Homes in ZIP Code 32789

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  /2

  Est $1,796,396

  Not Listed For Sale

  1755 Grinnell Terrace, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 4,021 Sq Ft
  • Built 2009

  1755 Grinnell Terrace, Winter Park, FL 32789

  Last Sold Summary

  • 142 Days On Market
• 

  

  

  /23

  $2,829,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,018 Sq Ft

  609 S Phelps Ave, Winter Park, FL 32789

  Under Construction. Under Construction. A timeless expression of modern luxury, this exceptional new residence by LUIH Luxury Homes brings together thoughtful architecture, designer finishes, and refined craftsmanship in one of Winter Park’s most desirable neighborhoods. Situated on an oversized homesite along a quiet, tree-lined street, the home offers approximately 4,018 square feet of

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  609 S Phelps 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 $561,029

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1875 Staunton Ave, Winter Park, FL 32789
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  /36

  Est $624,413

  Not Listed For Sale

  670 Osceola Ave Unit 670, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 1983

  670 Osceola Ave Unit 670, Winter Park, FL 32789

  Last Sold Summary

  • 152 Days On Market
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  /52

  $224,999

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool &

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
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  /2

  $2,100,000

  Sold Jul 07, 2025

  104 Cortland Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1926

  Last Sold Summary

  • 12% Below List Price
  • $660/SF
  • 36 Days On Market

  Current Estimated Value $2,097,262

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

  104 Cortland Ave, Winter Park, FL 32789
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  /2

  Est $1,589,309

  Not Listed For Sale

  660 Arjay Way, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,237 Sq Ft
  • Built 1957

  660 Arjay Way, Winter Park, FL 32789

  Last Sold Summary

  • 133 Days On Market
• 

  

  /58

  $2,095,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  1398 Grove Terrace, Winter Park, FL 32789

  Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a

  Liz Jones ORANGE SLICE PROPERTIES

  1398 Grove Terrace, Winter Park, FL 32789
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  /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 $614,190

  Last Listing Agent David Gallup RE/MAX 200 REALTY

  1137 Oaks Blvd, Winter Park, FL 32789
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  /38

  Est $1,281,382

  Not Listed For Sale

  401 N Interlachen Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft
  • Built 1971

  401 N Interlachen Ave, Winter Park, FL 32789

  Last Sold Summary

  • 39 Days On Market
• 

  

  /34

  $284,900

  $45K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you

  Mathew Kelly TURN-KEY MOVES REALTY

  311 E Morse Blvd Unit 7-19, 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 $3,139,915

  Last Listing Agent Mauro Costa VISTA CAY REALTY COMPANY

  2020 Via Tuscany, Winter Park, FL 32789
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  /2

  Est $2,937,250

  Not Listed For Sale

  266 Chase Ave, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,088 Sq Ft
  • Built 1930

  266 Chase Ave, Winter Park, FL 32789

  Last Sold Summary

  • 30 Days On Market
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  /32

  $1,299,000

  New Construction Open Sun 2PM - 4PM $126K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  1870 Walker Ave, Winter Park, FL 32789

  This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas,

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1870 Walker Ave, Winter Park, FL 32789
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  /2

  $749,000

  Sold Aug 01, 2025

  1429 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,939 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $386/SF
  • 63 Days On Market

  Current Estimated Value $761,130

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  1429 Indiana Ave, Winter Park, FL 32789
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  /67

  Est $828,091

  Not Listed For Sale

  1131 Oxford Rd, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,608 Sq Ft
  • Built 1925

  1131 Oxford Rd, Winter Park, FL 32789

  Last Sold Summary

  • 31 Days On Market
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  /27

  $1,195,000

  $255K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 2,096 Sq Ft

  1500 Harris Cir, Winter Park, FL 32789

  Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1500 Harris Cir, 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 $829,713

  Last Listing Agent Michael Domi COMPASS FLORIDA LLC

  734 Maryland Ave, Winter Park, FL 32789
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  /55

  Est $2,588,000

  Not Listed For Sale

  1444 Grove Terrace, Winter Park, FL 32789

  • 6 Beds
  • 7 Baths
  • 4,442 Sq Ft
  • Built 2024

  1444 Grove Terrace, Winter Park, FL 32789

  Last Sold Summary

  • 27 Days On Market
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  /37

  $1,375,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  266 W Lyman Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart of Winter Park, offering the perfect blend of luxury and convenience. Whether you're looking for a full-time residence or a lock-and-leave property, this home delivers on every level. Designed with entertaining in mind, the open-concept layout creates a seamless flow

  Larry Lanpher MAROON REALTY GROUP LLC

  266 W Lyman Ave, Winter Park, FL 32789

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