Winter Park, FL Homes

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  $1,725,000 Sold Mar 05, 2026

  617 Worthington Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,533 Sq Ft
  • Built 2018

  Last Sold Summary

  • 13% Below List Price
  • $488/SF
  • 215 Days On Market

  Current Estimated Value $1,745,870

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  617 Worthington Dr, Winter Park, FL 32789
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  /23

  Est $282,727 Not Listed For Sale

  3197 Crown Jewel Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Built 2019

  3197 Crown Jewel Ct, Winter Park, FL 32792

  Last Sold Summary

  • 17% Below List Price
  • $241/SF
  • 23 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Priscilla Chan FLORIDA REALTY INVESTMENTS
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  /47

  $6,450,000

  • 5 Beds
  • 5.5 Baths
  • 5,476 Sq Ft

  1200 Via Salerno, Winter Park, FL 32789

  Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1200 Via Salerno, Winter Park, FL 32789
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  $415,000 Sold Jun 10, 2025

  3063 Ash Park Loop, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $248/SF
  • 23 Days On Market

  Current Estimated Value $409,535

  Last Listing Agent Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

  3063 Ash Park Loop, Winter Park, FL 32792
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  /32

  Est $618,327 Not Listed For Sale

  1178 Wildmeadow Run, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 2021

  1178 Wildmeadow Run, Winter Park, FL 32792

  Last Sold Summary

  • 3% Above List Price
  • $340/SF
  • 6 Days On Market

  Last Sold Price $601,000

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
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  /9

  $165,000

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792

  Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community. 1,031 sq. ft. newer roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to shopping and dining, 15 minutes to

  Abranette Lopez LPT REALTY, LLC

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792
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  /2

  $385,000 Sold Nov 12, 2025

  4421 Steed Terrace, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $215/SF
  • 209 Days On Market

  Current Estimated Value $406,286

  Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

  4421 Steed Terrace, Winter Park, FL 32792
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  /18

  Not Listed For Sale

  1411 Miller Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft
  • Built 2023

  1411 Miller Ave, Winter Park, FL 32789

  Last Sold Summary

  • $430/SF
  • 30 Days On Market

  Last Sold Price $779,900

  Last Listing Agent Kimberly Griffin RE/MAX
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  /5

  $724,900

  • Land
  • 0.54 Acre
  • $1,342,407 per Acre

  1034 Turner Rd, Winter Park, FL 32789

  Rare opportunity to build your dream home on the shores of highly sought-after Lake Bell in the desirable 32789 Winter Parkzip code. This exceptional waterfront parcel offers direct access to one of the area’s beautiful skiable lakes, providing theperfect setting for luxury lakefront living. The current owners have already completed significant groundwork, includingprofessionally

  Parker Blanchard OLDE TOWN BROKERS INC

  1034 Turner Rd, Winter Park, FL 32789
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  $665,000 Sold Jun 18, 2025

  2817 Prince John Rd, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,183 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 37 Days On Market

  Current Estimated Value $651,410

  Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

  2817 Prince John Rd, Winter Park, FL 32792
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  /2

  Est $96,126 Not Listed For Sale

  3035 George Mason Ave Unit 18, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 549 Sq Ft
  • Built 1974

  3035 George Mason Ave Unit 18, Winter Park, FL 32792

  Last Sold Summary

  • 17% Below List Price
  • $211/SF
  • 196 Days On Market

  Last Sold Price $116,000

  Last Listing Agent Margarita Morales OLYMPUS EXECUTIVE REALTY INC
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  $665,000

  • 5 Beds
  • 3.5 Baths
  • 3,152 Sq Ft

  5275 Pine Lily Cir, Winter Park, FL 32792

  Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has abeautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 squarefeet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that

  Kathy Williams REAL BROKER, LLC

  5275 Pine Lily Cir, Winter Park, FL 32792
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  $2,835,000 Sold Nov 24, 2025

  255 Stirling Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,635 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $780/SF
  • 25 Days On Market

  Current Estimated Value $2,831,194

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

  255 Stirling Ave, Winter Park, FL 32789
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  /18

  Est $440,321 Not Listed For Sale

  1916 Erudite Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  1916 Erudite Way, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $262/SF
  • 146 Days On Market

  Last Sold Price $466,790

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /18

  $1,500,000 Under Contract

  • 4,056 Sq Ft

  1903 S Lakemont Ave, Winter Park, FL 32792

  Location, location, location! This is an amazing opportunity to build/renovate on a premier lakefront lot in the charming and upscale Winter Park neighborhood of Orlando, Florida. Located on Lake Spier and across the street from the beautiful Baldwin Park, this exceptional-almost one acre property-includes six 1/1 units. This prime property is minutes from award winning restaurants, sidewalk

  Maria Tenner Platinum Properties Int'l Inc.

  1903 S Lakemont Ave, Winter Park, FL 32792
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  $627,000 Sold Mar 23, 2026

  428 Selkirk Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,782 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $352/SF
  • 103 Days On Market

  Current Estimated Value $624,915

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  428 Selkirk Dr, Winter Park, FL 32792
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  Est $529,097 Not Listed For Sale

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft
  • Built 1987

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $342/SF
  • 104 Days On Market

  Last Sold Price $570,000

  Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES
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  /22

  $400,000 Pending

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

  1028 Lake Bell Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. WELCOME HOME to this rare Winter Park opportunity! Live minutes away Park Avenue in one of Winter Park’s most convenient hidden pockets. Rarely does a home become available on this quiet cul-de-sac directly across from Lake Bell — and this charming 2 bedroom, 2 bathroom bungalow delivers on location, character, and updates. Less than 5 minutes to Whole

  Maria Nunez COMPASS FLORIDA LLC

  1028 Lake Bell Dr, Winter Park, FL 32789
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  $1,430,000 Sold Nov 10, 2025

  1011 Mckean Cir, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1955

  Last Sold Summary

  • $641/SF
  • 0 Days On Market

  Current Estimated Value $1,454,862

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  1011 Mckean Cir, Winter Park, FL 32789
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  /2

  Est $374,760 Not Listed For Sale

  7632 Aloma Pines Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2018

  7632 Aloma Pines Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $198/SF
  • 129 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Dayanne Rivera PREFERRED REAL ESTATE BROKERS
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  /65

  $4,750,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,850 Sq Ft

  1150 Via Salerno, Winter Park, FL 32789

  In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Designed and developed by Steve and Jodie Warrick Konold of Scout & Co., the 3,850 sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway and

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1150 Via Salerno, Winter Park, FL 32789
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  $439,900 Sold Jul 22, 2025

  1945 Bering Ave, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft
  • Built 1958

  Last Sold Summary

  • $279/SF
  • 6 Days On Market

  Current Estimated Value $444,765

  Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

  1945 Bering Ave, Winter Park, FL 32789
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  Est $454,751 Not Listed For Sale

  2445 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft
  • Built 2018

  2445 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $229/SF
  • 41 Days On Market

  Last Sold Price $460,000

  Last Listing Agent Karen Wheeler RE/MAX CENTRAL REALTY
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  /23

  $380,000

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft

  765 Baffie Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Affordable 2-bedroom, 1-bath home in Winter Park with easy access to Downtown Winter Park, College Park, and the Dubsdread community. This spotless residence features fresh interior paint, an updated kitchen with granite countertops, a beautifully renovated shower bath, and continuous travertine flooring throughout for a clean, cohesive look. Major

  Anne Rogers ANNE ROGERS REALTY GROUP INC

  765 Baffie Ave, Winter Park, FL 32789
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  $385,000 Sold Feb 09, 2026

  5563 Garden Grove Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $268/SF
  • 36 Days On Market

  Current Estimated Value $407,893

  Last Listing Agent Anne Jones COLDWELL BANKER HUBBARD HANSEN

  5563 Garden Grove Cir, Winter Park, FL 32792
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  Est $2,032,522 Not Listed For Sale

  2156 Talman Ct, Winter Park, FL 32792

  • 5 Beds
  • 8 Baths
  • 7,762 Sq Ft
  • Built 2008

  2156 Talman Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $264/SF
  • 32 Days On Market

  Last Sold Price $2,050,000

  Last Listing Agent Abby Nguyen AGENCYONE
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  $779,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,778 Sq Ft

  5233 Lake Howell Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to 5233 Lake Howell Road, a thoughtfully updated residence offering modern finishes, extensive upgrades, and a private backyard retreat designed for both everyday living and effortless entertaining.Inside, white porcelain tile flooring and recessed lighting create a bright, cohesive atmosphere throughout the main living spaces. Expansive

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  5233 Lake Howell Rd, Winter Park, FL 32792
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  $2,575,000 Sold Oct 20, 2025

  1341 Place Picardy, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,469 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $576/SF
  • 95 Days On Market

  Current Estimated Value $2,552,810

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
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  /20

  Est $465,701 Not Listed For Sale

  2448 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2020

  2448 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 5% Above List Price
  • $214/SF
  • 89 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
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  $669,000 Pending

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

  681 Overspin Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Well-maintained and beautifully upgraded, this exceptional home is located in the highly desirable Dubsdread Heights neighborhood of Winter Park. Offering 4 bedrooms and 2.5 baths (with the 4th bedroom downstairs currently used as an office/den), every detail of this residence has been thoughtfully enhanced. Recent major upgrades include a new roof (2024),

  Gail Higley RE/MAX SELECT GROUP

  681 Overspin Dr, Winter Park, FL 32789
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  $435,000 Sold Aug 31, 2025

  2209 Fairglenn Way, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $215/SF
  • 54 Days On Market

  Current Estimated Value $440,485

  Last Listing Agent Benjamin Benami CHARLES RUTENBERG REALTY ORLANDO

  2209 Fairglenn Way, Winter Park, FL 32792
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  /22

  Est $186,025 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

  • 22% Below List Price
  • $243/SF
  • 4 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Tyler Reik KELLER WILLIAMS WINTER PARK
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  /89

  $1,799,999

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  Listed at APPRAISED VALUE **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
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  $714,000 Sold Feb 25, 2026

  1449 Pelican Bay Trail, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,928 Sq Ft
  • Built 1982

  Last Sold Summary

  • $244/SF
  • 2 Days On Market

  Current Estimated Value $703,394

  Last Listing Agent Steven Ritz KELLER WILLIAMS WINTER PARK

  1449 Pelican Bay Trail, Winter Park, FL 32792
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  Est $741,377 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

  • 7% Above List Price
  • $197/SF
  • 18 Days On Market

  Last Sold Price $690,000

  Last Listing Agent Jeremy Seymour KELLER WILLIAMS ADVANTAGE REALTY
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  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,249 Sq Ft

  1750 Carollee Ln, Winter Park, FL 32789

  Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. In one of Winter Park’s established neighborhoods, residents enjoy access to top-rated schools, tree-lined streets, and proximity to Park Avenue’s renowned dining and shopping, as well as the area’s scenic Chain of Lakes. Originally built in 2012, this four-bedroom, 3.5-bath home offers over 3,200 square feet of thoughtfully

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1750 Carollee Ln, Winter Park, FL 32789
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  $242,000 Sold Oct 15, 2025

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $199/SF
  • 125 Days On Market

  Current Estimated Value $229,294

  Last Listing Agent Jessica Geer A+ REALTY PROFESSIONALS, INC

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
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  /28

  Est $255,667 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

  • 18% Below List Price
  • $193/SF
  • 77 Days On Market

  Last Sold Price $311,000

  Last Listing Agent Jin Li ACHIEVA REALTY, INC
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  $1,850,000

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft

  1560 Woodland Ave, Winter Park, FL 32789

  Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend! Set on a beautifully landscaped 0.27-acre lot along Winter Park’s iconic tree lined, brick paved streets, this custom 5-bedroom, 4.5-bathroom residence with an office, a gym and attached in-law suite

  Chris Creegan CREEGAN GROUP

  1560 Woodland Ave, Winter Park, FL 32789
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  $535,000 Sold May 28, 2025

  4200 Bear Gully Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,945 Sq Ft
  • Built 2003

  Last Sold Summary

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

  Current Estimated Value $526,959

  Last Listing Agent Renee Killiri RED BIRD REALTY OF FLORIDA INC

  4200 Bear Gully Rd, Winter Park, FL 32792

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