Homes in ZIP Code 32789

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  /2

  $1,675,000

  Sold May 08, 2026

  1560 Woodland Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Below List Price
  • $435/SF
  • 16 Days On Market

  Current Estimated Value $1,717,691

  Last Listing Agent Chris Creegan CREEGAN GROUP

  1560 Woodland Ave, Winter Park, FL 32789
• 

  

  /2

  Est $1,194,068

  Not Listed For Sale

  100 S Virginia Ave Unit 201, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,756 Sq Ft
  • Built 2008

  100 S Virginia Ave Unit 201, Winter Park, FL 32789

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC
• 

  

  

  /37

  $1,540,000

  $255K PRICE DROP

  • 3 Beds
  • 5 Baths
  • 2,756 Sq Ft

  641 Northwood Cir, Winter Park, FL 32789

  Virtually Staged. 641 Northwood Circle is a rare opportunity to own newer construction in the heart of Winter Park at a newly repositioned price of $1,599,000. Tucked within an intimate residential enclave and surrounded by multimillion-dollar homes, and short distance to Winter Park Golf Course and Park Avenue, this stylish residence offers the location, lifestyle and long-term appeal that make

  Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY

  641 Northwood Cir, Winter Park, FL 32789
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  /2

  $360,000

  Sold Nov 20, 2025

  611 Ololu Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $314/SF
  • 7 Days On Market

  Current Estimated Value $377,542

  Last Listing Agent Amanda Johnson HOMERUN REALTY, LLC

  611 Ololu Dr, Winter Park, FL 32789
• 

  

  

  /17

  Est $314,682

  Not Listed For Sale

  500 N Pennsylvania Ave Unit F, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft
  • Built 1981

  500 N Pennsylvania Ave Unit F, Winter Park, FL 32789

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC
• 

  

  /25

  $439,000

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft

  950 Hanover Ave, Winter Park, FL 32789

  Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit,

  Michael Domi COMPASS FLORIDA LLC

  950 Hanover Ave, Winter Park, FL 32789
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  /2

  $1,535,000

  Sold Mar 30, 2026

  507 Country Club Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,985 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $514/SF
  • 27 Days On Market

  Current Estimated Value $1,562,585

  Last Listing Agent Lianna D'Angelo SOTERA LIVING

  507 Country Club Dr, Winter Park, FL 32789
• 

  

  /22

  Est $476,673

  Not Listed For Sale

  311 E Morse Blvd Unit 6-8, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 884 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 6-8, Winter Park, FL 32789

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES
• 

  $5,999,990

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,880 Sq Ft

  2661 Via Tuscany, Winter Park, FL 32789

  Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS.Set on a prominent corner lot within exclusive Via Tuscany, this extraordinary new-construction residence by Developer & Builder Group represents far more than exceptional modern design. Its distinction lies equally in what you see and in what you don't see, the extraordinary level of construction,

  Nohora Gomez COLDWELL BANKER REALTY

  2661 Via Tuscany, Winter Park, FL 32789
• 

  /2

  $1,000,500

  Sold Dec 11, 2025

  210 E Rockwood Way, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,431 Sq Ft
  • Built 1950

  Last Sold Summary

  • $699/SF
  • 0 Days On Market

  Current Estimated Value $1,097,800

  Last Listing Agent Penny Puente DALTON WADE INC

  210 E Rockwood Way, Winter Park, FL 32789
• 

  

  /6

  Est $1,980,793

  Not Listed For Sale

  140 E Morse Blvd Unit I, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,291 Sq Ft
  • Built 2008

  140 E Morse Blvd Unit I, Winter Park, FL 32789

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Andrea Sider, PA KELLER WILLIAMS WINTER PARK
• 

  

  /20

  $680,000

  $70K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,664 Sq Ft

  432 W Swoope Ave, Winter Park, FL 32789

  A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

  Thomas Bonner COLDWELL BANKER REALTY

  432 W Swoope Ave, Winter Park, FL 32789
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  /2

  $555,000

  Sold Jan 29, 2026

  1267 Michigan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft
  • Built 2019

  Last Sold Summary

  • 17% Below List Price
  • $309/SF
  • 88 Days On Market

  Current Estimated Value $564,039

  Last Listing Agent Megan Cross FANNIE HILLMAN & ASSOCIATES

  1267 Michigan Ave, Winter Park, FL 32789
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  /51

  Est $770,980

  Not Listed For Sale

  106 S Interlachen Ave Unit 416, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1971

  106 S Interlachen Ave Unit 416, Winter Park, FL 32789

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
• 

  

  /31

  $245,000

  • 2 Beds
  • 2 Baths
  • 913 Sq Ft

  1250 S Denning Dr Unit 233, Winter Park, FL 32789

  Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open

  Samuel Kingsford STOCKWORTH REALTY GROUP

  1250 S Denning Dr Unit 233, Winter Park, FL 32789
• 

  /2

  $450,000

  Sold Mar 31, 2026

  764 W Comstock Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1935

  Last Sold Summary

  • 5% Below List Price
  • $486/SF
  • 17 Days On Market

  Current Estimated Value $460,555

  Last Listing Agent Manny del Valle KELLER WILLIAMS WINTER PARK

  764 W Comstock Ave, Winter Park, FL 32789
• 

  

  /39

  Est $796,810

  Not Listed For Sale

  104 S Interlachen Ave Unit 414, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1971

  104 S Interlachen Ave Unit 414, Winter Park, FL 32789

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent James Lyon COLLADO REAL ESTATE
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  /13

  $589,000

  $6K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,126 Sq Ft

  1319 Bessmor Rd, Winter Park, FL 32789

  Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024.

  Sidney Galloway GALLOWAY REAL ESTATE

  1319 Bessmor Rd, Winter Park, FL 32789
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  /2

  $4,950,000

  Sold Jul 30, 2026

  1660 Palmer Ave, Winter Park, FL 32789

  • 5 Beds
  • 6.5 Baths
  • 5,636 Sq Ft
  • Built 2024

  Last Sold Summary

  • 13% Below List Price
  • $878/SF
  • 438 Days On Market

  Current Estimated Value $4,216,715

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
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  /2

  Est $802,559

  Not Listed For Sale

  106 S Interlachen Ave Unit 317, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 1971

  106 S Interlachen Ave Unit 317, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
• 

  

  /19

  $3,199,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,737 Sq Ft

  361 E Kings Way, Winter Park, FL 32789

  Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a rare opportunity to own a home where timeless architecture, refined craftsmanship, and an unrivaled location come together. A striking marble mosaic foyer creates an unforgettable first impression, immediately setting the tone

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  361 E Kings Way, Winter Park, FL 32789
• 

  /2

  $190,000

  Sold Mar 20, 2026

  1250 S Denning Dr Unit 104, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  Last Sold Summary

  • 17% Below List Price
  • $209/SF
  • 60 Days On Market

  Current Estimated Value $199,792

  Last Listing Agent John Harbuck SERHANT

  1250 S Denning Dr Unit 104, Winter Park, FL 32789
• 

  

  /56

  Est $1,507,055

  Not Listed For Sale

  106 S Interlachen Ave Unit 219, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1971

  106 S Interlachen Ave Unit 219, Winter Park, FL 32789

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
• 

  

  /46

  $1,600,000

  Open Sat 12AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,733 Sq Ft

  2207 Kindel Ave, Winter Park, FL 32789

  WELCOME TO LAKEFRONT LUXURY ON LAKE BELL. This exceptional custom residence brings together refined craftsmanship and design, and an extraordinary waterfront setting in the heart of Winter Park. Built in 2025 by Accent Homes & Development, this beautifully appointed home offers 2,733 square feet of living space, with 3 bedrooms and 2.5 baths.From the moment you enter, expansive windows

  Sandra Velasquez THE SIMON SIMAAN GROUP

  2207 Kindel Ave, Winter Park, FL 32789
• 

  /2

  $368,500

  Sold Apr 03, 2026

  958 Dupont Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Below List Price
  • $234/SF
  • 49 Days On Market

  Current Estimated Value $377,528

  Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

  958 Dupont Ave, Winter Park, FL 32789
• 

  

  /28

  Est $590,069

  Not Listed For Sale

  100 S Interlachen Ave Unit 108, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 901 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 108, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
• 

  

  /36

  $1,419,900

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,984 Sq Ft

  1546 Miller Ave, Winter Park, FL 32789

  Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunning new farmhouse-inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for,

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1546 Miller Ave, Winter Park, FL 32789
• 

  /2

  $1,650,000

  Sold May 01, 2026

  1016 Howell Branch Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,142 Sq Ft
  • Built 1959

  Last Sold Summary

  • 3% Below List Price
  • $525/SF
  • 7 Days On Market

  Current Estimated Value $1,642,454

  Last Listing Agent Andrew Birr PLAID PROPERTIES, LLC

  1016 Howell Branch Rd, Winter Park, FL 32789
• 

  /2

  Est $386,642

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Jennifer Cornette HOLT REAL ESTATE LLC
• 

  /2

  $2,450,000

  • 5 Beds
  • 5.5 Baths
  • 4,010 Sq Ft

  1771 Taylor Ave, Winter Park, FL 32789

  Custom Winter Park home completed in 2019 by FG Schaub Custom Home Builder. Contemporary Florida living awaits in this newly built home, boasting a spacious open floor plan spanning over 4,000 square feet with five bedrooms and five-and-a-half baths. Delight in the stunning gourmet kitchen, gas cooktop, oversized island and an extended walk-in pantry with cabinets. Distinctive features include

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1771 Taylor Ave, Winter Park, FL 32789
• 

  /2

  $810,000

  Sold Nov 26, 2025

  1314 Canterbury Rd, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 1950

  Last Sold Summary

  • $466/SF

  Current Estimated Value $825,479

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1314 Canterbury Rd, Winter Park, FL 32789
• 

  /2

  Est $640,103

  Not Listed For Sale

  350 Carolina Ave Unit 304, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 2005

  350 Carolina Ave Unit 304, Winter Park, FL 32789

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Jennifer Tyre REALTY AND COMPANY INT., LLC
• 

  

  /46

  $1,095,000

  • 4 Beds
  • 3 Baths
  • 2,803 Sq Ft

  443 Broadview Ave, Winter Park, FL 32789

  A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one home from Lake Killarney, the property is 2803sf, with a 3/2 main residence (approximately 2200sf) plus a detached 1/1 guest cottage (approximately 600sf). Beautiful curb appeal and a glass-enclosed front porch with beadboard

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  443 Broadview Ave, Winter Park, FL 32789
• 

  /2

  $892,500

  Sold Jun 25, 2026

  1960 E Winter Park Rd, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,864 Sq Ft
  • Built 1948

  Last Sold Summary

  • 1% Below List Price
  • $479/SF
  • 13 Days On Market

  Current Estimated Value $911,719

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1960 E Winter Park Rd, Winter Park, FL 32789
• 

  /2

  Est $659,540

  Not Listed For Sale

  250 Carolina Ave Unit 406, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1981

  250 Carolina Ave Unit 406, Winter Park, FL 32789

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Gina Johnson RE/MAX PREMIER REALTY
• 

  

  /4

  $750,000

  • 3 Beds
  • 1 Bath
  • 1,325 Sq Ft

  1421 Chestnut Ave, Winter Park, FL 32789

  Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or

  Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  1421 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  $1,755,000

  Sold Jul 24, 2026

  1813 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,551 Sq Ft
  • Built 2013

  Last Sold Summary

  • 12% Below List Price
  • $494/SF
  • 67 Days On Market

  Current Estimated Value $1,816,189

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1813 Harland Park Dr, Winter Park, FL 32789
• 

  /2

  Est $132,397

  Not Listed For Sale

  1695 Lee Rd Unit E213, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  1695 Lee Rd Unit E213, Winter Park, FL 32789

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Justin Adams EXP REALTY LLC
• 

  

  /48

  $1,095,000

  Open Sat 10AM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,135 Sq Ft

  1517 Harmon Ave, Winter Park, FL 32789

  Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining.The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen

  Steven Koleno BEYCOME OF FLORIDA LLC

  1517 Harmon Ave, Winter Park, FL 32789
• 

  /2

  $4,500,000

  Sold May 29, 2026

  1521 Harris Cir, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,922 Sq Ft
  • Built 2026

  Last Sold Summary

  • $1,147/SF
  • 0 Days On Market

  Current Estimated Value $3,635,666

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1521 Harris Cir, Winter Park, FL 32789

Showing Results 521 - 560, Page 14 of 18