Winter Park, FL Homes

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  $1,695,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  629 Country Club Dr, Winter Park, FL 32789

  Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views

  Randy Lazarus CLASSIC HOMES

  629 Country Club Dr, Winter Park, FL 32789
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  $2,595 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1128 Park Green Place, Winter Park, FL 32789

  Stylish Winter Park home available now! Split-plan, 3 bed, 2 bath layout with two car garage, fenced-in backyard with patio, and community pool with cabana. Pet-friendly (subject to deposit and approval). The master bedroom has trey ceilings and an en-suite bath with double vanity and double walk-in closets. Full-size washer and dryer, new A/C unit (2025) and fresh exterior paint (2025). Located

  1128 Park Green Place, Winter Park, FL 32789
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  $660,000 Sold May 23, 2025

  2732 Lion Heart Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 1962

  Last Sold Summary

  • $334/SF
  • 2 Days On Market

  Current Estimated Value $649,458

  Last Listing Agent Sue Grafton FANNIE HILLMAN & ASSOCIATES

  2732 Lion Heart Rd, Winter Park, FL 32792
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  /89

  Est $1,313,042 Not Listed For Sale

  3629 Midiron Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft
  • Built 2024

  3629 Midiron Dr, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $417/SF
  • 13 Days On Market

  Last Sold Price $1,355,000

  Last Listing Agent Amanda Wood RE/MAX
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  /26

  $189,000

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

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

  Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
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  $2,950 per month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
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  $685,000 Sold May 27, 2025

  1321 Medinah Ct, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,446 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $280/SF
  • 53 Days On Market

  Current Estimated Value $693,792

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792
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  /38

  Est $753,395 Not Listed For Sale

  1477 Lone Feather Trail, Winter Park, FL 32792

  • 5 Beds
  • 3.5 Baths
  • 2,894 Sq Ft
  • Built 2021

  1477 Lone Feather Trail, Winter Park, FL 32792

  Last Sold Summary

  • 3% Above List Price
  • $252/SF
  • 30 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Christopher Soucy REALTY ONE GROUP MVP
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  /28

  $445,000

  • 5 Beds
  • 3 Baths
  • 1,945 Sq Ft

  3642 Periwinkle Dr, Winter Park, FL 32792

  Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout,

  John Hwangbo HONEST REAL ESTATE COMPANY

  3642 Periwinkle Dr, Winter Park, FL 32792
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  /6

  $1,850 per month

  • 2 Beds
  • 2.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

  Close to Park Avenue Winter Park Restaurants and shopping near UCF and Full sail University also Rollins Colllege, Great Public schools. Close to the Orlando Airport and 30 minutes from Disney World and Universal Studios.

  2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792
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  $637,500 Sold Jan 16, 2026

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,951 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 149 Days On Market

  Current Estimated Value $637,523

  Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

  595 Huntington Ave Unit 4, Winter Park, FL 32789
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  /2

  Est $196,265 Not Listed For Sale

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

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

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $164/SF
  • 108 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Larry Ouellette MANA REAL ESTATE
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  $1,899,500 Open Sun 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  1840 Bryan Ave, Winter Park, FL 32789

  This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1840 Bryan Ave, Winter Park, FL 32789
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  /22

  $1,350 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792

  Great location in Winter Park! This 2-bedroom, 2-bath apartment offers comfortable living with easy access to everything you need. Open Parking in front and located close to Full Sail University, UCF, Valencia College, and major roads like University Blvd and SR-436 (Semoran Blvd). Enjoy being just minutes from shopping centers, grocery stores, coffee shops, and restaurants, including Publix,

  Julio Lopez JCL REALTY INC

  3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792
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  $400,000 Sold May 29, 2025

  5144 Goldenrod Place Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $273/SF
  • 36 Days On Market

  Current Estimated Value $398,228

  Last Listing Agent Rebecca Sparks C. APOLLO REALTY INC

  5144 Goldenrod Place Rd, Winter Park, FL 32792
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  Not Listed For Sale

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,079 Sq Ft
  • Built 1974

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  Last Sold Summary

  • $120/SF
  • 66 Days On Market

  Last Sold Price $130,000

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC
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  /16

  $154,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

  The Ultimate Winter Park is your every desire. Investment Potential, Student Sanctuary or just a long-awaited Life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within

  Kelly Flores COLDWELL BANKER REALTY

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
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  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • House for Rent

  1613 Winter Green Blvd, Winter Park, FL 32792

  Charming Single-Family Home in the Heart of Winter ParkWelcome home to this well-maintained 3-bedroom, 2-bath single-family residence located in a quiet, established Winter Park neighborhood. Enjoy the privacy of a detached home, abundant natural light, and a functional layout perfect for comfortable everyday living.The home features fresh, neutral interiors, updated bathrooms,

  1613 Winter Green Blvd, Winter Park, FL 32792
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  $1,250,000 Sold Dec 29, 2025

  359 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1979

  Last Sold Summary

  • $522/SF
  • 0 Days On Market

  Current Estimated Value $1,248,370

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  359 Beloit Ave, Winter Park, FL 32789
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  Est $452,978 Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  Unlisted Address

  Last Sold Summary

  • 3% Below List Price
  • $245/SF

  Last Sold Price $467,990

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  /42

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  1098 Wildmeadow Run, Winter Park, FL 32792

  In the gates of one of Winter Park’s most desirable communities, this elegant single-story residence offers an exceptional opportunity to experience refined Florida living in the sought-after enclave of Hawk’s Crest. Spanning more than 1,700 square feet, the home blends timeless architecture with a thoughtfully designed layout that balances comfort, style and functionality. From the moment you

  Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  1098 Wildmeadow Run, Winter Park, FL 32792
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  /18

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1148 Park Green Place, Winter Park, FL 32789

  Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

  Linda Baez DON ASHER & ASSOCIATES, INC.

  1148 Park Green Place, Winter Park, FL 32789
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  $468,470 Sold Jun 20, 2025

  1026 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 25 Days On Market

  Current Estimated Value $467,385

  Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, Winter Park, FL 32792
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  Est $439,075 Not Listed For Sale

  2838 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2838 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $237/SF
  • 8 Days On Market

  Last Sold Price $452,090

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  /29

  $635,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  218 Orange Terrace Dr, Winter Park, FL 32789

  Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new

  Arden Magee ANNE ROGERS REALTY GROUP INC

  218 Orange Terrace Dr, Winter Park, FL 32789
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  /15

  $2,900 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  5417 Ferrol Dr, Winter Park, FL 32792

  Beautifully Remodeled 3 Bed, 2 Bath Home Energy Efficient & Prime Location!Welcome to your dream rental! This stunning newly remodeled 3-bedroom, 2-bath home offers modern comfort with a touch of elegance. Featuring an open floor concept, the spacious living area is perfect for entertaining, complete with a cozy fireplace and abundant natural light from double-glazed windows.The

  5417 Ferrol Dr, Winter Park, FL 32792
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  $430,000 Sold Aug 08, 2025

  1006 Bradford Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $202/SF
  • 7 Days On Market

  Current Estimated Value $435,208

  Last Listing Agent Paul Giannotti TERZA REAL ESTATE

  1006 Bradford Dr, Winter Park, FL 32792
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  Est $220,080 Not Listed For Sale

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Built 1981

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • 17% Below List Price
  • $256/SF
  • 27 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Marina Gamundi KELLER WILLIAMS ADVANTAGE III
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  /11

  $630,000 Pending

  • Land
  • 0.31 Acre
  • $2,032,258 per Acre

  1860 Staunton Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Large double lot in the highly desirable Killarney Shores neighborhood of Winter Park. The property has already received county approval to revert to the original platting, subdivide into two 50' x 135' lots. Located just one block from Lake Killarney. This prime location is minutes from Park Avenue, College Park, and I-4, providing both convenience and

  Leighton Hope COMPASS FLORIDA LLC

  1860 Staunton Ave, Winter Park, FL 32789
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  $2,435 per month

  • 3 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • House for Rent

  1622 Arbor Park Dr, Winter Park, FL 32789

  Free 1/2 month's rent move in incentive! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room with plenty of natural light

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  1622 Arbor Park Dr, Winter Park, FL 32789
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  $390,000 Sold Feb 23, 2026

  1670 Clematis Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Below List Price
  • $278/SF
  • 81 Days On Market

  Current Estimated Value $375,356

  Last Listing Agent Gea Gomez LPT REALTY, LLC

  1670 Clematis Ln, Winter Park, FL 32792
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  Est $358,053 Not Listed For Sale

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1986

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Last Sold Summary

  • 16% Above List Price
  • $202/SF
  • 53 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP
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  $124,900

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E204, Winter Park, FL 32789

  Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

  Brandy Ray LOKATION

  1695 Lee Rd Unit E204, Winter Park, FL 32789
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  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792

  Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792
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  $1,595,000 Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,576,017

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
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  Est $317,552 Not Listed For Sale

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1980

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  Last Sold Summary

  • 19% Below List Price
  • $276/SF
  • 6 Days On Market

  Last Sold Price $394,000

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES
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  /55

  $1,500,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,281 Sq Ft

  246 Palmer Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  246 Palmer Ave, Winter Park, FL 32789
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  $702,000 per month

  • Property for Rent

  7839 University Garden Dr, Winter Park, FL 32792

  Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417,

  Shettle Huynh FLORIDA REALTY INVESTMENTS

  7839 University Garden Dr, Winter Park, FL 32792
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  $749,000 Sold Aug 13, 2025

  627 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,509 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $299/SF
  • 52 Days On Market

  Current Estimated Value $748,728

  Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

  627 Darcey Dr, Winter Park, FL 32792
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  /18

  Est $442,036 Not Listed For Sale

  2786 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2786 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • $233/SF
  • 7 Days On Market

  Last Sold Price $444,190

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

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