Winter Park, FL Homes

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  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,986 Sq Ft

  2299 Via Tuscany, Winter Park, FL 32789

  Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes.

  Vincent Scarlatos CORCORAN PREMIER REALTY

  2299 Via Tuscany, Winter Park, FL 32789
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  $1,850,000 Sold Dec 15, 2025

  419 W Morse Blvd, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $611/SF
  • 0 Days On Market

  Current Estimated Value $1,860,758

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

  419 W Morse Blvd, Winter Park, FL 32789
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  /22

  Est $198,416 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  Last Sold Summary

  • 17% Below List Price
  • $243/SF
  • 4 Days On Market

  • Last Sold Price $240,000
  • Aug 17, 2023

  Last Listing Agent Tyler Reik KELLER WILLIAMS WINTER PARK
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  /24

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,610 Sq Ft

  814 Densmore Dr, Winter Park, FL 32792

  Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home.Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for

  Liz Jones ORANGE SLICE PROPERTIES

  814 Densmore Dr, Winter Park, FL 32792
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  $470,000 Sold Aug 21, 2025

  2920 Abbey Ct, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,035 Sq Ft
  • Built 1964

  Last Sold Summary

  • 6% Below List Price
  • $231/SF
  • 2 Days On Market

  Current Estimated Value $572,804

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2920 Abbey Ct, Winter Park, FL 32792
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  /77

  Est $758,819 Not Listed For Sale

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft
  • Built 2014

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  Last Sold Summary

  • 10% Above List Price
  • $197/SF
  • 18 Days On Market

  • Last Sold Price $690,000
  • Aug 23, 2023

  Last Listing Agent Jeremy Seymour KELLER WILLIAMS ADVANTAGE REALTY
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  /25

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1807 Hammerlin Ave Unit G, Winter Park, FL 32789

  **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and

  Courtney Dietch ALL REAL ESTATE & INVESTMENTS

  1807 Hammerlin Ave Unit G, Winter Park, FL 32789
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  $280,000 Sold Jun 27, 2025

  2446 Lotafun Ave, Winter Park, FL 32789

  • Land
  • 7,405 Sq Ft
  • $1,647,059 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 123 Days On Market

  Current Estimated Value $284,333

  Last Listing Agent David Francetic COLDWELL BANKER REALTY

  2446 Lotafun Ave, Winter Park, FL 32789
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  Est $276,337 Not Listed For Sale

  7113 Swallow Run Unit 2, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 2011

  7113 Swallow Run Unit 2, Winter Park, FL 32792

  Last Sold Summary

  • 11% Below List Price
  • $193/SF
  • 77 Days On Market

  • Last Sold Price $311,000
  • Sep 18, 2023

  Last Listing Agent Jin Li ACHIEVA REALTY, INC
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  $1,890,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,953 Sq Ft

  640 Arjay Way, Winter Park, FL 32789

  Under contract-accepting backup offers. Motivated Sellers! Priced at $35,000 below recent Appraisal Price on this amazing oversized lot! Walk into this home with equity from the start! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless

  Farah Bloom KELLER WILLIAMS WINTER PARK

  640 Arjay Way, Winter Park, FL 32789
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  /2

  $684,000 Sold Dec 23, 2025

  1909 Cyril Ct, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 3,102 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Below List Price
  • $221/SF
  • 56 Days On Market

  Current Estimated Value $690,864

  Last Listing Agent James Hurst, II JAMES F. HURST II, BROKER

  1909 Cyril Ct, Winter Park, FL 32792
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  Est $446,495 Not Listed For Sale

  2748 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2023

  2748 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 5% Above List Price
  • $223/SF
  • 157 Days On Market

  • Last Sold Price $426,000
  • Feb 26, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  $490,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,378 Sq Ft

  958 Hanover Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Mother-in-Law suit attached with private entrance on a dead-end street with water view. Welcome to this beautifully remodeled home in the heart of Winter Park, offering the perfect blend of charm, privacy, and convenience. Situated at the end of a quiet street, this unique property provides exceptional privacy while showcasing peaceful views of nearby Lake

  Christopher Lyons AGILE GROUP REALTY

  958 Hanover Ave, Winter Park, FL 32789
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  $3,800,000 Sold Feb 24, 2026

  637 N Park Ave, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $897/SF
  • 24 Days On Market

  Current Estimated Value $3,476,043

  Last Listing Agent Whitney Johnson COLDWELL BANKER REALTY

  637 N Park Ave, Winter Park, FL 32789
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  /18

  Est $204,104 Not Listed For Sale

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Built 1983

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  Last Sold Summary

  • 15% Below List Price
  • $209/SF
  • 2 Days On Market

  • Last Sold Price $240,000
  • Jul 21, 2023

  Last Listing Agent John Goggin STOCKWORTH REALTY GROUP
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  $1,425,000

  • 4 Beds
  • 3.5 Baths
  • 2,170 Sq Ft

  1751 Goodrich Ave, Winter Park, FL 32789

  Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

  Stephanie Baldner EXP REALTY LLC

  1751 Goodrich Ave, Winter Park, FL 32789
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  $5,400,000 Sold Jul 14, 2025

  541 Virginia Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,725 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $1,143/SF
  • 152 Days On Market

  Current Estimated Value $5,253,998

  Last Listing Agent Keith Moore HOMEVEST REALTY

  541 Virginia Dr, Winter Park, FL 32789
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  Est $404,731 Not Listed For Sale

  7494 Betty St, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft
  • Built 2023

  7494 Betty St, Winter Park, FL 32792

  Last Sold Summary

  • 10% Below List Price
  • $305/SF
  • 52 Days On Market

  • Last Sold Price $450,000
  • Sep 22, 2023

  Last Listing Agent Douglas Herrold LIGHTHOUSE PROPERTY GRP INC
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  /19

  $510,000

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft

  2627 Ambergate Rd, Winter Park, FL 32792

  Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!Investors -- You will love the cash flow upside with this property.Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for

  Ryan Minadie COLDWELL BANKER REALTY

  2627 Ambergate Rd, Winter Park, FL 32792
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  $1,305,000 Sold Nov 05, 2025

  1600 Barcelona Way, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,014 Sq Ft
  • Built 1972

  Last Sold Summary

  • 12% Below List Price
  • $433/SF
  • 175 Days On Market

  Current Estimated Value $1,356,039

  Last Listing Agent Laura Ascenso CREEGAN GROUP

  1600 Barcelona Way, Winter Park, FL 32789

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