Winter Park Homes for Sale

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  $565,000

  • 3 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  1781 Indiana Ave Unit A, Winter Park, FL 32789

  Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed

  James Rouadi CARLISLE REALTY, LLC

  1781 Indiana Ave Unit A, Winter Park, FL 32789
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  /36

  $2,540,000 Open Tue 12PM - 2PM

  • 3 Beds
  • 3 Baths
  • 2,667 Sq Ft

  135 W Swoope Ave, Winter Park, FL 32789

  Luxury living in Winter Park 32789 in this well-appointed, fee-simple townhouse just steps from Park Avenue, with no HOA or condo fees. Three-story home features refinished hardwood floors (Knight Flooring), high ceilings, crown moldings and a PRIVATE ELEVATOR for easy access to all levels. The first floor offers a flexible bedroom, currently used as an office and bedroom along with a full bath,

  Jennifer Sloan COMPASS FLORIDA LLC

  135 W Swoope Ave, Winter Park, FL 32789
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  /18

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  1760 Greenwich Ave, Winter Park, FL 32789

  Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1760 Greenwich Ave, Winter Park, FL 32789
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  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1113 Via Del Mar, Winter Park, FL 32789

  Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceablehomesite offering rare scale, privacy, and extraordinary future build potential. The primaryvalue is in the land, presenting an unparalleled canvas for a custom luxury residence, withvirtually no comparable vacant land available in the immediate vicinity. Set on a tranquil smalllake that

  David Barany BAY HILL REALTY LLC

  1113 Via Del Mar, Winter Park, FL 32789
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  /43

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  512 N Lakemont Ave, Winter Park, FL 32792

  Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

  David Plasencia COLDWELL BANKER REALTY

  512 N Lakemont Ave, Winter Park, FL 32792
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  /35

  $775,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,038 Sq Ft

  350 Cornwall Rd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Fully reimagined and COMPLETELY RENOVATED with Custom features, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island,

  Kelly Butterfield RE/MAX TOWN & COUNTRY REALTY

  350 Cornwall Rd, Winter Park, FL 32792
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  /7

  $899,000

  • Land
  • 0.19 Acre
  • $4,731,579 per Acre

  731 Midget Dr, Winter Park, FL 32789

  Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and

  Juliana Usquiano EMPIRE NETWORK REALTY

  731 Midget Dr, Winter Park, FL 32789
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  /19

  $450,000

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  640 N Park Ave Unit 5, Winter Park, FL 32789

  Location, Location, Location!Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz.Enjoy a

  David Auerbach PARK TOWN REAL ESTATE LLC

  640 N Park Ave Unit 5, Winter Park, FL 32789
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  /60

  $2,100,000

  • 5 Beds
  • 3 Baths
  • 3,669 Sq Ft

  1711 Barcelona Way, Winter Park, FL 32789

  Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than 3⁄4 of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed

  Lindsay Kaye Voss VOSS REALTY INC

  1711 Barcelona Way, Winter Park, FL 32789
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  /20

  $650,000

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  2330 Coldstream Dr, Winter Park, FL 32792

  Completely renovated and move-in ready! This beautifully updated home has been fully remodeled with attention to detail and quality finishes throughout. Recent upgrades include brand-new flooring, modern appliances, fresh interior and exterior paint, and a new A/C system, offering comfort and peace of mind for years to come.The home is in excellent condition. Truly feels like new construction

  Marta Faustino DTB FLORIDA REALTY, INC.

  2330 Coldstream Dr, Winter Park, FL 32792
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  /3

  $1,895,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,617 Sq Ft

  914 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

  Matthew Burks CORCORAN PREMIER REALTY

  914 Enclave Place, Winter Park, FL 32792
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  /7

  $196,400

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792

  Condo in Winter Park, FL. 2923 Antique Oaks Cir, Unit 37. Updated 1,105 sq. ft. first-floor, North West corner condo. 2 bedrooms, 2 bathrooms. Located in the Winter Park School District: Updated Interiors: Recently remodeled with modern finishes, including brand-new appliances (convection oven, refrigerator, dishwasher), and a new LG stackable washer/dryer in the interior laundry room. Outdoor

  Cliff Glansen FLATFEE.COM

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792
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  /27

  $99,000

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  278 Scottsdale Square Unit 278, Winter Park, FL 32792

  Welcome to 278 Scottsdale Square in Winter Park, a well-maintained 2-bedroom, 2-bathroom condominium offering over 1,000 square feet of comfortable living space in a highly convenient location. This second-story unit features wood-like laminate flooring throughout, creating a clean and cohesive look that is both stylish and easy to maintain. The home has been carefully cared for and kept in

  Chris Creegan CREEGAN GROUP

  278 Scottsdale Square Unit 278, Winter Park, FL 32792
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  /25

  $150,000

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport.This unit offers a cozy living/dining area with sliding

  Maria Batista LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
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  /11

  $1,800,000

  • Land
  • 0.3 Acre
  • $6,000,000 per Acre

  1181 Via Capri, Winter Park, FL 32789

  Build your dream home in one of Winter Park’s most desirable areas. This exceptional vacant lot at 1181 Via Capri offers a rare opportunity to create a custom residence in a well-established neighborhood known for its charm, convenience, and strong property values. Ideally located just minutes from Park Avenue, top-rated schools, dining, shopping, and major roadways, this homesite provides both

  Ana Semmel KARDOSH REALTY

  1181 Via Capri, Winter Park, FL 32789
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  /19

  $929,900

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2823 Wright Ave, Winter Park, FL 32789

  Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows

  Tal Busidan TAL BUSIDAN PA

  2823 Wright Ave, Winter Park, FL 32789
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  /5

  $3,795,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,508 Sq Ft

  1811 Oneco Ave, Winter Park, FL 32789

  Under Construction. One of Winter Park's largest new construction homesites — 13,519 square feet, over a third of an acre — anchors this signature build, a three-story luxury residence on Oneco Avenue where scale, privacy, and architectural distinction rarely coexist at this price point.This home carries the mark of a builder renowned for delivering Winter Park's most trend-setting luxury

  Ahmad Hassan COMPASS FLORIDA LLC

  1811 Oneco Ave, Winter Park, FL 32789
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  /39

  $3,350,000

  • 5 Beds
  • 6 Baths
  • 4,636 Sq Ft

  2040 Randall Cir, Winter Park, FL 32789

  Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2040 Randall Cir, Winter Park, FL 32789
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  /2

  $1,495,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,738 Sq Ft

  901 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch

  Laura Earl CORCORAN PREMIER REALTY

  901 Enclave Place, Winter Park, FL 32792
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  /10

  $1,689,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  1810 Hollywood Ave, Winter Park, FL 32789

  Under Construction. Estimated completion August!! Experience modern luxury living in the heart of Winter Park with this beautifully designed pool home at 1810 Hollywood Avenue. Offering 4 bedrooms, 3.5 bathrooms, and 2,604 square feet of thoughtfully planned living space, this residence blends high-end finishes with everyday functionality in one of Central Florida’s most sought-after locations.

  Ken Pozek REAL BROKER, LLC

  1810 Hollywood Ave, Winter Park, FL 32789
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  /31

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  346 S Ranger Blvd, Winter Park, FL 32792

  PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

  Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

  346 S Ranger Blvd, Winter Park, FL 32792
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  /73

  $3,449,999

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  A New Standard of Modern Sophistication in Winter ParkIn a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living.Step

  Mark Anthony Buot ROI AVE LLC

  1742 Temple Dr, Winter Park, FL 32789

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