. A fully equipped secondary kitchen and butler’s pantry offers abundant storage, a built-in oven, a microwave and an additional refrigerator, making entertaining on any scale effortless. Privately situated on the first floor, the luxurious primary suite serves as a peaceful retreat with direct access to the lanai and outdoor living areas. The spa-inspired primary bath features a sculptural stone soaking tub, an oversized shower with multiple rain shower heads and a secluded outdoor patio complete with an open-air shower. A beautifully customized walk-in closet completes the suite. Additional first-floor amenities include a dedicated office, an elegant powder bath, and a unique dog room. A versatile flex space currently utilized as a spa room with laundry offers endless possibilities as a fitness room, expansive mudroom, storage area or wellness retreat, with direct access to one of the garage bays. The second level features a spacious family room along with two generously sized bedroom suites, each offering walk-in closets and private ensuite baths. One of the home's most remarkable features is the expansive rooftop balcony, complete with a gas fireplace and panoramic views overlooking both the front courtyard and backyard. Whether hosting guests or enjoying a quiet evening sunset, this elevated outdoor living space provides an unforgettable setting. Situated on a sprawling half-acre lot, the property offers exceptional outdoor space with room for future expansion or simply enjoying the privacy and beauty of the backyard, pool and lanai. Ideally located just minutes from vibrant Park Avenue, residents enjoy convenient access to Winter Park’s renowned dining, shopping, parks and cultural amenities, while major roadways provide easy commutes to downtown Orlando, Orlando Executive Airport and Orlando International Airport.
Lake Howell High - O6413717 - 5340 N LAKE BURKETT LN, WINTER PARK, FL 32792 8 Days on yellowkey
$495,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation just moments from home. This meticulously maintained residence stands out with fresh exterior paint, updated landscaping, and inviting curb appeal. Inside, soaring vaulted ceilings and abundant natural light create an open, airy atmosphere, enhanced by fresh interior paint throughout. The thoughtfully designed split-bedroom floor plan makes excellent use of every square foot, offering comfortable living with no wasted space. An indoor laundry room, spacious 2-car garage, and desirable semi cul-de-sac location add to the home's appeal. Beyond the lake, residents enjoy a community pool, playground, boat launch, and dock along with being located directly across the street from the Cross-Seminole Bike Trail, creating a true lifestyle community. Conveniently located with easy access to SR 417, shopping, dining, and everyday essentials, this home offers the perfect blend of recreation, convenience, and value. Experience the rare opportunity to enjoy private lake-access living in one of the area's most desirable neighborhoods.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY
Winter Park High - O6413398 - 2240 VENETIAN WAY, WINTER PARK, FL 32789 8 Days on yellowkey
$3,500,000 | Single Family Home | 4 beds | 3.5 baths | 2 gar
Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*
Winter Park High - O6413560 - 1760 ALABAMA DR, WINTER PARK, FL 32789 9 Days on yellowkey
$10,900 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Behind a gated courtyard entrance in the Vias of Winter Park, just around the corner from Kraft Azalea Garden on the shores of Lake Maitland, this move-in ready residence offers privacy, thoughtful design and exceptional indoor-outdoor living. Surrounded by mature landscaping and accessed from both front and rear driveways, the property provides a rare sense of seclusion while remaining minutes from Park Avenue, Winter Park Racquet Club, dining, shopping and top-rated schools. Designed to maximize natural light, the home features vaulted ceilings, skylights, walls of windows and seamless connections to multiple outdoor living areas. The main level includes formal living and dining rooms, a spacious family room, dedicated home office and powder bath. Custom built-ins, extensive storage and carefully planned living spaces support both everyday living and entertaining. The chef's kitchen is appointed with custom wood cabinetry, stone countertops, premium appliances, a large center island with seating and generous preparation space. Open sightlines and direct access to outdoor gathering areas create a natural flow throughout the home. Upstairs, three bedrooms and two full baths include a spacious primary suite featuring vaulted ceilings, hardwood flooring, private balcony access and a renovated bath with marble finishes and a walk-in shower. Additional storage throughout the second level enhances functionality and organization. Outdoor living is a defining feature of the property. Multiple gathering spaces include a welcoming front courtyard, fire pit area and a fully equipped outdoor kitchen and dining space featuring a Wolf grill, brick pizza oven and market lighting. Mature hedges and professionally designed landscaping create privacy throughout the grounds. Additional highlights include hardwood flooring, an oversized garage with substantial storage capacity, dedicated utility room with laundry and utility sink, rear motor court access and multiple outdoor entertaining areas designed for year-round enjoyment. Available for a one-year lease. Unfurnished. Pets considered on a case-by-case basis subject to landlord approval.
Winter Park High - O6413279 - 300 CAROLINA AVE #301, WINTER PARK, FL 32789 9 Days on yellowkey
$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.
Winter Park High - O6412857 - 230 E ROCKWOOD WAY, WINTER PARK, FL 32789 9 Days on yellowkey
$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.
Winter Park High - O6413554 - 311 E MORSE BLVD #6-12, WINTER PARK, FL 32789 10 Days 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.
Winter Park High - O6413563 - 2918 ANTIQUE OAKS CIR #26, WINTER PARK, FL 32792 10 Days 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