Homes in ZIP Code 32789

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  /2

  $600,000

  Sold Oct 17, 2025

  2812 Woodside Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Below List Price
  • $326/SF
  • 50 Days On Market

  Current Estimated Value $620,203

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  2812 Woodside Ave, Winter Park, FL 32789
• 

  

  /2

  Est $2,139,668

  Not Listed For Sale

  660 Osceola Ave Unit 104, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,632 Sq Ft
  • Built 1999

  660 Osceola Ave Unit 104, Winter Park, FL 32789

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  /81

  $1,875,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 3,127 Sq Ft

  1661 Laurel Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Set along the brick-lined streets of Charmont, one of Winter Park’s most coveted and established neighborhoods, 1661 Laurel Road presents a rare opportunity to own a home in an exceptional location just three houses from Lake Virginia. From the front yard, enjoy beautiful lake views and the timeless character of a neighborhood defined by mature trees,

  Carol van den Berg VAN DEN BERG REAL ESTATE GROUP

  1661 Laurel Rd, Winter Park, FL 32789
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  /2

  $400,000

  Sold Jun 24, 2026

  721 Dunbar St, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1950

  Last Sold Summary

  • $393/SF
  • 4 Days On Market

  Current Estimated Value $404,707

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  721 Dunbar St, Winter Park, FL 32789
• 

  

  /2

  Est $436,499

  Not Listed For Sale

  690 Osceola Ave Unit 308, Winter Park, FL 32789

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

  690 Osceola Ave Unit 308, Winter Park, FL 32789

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC
• 

  

  /3

  $4,325,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,853 Sq Ft

  250 W Reading Way, Winter Park, FL 32789

  Virtually Staged. Under Construction. Introducing THE READING RESIDENCE, an extraordinary NEW-CONSTRUCTION ESTATE by renowned luxury builder VIMARO HOMES, ideally situated at 250 WEST READING WAY IN WINTER PARK. Encompassing approximately 4,853 SQUARE FEET, WITH 5,922 TOTAL SQUARE FEET OF CONSTRUCTION, this FIVE-BEDROOM, FOUR-AND-ONE-HALF-BATH residence is a masterful expression of elevated

  Brian Mitnik RE/MAX 200 REALTY

  250 W Reading Way, Winter Park, FL 32789
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  /2

  $615,000

  Sold Jun 10, 2026

  1034 Turner Rd, Winter Park, FL 32789

  • Land
  • 23,522 Sq Ft
  • $1,138,889 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 77 Days On Market

  Current Estimated Value $629,494

  Last Listing Agent Parker Blanchard OLDE TOWN BROKERS INC

  1034 Turner Rd, Winter Park, FL 32789
• 

  

  /39

  Est $305,224

  Not Listed For Sale

  700 Melrose Ave Unit K3, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  700 Melrose Ave Unit K3, Winter Park, FL 32789

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE
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  /35

  $1,649,000

  Under Contract

  • 3 Beds
  • 3 Baths
  • 2,857 Sq Ft

  1200 Woodmere Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Picturesque and beautifully appointed, this three-bedroom, three-bath residence is ideally situated along the sought-after Vias of Winter Park, a charming brick-paved street framed by mature landscaping and distinguished residences. Meticulously maintained grounds surround the home, with brick-paver walkways and inviting side and rear courtyards creating a

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1200 Woodmere Dr, Winter Park, FL 32789
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  /2

  $405,000

  Sold Apr 01, 2026

  1028 Lake Bell Dr, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • Built 1956

  Last Sold Summary

  • 1% Above List Price
  • $286/SF
  • 4 Days On Market

  Current Estimated Value $401,861

  Last Listing Agent Maria Nunez COMPASS FLORIDA LLC

  1028 Lake Bell Dr, Winter Park, FL 32789
• 

  /2

  Est $176,994

  Not Listed For Sale

  700 Melrose Ave Unit G34, Winter Park, FL 32789

  • Studio
  • 1 Bath
  • 624 Sq Ft
  • Built 1964

  700 Melrose Ave Unit G34, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Luly Cueto-Lauridsen PARK PLACE REAL ESTATE
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  /36

  $630,000

  • 6 Beds
  • 3 Baths
  • 3,145 Sq Ft

  2600 Euston Rd, Winter Park, FL 32789

  INVESTMENT OPPORTUNITY near Lake Killarney! This Winter Park gem offers a flexible layout perfect for multigenerational living, house-hacking, or rental income that can exceed the mortgage payment — true positive cash flow potential! Bright, spacious interiors with indep living areas for privacy & functionality. Large lot w/ mature landscaping, great for entertaining or tenant appeal. Recent

  Suheil Flores AROD PARTNERS REALTY

  2600 Euston Rd, Winter Park, FL 32789
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  /2

  $1,480,000

  Sold Sep 19, 2025

  1742 Barcelona Way, Winter Park, FL 32789

  • 5 Beds
  • 8 Baths
  • 3,626 Sq Ft
  • Built 1973

  Last Sold Summary

  • 18% Below List Price
  • $408/SF
  • 81 Days On Market

  Current Estimated Value $1,614,543

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1742 Barcelona Way, Winter Park, FL 32789
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  /44

  Est $2,248,479

  Not Listed For Sale

  200 S Interlachen Ave Unit 400, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,074 Sq Ft
  • Built 2001

  200 S Interlachen Ave Unit 400, Winter Park, FL 32789

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES
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  /49

  $1,377,500

  Open Sat 1PM - 4PM $173K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,578 Sq Ft

  1421 Chapman Cir, Winter Park, FL 32789

  Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next

  Kelly Price KELLY PRICE & COMPANY LLC

  1421 Chapman Cir, Winter Park, FL 32789
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  /2

  $365,000

  Sold May 13, 2026

  765 Baffie Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Below List Price
  • $390/SF
  • 32 Days On Market

  Current Estimated Value $365,087

  Last Listing Agent Anne Rogers ANNE ROGERS REALTY GROUP INC

  765 Baffie Ave, Winter Park, FL 32789
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  /2

  Est $2,484,654

  Not Listed For Sale

  315 E New England Ave Unit 30, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,130 Sq Ft
  • Built 2008

  315 E New England Ave Unit 30, Winter Park, FL 32789

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Michelle Daniels COLDWELL BANKER REALTY
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  /31

  $540,000

  $1K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  1261 Indiana Ave, Winter Park, FL 32789

  Welcome to easy living in the heart of Winter Park. This beautifully bright end unit townhome offers 1,660 square feet of comfortable, move-in-ready living space with no carpet throughout. New luxury vinyl plank flooring was installed in August 2026 and includes a one-year transferable workmanship warranty. The main level offers a versatile layout with two distinct living areas, including a

  Megan Cross FANNIE HILLMAN & ASSOCIATES

  1261 Indiana Ave, Winter Park, FL 32789
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  /2

  $975,000

  Sold Mar 25, 2026

  456 Carolina Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,615 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $604/SF
  • 9 Days On Market

  Current Estimated Value $982,390

  Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES

  456 Carolina Ave, Winter Park, FL 32789
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  /2

  Est $1,479,329

  Not Listed For Sale

  315 E New England Ave Unit 9, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,637 Sq Ft
  • Built 2007

  315 E New England Ave Unit 9, Winter Park, FL 32789

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Anna Lohr URBANISTA BROKERS
• 

  

  /18

  $135,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit A116, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and

  Bianca Pierre REAL BROKER, LLC

  1695 Lee Rd Unit A116, Winter Park, FL 32789
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  /2

  $475,000

  Sold Oct 14, 2025

  621 Symonds Ave, Winter Park, FL 32789

  • Land
  • 5,662 Sq Ft
  • $3,653,846 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 147 Days On Market

  Current Estimated Value $492,638

  Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

  621 Symonds Ave, Winter Park, FL 32789
• 

  

  /100

  Est $3,205,966

  Not Listed For Sale

  300 S Interlachen Ave Unit 303, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,355 Sq Ft
  • Built 2005

  300 S Interlachen Ave Unit 303, Winter Park, FL 32789

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC
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  /58

  $6,900,000

  Open Sun 2PM - 4PM

  • 6 Beds
  • 7 Baths
  • 6,396 Sq Ft

  1260 Alabama Dr, Winter Park, FL 32789

  Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue.From the

  Kelly Price KELLY PRICE & COMPANY LLC

  1260 Alabama Dr, Winter Park, FL 32789
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  /2

  $735,000

  Sold Jun 30, 2026

  738 S Pennsylvania Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,739 Sq Ft
  • Built 1925

  Last Sold Summary

  • $423/SF
  • 2 Days On Market

  Current Estimated Value $760,164

  Last Listing Agent Justin Jodha COMPASS FLORIDA LLC

  738 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /24

  Est $226,393

  Not Listed For Sale

  1250 S Denning Dr Unit 126, Winter Park, FL 32789

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

  1250 S Denning Dr Unit 126, Winter Park, FL 32789

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Shahram Sondi SHAHRAM SONDI + CO.
• 

  

  /45

  $2,190,000

  • 4 Beds
  • 3 Baths
  • 3,463 Sq Ft

  1803 Barker Dr, Winter Park, FL 32789

  A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury

  Tiffany Score Denovo Realty

  1803 Barker Dr, Winter Park, FL 32789
• 

  /2

  $245,000

  Sold Jul 21, 2026

  700 Melrose Ave Unit K25, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft
  • Built 1964

  Last Sold Summary

  • $311/SF
  • 4 Days On Market

  Current Estimated Value $238,221

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit K25, Winter Park, FL 32789
• 

  /2

  Est $174,059

  Not Listed For Sale

  1250 S Denning Dr Unit 108, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 108, Winter Park, FL 32789

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Cleve Loveland LOVELAND PROPERTIES
• 

  

  /39

  $1,775,000

  $75K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,112 Sq Ft

  101 S New York Ave Unit 311, Winter Park, FL 32789

  Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort.Immediately captivating, the light-filled open floor plan showcases stunning new

  Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  101 S New York Ave Unit 311, Winter Park, FL 32789
• 

  /2

  $675,000

  Sold Aug 12, 2026

  1622 Arbor Park Dr, Winter Park, FL 32789

  • Land
  • 7,840 Sq Ft
  • $3,750,000 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 14 Days On Market

  Current Estimated Value $711,180

  Last Listing Agent Dawn Romance FANNIE HILLMAN & ASSOCIATES

  1622 Arbor Park Dr, Winter Park, FL 32789
• 

  

  /31

  Est $1,118,560

  Not Listed For Sale

  100 S Virginia Ave Unit 315, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,599 Sq Ft
  • Built 2009

  100 S Virginia Ave Unit 315, Winter Park, FL 32789

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
• 

  

  /22

  $154,900

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit A101, Winter Park, FL 32789

  Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

  Daniel Zheng CINO INTERNATIONAL INC

  1695 Lee Rd Unit A101, Winter Park, FL 32789
• 

  /2

  $2,755,000

  Sold Jun 25, 2026

  670 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 4,091 Sq Ft
  • Built 2016

  Last Sold Summary

  • 5% Below List Price
  • $673/SF
  • 18 Days On Market

  Current Estimated Value $2,749,999

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  670 Williams Dr, Winter Park, FL 32789
• 

  

  /34

  Est $1,413,625

  Not Listed For Sale

  101 S New York Ave Unit 309, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,966 Sq Ft
  • Built 2008

  101 S New York Ave Unit 309, Winter Park, FL 32789

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES
• 

  /2

  $1,319,950

  • 4 Beds
  • 5 Baths
  • 3,474 Sq Ft

  952 Moss Ln, Winter Park, FL 32789

  Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 4-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the

  Terry Connors MERIDIAN RESIDE

  952 Moss Ln, Winter Park, FL 32789
• 

  /2

  $669,000

  Sold Mar 26, 2026

  681 Overspin Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $301/SF
  • 34 Days On Market

  Current Estimated Value $680,592

  Last Listing Agent Gail Higley RE/MAX SELECT GROUP

  681 Overspin Dr, Winter Park, FL 32789
• 

  

  /22

  Est $1,734,091

  Not Listed For Sale

  101 S New York Ave Unit 304, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,118 Sq Ft
  • Built 2008

  101 S New York Ave Unit 304, Winter Park, FL 32789

  Last Sold Summary

  • 32 Days On Market

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

  

  /50

  $3,150,000

  $155K PRICE INCREASE

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

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

  Virtually Staged. Welcome to South Interlachen Place, an exceptional luxury townhome ideally positioned in the heart of downtown Winter Park. Just steps from Park Avenue, this sophisticated residence offers an unparalleled lifestyle defined by elegance, convenience, and access to the area’s finest dining, shopping, and cultural experiences. Thoughtfully designed with 3 bedrooms, 3 full bathrooms,

  Erin Legler CHARLES RUTENBERG REALTY ORLANDO

  125 S Interlachen Ave Unit 2, Winter Park, FL 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

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