Winter Park, FL Homes

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  $5,300,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,197 Sq Ft
  • House for Rent

  1518 Pinewood Dr, Winter Park, FL 32789

  Discover this delightful 2-bedroom, 1-bath bungalow perfectly situated at the intersection of Winter Park and College Park. This home offers convenient access to major hospitals and roadways, placing you just minutes away from downtown Orlando, 25 minutes from Disney World, 15 minutes from Universal Studios, and 20 minutes from MCO Airport. Enjoy nearby shopping and dining options within a

  1518 Pinewood Dr, Winter Park, FL 32789
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  $450,000 Sold Jul 22, 2025

  1624 Little Wren Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $195/SF
  • 23 Days On Market

  Current Estimated Value $456,062

  Last Listing Agent Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

  1624 Little Wren Ln, Winter Park, FL 32792
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  /27

  Est $168,822 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 759 Sq Ft

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

  603 Saint Johns Ct Unit S, Winter Park, FL 32792
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  $337,500

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  121 Stefanik Rd, Winter Park, FL 32792

  A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. This is a two bedroom and one bath in the front with a one bedroom one bath mother-in-law suite in the back, off of the laundry room with its own entrance as well. Main house has a large foyer and living room. Kitchen has beautiful cabinets and granite counter tops. Septic system was just replaced in September. Currently rented for $2,000

  Moe Mossa SAVVY AVENUE, LLC

  121 Stefanik Rd, Winter Park, FL 32792
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  /20

  $1,350 per month

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft
  • Condo for Rent

  4860 Tangerine Ave Unit 4860, Winter Park, FL 32792

  For Rent -- Immediate Move In!!!This 1 bedroom 1 bath condo is Now Available. No Carpet, Very Clean with updated Appliances. Located in the heart of Winter Park. The master bedroom is very spacious - there is a bed to use if you choose to. The community includes a pool and a Fitness Center. Very quiet neighborhood. Located within close distance to Valencia College, Rollins College and

  Kamla McGregor LPT REALTY, LLC

  4860 Tangerine Ave Unit 4860, Winter Park, FL 32792
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  $432,000 Sold May 08, 2025

  2472 Firstlight Way, Winter Park, FL 32792

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

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 53 Days On Market

  Current Estimated Value $441,299

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2472 Firstlight Way, Winter Park, FL 32792
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  Est $875,039 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  1403 Michigan Ave, Winter Park, FL 32789

  1403 Michigan Ave, Winter Park, FL 32789
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  /20

  $275,000

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 213, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Fully renovated two-bedroom, two-bath residence in the sought-after Mead Garden Condominium community. Spanning 908 square feet, this second-floor home offers a move-in-ready interior with a contemporary open-concept layout and elevated finishes throughout. The kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, a

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1250 S Denning Dr Unit 213, Winter Park, FL 32789
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  /20

  $4,150 per month

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • House for Rent

  1470 Lone Feather Trail, Winter Park, FL 32792

  Welcome to this inviting rental opportunity in the charming district of Winter Park, FL. Nestled in a vibrant area, this property offers a delightful experience for those looking to enjoy a serene lifestyle while still being close to modern conveniences.Key property features include spacious bedrooms and well-appointed bathrooms, all designed with comfort in mind. With ample square

  1470 Lone Feather Trail, Winter Park, FL 32792
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  $605,000 Sold Dec 22, 2025

  2478 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1965

  Last Sold Summary

  • 19% Below List Price
  • $268/SF
  • 123 Days On Market

  Last Listing Agent Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
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  Est $1,086,993 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,310 Sq Ft

  1780 Mondrian Cir, Winter Park, FL 32789

  1780 Mondrian Cir, Winter Park, FL 32789
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  /22

  $225,000

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  1913 Woodcrest Dr Unit B, Winter Park, FL 32792

  Winter Park gem! This tastefully updated 2-bedroom, 2-bath corner unit with a spacious patio offers a rare opportunity in a boutique community of only 11 residences, surrounded by million-dollar homes. The unit was repiped in October 2025 and features high-quality enhancements including plantation shutters, built-in closets, a hurricane-rated sliding glass door, smart recessed lighting

  Irina Paul FUTURE HOME REALTY INC

  1913 Woodcrest Dr Unit B, Winter Park, FL 32792
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  $3,000 per month

  • 5 Beds
  • 3 Baths
  • 1,442 Sq Ft
  • House for Rent

  2181 Linden Rd, Winter Park, FL 32792

  Modern Winter Park Living • Fully Renovated 2025 Home • Independent In-Law Suite • No HOAWelcome to your newly renovated 2025 residence at 2181 Linden Road, Winter Park, FL 32792, offering the perfect blend of style, functionality, and location. This stunning rental home is ideal for families, professionals, or anyone seeking a modern lifestyle in one of Central Florida’s most desirable

  Alejandro Rodriguez AROD PARTNERS REALTY

  2181 Linden Rd, Winter Park, FL 32792
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  $417,100 Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  /18

  Est $421,297 Not Listed For Sale

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

  2809 Bright Bird Ln, Winter Park, FL 32792

  2809 Bright Bird Ln, Winter Park, FL 32792
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  $475,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft

  2020 Cocos Ct, Winter Park, FL 32792

  Fully Renovated Home in Winter Park!Beautifully 3-bedroom, 2-bathroom POOL home located in the desirable Eastbrook community of Winter Park. Situated on an oversized .30-acre corner lot in a quiet cul-de-sac with no HOA.This property offers 1,715 sq. ft. of living space, a 1-car garage, and a spacious fenced backyard—the perfect combination of comfort, style, and location. Updates include

  Julimar Barreiro Pastrana SERHANT

  2020 Cocos Ct, Winter Park, FL 32792
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  /10

  $2,540 per month

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • House for Rent

  191 Jergo Rd, 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 $2684.90. That covers your base rent, $2540.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  191 Jergo Rd, Winter Park, FL 32792
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  $1,640,000 Sold Mar 06, 2025

  508 W Swoope Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,133 Sq Ft
  • Built 2021

  Last Sold Summary

  • 17% Below List Price
  • $397/SF
  • 258 Days On Market

  Last Listing Agent Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

  508 W Swoope Ave, Winter Park, FL 32789
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  /18

  Est $417,681 Not Listed For Sale

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

  2805 Bright Bird Ln, Winter Park, FL 32792

  2805 Bright Bird Ln, Winter Park, FL 32792
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  $619,500

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  1451 Cavendish Rd, Winter Park, FL 32789

  Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and prominent corner lot, this move-in-ready home perfectly balances charm, safety, and convenience just minutes from Park Avenue, Downtown Orlando, and the Mills District. Enjoy extensive upgrades including new AC, attic

  Spencer Flory LoKation

  1451 Cavendish Rd, Winter Park, FL 32789
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  $1,299 per month

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft
  • Condo for Rent

  3044 Antique Oaks Cir Unit 178, Winter Park, FL 32792

  Welcome home! This fantastic 1-bedroom, 1-bath home is available on November 4, 2025! Located conveniently in the desirable community of Parkview Village Condo, this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features such. Act now! This one won’t last long! All applicants are

  Steve Simpson 407 PROPERTIES

  3044 Antique Oaks Cir Unit 178, Winter Park, FL 32792
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  $380,000 Sold Feb 27, 2025

  3505 Balsam Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,709 Sq Ft
  • Built 1965

  Last Sold Summary

  • 9% Above List Price
  • $222/SF
  • 21 Days On Market

  Current Estimated Value $375,790

  Last Listing Agent Jennifer Clark GLORY INTL. REAL ESTATE CO

  3505 Balsam Dr, Winter Park, FL 32792
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  /18

  Est $430,619 Not Listed For Sale

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

  2821 Bright Bird Ln, Winter Park, FL 32792

  2821 Bright Bird Ln, Winter Park, FL 32792
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  $539,000

  • 4 Beds
  • 2 Baths
  • 1,885 Sq Ft

  2665 Tierra Cir, Winter Park, FL 32792

  Welcome to 2665 Tierra Circle, a captivating Mediterranean-inspired residence nestled in the desirable Casa Aloma neighborhood of Winter Park. This thoughtfully maintained 4-bedroom, 2-bath home spans 1,885 square feet and has been lovingly cared for by a single owner for the past 23 years, evident in every detail throughout. Step inside to discover a flowing floor plan featuring distinct living,

  Kelly Price KELLY PRICE & COMPANY LLC

  2665 Tierra Cir, Winter Park, FL 32792
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  /20

  $5,960 per month

  • 3 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789

  Feel at home in this tiny home with private space in the heart of Winter Park, Florida. This beautiful home is the perfect retreat for families, couples, or friends seeking a relaxing and comfortable stay.This home features three spacious queen bedrooms, a full bathroom with a walk-in shower, and a quaint farmhouse-styled studio with a queen bed and a full bathroom with a walk-in shower. The

  2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789
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  $1,206,400 Sold Oct 15, 2025

  4048 Gilder Rose Place, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,321 Sq Ft
  • Built 1992

  Last Sold Summary

  • $363/SF
  • 101 Days On Market

  Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
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  /18

  Est $435,854 Not Listed For Sale

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

  2796 Bright Bird Ln, Winter Park, FL 32792

  2796 Bright Bird Ln, Winter Park, FL 32792
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  $325,000

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  2401 Antilles Dr, Winter Park, FL 32792

  Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family

  George Freelove KELLER WILLIAMS WINTER PARK

  2401 Antilles Dr, Winter Park, FL 32792
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  $8,900 per month

  • 4 Beds
  • 5 Baths
  • 3,611 Sq Ft
  • House for Rent

  1442 Palm Ave, Winter Park, FL 32789

  Discover this exquisite property featuring a main house, complemented by a separate guest apartment equipped with one bedroom, one bathroom, a full living room, and a kitchen. The main house boasts an inviting open floor plan adorned with tall ceilings and beautiful hardwood floors throughout. On the upper level, relax in the luxurious master suite, accompanied by two additional bedrooms and

  Bianca Botelho RE/MAX ASSURED

  1442 Palm Ave, Winter Park, FL 32789
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  $72,000 Sold Jun 24, 2025

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

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

  Last Sold Summary

  • 24% Below List Price
  • $92/SF
  • 4 Days On Market

  Current Estimated Value $79,788

  Last Listing Agent Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  273 Scottsdale Square Unit 273, Winter Park, FL 32792
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  /88

  Est $1,910,791 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft

  1661 Hillcrest Ave, Winter Park, FL 32789

  1661 Hillcrest Ave, Winter Park, FL 32789
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  /25

  $428,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  5201 Ardmore Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully Renovated 3-Bed, 2-Bath Home in Winter Park!!! Experience modern living at its finest in this fully renovated 3-bedroom, 2-bathroom home located in the heart of Winter Park. Recently updated with a new roof (installed within the last six months), HVAC systembupdated within the last few years, and

  Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

  5201 Ardmore Dr, Winter Park, FL 32792
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  /45

  $3,000 per month

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

  4044 Tenita Dr, Winter Park, FL 32792

  Welcome to this beautiful and cozy single-story home with a pool, designed to captivate your senses from the moment you step inside. This thoughtfully laid-out residence offers a spacious living area, dining space, and an open-concept kitchen—the true heart of the home. Featuring elegant cascading quartz countertops, modern white and blue cabinetry, and stainless steel appliances, the kitchen is

  4044 Tenita Dr, Winter Park, FL 32792
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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 $648,867

  Last Listing Agent Sue Grafton FANNIE HILLMAN & ASSOCIATES

  2732 Lion Heart Rd, Winter Park, FL 32792
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  Est $427,152 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  2719 Bright Bird Ln, Winter Park, FL 32792

  2719 Bright Bird Ln, Winter Park, FL 32792
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  /35

  $449,000

  • 4 Beds
  • 2 Baths
  • 1,738 Sq Ft

  824 Garrett Ct, Winter Park, FL 32792

  Welcome to 824 Garrett Court, a beautifully updated 4-bedroom, 2-bath home located on a quiet cul-de-sac in the highly desirable Winter Park Forest community. This bright and spacious residence is one of the only homes listed in this sought-after neighborhood in 2025. The interior features luxury vinyl flooring throughout, 4inch baseboards, an updated kitchen with stainless steel appliances

  Shelby Serrao COMPASS FLORIDA LLC

  824 Garrett Ct, Winter Park, FL 32792
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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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  $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 $684,050

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792
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  /18

  Est $427,483 Not Listed For Sale

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

  2790 Bright Bird Ln, Winter Park, FL 32792

  2790 Bright Bird Ln, Winter Park, FL 32792

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