Winter Park FL. Homes For Sale

Looking for the quintessential Winter Park home? This exquisite, single story 3 bedroom, 3 bath, plus office home is located in the beautiful Lake Sylvan Shores neighbor...

Welcome Home! Located only MINUTES from the luxury Winter Park Village and Park Avenue. This home is situated exactly where you need to be in order to make the most of e...

Welcome to 550 Lake Front Boulevard, a luxurious haven situated in Winter Park, Florida. This remarkable residence, built in 2019, embodies elegance, meticulous craftsman...

Picturesque 4 Bedroom / 2 Bathroom Home on tranquil end of street. Don't Be fooled by the square footage. This home feels and lives much larger! Gorgeous Light and Bright...

A stunning home in Winter Park ready for the next lucky family to move in! This charming four-bedroom, 3.5-bath home has it all. The moment you walk in the front door fro...

Welcome to this newly constructed home in the beautiful, gated community of Hawks Crest. This stunning Anastasia model has 4 bedrooms 3.5 bathrooms that comes with 2 AC u...

Distinctive, private, unique and full of character is what sets this estate apart from all other properties on the market. Welcome home to your freshly built and highly u...

Welcome to the exclusive gated community, Meadows at Hawk's Crest, located in sought-after Winter Park northeast of Orlando. We promise that this house will not disappoin...

A timeless home awaits among the tree canopies of Kenilworth Shores, a tried-and-true Winter Park neighborhood steeped in history. A pristine property and beautifully app...

Attention All Buyers and Investors…This is a Must See 3br/2bath single story home in one of Winter Parks highly sought out neighborhoods in Eastbrook. This property has N...

Located in the quaint, desirable Kenilworth Shores of Winter Park is where you will find this UPDATED traditional home that features over 2100 sq. ft., boasting 3 bedroom...

Welcome to Old Winter Park's coveted Tree Streets - a place where your dream home is waiting for you! This truly sustainable 5/3 property rests in a neighborhood teeming ...

A truly stunning 2022 transitional, modern residence recently completed in the heart of the Vias by Z Properties Inc. Tremendous “off the charts” quality in this custom-d...

Terrific opportunity to renovate or restart and build new! Situated on a large .30 acre (13,035 sf) corner lot, the property offers lots of possibilities! Tucked away i...

Great Investment Opportunity (SOLD AS IS) This three bedroom one bath home is in need of a total makeover, or tear down and build your own new home. Home is situated in ...

Introducing a once-in-a-lifetime opportunity to own an exquisite multi-generational home in the coveted and exclusive neighborhood of Talman Mews, situated on not one, bu...

Highly sought after community of Park Grove 3 bedroom 2.5 bath pool home now available! This beautiful home is located in highly sought after Park Grove community, just...

Located in desirable Winter Park, this beautiful single-story home is situated on an oversized lot of 0.28 acres surrounded by mature oaks, magnolia and an array of lush ...

**YOUR SEARCH STOPS HERE** POOL HOME** SEPARATE TWO BEDROOM GUEST HOUSE** MASTER BEDROOM ON MAIN LEVEL** Experience luxury living at its finest in this beautiful two-stor...

Waterbridge of Winter Park! Rare opportunity to own in this fabulous Winter Park community being offered by the original owner. This one is ready for your special touch...

Unbelievable opportunity to own this 4 bedroom, 3 bath home nestled within a charming and highly sought-after Winter Park neighborhood. This older home exudes timeless ap...

Welcome to 220 Blossom Lane, an exquisite NEWLY RENOVATED single-family residence nestled in highly sought-after Winter Park, FL. This luxurious 3-bedroom, 2-bathroom hom...

Under Construction. Breathtaking modern home just weeks away from completion. This sleek five-bedroom, six-and-a-half-bath residence abounds with high-end details through...

One or more photo(s) has been virtually staged. Welcome to Vimaro Homes newest completed Project! This listing showcases a stunning new construction project with an impre...

!!!New Roof Coming soon!!! Welcome home to this 4 bedroom, 3 bathroom, single-family home located in the community of Winter Woods in Winter Park. All three bathrooms ha...

New Construction Custom Built Masterpiece located in one of Winter Park’s most desirable neighborhoods, zoned for top-rated schools in the county and only minutes away fr...

West Side Winter Park Investment Property

Proudly presenting a unique opportunity to acquire one of the most significant lakefront estates in Winter Park, on beloved Via Tuscany, moments from downtown Park Avenue...

Pre-Construction. To be built. Experience the perfect fusion of indoor-outdoor living, clean lines, and minimalist design in the heart of Winter Park. This California Mo...

You’ll be impressed with this well-cared for home in the desired Howell Estates Community of Winter Park. Extremely low yearly HOA fees of $25. You’ll notice the curb app...

This stunningly renovated ranch-style home is situated on a tranquil street in the charming Winter Park neighborhood, offering easy access to shopping and top-rated schoo...

Under Construction. Under construction. Beautiful New Construction home in the heart of Winter Park. This upscale Magnolia Home features upscale design features throughou...

SOLAR HOME!!!!!Beautiful 4 bedroom 2 bath with a large pool located in the Winter Park Pine. Features large kitchen with large island, granite counter tops and 42" upper ...

Are you looking to live in a prestige Winter Park Pool Home! You have found one! It is located in a quiet Eastbrook Subdivision and in the heart of Winter Park! Only a sh...

Welcome home to the desirable Eastbrook community located in Winter Park and zoned for top-rated schools! Currently tenant occupied through 12/31/23 but seller will reque...

This lovingly cared for transitional pool home with oversized lot is situated on a quiet tree-lined street. This spacious home is perfect for family living or entertainin...

Under Construction. New CUSTOM pool home a short walk to Winter Park High School. Private keyed ACCESS to beautiful LAKE BERRY with boat dock and ramp is available for on...

This exquisite French Country estate is a true masterpiece, boasting a grand total of 4900 square feet of luxurious living space. Located in the highly coveted Penn Place...

New Price!! Beautifully renovated four-bedroom, three-full-bath Winter Park home. The incredible curb appeal begins with new landscaping, exterior lighting, paver drive,...

Located in Winter Park this home was devised by architectural firm, Green Apple & built by E2 Homes. Contemporary living adheres to a few principles that define its simpl...

RARE FIND - *** LAKE FRONTAGE on Private Lake Spier with DOCK, POOL,& CABANA which could never be built today!!!*** This home is in the perfect location only 0.7 miles or...

Welcome to 2015 N. Park Avenue - your brand new modern construction home! This stunning property is designed with contemporary features and high-end finishes throughout....

BACK ON THE MARKET!!! This beautiful, lovingly cared for move-in ready, one story 4-bedroom 2.5 bath home offers you a unique opportunity to own in Winter park for under...

Luxurious and inviting, this custom one-owner home has it all and is on a quiet brick street in the desirable Via’s of Winter Park, elevated on a generous sized lot with ...

This beautiful 4-bedroom home (with a pool) sits close by between Lake Sue and Lake Virginia in one of the most sought-after neighborhoods of Winter Park. And in an area ...

Fabulous single story home in the heart of Winter Park! This 4 bed, 3 bath home is situated on a large CORNER lot with a highly desirable 3 car garage! Step inside the fo...

Serene and private estate on a half acre lot in the Heart of Olde Winter Park. A custom built estate with amazing detail throughout boasts 6 bedrooms (downstairs master p...

In the heart of Winter Park, next to 1-4 between Par and Fairbanks exits. This cute 2/1 house is ready for renovations which will make it a great home or rental. It is on...

Winter Park charmer with short term/rental possibilities, a brand NEW ROOF (2023), NEW KITCHEN (2022), UPDATED A/C (2022), WATER HEATER (2023), WOOD LOOK TILE throughout ...

Under Construction. New construction in Winter Park, Florida. Nestled amongst million-dollar properties, with Lake Killarney just down the street, this single-story conte...

! Attention Buyers! Live Your best life in the desirable Windsong Subdivision in Winter Park. This beautiful custom built home, with attention paid to every detail, wel...

PRICE REDUCTION! Simple Elegance! Just a stone's throw from Lake Baldwin! You will be captivated by this tastefully chic updated Home in the very sought after neighborho...

This custom four bedroom, three and one half bathroom, 4,610 square foot pool home is located in the heart of Olde Winter Park. From the paver covered circular drive you...

Pre-Construction. To be built. Modern Farmhouse with Pool is located in Winter Park and offers over 4500 sq. ft. of air-conditioned living space, with another 1,000 sq. ...

Absolutely gorgeous, executive home, located in a gated community in the beautiful Bear Gully Pointe, in Winter Park!. Masterfully designed with exquisite details of cont...

Deep lot one block from Dubsdread golf Course. You can use as your primary home or great for investor. Great location, minutes from Park Avenue, College Park and Downtown...

LOCATION, LOCATION, LOCATION!! in the hearth of winter park with no HOA, hard to find 1/2 Acres lot with a beautiful 3/2 move in ready, tile throughout. Roof was done in ...

Elegant Charleston style residence secluded on a "private lane" in the heart of Olde Winter Park, just one property removed from Lake Osceola. Resting on over a ½ acre ma...

LOCATION, LOCATION, LOCATION!! Amazing opportunity to own in the highly sought after, well established neighborhood of WINTER PARK PINES. Zoned for great schools Brookshi...

Perfect 4/2.5 home in the well-established subdivision of Eastbrook in Seminole County! This lovely home has NEW laminated floors in the bedrooms, and recently painted wa...

Price Improvement on the Lowest Priced Pool Home in 32789!! Welcome to this stunning bungalow featuring 3 bedroom, 2 bathrooms with a Pool situated in the historic and ch...

Fully remodeled home in Winter Park with no association and huge backyard space. New roof installed in 2021. This three-bedroom, two-bath, one-car garage home has new lam...

Welcome to Orwin Manor, a timeless Orlando-Winter Park neighborhood established in 1924, offering lifestyle and prime location. Come see this designer dream! Solidly buil...

Pre-inspected. Offered for the first time in over 30 years! Winter Park’s only original, charming and completely remodeled historical farmhouse. Known as the “Harris-Edis...

Magnificent lakeview estate in Windsong – 526 Genius Drive, Winter Park. For the first time, this stately residence is on the market and available for purchase. Custom bu...

This beautiful and remodeled home is turnkey and ready to move in. Investors -- You will love the cash flow upside with this property. Updated Roof, AC, Exterior Pain...

Build your dream home in the desirable Lake Sue area. Nestled amongst the majestic oaks on a quaint brick street, current home is a three bedroom, two bath home with a g...

Elegant French Mediterranean gated lakefront estate on premier exclusive and private setting in Olde Winter Park… This spectacular residence is located on the Isle of Sic...

Stunning new two-story home in Winter Park’s exclusive gated community of Hawk’s Crest. This 4-bedroom, 3 bathroom home has a great floor plan that features open dining a...

Click on link for walkthrough video Tour!!! Spacious well-kept home with over 2,036 SF of living space. Located on a quiet street, the property is set back on the lot wit...

PRICE IMPROVEMENT--Fabulous home in the Heart and Soul of Winter Park's Osceola Shores neighborhood. Walk to Polasek Museum, Rollins College, Dinky Dock Park and Park Ave...

*NOW READY TO SHOW*SCHEDULE TODAY*Welcome home to this Amazing Lake House situated just minutes away from the Charming and Historic Winter Park Avenue. This Wonderful Est...

Pre-Construction. To be built. Located on a rare “Vias” lot this new construction home was designed and developed by Scout + Company. In Pueblo Revival style, the home w...

Let yourself feel captivated by this Single-Family home recently remodeled, offering 3 bedrooms 2 bathrooms in the great neighborhood of Lake Killarney. Enjoy the opportu...

Stunning Two-Story Home in Winter Park's exclusive neighborhood. House is offering 4 Spacious bedrooms and 2.5 bathrooms has a great floor plan. The gourmet kitchen wit...

Residing in one of Winter Park’s most sought-after communities, this gorgeous Windsong Estate awaits. From the expansive layout and beautiful outdoor living space to the ...

This is YOUR NEW HOME located right in Winter Park. This THREE BEDROOM, ONE BATH home has over 1300 SQUARE FEET and is ready for YOU, its next owner! This home sits on a...

Lowest priced Waterfront in Winter Park! It’s rare to find. Plus, Seller to pay $10,000 toward buyers closing costs and/or interest rate buy down. This property is on L...

"THE TRIANGLE HOUSE" PROFESSIONALLY DECORATED! Has 2 fireplaces, one in the master bedroom and another in the living area. High ceilings throughout and a spectacular lot ...

Stunning Custom Designed POOL Home - 5 Bedroom, 4.5 Bath located in Osceola Shores. Which is a neighborhood of luxury homes in Winter Park, Florida. WALKABLE TO PARK AVEN...

One or more photo(s) has been virtually staged. Lakefront luxury on the beautiful shores of Lake Killarney! Custom built with attention paid to every detail, this Mediter...

Seller financing available on this incredible Winter Park home. An elegant custom home, designed & built by FG Shaub, is tucked away on a large corner lot on a pristine o...

***Location Location**Virginia Heights within Winter Park luxury living! Easy walk to Park Ave. and Rollins College. Lake Virginia is one block away with storage for you...

Create your Winter Park dream home! This property is less than 1 minute to Interlachen Country Club with multiple million dollar homes in close proximity. Great to remode...

Under Construction. Brand new construction!! Ready to move in! A stunning modern transitional home located in the heart of Winter park minutes from Park Ave. As you enter...

Pre-Construction. To be built. Pre-Construction. To be built. This Cape Cod inspired home provides a rare pre-construction opportunity in highly coveted Winter Park. Make...

One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of August. This custom built Winter Park home is the epitome of l...

Under Construction. UNDER CONSTRUCTION; Elegance, comfort, and a welcoming environment blend cohesively at this modern West Indies new construction home in one of the mos...

*** PRICE ADJUSTMENT & BACK ON THE MARKET!! SADLY DUE TO BUYER'S FINANCING. PASSED INSPECTION & APPRAISED OVER ASK at $630K! *** Reports available upon request. NEW backy...

Build your Dream Home ted on the shores of Lake Howell, this Lakefront property offers the potential buyer over 3.9 acres of High and Dry Land in a serene natural setting...

"Welcome to this exclusive contemporary luxury home, showcasing an architectural design that sets it apart. The house is characterized by a robust structure, boasting...

Pre-Construction. To be built. Custom transitional estate pool home on over 1 acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

Pre-Construction. To be built. Custom transitional estate pool home on over ¾-acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

Pre-Construction. To be built. Custom transitional estate pool home on over ¾-acre lot in coveted Winter Park. Nestled on a quiet cul-de-sac, yet situated within minutes ...

Pre-Construction. To be built. RE-DESIGNED and BACK ON MARKET APRIL 21, 2023. Ready to break ground! INQUIRE NOW for more details about this gorgeous MODERN COUNTY pool ...

One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acre...

NEW AND IMPROVED PRICE: Located in the heart of “The Golden Triangle” of Winter Park, this 0.43 acre property is approximately 125 feet wide by 150 feet deep. Discretely ...

Seller says "RANCH STYLE, ONE FLOOR 3/2 TOTAL AREA 2,382 SQ FEET, LIVING AREA 1,584 SQ FEET CONVENTIONAL AND CASH-ONLY SALE What I love about this home. Th...

Pre-Construction. To be built. Homes don’t come along like this very often! Here’s your opportunity to own a Magnificent Estate "Elanza on Lake Killarney." Enter through ...

WINDSONG - WINTER PARK. Designed to perfection, this exquisite Spanish-Mediterranean home sits on an oversized lot overlooking the tranquil pond and fountain. Grand curb...