Winter Park, FL Homes

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  $1,770,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,533 Sq Ft

  617 Worthington Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a

  Kelly Price KELLY PRICE & COMPANY LLC

  617 Worthington Dr, 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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  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,110,139

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  Est $266,066 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  7164 Swallow Run Unit GE, Winter Park, FL 32792

  7164 Swallow Run Unit GE, Winter Park, FL 32792
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  $6,600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMSIntroducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest

  Prescilla Vazquez COMPASS FLORIDA LLC

  2661 Vía Tuscany, Winter Park, FL 32789
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  $1,850 per month

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  7765 Fernbrook Way, Winter Park, FL 32792

  Come and see your new home!! In a great area. There are lots of updates they make this rental beautiful!! Come see all new bathrooms, new ceramic floors and completely new paint. Large rear yard for entertaining. Call today to see your new home!!!

  Jodi Nielsen OVER THE TOP REALTY LLC

  7765 Fernbrook Way, Winter Park, FL 32792
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  $699,000 Sold Jun 30, 2025

  1632 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $394/SF
  • 110 Days On Market

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
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  Not Listed For Sale

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

  681 Grenadine Ct Unit S, Winter Park, FL 32792

  681 Grenadine Ct Unit S, Winter Park, FL 32792
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  /30

  $698,000

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  2612 Roxbury Rd, Winter Park, FL 32789

  SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!!A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
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  /20

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,643 Sq Ft
  • House for Rent

  2852 Scarlet Rd, Winter Park, FL 32792

  BEAUTIFUL HOME IN WINTER PARK!!Delight in this stunning 3-bedroom, 2-bathroom home nestled in the charming locale of Winter Park. The residence boasts a spacious family room and a dining area adorned with elegant wood-like tile flooring, setting a warm and inviting atmosphere. Marvel at the stylish light fixtures that add a touch of sophistication to every room.The heart of the

  2852 Scarlet Rd, Winter Park, FL 32792
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  $689,500 Sold Jul 19, 2025

  1129 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $394/SF
  • 21 Days On Market

  Current Estimated Value $686,391

  Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

  1129 Golfside Dr, Winter Park, FL 32792
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  Est $467,607 Not Listed For Sale

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

  2260 Shadowland Loop, Winter Park, FL 32792

  2260 Shadowland Loop, Winter Park, FL 32792
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  $625,000

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  1500 Berkshire Ave, Winter Park, FL 32789

  Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Winter Park’s most treasured neighborhoods. Thoughtfully updated while preserving its timeless character, this 3 bedroom 1 and a half bath home blends classic architectural charm with today’s modern conveniences. Major system improvements include updated plumbing and electrical, a new roof in 2025, new HVAC in

  Lianna D'Angelo SOTERA LIVING

  1500 Berkshire Ave, Winter Park, FL 32789
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  $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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  $893,000 Sold Oct 09, 2025

  2890 Wild Ginger Ct, Winter Park, FL 32792

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft
  • Built 1993

  Last Sold Summary

  • 27% Below List Price
  • $262/SF
  • 78 Days On Market

  Current Estimated Value $930,896

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  2890 Wild Ginger Ct, Winter Park, FL 32792
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  Not Listed For Sale

  0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792
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  $1,375,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The

  Christina Fata REAL BROKER, LLC.

  2015 Summerfield Rd, Winter Park, FL 32792
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  /20

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft
  • Townhouse for Rent

  3050 Autumn Ct, Winter Park, FL 32792

  Property Id: 2344680 This could be your place to call home. This townhome is located off of 436 in Winter Park. It is in an A rated school district, and perfect for families. The home features 3 bedrooms and 2 full bathrooms, spacious corner lot, and porched back patio. There is also access to a beautifully kept community pool. Washer and dryer included in unit.

  3050 Autumn Ct, Winter Park, FL 32792
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  $800,200 Sold Oct 03, 2025

  4107 Gabriella Ln, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft
  • Built 1998

  Last Sold Summary

  • 33% Below List Price
  • $260/SF
  • 112 Days On Market

  Current Estimated Value $936,816

  Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  4107 Gabriella Ln, Winter Park, FL 32792
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  Est $719,197 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  1360 Blue Stem Ln, Winter Park, FL 32792

  1360 Blue Stem Ln, Winter Park, FL 32792
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  /25

  $284,900

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

  2335 Inagua Way, Winter Park, FL 32792

  Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

  Marion McGrath ABSOLUTE REALTY GROUP, LLC

  2335 Inagua Way, Winter Park, FL 32792
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  /15

  $1,320 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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  $350,000 Sold Feb 12, 2025

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789

  • 1 Bed
  • 1.5 Baths
  • 726 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $482/SF
  • 82 Days On Market

  Current Estimated Value $365,401

  Last Listing Agent Jennifer Cornette HOLT REAL ESTATE LLC

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789
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  /2

  Est $149,964 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  160 Lewfield Cir Unit 160, Winter Park, FL 32792

  160 Lewfield Cir Unit 160, Winter Park, FL 32792
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  $409,999 Pending

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft

  5563 Garden Grove Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Lovely pool home in the desirable community of Winter Park, conveniently located near shopping, medical offices, and UCF.Freshly painted inside and out, this home features a kitchen with tile and granite, and all appliances included. The kitchen opens to the great room, which offers easy-care tile flooring throughout the main living areas. Enjoy the

  Anne Jones COLDWELL BANKER HUBBARD HANSEN

  5563 Garden Grove Cir, Winter Park, FL 32792
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  $2,599 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 $2743.90. That covers your base rent, $2599.00 + 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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  $380,000 Sold Mar 27, 2025

  3877 Waterview Loop, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,527 Sq Ft
  • Built 1988

  Last Sold Summary

  • $249/SF

  Current Estimated Value $374,484

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

  3877 Waterview Loop, Winter Park, FL 32792
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  Est $441,085 Not Listed For Sale

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

  2953 Clever Ln, Winter Park, FL 32792

  2953 Clever Ln, Winter Park, FL 32792
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  $679,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,920 Sq Ft

  2087 Laurelwood Way, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between

  Brian Rotenberger COMPASS FLORIDA LLC

  2087 Laurelwood Way, Winter Park, FL 32792
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  /7

  $1,350 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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  $396,477 Sold May 20, 2025

  7543 Dockside St, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Above List Price
  • $276/SF
  • 7 Days On Market

  Current Estimated Value $401,857

  Last Listing Agent Juan Matias LPT REALTY, LLC

  7543 Dockside St, Winter Park, FL 32792
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  Est $188,523 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3351 River View Way Unit 41, Winter Park, FL 32792

  3351 River View Way Unit 41, Winter Park, FL 32792
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  $714,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,928 Sq Ft

  1449 Pelican Bay Trail, Winter Park, FL 32792

  Under contract-accepting backup offers. Fantastic, updated Winter Park abode with 4 bedrooms, 2.5 baths, beautiful soaring wood plank ceilings, sparkling salt-filtration pool, and almost 3,000 sq ft is available now. This executive home located in the upscale Pelican Bay neighborhood is sure to please with so many recent updates, an oversized lushly treed lot (.46 acre), a long paver driveway and

  Steven Ritz KELLER WILLIAMS WINTER PARK

  1449 Pelican Bay Trail, Winter Park, FL 32792
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  /15

  $2,115 per month

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

  1381 Viburnum Ln, 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

  1381 Viburnum Ln, Winter Park, FL 32792
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  $3,020,000 Sold Oct 02, 2025

  1820 Englewood Rd, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,263 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $708/SF
  • 70 Days On Market

  Current Estimated Value $3,029,401

  Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
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  Est $471,851 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  2444 Firstlight Way, Winter Park, FL 32792

  2444 Firstlight Way, Winter Park, FL 32792
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  /25

  $425,000 Pending

  • 2 Beds
  • 2 Baths
  • 760 Sq Ft

  875 W Lyman Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of

  Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

  875 W Lyman Ave, Winter Park, FL 32789
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  $2,675 per month

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Townhouse for Rent

  2460 Firstlight Way, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2460 Firstlight Way, Winter Park, FL 32792
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  $1,120,000 Sold Jan 08, 2026

  5236 Lake Howell Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,710 Sq Ft
  • Built 2025

  Last Sold Summary

  • 23% Below List Price
  • $302/SF
  • 129 Days On Market

  Last Listing Agent Troy Hensley BHHS FLORIDA REALTY

  5236 Lake Howell Rd, Winter Park, FL 32792
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

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