Winter Park, FL Homes

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  $750,000

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  2612 Roxbury Rd, Winter Park, FL 32789

  SELLER MOTIVATED!! CONTRIBUTING $10,000 FLEX CASH!!! Potential of an extra one percent for closing costs, just ask your agent!!A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
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  /21

  $1,850 per month

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

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
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  $450,000 Sold Mar 06, 2025

  236 N Ranger Blvd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 8 Days On Market

  Current Estimated Value $565,973

  Last Listing Agent Alexander Young FOLIO REALTY LLC

  236 N Ranger Blvd, Winter Park, FL 32792
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792
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  /52

  $1,195,000

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789

  Welcome to The Cloisters, an exclusive lakefront enclave located in the heart of Winter Park, offering a rare combination of walkability, lakefront serenity, and bespoke design. Situated on the fourth floor, this fully reimagined residence is the result of a meticulous, full-scale renovation by W Designs LTD and has never been occupied. A striking entry sets the tone with a black-and-white

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789
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  /11

  $2,395 per month

  • 3 Beds
  • 2.5 Baths
  • 1,518 Sq Ft
  • House for Rent

  3107 Ash Park Loop, Winter Park, FL 32792

  Discover comfort and charm in this beautifully maintained 3-bedroom, 2-bath home located in the desirable Winter Park area. Boasting bright, naturally lit rooms and a spacious layout, this home is perfect for both relaxing and entertaining. Enjoy the serenity of a big backyard—ideal for gathering or simply enjoying the Florida sunshine. Conveniently situated near top-rated schools, shopping,

  Justin V LaManna HOMEVEST REALTY

  3107 Ash Park Loop, Winter Park, FL 32792
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  $324,000 Sold Jun 17, 2025

  1920 Magnolia Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1986

  Last Sold Summary

  • $242/SF

  Current Estimated Value $328,442

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1920 Magnolia Ave, Winter Park, FL 32792
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  /2

  Est $207,380 Not Listed For Sale

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

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792
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  $250,000

  • 2 Beds
  • 1 Bath
  • 818 Sq Ft

  1996 Indiana Ave, Winter Park, FL 32789

  Investors/builders, here is your next project. This oversized lot (6,957 sf) on a dead-end street is perfect for our next investment opportunity. With a Winter Park address, this lot contains a spectacular location. In the bustling area of College Park/Winter Park, this lot sits near the main campus of Advent Health, the museums of Orlando, shopping on Park Avenue, and fine dining at the new

  Herb Baird, Jr MARKET CONNECT REALTY LLC

  1996 Indiana Ave, Winter Park, FL 32789
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  /29

  $4,995 per month

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  Nestled within the exclusive 400 West enclavean intimate community of just nine residences just moments from Park Avenuethis modern townhome seamlessly combines superior craftsmanship, elegant interiors, and outstanding walkability. Entering through either the private garage or the charming garden-style front path, you're welcomed into a luminous, open-concept main level that emphasizes comfort,

  438 W Swoope Ave, Winter Park, FL 32789
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  $850,000 Sold Dec 27, 2024

  1621 Lasbury Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,267 Sq Ft
  • Built 1986

  Last Sold Summary

  • 22% Below List Price
  • $375/SF
  • 211 Days On Market

  Current Estimated Value $913,476

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1621 Lasbury Ave, Winter Park, FL 32789
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  /2

  Est $426,124 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,214 Sq Ft

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /50

  $1,375,000

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The

  Christina Fata REAL BROKER, LLC

  2015 Summerfield Rd, Winter Park, FL 32792
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  /52

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  1730 Oneco Ave, Winter Park, FL 32789

  Just completed full interior home renovation and ready to lease for first time on the Flowered Streets of Winter Park. This 3/2 offers an exceptional opportunity in Winter Park 32789 and features a 3/2 split floorplan, all new luxury vinyl wide plank flooring and new doors/door hardware throughout home. The sleek brand new kitchen features stainless appliances, Quartz countertops, and chic 1/2

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1730 Oneco Ave, Winter Park, FL 32789
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  /2

  $485,000 Sold Aug 18, 2025

  1921 Japonica Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 1971

  Last Sold Summary

  • $223/SF
  • 11 Days On Market

  Current Estimated Value $481,344

  Last Listing Agent Jose Gabriel Rodriguez COLDWELL BANKER RESIDENTIAL RE

  1921 Japonica Rd, Winter Park, FL 32792
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  /2

  Est $591,554 Not Listed For Sale

  • 18 Beds
  • 18 Baths
  • 1,852 Sq Ft

  875 Miles Ave Unit 4, Winter Park, FL 32789

  875 Miles Ave Unit 4, Winter Park, FL 32789
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  /25

  $284,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2335 Inagua Way, Winter Park, FL 32792

  Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

  Marion McGrath ABSOLUTE REALTY GROUP, LLC

  2335 Inagua Way, Winter Park, FL 32792
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  $2,115 per month

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft
  • House for Rent

  7413 Fieldcrest Ave, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2259.90. That covers your base rent, $2115.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7413 Fieldcrest Ave, Winter Park, FL 32792
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  $335,000 Sold Oct 31, 2025

  3525 Baxter Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Above List Price
  • $215/SF
  • 5 Days On Market

  Last Listing Agent Ashley Fisak COLDWELL BANKER RESIDENTIAL RE

  3525 Baxter Dr, Winter Park, FL 32792
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  Est $435,106 Not Listed For Sale

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

  2931 Clever Ln, Winter Park, FL 32792

  2931 Clever Ln, Winter Park, FL 32792
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  $409,999 Pending

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

  5563 Garden Grove Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Lovely pool home in the desirable community of Winter Park, conveniently located near shopping, medical offices, and UCF.Freshly painted inside and out, this home features a kitchen with tile and granite, and all appliances included. The kitchen opens to the great room, which offers easy-care tile flooring throughout the main living areas. Enjoy the

  Anne Jones COLDWELL BANKER HUBBARD HANSEN

  5563 Garden Grove Cir, Winter Park, FL 32792
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  $2,275 per month

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft
  • Townhouse for Rent

  3055 Autumn Ct, Winter Park, FL 32792

  Welcome to this charming and modern village-style home ideally located near Winter Park, top-rated schools, major roads, shopping, and restaurants. This residence features an open-concept floor plan with stainless steel appliances, laminate flooring in the main living areas, and cozy carpet in the bedrooms. The fenced backyard provides the perfect space for outdoor enjoyment and privacy. Modern

  Elias Kilci AGENT TRUST REALTY CORPORATION

  3055 Autumn Ct, Winter Park, FL 32792
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  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,102,207

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  /2

  Est $446,269 Not Listed For Sale

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

  2939 Clever Ln, Winter Park, FL 32792

  2939 Clever Ln, Winter Park, FL 32792
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  /30

  $679,000

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2087 Laurelwood Way, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between

  Brian Rotenberger COMPASS FLORIDA LLC

  2087 Laurelwood Way, Winter Park, FL 32792
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  /15

  $2,330 per month

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • House for Rent

  1821 Carrigan Ave, Winter Park, FL 32789

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2474.90. That covers your base rent, $2330.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1821 Carrigan Ave, Winter Park, FL 32789
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  $175,000 Sold Jan 27, 2025

  7420 Woodburn Ct Unit 25, Winter Park, FL 32792

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

  Last Sold Summary

  • 12% Below List Price
  • $152/SF
  • 93 Days On Market

  Current Estimated Value $191,238

  Last Listing Agent Wendy Cheng INTERNATIONAL NETWORK REALTY

  7420 Woodburn Ct Unit 25, Winter Park, FL 32792
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  3065 George Mason Ave Unit B, Winter Park, FL 32792

  3065 George Mason Ave Unit B, Winter Park, FL 32792
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  $916,050 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft

  Lot #21 Karolina Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a thoughtfully designed masterpiece, blending elegant country charm with the comfort and functionality today’s homeowners crave. One of three consecutive custom builds — each with its own

  Laura Hope COMPASS FLORIDA LLC

  Lot #21 Karolina Ave, Winter Park, FL 32789
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  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Condo for Rent

  616 Montego Bay Ct Unit S, Winter Park, FL 32792

  Welcome to this charming 2-bedroom, 2-bath home located in the heart of Winter Park! This beautifully maintained residence offers 1,037 square feet of comfortable living space with a bright and open layout. Enjoy a spacious living room, a functional kitchen with plenty of cabinet space, and cozy bedrooms designed for comfort and privacy. The home also features a private patio—perfect for relaxing

  Carlos Ramirez AGENT TRUST REALTY CORPORATION

  616 Montego Bay Ct Unit S, Winter Park, FL 32792
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  $699,000 Sold Jun 30, 2025

  1632 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $394/SF
  • 110 Days On Market

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
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  Est $216,127 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  608 Montego Bay Ct Unit S, Winter Park, FL 32792
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  /25

  $475,000

  • 2 Beds
  • 2 Baths
  • 760 Sq Ft

  875 W Lyman Ave, Winter Park, FL 32789

  Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of only a handful of lots to have a view of

  Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

  875 W Lyman Ave, Winter Park, FL 32789
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  /45

  $2,724 per month

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Condo for Rent

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

  Feel at home in this cozy and inviting 2-bedroom, 1-bathroom home, ideal for couples, small families, or solo travelers looking to explore Central Florida.This charming property offers a full kitchen with stainless steel appliances, a full bathroom with a walk-in shower, and a free washer and dryer. There is also an outdoor sitting area.Free parking is available for up to two vehicles. A

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
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  $689,500 Sold Jul 19, 2025

  1129 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $394/SF
  • 21 Days On Market

  Current Estimated Value $668,146

  Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

  1129 Golfside Dr, Winter Park, FL 32792
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  Est $1,308,497 Not Listed For Sale

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

  3629 Midiron Dr, Winter Park, FL 32789

  3629 Midiron Dr, Winter Park, FL 32789
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  $739,900 Pending

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

  1909 Cyril Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. BEAUTIFULLY RENOVATED CUSTOM HOME IN WINTER PARK. THIS STUNNING 3 BEDROOM 3.5 BATH CUSTOM HOME BLENDS STYLE, COMFORT, AND CONVENIENCE IN ONE OF WINTER PARK'S MOST DESIRABLE NEIGHBORHOODS. ENJOY A NEW ROOF, RECENTLY RENOVATED KITCHEN AND MAIN LIVING AREA, CATHEDRAL CEILINGS THAT FILL THE HOME WITH NATURAL LIGHT. THE OPEN FLOOR PLAN IS PERFECT FOR FAMILY

  James Hurst, II JAMES F. HURST II, BROKER

  1909 Cyril Ct, Winter Park, FL 32792
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  /37

  $3,400 per month

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Condo for Rent

  690 Osceola Ave Unit 203, Winter Park, FL 32789

  Experience upscale living in this stunning 2-bedroom, 2-bath luxury condo featuring gorgeous raw wood floors in this breathtaking lakefront complex situated on the shores of the Winter Park Chain of Lakes and walking distance to Park Avenue, shopping, museums, restaurants and parks. The open-concept layout offers a seamless flow between the living, dining, and kitchen areas—perfect for both

  Nancy Bhavsar ANNE ROGERS REALTY GROUP INC

  690 Osceola Ave Unit 203, Winter Park, FL 32789
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  $893,000 Sold Oct 09, 2025

  2890 Wild Ginger Ct, Winter Park, FL 32792

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft
  • Built 1993

  Last Sold Summary

  • 27% Below List Price
  • $262/SF
  • 78 Days On Market

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

  2890 Wild Ginger Ct, Winter Park, FL 32792
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  Est $756,863 Not Listed For Sale

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

  1477 Lone Feather Trail, Winter Park, FL 32792

  1477 Lone Feather Trail, Winter Park, FL 32792

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