Homes in ZIP Code 32789

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  /58

  $1,750,000

  • 3 Beds
  • 4.5 Baths
  • 3,164 Sq Ft

  1630 Chestnut Ave, Winter Park, FL 32789

  Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets." This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets a relaxed tone throughout, blending timeless design elements with contemporary

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1630 Chestnut Ave, Winter Park, FL 32789
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  /57

  $3,225 per month

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • House for Rent

  1835 Edwin Blvd, Winter Park, FL 32789

  Welcome to this charming bungalow located near the historic district of Winter Park, FL. This home boasts three spacious bedrooms and two fully renovated bathrooms, featuring beautiful tile finishes. The kitchen is a chef's dream with stainless steel appliances, granite countertops, travertine floors and a modern design. The living room and bedrooms are adorned with beautiful wood flooring,

  Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

  1835 Edwin Blvd, Winter Park, FL 32789
• 

  

  

  /45

  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,102,207

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
• 

  

  /2

  Est $523,051 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789
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  /58

  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 3,423 Sq Ft

  1540 Palm Ave, Winter Park, FL 32789

  Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of

  John McDade FANNIE HILLMAN & ASSOCIATES

  1540 Palm Ave, Winter Park, FL 32789
• 

  

  /18

  $2,395 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1148 Park Green Place, Winter Park, FL 32789

  Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

  Linda Baez DON ASHER & ASSOCIATES, INC.

  1148 Park Green Place, Winter Park, FL 32789
• 

  /2

  $699,000 Sold Jun 30, 2025

  1632 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $394/SF
  • 110 Days On Market

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
• 

  

  /39

  Est $1,613,998 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,345 Sq Ft

  1007 S Pennsylvania Ave, Winter Park, FL 32789

  1007 S Pennsylvania Ave, Winter Park, FL 32789
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  /53

  $2,775,000

  • 5 Beds
  • 5 Baths
  • 4,026 Sq Ft

  2503 Versailles Ave, Winter Park, FL 32789

  Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered lanai with full summer kitchen, and a backyard putting green. Additional highlights include a 3-car garage, a gated parking pad ideal

  Sarah Tomlinson COMPASS FLORIDA LLC

  2503 Versailles Ave, Winter Park, FL 32789
• 

  

  /19

  $4,695 per month

  • 3 Beds
  • 5 Baths
  • 2,659 Sq Ft
  • House for Rent

  1166 Palmer Ave, Winter Park, FL 32789

  1166 Palmer Ave Winter Park, Fl 32789 - Available December 1st - March 31st! Welcome home to this absolutely stunning property boasting an exceptionally open floor plan with loads of character! Located in the heart of Winter Park minutes from Downtown you will not find this opportunity arise often. This must see spacious home features 3 bedrooms, 3 full bathrooms, and 2 half bathrooms. Gorgeous

  Brock Stocksett HOMEVEST REALTY

  1166 Palmer Ave, Winter Park, FL 32789
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  /2

  $350,000 Sold Feb 12, 2025

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789

  • 1 Bed
  • 1.5 Baths
  • 726 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $482/SF
  • 82 Days On Market

  Current Estimated Value $356,524

  Last Listing Agent Jennifer Cornette HOLT REAL ESTATE LLC

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789
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  /3

  Est $2,244,348 Not Listed For Sale

  150 Whipple Ave, Winter Park, FL 32789

  150 Whipple Ave, Winter Park, FL 32789
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  /57

  $1,525,000

  • 4 Beds
  • 4 Baths
  • 3,237 Sq Ft

  1408 Chapman Cir, Winter Park, FL 32789

  Nestled in the Elizabeth’s Walk subdivision in the highly desirable Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2.5-ton Trane

  Jennifer Sloan COMPASS FLORIDA LLC

  1408 Chapman Cir, Winter Park, FL 32789
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  /33

  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • House for Rent

  1622 Arbor Park Dr, Winter Park, FL 32789

  Offering a $500 move-in incentive if moved in by the end of December! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  1622 Arbor Park Dr, Winter Park, FL 32789
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  /2

  $3,020,000 Sold Oct 02, 2025

  1820 Englewood Rd, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,263 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $708/SF
  • 70 Days On Market

  Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
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  /14

  Est $730,969 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1407 Miller Ave, Winter Park, FL 32789

  1407 Miller Ave, Winter Park, FL 32789
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  /58

  $2,900,000

  • 3 Beds
  • 7 Baths
  • 5,483 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private

  Adriana Oyarce ANCHOR REAL ESTATE

  1401 Green Cove Rd, Winter Park, FL 32789
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  /90

  $16,550 per month

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft
  • House for Rent

  1860 Via Contessa, Winter Park, FL 32789

  Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Viasneighborhood,offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcomingatmosphere.Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

  Sylvester Harding SIERRA REALTY GROUP LLC

  1860 Via Contessa, Winter Park, FL 32789
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  /2

  $799,000 Sold Apr 30, 2025

  2320 Janice Ave, Winter Park, FL 32789

  • Land
  • 0.28 Acre
  • $2,853,571 per Acre

  Last Sold Summary

  • 2 Days On Market

  Current Estimated Value $790,000

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2320 Janice Ave, Winter Park, FL 32789
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  /11

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1405 Miller Ave, Winter Park, FL 32789

  1405 Miller Ave, Winter Park, FL 32789
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  /60

  $2,345,000

  • 4 Beds
  • 3.5 Baths
  • 3,986 Sq Ft

  2299 Via Tuscany, Winter Park, FL 32789

  Stunning 4-bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardwood oak floors, two fireplaces, and a chef’s kitchen offering premium appliances including SubZero Refrigeration and Viking 6-Burner Gas Cooktop. The private backyard features a large pool, covered

  Vincent Scarlatos CORCORAN PREMIER REALTY

  2299 Via Tuscany, Winter Park, FL 32789
• 

  

  /25

  $9,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • House for Rent

  1530 Via Tuscany, Winter Park, FL 32789

  Newly Remodeled Pool home located on premier street in Winter Park. This 4 bedroom home has just been totally updated with very tasteful upgrades. Notable items include: new paint in and out, new flooring in foyer, kitchen, baths. All baths remodeled, new light fixtures, new pavers on rear patio and pool, new landscaping package. The kitchen features new stone counters and backsplash. Also there

  Dan Haber CORCORAN PREMIER REALTY

  1530 Via Tuscany, Winter Park, FL 32789
• 

  /2

  $417,100 Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  /9

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /54

  $950,000

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  668 Overspin Dr, Winter Park, FL 32789

  Modern Elegance Meets Custom Craftsmanship in the Heart of Winter ParkWelcome to your dream home — a custom-built Winter Park masterpiece blending modern luxury with thoughtful design. With over 2,500 sq/ft of stunning living space, this 4-bedroom, 3-bathroom home was built to impress and designed to entertain.Step inside and be captivated by the seamless open layout, drenched in natural

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  668 Overspin Dr, Winter Park, FL 32789
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  /33

  $1,595 per month

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Condo for Rent

  851 Miles Ave Unit 21, Winter Park, FL 32789

  Imagine living in this beautiful two-bedroom, one-bathroom condominium near downtown Winter Park at Aragon Condos. This intimate, two-building, two-story condominium community comprises just twenty-eight units focused around a central courtyard.This first-floor corner unit allows for privacy with only one adjoining neighbor.Features include:Granite kitchen countertops;

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  851 Miles Ave Unit 21, Winter Park, FL 32789
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  /2

  $1,640,000 Sold Mar 06, 2025

  508 W Swoope Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,133 Sq Ft
  • Built 2021

  Last Sold Summary

  • 17% Below List Price
  • $397/SF
  • 258 Days On Market

  Last Listing Agent Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

  508 W Swoope Ave, Winter Park, FL 32789
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  /9

  Est $419,275 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  1768 Miller Ave, Winter Park, FL 32789

  1768 Miller Ave, Winter Park, FL 32789
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  /45

  $399,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price of $399,000. This fully renovated one-bedroom, one-bathroom condo spans 900 square feet and offers single-story, ground-floor, corner-unit living just steps from Park Avenue. The 2018 full renovation was extensive and included new electrical

  Padgett McCormick KELLY PRICE & COMPANY LLC

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
• 

  

  /57

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • House for Rent

  2128 Sycamore Dr, Winter Park, FL 32789

  MOVE-IN READY! Don’t miss this fantastic opportunity to rent a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to the home’s longevity.

  Luis Perez Garcia EXP REALTY LLC

  2128 Sycamore Dr, Winter Park, FL 32789
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  /2

  $1,242,000 Sold Feb 07, 2025

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,734 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $454/SF
  • 184 Days On Market

  Current Estimated Value $1,241,199

  Last Listing Agent Gernelle Bokuniewicz LIVELY REAL ESTATE

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789
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  /9

  Est $402,172 Not Listed For Sale

  • 2 Beds

  822 Symonds Ave, Winter Park, FL 32789

  822 Symonds Ave, Winter Park, FL 32789
• 

  

  /55

  $1,599,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,964 Sq Ft

  1270 Arlington Place, Winter Park, FL 32789

  Modern Elegance in the Heart of Winter Park! Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste. A long paver driveway welcomes you with ample

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
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  /16

  $2,510 per month

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • House for Rent

  2843 Riddle Dr, Winter Park, FL 32789

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Daniel Reyes MAIN STREET RENEWAL LLC

  2843 Riddle Dr, Winter Park, FL 32789
• 

  /2

  $1,595,000 Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,568,298

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
• 

  

  /46

  Est $1,814,726 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  660 W Morse Blvd, Winter Park, FL 32789

  660 W Morse Blvd, Winter Park, FL 32789
• 

  

  /34

  $2,499,000

  • 4 Beds
  • 5 Baths
  • 4,875 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  "The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, derives it's over 4800 sq/ft of essence and uniqueness by fusing vibrant colors and eloquence with

  Brian Rotenberger COMPASS FLORIDA LLC

  2550 Venetian Way, Winter Park, FL 32789
• 

  

  /9

  $3,350 per month

  • 6 Beds
  • 3 Baths
  • 2,722 Sq Ft
  • House for Rent

  1288 Michigan Ave, Winter Park, FL 32789

  5 bedrooms, 3 bathrooms super close to Winter Park Village and conveniently located close to all Winter Park activities. Lots of remodeling!! No garage, large treed backyard!

  Eric Weigand CQ ORLANDO REALTY INC

  1288 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $380,000 Sold May 02, 2025

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $266/SF
  • 42 Days On Market

  Current Estimated Value $390,177

  Last Listing Agent Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /29

  Est $460,133 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  1114 Washington Ave Unit 3, Winter Park, FL 32789

  1114 Washington Ave Unit 3, Winter Park, FL 32789

Showing Results 201 - 240, Page 6 of 18