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Winter Park Real Estate Search

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Winter Park Listings

1220 N Park Avenue, Winter Park image
1220 N Park Avenue, Winter Park $17,486,000 ▲

Casa del Mondo, known as House of the World on Park Avenue in Winter Park, is a gated estate situated on Winter Park Chain of Lakes in the the most exclusive location in ...

  • 7 Beds
  • 5.5 Baths
  • Twelve Oaks SubDv.
  • 32789 Zip Code
1461 Via Tuscany, Winter Park image
1461 Via Tuscany, Winter Park $16,000,000

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...

  • 5 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
4 Isle Of Sicily, Winter Park image
4 Isle Of Sicily, Winter Park $10,950,000

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...

  • 5 Beds
  • 5.5 Baths
  • Isle Of Sicily SubDv.
  • 32789 Zip Code
1190 N Park Avenue, Winter Park image
1190 N Park Avenue, Winter Park $8,500,000 ▼

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...

  • 8 Beds
  • 5.5 Baths
  • 0000 SubDv.
  • 32789 Zip Code
671 Via Lugano, Winter Park image
671 Via Lugano, Winter Park $4,950,000

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...

  • 6 Beds
  • 6.5 Baths
  • Sicilian Shores SubDv.
  • 32789 Zip Code
550 Palmer Avenue, Winter Park image
550 Palmer Avenue, Winter Park $4,900,000

Pre-Construction. To be built. This Incredible Modern Transitional Home will be Breaking Ground Soon! It will be built on an Oversized Lot and is just Minutes to Park Ave...

  • 5 Beds
  • 5.5 Baths
  • Osceola Place SubDv.
  • 32789 Zip Code
466 Henkel Circle, Winter Park image
466 Henkel Circle, Winter Park $4,500,000 ▼

*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...

  • 4 Beds
  • 5 Baths
  • Thomas M Henkels Add SubDv.
  • 32789 Zip Code
664 W Morse Boulevard, Winter Park image
664 W Morse Boulevard, Winter Park $4,299,000

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...

  • 4 Beds
  • 4.5 Baths
  • Morse And Pennsylvania SubDv.
  • 32789 Zip Code
1106 Palmer Avenue, Winter Park image
1106 Palmer Avenue, Winter Park $4,250,000

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...

  • 4 Beds
  • 5.5 Baths
  • Winter Park Town Of SubDv.
  • 32789 Zip Code
2056 Lake Drive, Winter Park image
2056 Lake Drive, Winter Park $3,999,999 ▼

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 ...

  • 5 Beds
  • 5.5 Baths
  • Lords Sub SubDv.
  • 32789 Zip Code
637 N Park Avenue, Winter Park image
637 N Park Avenue, Winter Park — Park Hill $3,895,000

Here is your opportunity to live on Park Avenue in beautiful Winter Park! Walk to your favorite shops and restaurants. This classically styled luxurious Park Hill townho...

  • 3 Beds
  • 3.5 Baths
  • Park Hill SubDv.
  • 32789 Zip Code
222 W Rockwood Way, Winter Park image
222 W Rockwood Way, Winter Park $3,600,000

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...

  • 5 Beds
  • 5.5 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
526 Genius Drive, Winter Park image
526 Genius Drive, Winter Park $3,500,000 ▼

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...

  • 4 Beds
  • 4.5 Baths
  • Windsong North Shore 43/74 SubDv.
  • 32789 Zip Code
617 Penn Place, Winter Park image
617 Penn Place, Winter Park $3,495,000

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...

  • 4 Beds
  • 3.5 Baths
  • Pennsylvania Place Rep SubDv.
  • 32789 Zip Code
1150 Via Salerno, Winter Park image
1150 Via Salerno, Winter Park $3,495,000

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...

  • 4 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
1271 Via Capri, Winter Park image
1271 Via Capri, Winter Park $3,150,000 ▼

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 ...

  • 5 Beds
  • 4.5 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
4572 Palmetto Avenue Unit A, Winter Park image
4572 Palmetto Avenue Unit A, Winter Park $3,100,000 ▲

Location! Location! Location! MAJOR PRICE CHANGE, AI OFFICER AUTHORIZED THE NEW PRICE. WAREHOUSE building located in Winter Park with OFFICE and SHOWROOM space. ~ ZONED I...

  • 4572 Palmetto Condo SubDv.
  • 32792 Zip Code
2138 Lake Drive, Winter Park image
2138 Lake Drive, Winter Park $3,050,000 ▼

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...

  • 4 Beds
  • 3.5 Baths
  • Killarney Point SubDv.
  • 32789 Zip Code
1530 Mayfield Avenue, Winter Park image
1530 Mayfield Avenue, Winter Park $2,995,000 ▲

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...

  • 4 Beds
  • 4 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
5510 Howell Branch Road, Winter Park image
5510 Howell Branch Road, Winter Park $2,899,000

10.26 acres located in Winter Park, Fl. 3 different parcels with 6 total structures, 2 structures are large barns / outdoor buildings with one having a large loft - large...

  • Woodcrest Unit 8 SubDv.
  • 32792 Zip Code
2726 Lake Howell Lane, Winter Park image
2726 Lake Howell Lane, Winter Park $2,899,000 ▼

Build your Dream Home on the shores of Lake Howell, this rare Lakefront property offers the potential buyer over 5 acres of High and Dry Land in a serene natural setting....

  • Lake Howell SubDv.
  • 32792 Zip Code
1741 Glencoe Road, Winter Park image
1741 Glencoe Road, Winter Park $2,850,000

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 ...

  • 4 Beds
  • 4.5 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
170 S Phelps Avenue, Winter Park image
170 S Phelps Avenue, Winter Park $2,800,000

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...

  • 4 Beds
  • 4.5 Baths
  • Green Terrace SubDv.
  • 32789 Zip Code
1745 Lake Berry Drive, Winter Park image
1745 Lake Berry Drive, Winter Park $2,750,000 ▼

WINTER PARK LAKEFRONT – 1745 Lake Berry Drive. Stunning lakefront estate with 80’ of waterfront on Winter Park’s private Lake Berry. Recently remodeled by award-winning E...

  • 4 Beds
  • 3.5 Baths
  • Waterbridge SubDv.
  • 32789 Zip Code
1420 Holts Grove Circle, Winter Park image
1420 Holts Grove Circle, Winter Park $2,750,000 ▼

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

  • 4 Beds
  • 4.5 Baths
  • Windsong Lakeside Sec 02 43/71 SubDv.
  • 32789 Zip Code
125 S Interlachen Avenue Unit 2, Winter Park image
125 S Interlachen Avenue Unit 2, Winter Park — South Interlachen Place $2,699,000 ▼

****NEW PRICE!******HERE IS YOUR OPPORTUNITY! Welcome to South Interlachen Place, a luxury townhome located in downtown Winter Park. If you are looking for the perfect co...

  • 3 Beds
  • 3.5 Baths
  • South Interlachen Place SubDv.
  • 32789 Zip Code
1840 Via Genoa, Winter Park image
1840 Via Genoa, Winter Park $2,650,000

Welcome home to this completely updated home located in the Via’s, one of the most sought-after neighborhoods in the heart of Winter Park. This home truly has it all and ...

  • 4 Beds
  • 5 Baths
  • Lugano Terrace SubDv.
  • 32789 Zip Code
2172 Temple Drive, Winter Park image
2172 Temple Drive, Winter Park $2,650,000

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...

  • 5 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
2412 Chantilly Avenue, Winter Park image
2412 Chantilly Avenue, Winter Park $2,600,000

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...

  • 5 Beds
  • 6.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1400 Elizabeth Dr, Winter Park image
1400 Elizabeth Dr, Winter Park $2,580,000

Beautiful and secluded lakefront lot on quiet cove on Lake Osceola. Opportunity to design and Build with Z Properties.

  • Comstock Park SubDv.
  • 32789 Zip Code
Grove Avenue, Winter Park image
Grove Avenue, Winter Park $2,569,100 ▲

Custom Build a quaint community in Winter Park! A rare opportunity to develop with Conceptual completed making this an ideal site for the construction of 9 custom single ...

  • Mossy Oaks SubDv.
  • 32792 Zip Code
2156 Talman Court, Winter Park image
2156 Talman Court, Winter Park $2,495,000

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...

  • 5 Beds
  • 5.5 Baths
  • Talman Mews Ph 2 SubDv.
  • 32792 Zip Code
2819 Parkland Drive, Winter Park image
2819 Parkland Drive, Winter Park $2,395,000

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...

  • 4 Beds
  • 4.5 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1022 Mckean Circle, Winter Park image
1022 Mckean Circle, Winter Park $2,395,000

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...

  • 4 Beds
  • 3.5 Baths
  • Palmer Park SubDv.
  • 32789 Zip Code
660 W Morse Boulevard, Winter Park image
660 W Morse Boulevard, Winter Park — Morse $2,395,000 ▲

Welcome to your dream home! This luxurious townhome in Winter Park was designed by renowned architect Phil Kean and is a 3 bedroom (plus office), 3.5 bathroom gem with go...

  • 3 Beds
  • 3.5 Baths
  • Morse & Pennsylvania Twnhms SubDv.
  • 32789 Zip Code
1772 Chestnut Avenue, Winter Park image
1772 Chestnut Avenue, Winter Park $2,275,000

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...

  • 5 Beds
  • 4.5 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
419 W Morse Boulevard, Winter Park image
419 W Morse Boulevard, Winter Park — Virginia And Morse Brownstones $2,250,000

Stunning 3 bedroom (plus Office), 3.5 bathroom townhome designed by Phil Kean. Turn-key living at its finest. Light-Filled and Spacious, this beautiful home showcases the...

  • 3 Beds
  • 3.5 Baths
  • Virginia & Morse Brownstones SubDv.
  • 32789 Zip Code
1619 Elizabeths Walk, Winter Park image
1619 Elizabeths Walk, Winter Park $2,250,000

! 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...

  • 4 Beds
  • 3.5 Baths
  • Windsong Community Association, Inc. SubDv.
  • 32789 Zip Code
465 N Phelps Avenue, Winter Park image
465 N Phelps Avenue, Winter Park $2,200,000

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. ...

  • 7 Beds
  • 6 Baths
  • Ethel Park SubDv.
  • 32789 Zip Code
2723 Norris Avenue, Winter Park image
2723 Norris Avenue, Winter Park $2,175,000 ▼

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...

  • 4 Beds
  • 3.5 Baths
  • Parklando 02 SubDv.
  • 32789 Zip Code
1461 Palm Avenue, Winter Park image
1461 Palm Avenue, Winter Park $2,100,000

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

  • 4 Beds
  • 4.5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
1618 Lookout Landing Circle, Winter Park image
1618 Lookout Landing Circle, Winter Park $2,100,000

Welcome to Windsong! One of the most sought-after communities in the heart of Winter Park with access to the historic Winter Park Chain of Lakes and near Park Avenue. Win...

  • 4 Beds
  • 3.5 Baths
  • Windsong Lookout Landing 43/79 SubDv.
  • 32789 Zip Code
870 Georgia Avenue, Winter Park image
870 Georgia Avenue, Winter Park $2,095,000 ▼

NEW AND IMPROVED PRICE: Located in the heart of Winter Park this 0.43 acre property is approximately 125 feet wide by 150 feet deep. Discretely hidden behind a wall of po...

  • Winter Park Old Town SubDv.
  • 32789 Zip Code
870 Georgia Avenue, Winter Park image
870 Georgia Avenue, Winter Park $2,095,000 ▼

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 ...

  • 3 Beds
  • 2.5 Baths
  • Winter Park Old Town SubDv.
  • 32789 Zip Code
101 S New York Avenue Unit 309, Winter Park image
101 S New York Avenue Unit 309, Winter Park — Douglas Grand $1,999,000 ▼

Welcome to this stunning condo at The Douglas Grand, a true gem in the heart of downtown Winter Park. Located just one block from Park Avenue, this luxury condominium wil...

  • 3 Beds
  • 3.5 Baths
  • Winter Park Residential SubDv.
  • 32789 Zip Code
180 Whipple Avenue, Winter Park image
180 Whipple Avenue, Winter Park $1,960,000

Listing price is at appraised value as of 10/24/22 Appraisal. A++ Location (75% FAR) Buyer can bring their own builder. Only 3 Lots left! If you want true walkability...

  • 32789 Zip Code
2015 N Park Avenue, Winter Park image
2015 N Park Avenue, Winter Park — Park Ave $1,925,000

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....

  • 4 Beds
  • 4.5 Baths
  • N Park Ave SubDv.
  • 32789 Zip Code
1531 Place Picardy, Winter Park image
1531 Place Picardy, Winter Park $1,895,000

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...

  • 4 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
4091 Scarlet Iris Place, Winter Park image
4091 Scarlet Iris Place, Winter Park $1,800,000

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...

  • 6 Beds
  • 5.5 Baths
  • Bear Gully Pointe SubDv.
  • 32792 Zip Code
698 N New York Avenue, Winter Park image
698 N New York Avenue, Winter Park $1,800,000

Just Listed!! Impeccable location a half block off Park Avenue with incredible views of the golf course. Listed $130,000.00 below appraised value as of Oct 2022. This won...

  • 32789 Zip Code
2726 Lake Howell Lane, Winter Park image
2726 Lake Howell Lane, Winter Park $1,800,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • Lake Howell SubDv.
  • 32792 Zip Code
Howell Branch, Winter Park image
Howell Branch, Winter Park $1,800,000

2 parcels located at Dodd Rd. and Howell Branch Rd. Winter Park, Fl Over 1 acre of redevelopment land with a future land use of OFFICE! Great location, high daily traffic...

  • 32792 Zip Code
102 S Virginia Avenue Unit 110, Winter Park image
102 S Virginia Avenue Unit 110, Winter Park — Douglas Grand $1,795,000

Welcome to historic downtown Winter Park and one of Central Florida's most distinctive, established in-town living experiences, the Douglas Grand. <br><br> The two-sto...

  • 3 Beds
  • 3.5 Baths
  • Winter Park Residential SubDv.
  • 32789 Zip Code
1318 Morton Road, Winter Park image
1318 Morton Road, Winter Park $1,790,000 ▼

Under Construction. Brand New Contemporary Luxury Masterpiece Home with Exclusive Architectural Design, strong structure with two-story concrete-filled walls, steel joist...

  • 4 Beds
  • 3.5 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1451 Lyndale Boulevard, Winter Park image
1451 Lyndale Boulevard, Winter Park $1,750,000

Experience luxury living at its finest in this beautiful two-story pool home located in the highly desirable and historic Winter Park, FL. This stunning property boasts 5...

  • 5 Beds
  • 3.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
1640 Mayfield Ave, Winter Park image
1640 Mayfield Ave, Winter Park $1,725,000

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 ...

  • 3 Beds
  • 2.5 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
1166 Oaks Boulevard, Winter Park image
1166 Oaks Boulevard, Winter Park $1,699,999 ▼

Priced below market value! Welcome to your dream custom Winter Park estate located in the highly desirable and sought-after subdivision of Dixie Terrace. Situated on a pr...

  • 4 Beds
  • 3.5 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
270 E Lake Sue Avenue, Winter Park image
270 E Lake Sue Avenue, Winter Park $1,699,900 ▲

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 ...

  • 5 Beds
  • 4.5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
2161 N Park Avenue, Winter Park image
2161 N Park Avenue, Winter Park $1,650,000

One of a kind very rare piece of land for a commercial building on N Park Ave in Winter Park leading to the Shoppes of Winter Park. See attached proposed preliminary dra...

  • 32789 Zip Code
281 Brewer Avenue, Winter Park image
281 Brewer Avenue, Winter Park $1,600,000 ▼

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...

  • 5 Beds
  • 4.5 Baths
  • Osceola Shores Sec 02 SubDv.
  • 32789 Zip Code
401 N Interlachen Avenue, Winter Park image
401 N Interlachen Avenue, Winter Park — Village At Winterset $1,570,000

Discover the essence of luxury living in this exceptional end unit townhome, located just steps away from Park Avenue. Rarely available, this exquisite residence showcase...

  • 3 Beds
  • 2.5 Baths
  • Village Winterset Inc SubDv.
  • 32789 Zip Code
3520 Wilde Avenue, Winter Park image
3520 Wilde Avenue, Winter Park $1,500,000

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 ...

  • 6 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
3580 Wilde Avenue, Winter Park image
3580 Wilde Avenue, Winter Park $1,500,000

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 ...

  • 6 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
1503 Palmer Avenue, Winter Park image
1503 Palmer Avenue, Winter Park $1,499,000

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...

  • 4 Beds
  • 3 Baths
  • Temple Estates SubDv.
  • 32789 Zip Code
690 Osceola Avenue Unit 504, Winter Park image
690 Osceola Avenue Unit 504, Winter Park — 505 $1,495,000 ▼

***NEW PRICE***3 BEDROOMS & 3 BATH split floor plan located in the highly sought-after Lake Virginia Condos nestled in the heart of Winter Park. As soon as you enter this...

  • 3 Beds
  • 3 Baths
  • Lake Virginia Condo SubDv.
  • 32789 Zip Code
601 Ellen Drive, Winter Park image
601 Ellen Drive, Winter Park $1,399,000 ▲

Under Construction. Take advantage of one of the last chances to live in Lake Killarney Shores, one of Winter Park's newest communities - a collection of 30 custom homes ...

  • 4 Beds
  • 4.5 Baths
  • Lake Killarney Shores SubDv.
  • 32789 Zip Code
2019 Natalen Road, Winter Park image
2019 Natalen Road, Winter Park $1,395,000

Under Construction. New CUSTOM pool home a short walk to Winter Park High School. Open floor plan perfect for entertaining! Inviting front porch draws you in to spacious ...

  • 3 Beds
  • 4 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
1320 Orchid Avenue, Winter Park image
1320 Orchid Avenue, Winter Park $1,390,000 ▲

One or more photo(s) has been virtually staged. Under Construction. Introducing contemporary design and luxury living in Winter Park! This stunning new construction home,...

  • 4 Beds
  • 4 Baths
  • Elizabeth Heights Sub SubDv.
  • 32789 Zip Code
840 W Comstock Avenue, Winter Park image
840 W Comstock Avenue, Winter Park $1,300,000

Pre-Construction. To be built. Customizable Pre-Construction Home in Prime Location: Design Your Dream Residence with Valdara Custom Homes or Your Preferred Builder Se...

  • 4 Beds
  • 3.5 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
424 Turkey Run, Winter Park image
424 Turkey Run, Winter Park $1,297,500

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...

  • 4 Beds
  • 3.5 Baths
  • Quail Hollow SubDv.
  • 32789 Zip Code
617 Balmoral Road, Winter Park image
617 Balmoral Road, Winter Park $1,250,000 ▼

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

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
4765 Seminole Avenue, Winter Park image
4765 Seminole Avenue, Winter Park $1,200,000

Commercial property located on a little over a half acre, fully fenced lot in booming Winter Park. Currently houses 3 suites (A, B, and C), full kitchen, 2 full bathroom...

  • 32792 Zip Code
2315 Janice Avenue, Winter Park image
2315 Janice Avenue, Winter Park $1,200,000 ▼

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...

  • 5 Beds
  • 3 Baths
  • Parklando 03 SubDv.
  • 32789 Zip Code
3540 Wilde Avenue, Winter Park image
3540 Wilde Avenue, Winter Park $1,200,000

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 ...

  • 5 Beds
  • 5.5 Baths
  • No Subdivision SubDv.
  • 32792 Zip Code
1832 Pineview Circle, Winter Park image
1832 Pineview Circle, Winter Park $1,195,000

Pre-Construction. To be built. Looking to purchase a new home in Winter Park? Barefoot Brothers Construction group presents this opportunity to build on a quiet street, b...

  • 3 Beds
  • 3.5 Baths
  • Lakemont Heights SubDv.
  • 32792 Zip Code
1863 Lake Spier Dr, Winter Park image
1863 Lake Spier Dr, Winter Park $1,175,000 ▼

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...

  • 4 Beds
  • 3 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
911 Osceola Avenue, Winter Park image
911 Osceola Avenue, Winter Park $1,125,000

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 Avenue shops and resta...

  • 3 Beds
  • 3.5 Baths
  • Osceola Shores Sec 01 SubDv.
  • 32789 Zip Code
7448 Aloma Avenue, Winter Park image
7448 Aloma Avenue, Winter Park $1,100,000

Nice 5-tenant retail strip center.

  • Suburban Homes SubDv.
  • 32792 Zip Code
210 Laurel Park Court, Winter Park image
210 Laurel Park Court, Winter Park $1,100,000

Welcome home to this luxury custom-built home by award-winning Arthur Rutenberg Homes. Featuring 9'-12' ceilings w/ 4 bedrooms, 3 bathrooms and a private office. This gor...

  • 4 Beds
  • 3 Baths
  • Sanctuary At Lake Ann SubDv.
  • 32792 Zip Code
2726 Lake Howell Lane, Winter Park image
2726 Lake Howell Lane, Winter Park $1,049,900 ▼

Build your Dream Home on the shores of Lake Howell, this Lakefront property offers the potential buyer over 2 acres of High and Dry Land in a serene natural setting. Aft...

  • Lake Howell SubDv.
  • 32792 Zip Code
2430 Roxbury Road, Winter Park image
2430 Roxbury Road, Winter Park $995,000

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

  • 4 Beds
  • 3.5 Baths
  • Glencoe Sub SubDv.
  • 32789 Zip Code
100 S Interlachen Avenue Unit 201, Winter Park image
100 S Interlachen Avenue Unit 201, Winter Park — The Cloisters $975,000 ▼

One or more photo(s) has been virtually staged. Beautifully renovated, this downtown Winter Park three-bedroom, two-bath condominium on Lake Osceola embodies the art of t...

  • 3 Beds
  • 2 Baths
  • Cloisters Condo SubDv.
  • 32789 Zip Code
1500 Harris Circle, Winter Park image
1500 Harris Circle, Winter Park $949,900

"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 ...

  • 2 Beds
  • 2.5 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
357 Vitoria Ave, Winter Park image
357 Vitoria Ave, Winter Park $875,000

Be advised: multiple offer situation. Welcome to the most enchanting historic neighborhood in the most special little town in all of Florida. Bordering Lake Virginia and ...

  • 4 Beds
  • 3 Baths
  • College Place Rep SubDv.
  • 32789 Zip Code
1915 S Lakemont Avenue Unit 1, Winter Park image
1915 S Lakemont Avenue Unit 1, Winter Park — 1 $874,000 ▲

Under Construction. Located between the shores of Lake Spier and Lake Compton you'll discover Lake Spier Crossing. This exclusive lakefront community, nestled in the hear...

  • 3 Beds
  • 3.5 Baths
  • Maccallum Sub SubDv.
  • 32792 Zip Code
210 E Lake Sue Avenue, Winter Park image
210 E Lake Sue Avenue, Winter Park $850,000

This is an excellent opportunity to renovate or build your dream home in the beautiful City of Winter Park. It is rare to find a lot in one of the most popular areas of C...

  • 5 Beds
  • 3.5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1714 Westchester Avenue, Winter Park image
1714 Westchester Avenue, Winter Park $850,000 ▲

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...

  • 3 Beds
  • 2.5 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
358 W Comstock Avenue, Winter Park image
358 W Comstock Avenue, Winter Park $850,000

Residential Land Opportunity in Downtown Winter Park. Zoned R1-A this premium lot is ready for something new and exciting to be built on it. Featuring 107' road frontage ...

  • Winter Park SubDv.
  • 32789 Zip Code
903 Bungalow Avenue Unit 903, Winter Park image
903 Bungalow Avenue Unit 903, Winter Park — 903 $849,900 ▼

Gorgeous custom Mediterranean 3-level townhome in the middle of Winter Park! The incredible design and details in this residence will have you feeling like you’re living ...

  • 3 Beds
  • 2.5 Baths
  • Bungalow Park SubDv.
  • 32789 Zip Code
2227 Howard Drive, Winter Park image
2227 Howard Drive, Winter Park $825,000

Fractional Ownership. WINTER PARK, FLORIDA! Gorgeous ONE STORY lakefront home in Winter Park. 2227 Howard Drive | Offered at $825,000 Beautiful inside and out, this mid...

  • 3 Beds
  • 2.5 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1489 Lone Feather Trail, Winter Park image
1489 Lone Feather Trail, Winter Park $799,900 ▲

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...

  • 4 Beds
  • 3.5 Baths
  • Landings At Hawks Crest SubDv.
  • 32792 Zip Code
1437 Miller Avenue, Winter Park image
1437 Miller Avenue, Winter Park $799,000 ▼

ATTENTION developers/investors!!!! Winter Park investment property on a double lot. The lot is 100 X 140 and was originally platted as two 50 foot lots and zoned R2. Just...

  • Lawndale SubDv.
  • 32789 Zip Code
1231 Kenwood Avenue, Winter Park image
1231 Kenwood Avenue, Winter Park $799,000 ▼

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...

  • 3 Beds
  • 2 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
1321 Bridgeport Drive, Winter Park image
1321 Bridgeport Drive, Winter Park $790,000

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...

  • 4 Beds
  • 2 Baths
  • Waterbridge SubDv.
  • 32789 Zip Code
27 Stymie Place, Winter Park image
27 Stymie Place, Winter Park $784,990 ▼

Under Construction. Rare opportunity for affordable new construction in Winter Park! Construction has commenced! Park Avenue, Historic Dubsdread Golf Course, and the fut...

  • 5 Beds
  • 3 Baths
  • Golfview SubDv.
  • 32789 Zip Code
1407 Miller Avenue, Winter Park image
1407 Miller Avenue, Winter Park — Makeur Construction $784,900

Under Construction. WINTER PARK NEW CONSTRUCTION!! Welcome to an amazing opportunity to own a brand new 3 bedroom 2.5 bath townhome in an incredible location! This Stunni...

  • 3 Beds
  • 2.5 Baths
  • H. Vanwies SubDv.
  • 32789 Zip Code
640 Dunblane Drive, Winter Park image
640 Dunblane Drive, Winter Park $776,900 ▼

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...

  • 3 Beds
  • 3 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
1047 N Kentucky Avenue, Winter Park image
1047 N Kentucky Avenue, Winter Park — 1047 $749,900

This meticulous Winter Park townhouse is the epitome of thoughtful design and impeccable quality. Designed by Award-Winning modern architect Phil Kean, this unique 3-bedr...

  • 3 Beds
  • 2.5 Baths
  • Fairbanks Park SubDv.
  • 32789 Zip Code
1131 Oxford Road, Winter Park image
1131 Oxford Road, Winter Park $730,000 ▼

***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...

  • 3 Beds
  • 2 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
100 S Interlachen Avenue Unit 506E, Winter Park image
100 S Interlachen Avenue Unit 506E, Winter Park — The Cloisters $729,000 ▼

This exquisite top-level, corner unit condominium boasts 2 bedrooms and 2 bathrooms, located in downtown Winter Park. The unit's open floor plan provides a seamless flow ...

  • 2 Beds
  • 2 Baths
  • Cloisters Condo SubDv.
  • 32789 Zip Code
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  • Altamonte Springs
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  • College Park
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  • Debary
  • Deltona
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  • Lake Mary
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