Homes in ZIP Code 32789

• 

  

  /2

  Est $1,248,146

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • 184 Days On Market

  Last Listing Agent Gernelle Bokuniewicz LIVELY REAL ESTATE
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  /63

  $2,475,000

  • 3 Beds
  • 3 Baths
  • 2,316 Sq Ft

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

  Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out

  Skip Kirst COLLADO REAL ESTATE

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
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  /2

  $367,500

  Sold Nov 17, 2025

  1975 Staunton Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1949

  Last Sold Summary

  • 15% Below List Price
  • $306/SF
  • 225 Days On Market

  Current Estimated Value $371,359

  Last Listing Agent Marion McGrath ABSOLUTE REALTY GROUP, LLC

  1975 Staunton Ave, Winter Park, FL 32789
• 

  

  /2

  Est $439,596

  Not Listed For Sale

  535 N Interlachen Ave Unit 107, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1972

  535 N Interlachen Ave Unit 107, Winter Park, FL 32789

  Last Sold Summary

  • 127 Days On Market

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
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  /63

  $649,900

  $25K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,370 Sq Ft

  840 W Canton Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the heart of Winter Park. Every detail has been updated, including new mechanical systems, electrical, plumbing, custom doors and windows, gutters, stucco finishes, fixtures, fresh landscaping, and new sod. Inside, you'll find an open-concept floor plan with professionally

  Ken Pozek REAL BROKER, LLC

  840 W Canton Ave, Winter Park, FL 32789
• 

  /2

  $6,300,000

  Sold Nov 04, 2025

  1308 Green Cove Rd, Winter Park, FL 32789

  • 4 Beds
  • 5.5 Baths
  • 6,981 Sq Ft
  • Built 1990

  Last Sold Summary

  • $902/SF
  • 0 Days On Market

  Current Estimated Value $6,391,253

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  1308 Green Cove Rd, Winter Park, FL 32789
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  /2

  Est $312,697

  Not Listed For Sale

  1132 Park Green Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1991

  1132 Park Green Place, Winter Park, FL 32789

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Christi Nixon CHARLES RUTENBERG REALTY ORLANDO
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  /28

  $525,000

  $64K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,709 Sq Ft

  2803 Riddle Dr, Winter Park, FL 32789

  Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities.The heart of the home

  Allie George CORCORAN PREMIER REALTY

  2803 Riddle Dr, Winter Park, FL 32789
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  /2

  $1,635,000

  Sold May 11, 2026

  1841 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft
  • Built 2014

  Last Sold Summary

  • 18% Below List Price
  • $471/SF
  • 103 Days On Market

  Current Estimated Value $1,660,142

  Last Listing Agent Shanon Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
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  /2

  Est $2,440,702

  Not Listed For Sale

  1700 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,770 Sq Ft
  • Built 2016

  1700 Palm Ave, Winter Park, FL 32789

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  /11

  $1,800,000

  Under Contract

  • Land
  • 17,424 Sq Ft
  • $4,500,000 per Acre

  1220 Sharon Place, Winter Park, FL 32789

  Under contract-accepting backup offers. A rare opportunity to create your own vision in the heart of Winter Park. This exceptional 17,624-square-foot (0.40-acre) oversized corner lot offers approximately 112' x 145' of space and is ideally situated on a quiet, dead-end street just steps from the Winter Park Racquet Club. Opportunities to acquire a homesite of this size in Winter Park are

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1220 Sharon Place, Winter Park, FL 32789
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  /2

  $1,450,000

  Sold Jul 31, 2026

  1660 Walnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,249 Sq Ft
  • Built 2026

  Last Sold Summary

  • 12% Below List Price
  • $645/SF
  • 43 Days On Market

  Current Estimated Value $1,355,376

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1660 Walnut Ave, Winter Park, FL 32789
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  /2

  Est $1,512,140

  Not Listed For Sale

  1327 Bridgeport Dr, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 4,181 Sq Ft
  • Built 1979

  1327 Bridgeport Dr, Winter Park, FL 32789

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Jennifer Christ RE/MAX TOWN & COUNTRY REALTY
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  /29

  $899,000

  $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  560 Ololu Dr, Winter Park, FL 32789

  Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this

  Tiffany Yates COMPASS FLORIDA LLC

  560 Ololu Dr, Winter Park, FL 32789
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  /2

  $315,000

  Sold Mar 27, 2026

  2249 Minnesota Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1955

  Last Sold Summary

  • 28% Below List Price
  • $205/SF
  • 42 Days On Market

  Current Estimated Value $387,493

  Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

  2249 Minnesota Ave, Winter Park, FL 32789
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  /2

  Est $712,126

  Not Listed For Sale

  1580 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1971

  1580 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
• 

  

  /22

  $700,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,016 Sq Ft

  1592 Arbor Park Dr, Winter Park, FL 32789

  This exceptional homesite on Arbor Ridge sits in one of Winter Park's most prestigious and tightly held residential pockets—where elegant estates, mature canopy trees, and enduring property values define the neighborhood. Perfectly positioned, and ready for your vision, the lot places you just two blocks from the Winter Park YMCA and half a mile from highly regarded Lakemont Elementary. The

  David Welch CHARLES RUTENBERG REALTY ORLANDO

  1592 Arbor Park Dr, Winter Park, FL 32789
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  /2

  $407,000

  Sold Sep 03, 2026

  2323 Devon Ct, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,403 Sq Ft
  • Built 1951

  Last Sold Summary

  • 5% Below List Price
  • $169/SF
  • 13 Days On Market

  Current Estimated Value $620,399

  Last Listing Agent Renee Taylor CREEGAN GROUP

  2323 Devon Ct, Winter Park, FL 32789
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  /2

  Est $917,792

  Not Listed For Sale

  1762 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1957

  1762 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES
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  /24

  $3,300,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,421 Sq Ft

  1627 Mizell Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms

  Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  1627 Mizell Ave, Winter Park, FL 32789
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  /2

  $4,430,000

  Sold Oct 09, 2025

  2161 Sharon Rd, Winter Park, FL 32789

  • 5 Beds
  • 6.5 Baths
  • 6,338 Sq Ft
  • Built 2023

  Last Sold Summary

  • 11% Below List Price
  • $699/SF
  • 247 Days On Market

  Current Estimated Value $4,637,575

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  2161 Sharon Rd, Winter Park, FL 32789
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  /28

  Est $1,200,585

  Not Listed For Sale

  1500 Harris Cir, Winter Park, FL 32789

  • 2 Beds
  • 3 Baths
  • 1,950 Sq Ft
  • Built 1994

  1500 Harris Cir, Winter Park, FL 32789

  Last Sold Summary

  • 217 Days On Market

  Last Listing Agent Jean Gillen GILLEN & ASSOCIATES
• 

  

  /34

  $589,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1313 S Denning Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to a beautifully renovated 3-bedroom, 2-bath residence offering approximately 1,700 square feet of thoughtfully designed living space in the heart of Winter Park. Step inside to a fresh, inviting interior where timeless travertine flooring complements a beautifully updated kitchen featuring new cabinetry, new appliances, and a spacious new pantry.

  Elizabeth Sanchez THE AGENCY FL

  1313 S Denning Dr, Winter Park, FL 32789
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  /2

  $913,000

  Sold Jul 27, 2026

  422 Balmoral Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1957

  Last Sold Summary

  • $507/SF
  • 0 Days On Market

  Current Estimated Value $863,801

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

  422 Balmoral Rd, Winter Park, FL 32789
• 

  /2

  Est $1,965,412

  Not Listed For Sale

  1530 Via Tuscany, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • Built 1972

  1530 Via Tuscany, Winter Park, FL 32789

  Last Sold Summary

  • 377 Days On Market

  Last Listing Agent Mark Squires COLDWELL BANKER REALTY
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  /46

  $950,000

  Open Sat 1PM - 3PM $350K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,075 Sq Ft

  3006 Northwood Blvd, Winter Park, FL 32789

  Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character with all-new finishes and systems. An open living, dining, and kitchen core opens to a light-filled sitting area, with white oak floors and designer lighting and ceiling fans throughout. The kitchen stuns with Taj Mahal quartzite

  Daren Ellington ORLANDO HOMES GROUP LLC

  3006 Northwood Blvd, Winter Park, FL 32789
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  /2

  $1,565,000

  Sold Sep 24, 2025

  1450 Glencoe Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 1952

  Last Sold Summary

  • 1% Below List Price
  • $588/SF
  • 42 Days On Market

  Current Estimated Value $1,629,939

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1450 Glencoe Rd, Winter Park, FL 32789
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  /2

  Est $1,223,122

  Not Listed For Sale

  363 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,871 Sq Ft
  • Built 1950

  363 N Phelps Ave, Winter Park, FL 32789

  Last Sold Summary

  • 144 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC
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  /8

  $339,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  310 Granada Dr, Winter Park, FL 32789

  Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced

  William Ward A-WARD WINNING REALTY LLC

  310 Granada Dr, Winter Park, FL 32789
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  /2

  $414,000

  Sold Feb 19, 2026

  740 Baffie Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $284/SF
  • 94 Days On Market

  Current Estimated Value $424,704

  Last Listing Agent Chris Creegan CREEGAN GROUP

  740 Baffie Ave, Winter Park, FL 32789
• 

  /2

  Est $749,018

  Not Listed For Sale

  678 Depugh St, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 1952

  678 Depugh St, Winter Park, FL 32789

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
• 

  

  /41

  $4,400,000

  • 4 Beds
  • 5.5 Baths
  • 3,720 Sq Ft

  702 Via Bella, Winter Park, FL 32789

  Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmanship to one of Winter Park’s coveted residential corridors. Encompassing 3,720 square feet, the four-bedroom, five-and-one-half-bath home blends sophisticated interiors with contemporary systems and inviting spaces designed for

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  702 Via Bella, Winter Park, FL 32789
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  /2

  $2,250,000

  Sold Nov 17, 2025

  600 Ololu Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,749 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $600/SF
  • 2 Days On Market

  Current Estimated Value $2,294,837

  Last Listing Agent David Francetic COLDWELL BANKER REALTY

  600 Ololu Dr, Winter Park, FL 32789
• 

  /2

  Est $1,014,598

  Not Listed For Sale

  1875 Lake Spier Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 1958

  1875 Lake Spier Dr, Winter Park, FL 32789

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Angelina Cyprich FLORIDA REALTY INVESTMENTS
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  /7

  $1,295,000

  • Land
  • 22,215 Sq Ft
  • $2,539,216 per Acre

  1021 N Pennsylvania Ave, Winter Park, FL 32789

  A rare opportunity to build your custom dream home on a cleared homesite spanning more than one-half acre in a prime Winter Park location. Large, buildable parcels of this size are becoming increasingly difficult to find, making this an exceptional offering for those seeking space, flexibility and freedom to create a custom residence. Along Pennsylvania Avenue, this expansive homesite is ready

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1021 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $560,000

  Sold Jan 27, 2026

  1875 Staunton Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 89 Days On Market

  Current Estimated Value $574,509

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1875 Staunton Ave, Winter Park, FL 32789
• 

  /2

  Est $971,357

  Not Listed For Sale

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  1265 Park Pointe Ln, Winter Park, FL 32789

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III
• 

  

  /92

  $985,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,868 Sq Ft

  2667 Cochise Trail, Winter Park, FL 32789

  A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN but THERE ARE MANY FEATURES TO POINT OUT - THIS 2868 SQFT HOME has a 3-WAY SPLIT with 4 BEDROOMS, 3 FULL BATHROOMS, plus BONUS ROOM & OFFICE. YOU WILL NOT BELIEVE ALL THE STORAGE, STORAGE, STORAGE UNDER AIR! The BONUS ROOM (12.4 X

  Beverley Kistler COLDWELL BANKER REALTY

  2667 Cochise Trail, Winter Park, FL 32789
• 

  /2

  $620,000

  Sold Apr 10, 2026

  1137 Oaks Blvd, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,149 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $540/SF
  • 44 Days On Market

  Current Estimated Value $626,744

  Last Listing Agent David Gallup RE/MAX 200 REALTY

  1137 Oaks Blvd, Winter Park, FL 32789
• 

  /2

  Est $453,515

  Not Listed For Sale

  1501 Michigan Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 853 Sq Ft
  • Built 1936

  1501 Michigan Ave, Winter Park, FL 32789

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Brad Corbitt CREEGAN GROUP

Showing Results 641 - 680, Page 17 of 18