Homes in ZIP Code 32789

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  /25

  $3,500,000

  • 4 Beds
  • 3.5 Baths
  • 4,036 Sq Ft

  2240 Venetian Way, Winter Park, FL 32789

  Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting

  Johnny Hurlburt COLDWELL BANKER REALTY

  2240 Venetian Way, Winter Park, FL 32789
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  /2

  $3,978,550

  Sold May 18, 2026

  2020 Via Tuscany, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,665 Sq Ft
  • Built 2026

  Last Sold Summary

  • 5% Below List Price
  • $853/SF
  • 4 Days On Market

  Current Estimated Value $3,943,615

  Last Listing Agent Mauro Costa WILLIAM RAVEIS FLORIDA, LLC

  2020 Via Tuscany, Winter Park, FL 32789
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  /56

  Est $1,994,100

  Not Listed For Sale

  914 Moss Ln, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,431 Sq Ft
  • Built 1955

  914 Moss Ln, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  /12

  $4,500,000

  $499K PRICE DROP

  • Land
  • 20,908 Sq Ft
  • $9,375,000 per Acre

  503 N Interlachen Ave, Winter Park, FL 32789

  RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses.

  Kelly Price KELLY PRICE & COMPANY LLC

  503 N Interlachen Ave, Winter Park, FL 32789
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  /2

  $920,000

  Sold Jul 22, 2026

  250 Cortland Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $435/SF
  • 73 Days On Market

  Current Estimated Value $958,835

  Last Listing Agent James Ferngren CREEGAN GROUP

  250 Cortland Ave, Winter Park, FL 32789
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  /39

  Est $1,159,522

  Not Listed For Sale

  1771 Bryan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,507 Sq Ft
  • Built 1993

  1771 Bryan Ave, Winter Park, FL 32789

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Chase Morton Tate COMPASS FLORIDA LLC
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  /35

  $1,625,000

  Open Sun 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,133 Sq Ft

  2407 Lafayette Ave, Winter Park, FL 32789

  Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spacious residence offers 5 bedrooms, 4.5 bathrooms, and a large upstairs loft—providing the perfect blend of luxury, comfort, and functionality. From the moment you enter, you'll be captivated by the abundance of natural light and

  Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2407 Lafayette Ave, Winter Park, FL 32789
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  /2

  $3,443,500

  Sold Aug 17, 2026

  2905 Parkland Dr, Winter Park, FL 32789

  • 6 Beds
  • 8 Baths
  • 4,850 Sq Ft
  • Built 2026

  Last Sold Summary

  • 1% Above List Price
  • $710/SF
  • 5 Days On Market

  Current Estimated Value $648,034

  Last Listing Agent Clay Wooten UNITED REAL ESTATE PREFERRED

  2905 Parkland Dr, Winter Park, FL 32789
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  /38

  Est $1,831,737

  Not Listed For Sale

  580 Palmer Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 3,055 Sq Ft
  • Built 1950

  580 Palmer Ave, Winter Park, FL 32789

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES
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  /44

  $989,500

  • 1 Bed
  • 1.5 Baths
  • 1,109 Sq Ft

  269 E Canton Ave Unit 269, Winter Park, FL 32789

  Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine

  Catherine Williams COLDWELL BANKER REALTY

  269 E Canton Ave Unit 269, Winter Park, FL 32789
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  /2

  $819,000

  Sold Oct 31, 2025

  734 Maryland Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 1926

  Last Sold Summary

  • 3% Below List Price
  • $655/SF
  • 44 Days On Market

  Current Estimated Value $847,774

  Last Listing Agent Michael Domi COMPASS FLORIDA LLC

  734 Maryland Ave, Winter Park, FL 32789
• 

  /2

  Est $3,364,613

  Not Listed For Sale

  641 Virginia Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,223 Sq Ft
  • Built 1966

  641 Virginia Dr, Winter Park, FL 32789

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Audra Wilks PREMIER SOTHEBY'S INTL. REALTY
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  /33

  $1,595,000

  Open Sat 12PM - 2PM $95K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,048 Sq Ft

  1570 Palmer Ave, Winter Park, FL 32789

  Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functionality. Freshly painted throughout and move-in ready, the home features an open and inviting floor plan filled with natural light and high-end finishes.The gourmet kitchen is equipped with granite countertops, stainless

  David Auerbach PARK TOWN REAL ESTATE LLC

  1570 Palmer Ave, Winter Park, FL 32789
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  /2

  $715,000

  Sold Sep 26, 2025

  438 W Swoope Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Built 2014

  Last Sold Summary

  • 9% Below List Price
  • $275/SF
  • 46 Days On Market

  Current Estimated Value $782,205

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  438 W Swoope Ave, Winter Park, FL 32789
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  /64

  Est $748,140

  Not Listed For Sale

  260 Rippling Ln, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,179 Sq Ft
  • Built 1954

  260 Rippling Ln, Winter Park, FL 32789

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Brian Hyser THE AGENCY FL
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  /30

  $439,900

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  2041 Jewell Ave, Winter Park, FL 32789

  Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Located in the highly desirable Winter Park 32789 ZIP code, 2041 Jewell Avenue offers an unbeatable location just minutes from

  Martha Coronel IAD REAL ESTATE

  2041 Jewell Ave, Winter Park, FL 32789
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  /2

  $287,500

  Sold Jun 12, 2026

  119 Oak Grove Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,134 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Above List Price
  • $254/SF
  • 2 Days On Market

  Current Estimated Value $286,858

  Last Listing Agent Lorena Ortega INTERNATIONAL PROFESSIONAL REALTY INC

  119 Oak Grove Rd, Winter Park, FL 32789
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  /21

  Est $426,061

  Not Listed For Sale

  3508 Midiron Dr, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,036 Sq Ft
  • Built 1951

  3508 Midiron Dr, Winter Park, FL 32789

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Catherine Lambert BHHS FLORIDA REALTY
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  /75

  $6,000,000

  • 5 Beds
  • 8 Baths
  • 7,397 Sq Ft

  1571 Woodland Ave, Winter Park, FL 32789

  Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of-a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blendingrefined luxury with modern comfort.Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stackedcrown

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  1571 Woodland Ave, Winter Park, FL 32789
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  /2

  $410,000

  Sold Dec 02, 2025

  2464 Lotafun Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,804 Sq Ft
  • Built 1951

  Last Sold Summary

  • 9% Below List Price
  • $227/SF
  • 112 Days On Market

  Current Estimated Value $429,471

  Last Listing Agent Irina Paul FUTURE HOME REALTY INC

  2464 Lotafun Ave, Winter Park, FL 32789

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