Homes in ZIP Code 32789

• 

  

  

  /21

  Est $246,433 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 25A, Winter Park, FL 32789

  1500 Gay Rd Unit 25A, Winter Park, FL 32789
• 

  

  

  /20

  $750,000

  • 4 Beds
  • 3.5 Baths
  • 2,317 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 RESIDENTIAL RE

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

  $315,000 Sold Apr 14, 2025

  690 Osceola Ave Unit 308, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1969

  Last Sold Summary

  • 15% Below List Price
  • $274/SF
  • 35 Days On Market

  Current Estimated Value $352,113

  Last Listing Agent Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

  690 Osceola Ave Unit 308, Winter Park, FL 32789
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  /20

  Est $200,498 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 136, Winter Park, FL 32789

  2500 Lee Rd Unit 136, Winter Park, FL 32789
• 

  

  

  /15

  $750,000 Pending

  • Land
  • 0.45 Acre
  • $1,666,667 per Acre

  2002 Karolina Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. A unique opportunity in unincorporated Orange County, these three contiguous residential lots, each approximately 0.15 acres, totaling 0.45 acres or 20,244 square feet, are offered together as a prime redevelopment site. Zoned R-2, this assemblage is positioned adjacent to some of Winter Park’s most vibrant retail and restaurant corridors, including

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  2002 Karolina Ave, Winter Park, FL 32789
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  /2

  $440,000 Sold Aug 22, 2025

  3019 Northwood Blvd, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,662 Sq Ft
  • Built 1953

  Last Sold Summary

  • 35% Below List Price
  • $265/SF
  • 98 Days On Market

  Current Estimated Value $456,086

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

  3019 Northwood Blvd, Winter Park, FL 32789
• 

  

  /20

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 6C, Winter Park, FL 32789

  1500 Gay Rd Unit 6C, Winter Park, FL 32789
• 

  

  /49

  $1,215,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 and 720 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 and 720 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $312,500 Sold Oct 21, 2025

  1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 823 Sq Ft
  • Built 1983

  Last Sold Summary

  • 4% Below List Price
  • $380/SF
  • 9 Days On Market

  Current Estimated Value $311,746

  Last Listing Agent Livia Petraru EXP REALTY LLC

  1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789
• 

  

  /73

  Est $2,460,517 Not Listed For Sale

  • 3 Beds
  • 5 Baths
  • 3,244 Sq Ft

  125 S Interlachen Ave Unit 2, Winter Park, FL 32789

  125 S Interlachen Ave Unit 2, Winter Park, FL 32789
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  /8

  $295,000

  • 2 Beds
  • 1 Bath
  • 754 Sq Ft

  600 W Webster Ave, Winter Park, FL 32789

  Discover a rare opportunity in the heart of Winter Park, where classic charm meets modern potential. Situated on one of the area’s most coveted streets, this residence is just minutes from Park Avenue, Rollins College, and Winter Park Village. The home features a light-filled, thoughtful layout with hard-to-find character. Offering incredible flexibility, buyers may choose to renovate and expand

  Nicholas Cadwallader REALTY ONE GROUP MVP

  600 W Webster Ave, Winter Park, FL 32789
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  /2

  $520,000 Sold May 30, 2025

  2507 Lafayette Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 943 Sq Ft
  • Built 1956

  Last Sold Summary

  • 1% Below List Price
  • $551/SF
  • 41 Days On Market

  Current Estimated Value $516,186

  Last Listing Agent William Grim, III RE/MAX ASSURED

  2507 Lafayette Ave, Winter Park, FL 32789
• 

  

  /31

  Est $225,374 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 207, Winter Park, FL 32789

  2500 Lee Rd Unit 207, Winter Park, FL 32789
• 

  /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
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  /2

  $425,000 Sold Aug 21, 2025

  535 N Interlachen Ave Unit 205, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 986 Sq Ft
  • Built 1972

  Last Sold Summary

  • $431/SF
  • 0 Days On Market

  Current Estimated Value $426,986

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

  535 N Interlachen Ave Unit 205, Winter Park, FL 32789
• 

  

  /23

  Est $223,165 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  700 Melrose Ave Unit K4, Winter Park, FL 32789
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  /47

  $716,000

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft

  3018 Northwood Blvd, Winter Park, FL 32789

  PRICE IMPROVEMENT - "MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH A LARGE PRIVATE YARD, WINTER PARK, FL 32789. AWESOME LOCATION just off Corrine Drive. WALKING DISTANCE to East End Market. TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a DETAILED HOME ADDITION & UPDATE in 2020 with over $115,000.00 of improvements, including a NEW

  Joe Bornstein ROCK SPRINGS REALTY, LLC

  3018 Northwood Blvd, Winter Park, FL 32789
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  /2

  $610,000 Sold Dec 18, 2025

  1620 Howell Branch Rd, Winter Park, FL 32789

  • 3 Beds
  • 4 Baths
  • 1,984 Sq Ft
  • Built 1985

  Last Sold Summary

  • 13% Below List Price
  • $307/SF
  • 97 Days On Market

  Last Listing Agent Michelle Rhea THE WILKINS WAY LLC

  1620 Howell Branch Rd, Winter Park, FL 32789
• 

  

  /22

  Est $223,830 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  700 Melrose Ave Unit E26, Winter Park, FL 32789
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  /34

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  244 Osceola Ct, Winter Park, FL 32789

  Set in one of Winter Park’s most sought-after locations, this 1940 home delivers something that’s hard to recreate: walkability, character, and flexibility. Just steps from Downtown Winter Park, iconic Park Avenue, and Rollins College, with private access to Lake Osceola, the location alone sets this property apart. The home offers the charm of a historic build without the restrictions of a

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  244 Osceola Ct, Winter Park, FL 32789
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  /2

  $3,130,000 Sold Mar 27, 2025

  210 E Lake Sue Ave, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,188 Sq Ft
  • Built 2025

  Last Sold Summary

  • $747/SF
  • 6 Days On Market

  Current Estimated Value $3,085,263

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  210 E Lake Sue Ave, Winter Park, FL 32789
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  /18

  Est $191,317 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  1250 S Denning Dr Unit 107, Winter Park, FL 32789
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  /7

  $800,000

  • Land
  • 0.19 Acre
  • $4,210,526 per Acre

  1770 Bryan Ave, Winter Park, FL 32789

  Discover a truly unique offering in the heart of Winter Park! 1770 Bryan Avenue is now on the market along with the adjoining lots at 1760 and 1780 Bryan Avenue, creating a rare opportunity to own three consecutive parcels in one of Central Florida’s most desirable communities.While each property is being sold and priced separately, buyers have the option to purchase one, two, or all three

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1770 Bryan Ave, Winter Park, FL 32789
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  /2

  $385,000 Sold Jun 11, 2025

  1930 Albert Lee Pkwy, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,262 Sq Ft
  • Built 1955

  Last Sold Summary

  • 4% Below List Price
  • $305/SF
  • 101 Days On Market

  Current Estimated Value $387,890

  Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP

  1930 Albert Lee Pkwy, Winter Park, FL 32789
• 

  

  /30

  Est $733,077 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789
• 

  

  /37

  $169,000

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 219, Winter Park, FL 32789

  Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  2500 Lee Rd Unit 219, Winter Park, FL 32789
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  /2

  $1,600,000 Sold Dec 15, 2025

  825 Palmer Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft
  • Built 1953

  Last Sold Summary

  • 11% Below List Price
  • $485/SF
  • 87 Days On Market

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  825 Palmer Ave, Winter Park, FL 32789
• 

  

  /29

  Est $1,011,324 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

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

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789
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  /7

  $1,390,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  501 Lakeview Ave, Winter Park, FL 32789

  Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  501 Lakeview Ave, Winter Park, FL 32789
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  /2

  $1,800,000 Sold Oct 24, 2025

  1682 Arbor Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $610/SF
  • 16 Days On Market

  Current Estimated Value $1,767,811

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1682 Arbor Park Dr, Winter Park, FL 32789
• 

  

  /9

  Est $154,914 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit B103, Winter Park, FL 32789

  1695 Lee Rd Unit B103, Winter Park, FL 32789
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  /48

  $2,295,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft

  2412 Chantilly Ave, Winter Park, FL 32789

  Step into a world of modern elegance in this newly completed estate in the heart of Winter Park. Masterfully constructed, this five-bedroom residence with six full and one half baths spans over 4,500 square feet of luxurious design and comfort. From the moment you enter the soaring foyer, light pours through expansive windows that frame every angle of the open floor plan, creating a seamless

  Josh Hill THE AGENCY FL

  2412 Chantilly Ave, Winter Park, FL 32789
• 

  /2

  $550,000 Sold Nov 10, 2025

  2612 Lafayette Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,447 Sq Ft
  • Built 1956

  Last Sold Summary

  • 39% Below List Price
  • $225/SF
  • 573 Days On Market

  Last Listing Agent Maoline Herrera EXP REALTY LLC

  2612 Lafayette Ave, Winter Park, FL 32789
• 

  /2

  Est $249,079 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

  1250 S Denning Dr Unit 105, Winter Park, FL 32789
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  /6

  $1,550,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,164 Sq Ft

  1523 Miller Ave, Winter Park, FL 32789

  Under Construction. UNDER CONSTRUCTION. This 3,164 sq ft new construction home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area

  Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

  1523 Miller Ave, Winter Park, FL 32789
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  /2

  $1,063,303 Sold Dec 10, 2025

  1835 Karolina Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft
  • Built 2025

  Last Sold Summary

  • 23% Above List Price
  • $399/SF
  • 50 Days On Market

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  1835 Karolina Ave, Winter Park, FL 32789
• 

  

  /33

  Est $1,207,261 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789
• 

  

  /30

  $509,900

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  240 Orange Terrace Dr, Winter Park, FL 32789

  MOVE IN READY - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to offer.Fully renovated in 2021—including new

  Susan Pinnock A+ REALTY PROFESSIONALS, INC

  240 Orange Terrace Dr, Winter Park, FL 32789
• 

  /2

  $312,000 Sold Oct 16, 2025

  1921 Dartmouth Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1956

  Last Sold Summary

  • 16% Below List Price
  • $316/SF
  • 76 Days On Market

  Current Estimated Value $316,689

  Last Listing Agent Pat Hancock THOMAS LYNNE REALTY GROUP LLC

  1921 Dartmouth Ave, Winter Park, FL 32789
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  /28

  Est $180,819 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 211, Winter Park, FL 32789

  2500 Lee Rd Unit 211, Winter Park, FL 32789

Showing Results 401 - 440, Page 11 of 18