Winter Park, FL Homes

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  /42

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,308 Sq Ft

  2224 Shadowland Loop, Winter Park, FL 32792

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 450-7733

  2224 Shadowland Loop, Winter Park, FL 32792
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  /28

  $1,615 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
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  /2

  $2,295,000 Sold Dec 16, 2025

  1661 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,570 Sq Ft
  • Built 2025

  Last Sold Summary

  • 12% Below List Price
  • $643/SF
  • 26 Days On Market

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
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  /2

  Est $446,905 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft

  1401 Devon Rd, Winter Park, FL 32789

  1401 Devon Rd, Winter Park, FL 32789
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  /42

  $715,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  2418 Whitehall Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Don't miss out!!! MOTIVATED SELLER! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 485-6759

  2418 Whitehall Cir, Winter Park, FL 32792
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  /40

  $2,650 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  1994 Canny Cove, Winter Park, FL 32792

  This beautiful three bedroom, two and a half bath townhome is located in the newly developed Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch with a beautiful water view. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features

  Vildan Nigro RIVA REALTY GROUP LLC

  1994 Canny Cove, Winter Park, FL 32792
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  /2

  $2,700,000 Sold Oct 30, 2025

  1020 Mayfield Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $1,014/SF
  • 149 Days On Market

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
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  /2

  Est $632,060 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft

  2756 Lion Heart Rd, Winter Park, FL 32792

  2756 Lion Heart Rd, Winter Park, FL 32792
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  /23

  $449,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  2148 Blossom Ln, Winter Park, FL 32789

  Under contract-accepting backup offers. Located in the desirable Winter Park area, this newly listed 3-bedroom, 2-bathroom home at 2148 Blossom Lane offers excellent value and investment potential. This well-maintained house features 1,685 square feet of comfortable living space, perfect for families or investors looking for a solid opportunity. The home's prime location puts you just minutes

  

  Scot Hartwell

  PLATINUM REAL ESTATE

  (321) 478-2108

  2148 Blossom Ln, Winter Park, FL 32789
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  /53

  $1,850 - $8,285 per month

  Juno Winter Park

  Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  1305 Morgan Stanley Ave, Winter Park, FL 32789
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  /89

  $830,000 Sold Mar 11, 2025

  1223 Formosa Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,834 Sq Ft
  • Built 1940

  Last Sold Summary

  • 31% Below List Price
  • $216/SF
  • 240 Days On Market

  Current Estimated Value $849,806

  Last Listing Agent Farah Bloom KELLER WILLIAMS WINTER PARK

  1223 Formosa Ave, Winter Park, FL 32789
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  /2

  Est $384,881 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,823 Sq Ft

  3237 Black Pine Ave, Winter Park, FL 32792

  3237 Black Pine Ave, Winter Park, FL 32792
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  /33

  $200,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
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  /15

  $1,395 per month

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Condo for Rent

  3011 George Mason Ave Unit 3, Winter Park, FL 32792

  This 2 bedroom, 2 bathroom condo is located in the Colonies community near local shops, restaurants, and schools. Features include a spacious floor plan with a large main living room area, a lovely kitchen, a dining room, a wonderful primary suite, a laundry closet, a rear patio, and a community pool. Schedule a showing or submit an application online. All Real Property Management & Realty

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  3011 George Mason Ave Unit 3, Winter Park, FL 32792
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  /2

  $4,100,000 Sold Apr 18, 2025

  1691 Chestnut Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 4,582 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $895/SF
  • 1 Day On Market

  Current Estimated Value $3,840,500

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  1691 Chestnut Ave, Winter Park, FL 32789
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  /2

  Est $933,674 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  251 Dana Way, Winter Park, FL 32789

  251 Dana Way, Winter Park, FL 32789
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  $1,499,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  102 Bell Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

  102 Bell Place, Winter Park, FL 32792
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  /103

  $2,027 - $4,366 per month

  Paseo at Winter Park Village

  1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  940 W Canton Ave, Winter Park, FL 32789
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  /2

  $3,900,000 Sold Feb 18, 2025

  1341 College Point, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,279 Sq Ft
  • Built 2005

  Last Sold Summary

  • 8% Below List Price
  • $911/SF
  • 66 Days On Market

  Current Estimated Value $3,820,842

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1341 College Point, Winter Park, FL 32789
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  /2

  Est $625,371 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  1419 Miller Ave, Winter Park, FL 32789

  1419 Miller Ave, Winter Park, FL 32789
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  /27

  $320,000 Pending

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

  615 Warrenton Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Don’t miss out on this beautifully maintained, 2 bed, 2 bath, single story townhome in the sought after Winter Park Pines with a LOW HOA! As you make your way towards the entrance you have 2 private, fenced-in courtyard areas for sitting out for a morning coffee, home gardening, or just getting out to enjoy

  Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
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  /7

  $1,475 per month

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

  1250 S Denning Dr Unit 208, Winter Park, FL 32789

  A+++ Location in Winter Park. Remodeled 1 bedroom and bath apartment. Close to everything Advent Health, Park Avenue, Rollins College, Orange Avenue, Fairbanks, 17-92 and 1-4. No pets please.

  Ruth Harris COLDWELL BANKER RESIDENTIAL RE

  1250 S Denning Dr Unit 208, Winter Park, FL 32789
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  /2

  $638,250 Sold Sep 02, 2025

  1536 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1980

  Last Sold Summary

  • $338/SF
  • 3 Days On Market

  Current Estimated Value $635,045

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1536 Golfside Dr, Winter Park, FL 32792
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  /2

  Est $468,170 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1052 Manchester Cir, Winter Park, FL 32792

  1052 Manchester Cir, Winter Park, FL 32792
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  /25

  $375,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  3083 Crane Strand Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. 2024 ROOF! NO HOA!! This 3 bedroom, 2 bathroom property offers a split plan bedroom arrangement with walk-in closets in every room. There are ceiling fans in every bedroom & common area, and the floors throughout have tile or luxury vinyl plank (LVP) - no carpets! The primary suite and dining room both exit out onto a covered, screen-enclosed back porch

  Sheri Malin REDFIN CORPORATION

  3083 Crane Strand Dr, Winter Park, FL 32792
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  /40

  $1,316 - $1,711 per month

  Seabrook

  1 - 2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  3114 Terry Brook Dr, Winter Park, FL 32792
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  /2

  $401,000 Sold Oct 15, 2025

  1809 Palmer Ave, Winter Park, FL 32792

  • Land
  • 0.21 Acre
  • $1,909,524 per Acre

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Christina Munkberg COLDWELL BANKER RESIDENTIAL RE

  1809 Palmer Ave, Winter Park, FL 32792
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  /2

  Est $448,138 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  3241 Raiders Run, Winter Park, FL 32792

  3241 Raiders Run, Winter Park, FL 32792
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  /40

  $243,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  Come to your new home centrally located between Downtown Maitland and Winter Park. Close to the conveniences of retail shopping, restaurants, the Sunrail Station and I-4 to get you around Central Florida quickly. Enter into your one story condo to an open living, dining and kitchen floorplan for lots of space and flexibility. Ceramic tile throughout, 5" base molding, 6 panel doors and updated

  Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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  /25

  $1,350 per month

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

  3045 Aaron Burr Ave Unit 10, Winter Park, FL 32792

  Completely remodeled, come enjoy this amazing 1 bedroom 1 bathroom condo in winter park, Close to UCF, Full Sail University and centrally located to shopping malls, major highways, restaurants and theme parks. Just 11 minutes from Orlando international Airport, COMPLETELY REMODELED BRAND NEW A/C, NEW FLOORS, NEW BASEBOARDS, NEW VANITY, NEW TOILET, NEW PAINTING, NEW APPLIANCES, WASHER AND DRYER

  Tatiana Rojas TBO REAL ESTATE PARTNERS INC

  3045 Aaron Burr Ave Unit 10, Winter Park, FL 32792
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  /2

  $775,000 Sold May 21, 2025

  1818 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 189 Days On Market

  Current Estimated Value $802,463

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1818 Mondrian Cir, Winter Park, FL 32789
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  /2

  Est $681,296 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,746 Sq Ft

  2703 Summerfield Rd, Winter Park, FL 32792

  2703 Summerfield Rd, Winter Park, FL 32792
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  /33

  $650,000

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

  428 Selkirk Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Income-Producing Opportunity! Welcome to this versatile Winter Park POOL HOME! At present, this property is split into two separate living quarters with the main house offering 3 bedrooms & 2 bathrooms and the adjoining guest suite offering 1 bedroom & 1 bathroom. Each living quarter has its own kitchen, laundry, climate control & outdoor living

  Sheri Malin REDFIN CORPORATION

  428 Selkirk Dr, Winter Park, FL 32792
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  $1,681 - $5,232 per month

  Vintage Winter Park Apartments

  1 - 3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  7490 Dwell Well Way, Winter Park, FL 32792
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  /2

  $690,000 Sold Aug 14, 2025

  2433 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Above List Price
  • $375/SF
  • 2 Days On Market

  Current Estimated Value $637,887

  Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2433 Whitehall Cir, Winter Park, FL 32792
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  /2

  Est $609,192 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,551 Sq Ft

  2765 Banchory Rd, Winter Park, FL 32792

  2765 Banchory Rd, Winter Park, FL 32792
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  /26

  $439,900 Pending

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Opportunities like this are rare. Perfectly suited for multi-generational living, mother-in-law suite potential, or rental income, this versatile POOL home sits on an oversized lot with no HOA in one of Central Florida’s most desirable locations — Winter Park.The flexible floor plan allows for comfortable

  Irina Paul FUTURE HOME REALTY INC

  2835 Bongart Rd, Winter Park, FL 32792
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  /21

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • House for Rent

  216 Rippling Ln, Winter Park, FL 32789

  Welcome to this inviting home located in a private neighborhood just minutes from top restaurants, shops, and playgrounds. The open floor plan is filled with natural light, creating a warm and spacious living environment that’s perfect for everyday living and entertaining. Step outside to the gated, oversized backyard, ideal for relaxing, hosting gatherings, or enjoying outdoor activities in a

  Lorena Hernandez SAFETYNET REALTY

  216 Rippling Ln, Winter Park, FL 32789
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  /2

  $555,000 Sold Apr 25, 2025

  633 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $549,341

  Last Listing Agent Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  633 London Rd, Winter Park, FL 32792
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  /2

  Est $392,722 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,919 Sq Ft

  3458 Arbutus Ln, Winter Park, FL 32792

  3458 Arbutus Ln, Winter Park, FL 32792

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