Winter Park, FL Homes

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  $550,000

  • 3 Beds
  • 3 Baths
  • 1,602 Sq Ft

  7641 Village Green Dr, Winter Park, FL 32792

  Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter Park, FL. This well-maintained residence features 3 bedrooms and 3 full bathrooms across approximately 1,958 square feet of living space — perfect for comfortable daily living and entertaining. Set on a generous lot of nearly 0.30 acres, the property includes a private fenced-in backyard with an in-ground

  Jannett Marten Compass Florida, LLC

  7641 Village Green Dr, Winter Park, FL 32792
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  /20

  $1,750 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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  $3,450,000 Sold Jul 25, 2025

  182 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 4,812 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 61 Days On Market

  Current Estimated Value $3,422,449

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  Est $195,321 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792
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  $145,000

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792

  Townhouse 2 bedroom 2.5 bath, both bathrooms on the second floor are remodeled. The Townhome is rent $1,600. The unit is located in Winter Park Area and is close to the shopping and dining. It is also close to public transportation. HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

  Daiana Garcia Medrano LA ROSA REALTY ORLANDO LLC

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792
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  /25

  $2,600 per month

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

  1575 Lawndale Cir, Winter Park, FL 32792

  **WASHER AND DRYER INCLUDED** Welcome to your dream home at 1575 Lawndale Cir, Winter Park, FL 32792! Nestled in the heart of the highly coveted Winter Park, this 2-story gem offers the perfect blend of comfort and style. Step into a world of elegance with laminate wood and ceramic tile flooring gracing every corner of this home. The spacious living areas have great natural light for a warm and

  Dean Itani KELLER WILLIAMS ADVANTAGE REALTY

  1575 Lawndale Cir, Winter Park, FL 32792
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  $180,000 Sold Jan 06, 2026

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 8 Days On Market

  Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
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  Est $823,698 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1776 Mondrian Cir, Winter Park, FL 32789

  1776 Mondrian Cir, Winter Park, FL 32789
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  /14

  $2,289,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,334 Sq Ft

  2722 Eastern Pkwy, Winter Park, FL 32789

  Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence has been crafted for those who expect the

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  2722 Eastern Pkwy, Winter Park, FL 32789
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  /20

  $4,495 per month

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

  438 W Swoope Ave, Winter Park, FL 32789

  SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 2/28!!$4495.00 for a 15 MO LEASE$4695.00 12 MO LEASENestled 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

  438 W Swoope Ave, Winter Park, FL 32789
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  $1,950,000 Sold Sep 16, 2025

  141 Oakwood Way, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft
  • Built 2015

  Last Sold Summary

  • 14% Below List Price
  • $499/SF
  • 170 Days On Market

  Current Estimated Value $1,955,862

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
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  /2

  Est $957,871 Not Listed For Sale

  • 3 Beds

  2726 Lake Howell Ln, Winter Park, FL 32792

  2726 Lake Howell Ln, Winter Park, FL 32792
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  $509,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  422 S Ranger Blvd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. ?? Mid-Century Modern Gem in Sought-After Winter Park Pines Lovingly maintained and move-in ready, this Mid-Century Modern 4-bedroom, 2-bath home (just under 1,700 sq. ft.) offers light-filled living and timeless style in the heart of Winter Park Pines. Set beneath graceful mature oaks, the landscaped front yard provides a welcoming canopy. Step

  David Perez COLDWELL BANKER RESIDENTIAL RE

  422 S Ranger Blvd, Winter Park, FL 32792
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  /35

  $3,599 per month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  1945 Gunn Rd, Winter Park, FL 32792

  Fantastic Winter Park renovation. This 3 bedroom, 2 bathroom, plus an office home has been turned into a showplace. Great location zoned for Brookshire, Glenridge and Winter Park High School. The home features upscale fixtures, open floor plan, huge laundry room, office nook, new windows, ample dining space, new appliances and large fenced in backyard. A must see! Not furnished.

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1945 Gunn Rd, Winter Park, FL 32792
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  $170,000 Sold Jun 09, 2025

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $165/SF
  • 53 Days On Market

  Current Estimated Value $172,709

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792
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  Est $309,893 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  5879 Marble Ct, Winter Park, FL 32792

  5879 Marble Ct, Winter Park, FL 32792
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  $214,900

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792

  THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESTLED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING QUARTZITE COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGERATOR AND

  Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792
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  $750 per month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  2337 Inagua Way, Winter Park, FL 32792

  Property Id: 2352597Room for rent in beautiful 2 bedroom 2 bathroom condo. Full use of entire house. You get your own bathroom. The other room is rented out also, so it's 2 people sharing the house. Nice kitchen, new appliances. Big living room with vaulted ceilings, very spacious and sunny. Sun room with deck and fenced in backyard. New central A/C. Great community, pool and amenities.

  2337 Inagua Way, Winter Park, FL 32792
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  $625,000 Sold May 09, 2025

  1401 Lone Feather Trail, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $353/SF
  • 75 Days On Market

  Current Estimated Value $622,819

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  1401 Lone Feather Trail, Winter Park, FL 32792
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  Est $1,562,703 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,287 Sq Ft

  1005 S Pennsylvania Ave, Winter Park, FL 32789

  1005 S Pennsylvania Ave, Winter Park, FL 32789
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  /36

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,725 Sq Ft

  1816 Ivy Ln, Winter Park, FL 32792

  NEW REDUCED PRICE BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All

  Michael Cameron CAMERON REALTY GROUP LLC

  1816 Ivy Ln, Winter Park, FL 32792
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  $2,675 per month

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

  1986 Canny Cove, Winter Park, FL 32792

  This beautiful 3-bedroom, 2.5-bathroom two-story townhome is located in 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. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features stainless steel appliances, including a refrigerator,

  Vildan Nigro RIVA REALTY GROUP LLC

  1986 Canny Cove, Winter Park, FL 32792
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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 $569,575

  Last Listing Agent Alexander Young FOLIO REALTY LLC

  236 N Ranger Blvd, Winter Park, FL 32792
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  /2

  Est $734,476 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1166 Wildmeadow Run, Winter Park, FL 32792

  1166 Wildmeadow Run, Winter Park, FL 32792
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  $335,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  Unlisted Address

  Charming 3-bedroom, 2-bathroom single-family home nestled on a generous 9,626 sq ft lot in Winter Park’s desirable Goldenrod area. Built in 1972, this cozy one-story home offers 1,104 sq ft of living space with a classic split-bedroom floor plan — perfect for privacy while entertaining. The residence features tile and carpet flooring, central air conditioning, and a functional kitchen complete

  Rosa Rivera SKINNER REALTY, INC.

  Unlisted Address
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  /45

  $3,180 per month

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

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

  Experience a Central Florida retreat and feel at home in this Winter Park apartment, perfect for couples, families, or solo travelers. Sunlight filters through the leafy canopy onto a modest porch where you can unwind after a day of theme park thrills or downtown exploring.The full kitchen is equipped with stainless steel appliances, a stovetop, oven, microwave, and a refrigerator. A full

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
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  $912,500 Sold Jan 14, 2026

  210 Laurel Park Ct, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,838 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $322/SF
  • 25 Days On Market

  Last Listing Agent Alireza Partovi EXP REALTY LLC

  210 Laurel Park Ct, Winter Park, FL 32792
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  Est $434,439 Not Listed For Sale

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

  1935 Canny Cove, Winter Park, FL 32792

  1935 Canny Cove, Winter Park, FL 32792
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  $749,900

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  860 N Denning Dr, Winter Park, FL 32789

  FULLY FURNISHED | NEW CONSTRUCTION–QUALITY | WALKABLE WINTER PARK | FULL SMART HOME This is not a renovation—this is a complete architectural transformation. Taken down to the studs and roofline, expanded, and rebuilt with intention, this custom luxury residence is ideally located just steps from Winter Park Village and minutes from iconic Park Avenue, offering a truly walkable, car-optional

  LaDarrius Sanders OUTLET REALTY

  860 N Denning Dr, Winter Park, FL 32789
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  /18

  $1,495 per month

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

  3651 N Goldenrod Rd Unit 106, Winter Park, FL 32792

  Recently renovated first floor 2-bedroom, 2 bathroom, 840sqft condominium is located in Lancelot at Winter Park just off of University Blvd and Goldenrod Road. It's been beautifully updated with brand new 42" cabinets and new counter tops, vinyl plank floors throughout, new bathroom vanities, high efficiency AC system, window blinds and fresh paint. The newly renovated kitchen is expansive and

  Justin Recca INNOVATIVE REALTY, LLC

  3651 N Goldenrod Rd Unit 106, 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 $323,608

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

  1920 Magnolia Ave, Winter Park, FL 32792
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  Est $748,458 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft

  1421 Wooddale Ave, Winter Park, FL 32789

  1421 Wooddale Ave, Winter Park, FL 32789
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  $3,180,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 4,129 Sq Ft

  151 Oakwood Way, Winter Park, FL 32789

  Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

  Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
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  /15

  $2,120 per month

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft
  • House for Rent

  2045 Houndslake Dr, Winter Park, FL 32792

  Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

  2045 Houndslake Dr, Winter Park, FL 32792
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  $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 $484,677

  Last Listing Agent Jose Gabriel Rodriguez COLDWELL BANKER RESIDENTIAL RE

  1921 Japonica Rd, Winter Park, FL 32792
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  /2

  Est $308,733 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft

  5804 Shale Ct, Winter Park, FL 32792

  5804 Shale Ct, Winter Park, FL 32792
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  $1,359,950

  • 4 Beds
  • 4 Baths
  • 3,474 Sq Ft

  952 Moss Ln, Winter Park, FL 32789

  Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s

  Terry Connors THE SHOP REAL ESTATE CO.

  952 Moss Ln, Winter Park, FL 32789
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  /20

  $1,600 per month

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Townhouse for Rent

  2523 Alexa Ct, Winter Park, FL 32792

  Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

  Jaleel Smith LA ROSA REALTY LLC

  2523 Alexa Ct, 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

  Current Estimated Value $326,089

  Last Listing Agent Ashley Fisak COLDWELL BANKER RESIDENTIAL RE

  3525 Baxter Dr, Winter Park, FL 32792
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft

  677 Grenadine Ct Unit S, Winter Park, FL 32792

  677 Grenadine Ct Unit S, Winter Park, FL 32792

Showing Results 361 - 400, Page 10 of 18