Winter Park FL. Homes For Sale

Welcome Home to this charming single story 2 bedroom 2 bath home located in desirable Winter Park. Built in 1946, this home exudes charm, boasting original bathrooms and...

Do not miss your opportunity to call this lovely 3 bedroom, 2 bathroom property in Winter Park your NEW HOME!!! This bright and airy home has a great split bedroom open f...

DESIREABLE LAKE KILLARNEY CLASSIC HOME WITH MODERN UPDATES JUST BEGINS TO DESCRIBE THIS 4 BEDROOM 4 BATH POOL HOME SEATED ON A CORNER LOT IN THE VERY PRIVATE NEIGHBORHOOD...

Discover an exceptional opportunity in the heart of Winter Park. This beautiful custom-built two-story modern home is very bright with southern exposure on the rear of th...

This Brookshire Heights Mid-century Modern home has an oversized newly added master bedroom and en-suite. This home lives large with three bathrooms and four bedrooms on ...

An exceptional opportunity awaits in the heart of Winter Park. This transitional-style custom home is comprised of four bedrooms and three baths over 3,113 square feet of...

Presenting to the market for the first time in 54 years and the first time ever as three properties combined over the years all within footsteps of Park Avenue and situat...

Absolutely lovely 3-bedroom, 2.5-bath renovated home in highly desirable Timberlane Shores. Split level floor plan with walk out basement to patio and large private fully...

Opportunity knocks - ACT FAST!!! This beautiful fully remodeled 3 bedroom, 2 bath home is not going to last! Wood plank tile flooring throughout with rugs in the bedrooms...

Brand new home. 10 foot ceilings. Front and back porches. Engineered wood floors. Thermidor appliances. Upgraded windows. Huge attic storage. Surrounded by 6 foot block w...

Come take a look at this lovely home located in the desirable Dubsdread Heights neighborhood in Winter Park. After a long week of work, invite the neighbors over for a BB...

***GREAT SOLID BLOCK CORNER LOT HOUSE***3 BEDROOMS*** 2 FULL BATHS***FORMAL LIVING ROOM***DINING ROOM***FULL KITCHEN***FAMILY ROOM***INGROUND POOL***FENCED IN YARD***OVER...

CHARMING HOME IN GARDEN LAKE ESTATES WITH NO HOA!!! VERY LARGE LOT!!! This well cared for three bedroom/ two bath home is one you do not want to miss! Sought after commun...

This charming house is located in heart of Seminole County and located in very quite neighborhood. The neighborhood is zoned in best of Seminole County School District a...

Presenting an exquisite new listing in the Heart of Winter Park. Completely remodeled in 2019 from floor to ceiling, this casually elegant, single-story residence feature...

MULTIPLE OFFERS RECEIVED, please submit BEST OFFER by 3pm on Monday 1/18/2021. Welcome home to this beautiful bungalow right on the border of College Park and Winter Park...

Welcome to Park Grove! Here is your opportunity to live in Winter Park's most desired neighborhood! Park Grove, with it's tree lined streets, has been Winter Park's most ...

Don't miss your chance to own this spacious 4 bedroom 3 bath beautifully remodeled home located on the 4th fairway of the historic Dubstread Golf Course! This move-in rea...

Welcome to Winter Park! Charming 3 bedroom 2 bathroom home with 1 car garage in the Tanglewood community with no HOA. Updated kitchen with stainless steal appliances. Ne...

Renovated home in Winter Park in Winter Woods backs up to a wooded backdrop with no neighbors in the back providing tremendous privacy. This 3-bedroom, 2-bath split plan ...

Remodel existing home or it is a perfect location to build your custom home on this oversized lot off Park Avenue in Winter Park. The property measures 15,836 square feet...

This is a wonderful opportunity to purchase in one of the most sought after neighborhoods in Winter Park. Beautiful oak tree lined brick streets make this one of the pret...

Welcome to this updated 3 Bedroom pool home with a Mother-in-law suite. New roof 2020, hot and cold pipes replumbed 2015 and HVAC new in 2020. This home has beautiful new...

Located in beautiful Winter Park, FL. with 4 bedrooms 2 baths and 2,121 Sq. Ft. his is the perfect home with a pool you've been dreaming of. The home’s location just minu...

Fantastic 2 bed, 1 Bath + Bonus Room home located in Winter Park. Conveniently nestled between all the shops and dining College Park AND Winter Park have to offer. Cute ...

One or more photo(s) has been virtually staged. Built in 2015, this Winter Park two-story home offers granite countertops and a two-car garage. This home is vacant and cl...

RECENTLY RENOVATED. New kitchen cabinets with granite counter tops, brand new stainless steel appliances, updated bathrooms with custom tile work, fresh paint inside and ...

Under Construction. Your Brand New 2021 Custom Home is almost ready for your family. Rex-Tibbs Construction has been building timeless homes in Winter Park for over 35 ye...

Picturesque luxury. This delightful 4 bedroom, 3 bathroom house, plus office, marries the charm of a timeless transitional home with all of the hi-tech modern convenience...

Welcome home to this beautiful spacious 4 bedroom 3 bath home located in desirable gated community of Enclave at Aloma. First floor has an open floor plan with one bedroo...

An exceptional offering awaits in the heart of Winter Park. Built in 1925 and completely renovated in 2003, this remarkable residence retains its original charm while adh...

Under Construction. Another meticulously custom built masterpiece by award winning Austin Homes w/ interior design selections by Steele Street Studios. This timeless 4 b...

Updated Winter Park transitional ranch home close to city parks, bike trails and downtown Park Avenue. This home features completely remodeled kitchen with GE stainless ...

Charming 3 bed 1 bath home located in the heart of Winter Park. This property has so much potential located on an oversized double lot. Walking distance to Park Avenue re...

Take the virtual tour: https://my.matterport.com/show/?m=ti1mdHMXxU9. This gorgeous custom-built 4 bedroom, 3.5 bathroom home is located in the exclusive Windsong subdivi...

Come take a look at this tremendous opportunity to buy a house within 2 miles of Downtown Winter Park and Rollins College. You have a ton of Restaurants and Shopping wit...

This NEW smart and energy efficient custom home, located in the desirable Winter Park, projects sophistication and comfort. At 3 beds and 2 baths, it was created with ple...

Charming Craftsmen built in 1926 located in the Dubsdread Golf Course area. Completely Updated and Move In Ready. Walk up the steps onto the large front patio, Enter the...

Come see this adorable move in ready home in highly desirable Winter Park location. This lovely 3 bedroom, 2 bath home with detached studio offers an updated kitchen wit...

ORIGINAL OWNER! THIS SPECTACULAR AND BEAUTIFULLY APPOINTED WINTER PARK HOME IS ON A TRANQUIL CUL-DE-DAC LOT LOCATED IN THE ENCLUSIVE GATED BEAR GULLY POINTE COMMUNITY. T...

Welcome to 1807 Barker Drive, a lakefront home that includes tranquil views of a natural habitat, with magnificent sunsets off the water. Approximately 40% of the shoreli...

Location Location Location!! This is an amazing opportunity to live near Park Avenue, Rollins College, and Hannibal Square, an Historic Community of shops, restaurants, ...

Rare Opportunity to live in Winter Park, in a secluded beautiful Cul-de-Sac overlooking a wide open green area with a great privacy. Only a steps away from all the Major ...

WINTER PARK ADDRESS! New vinyl fence in the backyard, 2020. New hot water heater-2018. Kitchen appliances are smudge-proof stainless steel! -new stove, refrigerator, & di...

Magnificent New construction Downtown Winter Park estate, built by one of the country’s top builders, this architectural masterpiece is situated just steps from Park Aven...

Be the next owner of this cute 3 bedroom/1.5 bath Winter Park home located close to Lake Killarney! The home is in a desirable location with easy access to I-4 and 17-92....

Charming four bedroom two bathroom Winter Park gem with updated and great design touches. This home boasts a large open front porch, beautiful hardwood floors, a light ...

One-hundred-four expansive feet of Lake Maitland lakefront awaits on a quiet Olde Winter Park street just minutes away from Park Avenue. The home in mid-renovation, sold ...

Welcome to this elegant, one-of-a-kind, colonial-style home in Winter Park’s Windsong community. The classic brick exterior is remarkable and graciously invites you into ...

Sitting on a large oversized corner lot, this charming Winter Park home has been completely remodeled and wonderfully updated with today’s style and design in mind. A fun...

Builder/Investor opportunity in Winter Park. This is the last splittable double lot in Lakemont Heights. Lot size is approximately 122x150 (+/-)...owner has verbal from c...

One of a kind meticulously maintained ONE STORY Winter Park Charmer within walking distance to Downtown Park Avenue. Originally custom built for the local Miller hardware...

Extraordinary opportunity to live on a 1.88 acre lot directly on the banks of Bear Gully Lake with breathtaking views. This secluded lakeside retreat located in one of Wi...

New Price!! Elegant Spanish revival home on a paver circular drive in Old Winter Park. Extensive upgrades have been completed by the current owner including but not limi...

WOW! Incredible opportunity to own this 4 bedroom, 3 bath home located in the highly desirable Winter Park Pines Golf Community. Features include a driveway, tray ceiling...

Winter Parks Hidden Gem Seranza Park. This Almost-New Home is a Must for any buyer. Located in Seminole county with an A rated school district. Conveniently located near...

Charming 3/2 block home in a prime location! Enjoy everything Winter Park has to offer: short drive to Winter Park Village with its abundant shopping and dining, popular ...

This gorgeous model-like home is back in the market and priced to sell. This charming and unique style home was built in 1927 and restructured in 1975. This beauty is pa...

Fabulous Winter Park townhouse available now! This two-story property has 3 bedrooms with ample closet space and 3 full bathrooms. The open floor plan makes a wonderful e...

Looking for a family home/country club? This home is for you if you like the idea of living in a large grand pool home with high ceilings, on a private road within 3 bloc...

One or more photo(s) has been virtually staged. Move-in ready, 2018 newer construction home with spacious, open and flexible floorplan in convenient Winter Park location....

New Listing! Motivated Sellers! This property is located in the heart of lovely Winter Park, FL. This beautiful single family home contains 3,948 sq ft of Heated Space. S...

Three Bedroom Two Bathroom Home Located Close To All Shopping. This One Has A New Air Conditioning HVAC AND Compressor, New Water Heater, New Electrical Panels, Inside An...

Start off the new year #2021 in this Winter Park Home! Move right in and enjoy the gorgeous space with a very flexible floor plan offering 4 bedrooms, plus an extra room...

Welcome home to the charm of Winter Park. This executive pool home is situated in the perfect location with NO HOA, convenient to Lake Sue, Parks, World Class Shopping, a...

This adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods. Located on a shady, brick street surrounded by upsca...

An exceptionally designed single-story modern home situated on over a 1/3 of an acre in the Via’s of Winter Park showcases a beautiful balance of bringing the outdoors in...

Charming 3 bedroom, 2 bathroom, single-family pool home located in the community of Winter Park Estates. This home features a living room with a brick fireplace and a din...

"The Herringbone" This beautifully appointed 3 bedroom 2 bath home offers the same attention to detail the million dollar mansions surrounding it have but at a fraction ...

MOVE IN TODAY! This charming, updated 3/2 Winter Park home features 1,490 sq.ft. of living space, a split floor plan, crown molding, two-car garage with AC and an epoxy ...

One or more photo(s) has been virtually staged. New Construction home built by Integrity Remodeling and Custom Homes, Inc., one of the area's premier builders. Recently ...

Back on the market. What a location! This home is situated on a large corner lot in Park Grove, one of Winter Parks most desirable neighborhoods! Enjoy your weekends wal...

Don't miss out on this beautiful home located in a prime, tree-lined Winter Park neighborhood. A short walk from downtown Winter Park, Kraft Azalea Gardens on Lake Maitla...

This truly unique historic property built in the 1880's has been described as the most Victorian cottage still standing in Winter Park and perhaps the finest example of V...

Beautiful two-story traditional pool home in the Vias. The first floor boasts a formal living room with fireplace and separate dining room, spacious eat-in kitchen with s...

A timeless Gary Hancock Mediterranean designed estate situated on a wrapping corner on Park Avenue, truly one of the finest streets in Winter Park. This one-of-a-kind gat...

Luxury and elegance abound in this private, gated Winter Park Chain of Lakes estate, nestled on almost an acre at the end of a secluded cul-de-sac, with elevated views of...

LAKEFRONT ONE STORY- Priced to Sell !!! Winter Park Stunning 4 Beds 3 Full Bath pool home located on beautiful Lake Waunatta. This 3,417 Sqft one story home completely re...

Welcome Home! $20K Price Reduction! Rare opportunity to own a Winter Park Heated Pool Home with Guest Cottage & NO HOA! Visit https://tinyurl.com/1442palm for a custom vi...

Location, location, Location! Walk to Park Avenue, Winter park Racquet Club, Phelps Park, YMCA and Kraft Azalea Gardens, this lovely home has 4 bedrooms/2.5 bath with pri...

Fantastic waterfront opportunity in Winter Park’s The Vias. This 1.08 acre lot features 140’ of frontage on Lake Maitland’s quiet lagoon and easy access to the Chain of L...

Stunning 3 bedroom 2 bath pool home minutes to the prestigious Park Avenue. This home sits on a large lot with a huge driveway and two car garage. Step inside to an amazi...

Under Construction. (Under Construction) Winter Park luxury living at its absolute finest! Multiple Award-Winning Builder Ira Kitograd of IBK Construction, who has over ...

Set on an oversized 0.45 acre lot (125’x157’) this sprawling Winter Park home features 4,577 sf of interior living space complimented by beautiful hardwood floors, high c...

Incredible home on sought after McKean Circle walking distance to Park Ave in Winter Park. This Contemporary Spanish home exudes the classic and charm the community is al...

Enjoy the best Winter Park has to offer. Located just blocks from upscale dining, boutique shops and Rollins College. Relax in your private oasis backyard pool spa deck a...

Welcome home to a beautiful Winter Park move-in ready lakefront house on scenic and water ski-friendly Lake Spier. Near the intersection of Glenridge Way and Lakemont Ave...

THE PROPERTY IS FOR LAND SALE WITH 3BR/2BA HOUSE INCLUDED. IT IS LOCATED IN A VERY CONVENIENT AREA; APPROXIMATELY 4 MILES TO DOWNTOWN OF WINTER PARK, 2 MILES TO WINTER PA...

Pre-Construction. To be built. Pre-construction! Perfectly situated - close to Winter Park shopping and dining, Mead Botanical Gardens, College Park and Lake Ivanhoe. Gre...

Pre-Construction. To be built. Modern French country villa, situated on an oversized 0.36-acre lot located along the beautiful tree-lined Palmer Avenue. This villa is des...

Under Construction. BRAND NEW CONSTRUCTION IN WINTER PARK! Scheduled to be completed in October 2020 this stunning modern farmhouse was designed and built by Homes by Car...

Custom built home located Inside the beautiful, gated, Cypress Reserve neighborhood. Spacious 6 bedroom, 5 bathrooms and 3983 Square feet. This house has LOTS of room f...

One or more photo(s) has been virtually staged. Welcome to this one-of-a-kind contemporary masterpiece, custom-built by LunDev in the heart of highly desired Winter Park!...

Stop the car and bring your suitcase! This Winter Park updated bungalow with 3 bedrooms and 2 baths is move in ready! Front walkway welcomes friends and family members in...

WATERFRONT ESTATE: .58 acre tree canopied property framed by 300 feet on Howell Creek (with riparian rights, fishing platform, wildlife feeder & canoe) & wooded lot is t...

Great opportunity. Cute home in Winter Park with Winter Park Schools. Huge backyard. Split AC for every room. FOREIGN SELLER. Buy now build later on this big lot. Short d...

This almost-new light and bright home with top of the line finishes was fully renovated in 2019. Seller will provide 1 year home warranty. 2,172 sq ft under air, 4 Beds, ...

One or more photo(s) has been virtually staged. Located in the heart of Winter Park, this virtually new Modern Florida Coastal custom pool home was built by David Cahill ...

Back on the market!! Owners wanted one more holiday season of memories before parting with their home of 35 years. This home provides a popular 5/2.5 three way split poo...

WELCOME TO YOUR FOREVER HOME - LOCATION! LOCATION!! THIS IS A MUST SEE HOME!!! THIS METI...

LOCATION, LOCATION, LOCATION- "THE TRIANGLE HOUSE"- beautifully landscaped, professionally decorated, amazing Master Bedroom - 3 full baths and 2 bedrooms. This house ha...

Former model home available now as-is! Beautiful model home with a gourmet kitchen featuring designer curated finishes that overlooks the spacious great room, dining area...

OVERSIZED CORNER LOT....WELCOME TO PARK GROVE, ONE OF WINTER PARK'S HOTTEST NEIGHBORHOODS. RECENTLY APPRAISED. LOCATED ON A BEAUTIFUL TREE LINED STREET ONE BLOCK OFF PARK...

One or more photo(s) has been virtually staged. Charming home located in the heart of Winter Park Historical District. Split floor plan with upgraded laminate floors thro...

Heart of Winter Park! 2 Lots! Build on 14,867 sq ft of land (.34 acres, 2 lots) - - One Block to Park Avenue - - with upscale restaurants and shopping! Two single-family ...

Designed with the resort lifestyle in mind, this magnificent contemporary home is meticulously crafted with thoughtful architecture, new interiors and landscaping for a m...

Pristine Mediterranean highend upgrades on quiet, private cul-de-sac. Hardwood floors, chef kitchen, large covered and opened deck overlooking huge private park. Grand 1s...

Charmer in Olde Winter Park, rare renovation opportunity in Virginia Heights! Mother-in-Law rental above the garage rents at $1000 per month. Lots of unique features in ...

Absolutely gorgeous renovation of this 1930’s Winter Park bungalow. The home has been impeccably restored to save the historic architectural details and adding the mode...

Don't wait to view this Beautiful New Construction home! Meticulously built with five bedrooms and 3.5 bathrooms,including a master on the first and second floor! This l...

This beautiful, charming and cozy 4 bedroom 2 bathroom is in one of the most desired Winter Park neighborhood. Winter Park Pines! Zoned for all A-Rated Winter Park School...

Under Construction. Native Homes presents Milan - a one of a kind home designed by Dan Delong of Origins Residential Designs with custom interior by Pasternack Designs, P...

Elegant waterfront residence in Winter Park. This impeccable Mediterranean home features five bedrooms and four baths and is located on Howell Creek canal off Lake Maitla...

Entertain! Entertain! Entertain! Beautiful 2018 Custom built Winter Park lake front home on one of the most desired lakes in the area. This home features all the amenitie...

Beautiful traditional home with amazing curb appeal and large, oversized lot. Interior features approximately 3,000 SF including 4 bedrooms, 2.5 baths, formal living and ...

This custom 5-Bd/5-Ba/2-HBa contemporary/transitional luxury home has been uniquely designed with an exceptional selection of neutral materials, finishes, and lighting to...

Location, Location, Location. Own a piece of history! Next to Winter Park's downtown Park Ave, Winter Park Village and Rollins College. This home has a new Roof, new w...

Greens Cottage is one of Dubsdread's original, unique homes. Built in 1925, this two story Cedar Shake style home has been updated in keeping with its historic charm. The...

Beautiful one-owner custom-built home. All richly appointed with beautiful moldings, stunning wood floors throughout, with Grand Foyer & Entry. Formal living and family ...

Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150’ on the shores of Lake Berry. Custom built and architecturally stunning, this 5 bedroom, 4....

IMMEDIATE SALE!! Don't miss out on this one of a kind, 3 story home. This home is 5 bedroom, 3.5 bathroom homes zoned for a work/live so you can easily make this space yo...

Under Construction. Introducing Phil Kean's latest project - The Morse + Pennsylvania Townhomes. A private enclave of high-end urban lock + leave residences comprised of ...

A unique offering to say the least. Originally built in 1920, the woodwork highlights the best of lost skills retained in the massive renovation done in 2009. Sitting on...

Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge ...

Beautiful 5 Bedroom 3 Bath home in Winter Park's Kenilworth Shores, near the best area schools. An example of timeless design, quality construction, and tasteful updates,...

VALUE IS IN THE LAND! Prime real estate situated on the corner of Moray Lane and Loch Lomond Dr is being sold as a 3 Lot package, with all three lots facing Cady Way Par...

Lake Front on large, clear, spring fed Lake Waunatta. Bass fishing / water ski / jet ski. 3 Bed 2 Bath. Approx 3244 SF single story home. 2 year new roof. Ceramic tile t...

Winter Park Gem!! Don't miss this incredible investment possibility. A builders DREAM property, on a quiet cul de sac, over sized lot of almost 10000 sq ft. Great for bu...

If you’re looking for the quintessential Winter Park Lakefront Estate Home this is it! Designed by acclaimed architect Gamble Rogers this magnificent home has double wat...