Winter Park, FL Homes

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  /5

  $740,000

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  841 W Swoope Ave, Winter Park, FL 32789

  Prime Winter Park Redevelopment Opportunity – R-2 Zoned Rare opportunity to acquire an R-2 zoned parcel in one of Winter Park’s fastest-transforming corridors. This approximately 9,752 SF lot is ideally positioned between Park Avenue and Orlando Avenue and is within walking distance to Winter Park Village, offering convenient access to shopping, dining, and entertainment. Surrounded by active and

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 468-9259

  841 W Swoope Ave, Winter Park, FL 32789
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  /53

  $1,683 - $9,184 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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  $374,900 Sold Oct 10, 2025

  2028 Leanne Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 1968

  Last Sold Summary

  • $244/SF
  • 9 Days On Market

  Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

  2028 Leanne Ct, Winter Park, FL 32792
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  /2

  Est $1,169,273 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,871 Sq Ft

  363 N Phelps Ave, Winter Park, FL 32789

  363 N Phelps Ave, Winter Park, FL 32789
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  /36

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,495 Sq Ft

  2501 Tahoe Cir Unit 32501, Winter Park, FL 32792

  Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location.The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning

  

  Sarah Doyer

  COLDWELL BANKER RESIDENTIAL RE

  (321) 510-4129

  2501 Tahoe Cir Unit 32501, Winter Park, FL 32792
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  /25

  $6,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft
  • Condo for Rent

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

  Steven Koleno BEYCOME OF FLORIDA LLC

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
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  /2

  $750,000 Sold Jun 09, 2025

  2756 Summerfield Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Above List Price
  • $431/SF
  • 4 Days On Market

  Current Estimated Value $737,298

  Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

  2756 Summerfield Rd, Winter Park, FL 32792
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  /2

  Est $700,271 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,940 Sq Ft

  678 Depugh St, Winter Park, FL 32789

  678 Depugh St, Winter Park, FL 32789
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  /87

  $774,900

  • 5 Beds
  • 2.5 Baths
  • 2,646 Sq Ft

  2215 Marsh Sedge Ln, Winter Park, FL 32792

  NEW PRICE – Preserve-View Pool Retreat in a Gated, Family-Friendly Winter Park Community This is the one buyers wait for — and it’s finally here at a new price. Perfectly positioned on a premium preserve lot with no rear neighbors, this beautifully upgraded 2,645 sq ft Winter Park home offers rare privacy, peaceful green views, and your own screened in-ground pool — a combination that almost

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 463-5067

  2215 Marsh Sedge Ln, Winter Park, FL 32792
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  /103

  $1,991 - $6,413 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

  $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 $818,970 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,861 Sq Ft

  439 N Capen Ave, Winter Park, FL 32789

  439 N Capen Ave, Winter Park, FL 32789
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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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  /20

  $2,600 per month

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Townhouse for Rent

  2344 Flamingo Way, Winter Park, FL 32792

  Discover 2344 Flamingo Way in Winter Park, FL. This well maintained townhome offers comfort and convenience in a prime location. The home features 1,536 square feet with three bedrooms and two bathrooms. The layout includes a living room, dining room, dinette, and a modern kitchen. The kitchen offers a tile backsplash, decorative countertops, and stainless steel appliances including a flat

  Rodrigo Marsal LIFESTYLE INTERNATIONAL REALTY

  2344 Flamingo Way, 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

  Current Estimated Value $2,662,282

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
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  /2

  Est $483,012 Not Listed For Sale

  • 1 Bed

  2313 Loch Lomond Dr, Winter Park, FL 32792

  2313 Loch Lomond Dr, Winter Park, FL 32792
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  /51

  $1,489,000 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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  /37

  $1,210 - $1,823 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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  /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 $857,873

  Last Listing Agent Farah Bloom KELLER WILLIAMS WINTER PARK

  1223 Formosa Ave, Winter Park, FL 32789
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  /2

  Est $2,297,669 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,467 Sq Ft

  2172 Temple Dr, Winter Park, FL 32789

  2172 Temple Dr, Winter Park, FL 32789
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  /44

  $3,399,999

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /27

  $2,450 per month

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Townhouse for Rent

  1256 Michigan Ave, Winter Park, FL 32789

  Completely renovated. Beautiful two bedrooms, two baths with laundry room and private fenced backyard and carport. Close to upscale restaurants and shopping, and Interstate 4. This beautiful property is between Winter Park and downtown Orlando.

  Farah Novin PREMIER SOTHEBY'S INTL. REALTY

  1256 Michigan Ave, Winter Park, FL 32789
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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 $3,851,500

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  1691 Chestnut Ave, Winter Park, FL 32789
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  /2

  Est $438,692 Not Listed For Sale

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

  3092 Nicholson Dr, Winter Park, FL 32792

  3092 Nicholson Dr, Winter Park, FL 32792
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  /33

  $635,000 Pending

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

  428 Selkirk Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. 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,

  Sheri Malin REDFIN CORPORATION

  428 Selkirk Dr, Winter Park, FL 32792
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  /74

  $1,610 - $5,139 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

  $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 $3,831,882

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1341 College Point, Winter Park, FL 32789
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  /2

  Est $418,331 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft

  5201 Lake Howell Rd, Winter Park, FL 32792

  5201 Lake Howell Rd, Winter Park, FL 32792
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  /39

  $1,675,000

  • 5 Beds
  • 4.5 Baths
  • 3,033 Sq Ft

  501 Darcey Dr, Winter Park, FL 32792

  Welcome to this stunning modern custom smart home, a true statement of luxury and design offering 3,033 square feet of impeccably curated living space with 5 bedrooms and 4.5 bathrooms. From the moment you arrive, the pavered driveway, architectural lighting, and manicured landscaping set the tone for a home built for both elegance and ease.The heart of the home is bathed in natural light,

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  501 Darcey Dr, Winter Park, FL 32792
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  /21

  $2,375 per month

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • House for Rent

  1812 Pineview Cir, Winter Park, FL 32792

  WOW!! Renovated to perfection. Recently painted inside and out and a newer kitchen featuring white shaker cabinets with quartz countertops plus new appliances make this home a great find in an amazing location. This adorable and spotless Winter Park charmer is nestled on a quiet street a stone's throw to Lakemont Elementary. Tile and laminate throughout makes this home easy breezy to maintain.

  Sherrie Pillat RE/MAX ASSURED

  1812 Pineview Cir, Winter Park, FL 32792
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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 $639,424

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1536 Golfside Dr, Winter Park, FL 32792
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  /2

  Est $349,081 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft

  5229 N Woodcrest Dr, Winter Park, FL 32792

  5229 N Woodcrest Dr, 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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  /51

  $1,311 - $2,085 per month

  Cranes Landing Apartments

  1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

  3440 N Goldenrod Rd, 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

  Current Estimated Value $390,328

  Last Listing Agent Christina Munkberg COLDWELL BANKER RESIDENTIAL RE

  1809 Palmer Ave, Winter Park, FL 32792
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  /2

  Est $305,235 Not Listed For Sale

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

  2327 Antilles Dr, Winter Park, FL 32792

  2327 Antilles Dr, Winter Park, FL 32792
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  /54

  $439,900

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers

  Brian Bauer SOUTHERN LAND & HOMES

  1367 Tierra Cir, Winter Park, FL 32792
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  /28

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft
  • Condo for Rent

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

  Renovated ONE story condo available in Wrenwood. Light and Bright 2 BEDROOM, 2 BATH unit features neutral tile and LVT flooring (no carpet), Quartz counters, Stainless Steel appliances, Full size all-in-one WASHER/DRYER. Freshly Painted with UPDATES throughout- ready for occupancy! Generously sized bedrooms with ample closet space; Sliding doors from living room lead to a private Screened-in

  Emily Lemieux RE/MAX TOWN & COUNTRY REALTY

  4858 Tangerine Ave Unit 4858, 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 $806,281

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1818 Mondrian Cir, Winter Park, FL 32789
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  /2

  Est $542,217 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,040 Sq Ft

  1981 Japonica Rd, Winter Park, FL 32792

  1981 Japonica Rd, Winter Park, FL 32792

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