Winter Park, FL Homes

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  $349,500 Pending

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft

  7580 Aloma Pines Ct, Winter Park, FL 32792

  Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location and this 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with

  Simon Colak USCO CAPITAL GROUP

  7580 Aloma Pines Ct, Winter Park, FL 32792
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  $1,286 - $3,239 per month

  Liv at Winter Park Apartment Homes

  Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  $1,088,000 Sold Jan 30, 2026

  1092 Wading Waters Cir, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $356/SF
  • 60 Days On Market

  Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

  1092 Wading Waters Cir, Winter Park, FL 32792
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  Est $1,398,950 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,446 Sq Ft

  1458 Aloma Ave, Winter Park, FL 32789

  1458 Aloma Ave, Winter Park, FL 32789
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  $800,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  1780 Bryan Ave, Winter Park, FL 32789

  Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with theadjoining lots at 1760 and 1770 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three.

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1780 Bryan Ave, Winter Park, FL 32789
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  /31

  $3,400 per month

  • 4 Beds
  • 3.5 Baths
  • 3,215 Sq Ft
  • House for Rent

  8077 Pleasant Pine Cir, Winter Park, FL 32792

  This stunning Winter Park home, AVAILABLE April 01, features 4 bedrooms and 3.5 bathrooms, plus a fenced backyard for added privacy. The open-concept living and dining area is filled with natural light and boasts hardwood floors and elegant crown molding. The kitchen, perfect for entertaining, includes a large island, stainless steel appliances, and quartz countertops. Upstairs, you’ll find a

  Tatiana Diaz FLORIDA LAKES REALTY

  8077 Pleasant Pine Cir, Winter Park, FL 32792
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  /2

  $1,575,000 Sold Aug 14, 2025

  1394 Grove Terrace, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,958 Sq Ft
  • Built 2002

  Last Sold Summary

  • $532/SF
  • 5 Days On Market

  Current Estimated Value $1,567,532

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
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  /2

  Est $480,578 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,812 Sq Ft

  2667 Fitzhugh Rd, Winter Park, FL 32792

  2667 Fitzhugh Rd, Winter Park, FL 32792
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  /17

  $918,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,598 Sq Ft

  5325 Cypress Reserve Place, Winter Park, FL 32792

  Under contract-accepting backup offers. ATTENTION BUYERS!! Price adjusted to $918,000 and $15K SELLER CONCESSION TOWARDS BUYERS CLOSING COST WITH FULL ASKING PRICE!! The Winter Park Oasis You've Been Waiting For:Imagine waking up in an expansive primary suite, enjoying a cup of coffee by the fireplace, and then stepping out to your backyard oasis the heated, screened-in pool and spa, warmed

  Dori Estrada LPT REALTY, LLC

  5325 Cypress Reserve Place, Winter Park, FL 32792
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  /50

  $1,311 - $1,627 per month

  Winter Park Woods Apartments

  1 - 3 Beds

  349 Scottsdale Square, Winter Park, FL 32792

  This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

  349 Scottsdale Square, Winter Park, FL 32792
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  /2

  $625,000 Sold Sep 29, 2025

  3759 Kinsley Place, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,251 Sq Ft
  • Built 1988

  Last Sold Summary

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

  Current Estimated Value $632,518

  Last Listing Agent Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
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  /2

  Est $1,861,816 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,101 Sq Ft

  1660 Oneco Ave, Winter Park, FL 32789

  1660 Oneco Ave, Winter Park, FL 32789
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  /20

  $220,000

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

  This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

  Manny Celi YOUNG REAL ESTATE

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
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  /23

  $2,150 per month

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

  1250 S Denning Dr Unit 112, Winter Park, FL 32789

  Nestled in one of Winter Park’s most desirable pockets, the Mead Garden Condominium offers the perfect blend of tranquility and convenience. Set beside the lush, 47-acre Mead Botanical Garden, the community provides a peaceful, nature-rich backdrop while keeping you just minutes from everything that makes Winter Park exceptional. This ground floor unit boasts its own washer/dryer combo for

  Catherine Williams COLDWELL BANKER RESIDENTIAL RE

  1250 S Denning Dr Unit 112, Winter Park, FL 32789
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  /2

  $285,000 Sold Sep 24, 2025

  7777 Fernbrook Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Above List Price
  • $261/SF
  • 3 Days On Market

  Current Estimated Value $286,688

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  7777 Fernbrook Way, Winter Park, FL 32792
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  /2

  Est $784,061 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  1520 Palmer Ave, Winter Park, FL 32789

  1520 Palmer Ave, Winter Park, FL 32789
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  $380,000

  • 3 Beds
  • 2.5 Baths
  • 1,787 Sq Ft

  7506 Aloma Pines Ct, Winter Park, FL 32792

  Aloma Trails is a gated townhome community, built by Ryan Homes, located in Winter Park. Conveniently you'll find it's location between UCF and Rollins College. Seminole County is known for its highly rated public schools. Only minutes from Park Avenue shopping and restaurants. This END UNIT townhome features 3 bedrooms, 2 1/2 bathrooms, and a TWO car garage. Granite countertops, 42” upper

  Corey Van Dyke HOMEVEST REALTY

  7506 Aloma Pines Ct, Winter Park, FL 32792
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  $1,199 - $2,880 per month

  Summerlin at Winter Park Apartments

  1 - 3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
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  /2

  $315,000 Sold Jan 01, 2026

  615 Warrenton Rd, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 50 Days On Market

  Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
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  /2

  Est $3,715,233 Not Listed For Sale

  • 3 Beds
  • 5.5 Baths
  • 4,627 Sq Ft

  850 Georgia Ave, Winter Park, FL 32789

  850 Georgia Ave, Winter Park, FL 32789
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  $999,950 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,121 Sq Ft

  1444 Pelican Bay Trail, Winter Park, FL 32792

  Seller Financing Available--Attractive Terms--Potentially Below Market Rate. A True Gem on the Lake! If you've been dreaming of owning a lakefront property with a Winter Park address, this is your chance! This stunning 4-bedroom, 2.5-bathroom home in the tranquil Pelican Bay Subdivision is move-in ready and full of charm. As you approach, you'll be greeted by lush landscaping. Step through the

  Jacob Hara TRANSCEND REALTY

  1444 Pelican Bay Trail, Winter Park, FL 32792
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  /43

  $1,795 per month

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

  627 Grenadine Ct Unit S, Winter Park, FL 32792

  Cute 2 bed 2 bath, 2nd floor condo in quiet community of Winter Park Villas. Step into the spacious Family room that has a wood burning fireplace. Kitchen overlooks the family room and dining room. The dining room has a quaint bar area complete with sink. The balcony is perfect to enjoy morning coffee and balmy Florida evenings overlooking the trees. There is also an additional small storage

  Reeta Gulati RE REALTY

  627 Grenadine Ct Unit S, Winter Park, FL 32792
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  /2

  $325,000 Sold Dec 30, 2025

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

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 6 Days On Market

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /2

  Est $740,188 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,347 Sq Ft

  2235 Coldstream Dr, Winter Park, FL 32792

  2235 Coldstream Dr, Winter Park, FL 32792
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  $1,140,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft

  1150 Kenwood Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welcoming living room, versatile bonus/flex space, dining room

  JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
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  $910 - $1,544 per month

  San Jose Apartments

  1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  2353 Winter Woods Blvd, Winter Park, FL 32792
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  $790,000 Sold Jun 05, 2025

  600 Brechin Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 12 Days On Market

  Current Estimated Value $777,635

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  Est $747,282 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  800 Greens Ave, Winter Park, FL 32789

  800 Greens Ave, Winter Park, FL 32789
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  $960,000

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft

  1521 Heron Wood Place, Winter Park, FL 32792

  Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation.One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare

  Ronald Trotter RE/MAX INNOVATION

  1521 Heron Wood Place, Winter Park, FL 32792
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  /17

  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • House for Rent

  1621 Winter Green Blvd, Winter Park, FL 32792

  Are you looking for a well maintained, updated single family home in Winter Park? Presenting this 3 bedroom 2 bath home in a quiet little community conveniently located to all the conveniences Winter Park has to offer. This charming home has a beautifully updated gourmet kitchen with quartz counters and a substantial amount of cabinetry and newer stainless appliances. There is new vinyl planking

  Beatrice Palladino GALLERY PROPERTIES INTERNATIONAL

  1621 Winter Green Blvd, Winter Park, FL 32792
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  $690,000 Sold May 08, 2025

  1806 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  Last Sold Summary

  • 1% Below List Price
  • $342/SF
  • 61 Days On Market

  Current Estimated Value $718,817

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1806 Mondrian Cir, Winter Park, FL 32789
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  Est $510,589 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,048 Sq Ft

  2842 Eastern Pkwy, Winter Park, FL 32789

  2842 Eastern Pkwy, Winter Park, FL 32789
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  /22

  $225,000 Pending

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  1913 Woodcrest Dr Unit B, Winter Park, FL 32792

  Under contract-accepting backup offers. 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

  Irina Paul FUTURE HOME REALTY INC

  1913 Woodcrest Dr Unit B, Winter Park, FL 32792
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  $1,200 - $2,075 per month

  Central Place At Winter Park

  1 - 3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  7000 University Blvd, Winter Park, FL 32792
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  $360,000 Sold Apr 30, 2025

  1493 Hyde Park Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $256/SF
  • 4 Days On Market

  Current Estimated Value $360,738

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  1493 Hyde Park Dr, Winter Park, FL 32792
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  Est $3,490,684 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,097 Sq Ft

  1821 Summerland Ave, Winter Park, FL 32789

  1821 Summerland Ave, Winter Park, FL 32789
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  /30

  $214,990

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7744 Country Place Unit C4, Winter Park, FL 32792

  Location, Location, Location! This highly sought-after two-bedroom, two-bath condo in Winter Park won’t last long! Ideally situated close to the University of Central Florida, it's a perfect investment opportunity for parents offering lower monthly payments compared to the high costs of on-campus housing. Upgrades made in 2020 include a new roof, air conditioning system, and enhanced attic

  David Knight EXP REALTY LLC

  7744 Country Place Unit C4, Winter Park, FL 32792
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  /24

  $3,650 per month

  • 3 Beds
  • 2 Baths
  • 2,064 Sq Ft
  • House for Rent

  1329 Medinah Ct, Winter Park, FL 32792

  Welcome to this fully rehabbed rental home located in the highly sought-after Winter Park Pines neighborhood. Situated right near the golf course and within a desirable school district, this home offers both comfort and convenience in a prime location. Inside, you’ll find a completely refreshed interior featuring new flooring and fresh paint throughout, creating a bright and modern living space.

  Alex Scures COLONIALTOWN REALTY

  1329 Medinah Ct, Winter Park, FL 32792
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  $351,000 Sold Sep 09, 2025

  1041 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $209/SF
  • 147 Days On Market

  Current Estimated Value $373,126

  Last Listing Agent Bob Paulson COLDWELL BANKER RESIDENTIAL RE

  1041 Manchester Cir, Winter Park, FL 32792
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  Est $453,742 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  3304 Ellwood Ct, Winter Park, FL 32792

  3304 Ellwood Ct, Winter Park, FL 32792

Showing Results 121 - 160, Page 4 of 18