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Vacation Homes for Sale in Winter Park, FL

14 homes
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840 W Comstock Ave, Winter Park, FL 32789

Immerse yourself in the serenity this modern boutique home offers in the heart of Winter Park, FL. Walking up you are greeted by an adorable front patio enticing you to enjoy your favorite beverage ...
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100 S Interlachen Ave Unit 410, Winter Park, FL 32789

Welcome to The Cloisters Condominiums, a sanctuary nestled between the serene Winter Park Chain of Lakes and the vibrant Park Avenue. This sophisticated condominium embodies the essence of Winter Par...
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1269 Wading Waters Cir, Winter Park, FL 32792

Location Location Location. WINTER PARK. Built in 2021 and upgraded this year. This Meritage Homes Wimberley 11 model sits on a premium lot that backs onto conservation and is next to the playgro...
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2530 Franklin Ave, Winter Park, FL 32789

***SELLER IS WILLING TO ASSIST BUYER WITH CLOSING COSTS OR INTEREST RATE BUY-DOWN!*** Masterful design and modern luxury are uniquely embodied in this beautiful Winter Park home. As you drive up the ...
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629 Country Club Dr, Winter Park, FL 32789

Pre-Construction. To be built. ***NEW CONSTRUCTION*** Welcome to Winter Park! Bring your boat- deeded lake access on Lake Killarney! This stunning new modern home is meticulously designed and conveni...
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5330 N Lake Burkett Ln, Winter Park, FL 32792

JUST REDUCED.Seller needs to sale Better-Than-New Home in Winter Park! Welcome to your better-than-new home in a highly desirable, well-established Winter Park neighborhood! This exceptional proper...
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2437 Eastbrook Blvd, Winter Park, FL 32792

NEW PRICE!!! NEW ROOF!!! NEW HVAC!!! This established and desirable Winter Park neighborhood enjoys access to the excellent, top-rated Seminole County schools, with an elementary school just a ha...
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2804 Dike Rd, Winter Park, FL 32792

Welcome to your very own private personal retreat! This truly one of a kind oasis of a property features 1.9 acres of lushly landscaped garden in Winter Park. A four-bedroom, three-bathroom main hous...
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2408 Lafayette Ave, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Nestled within the charming enclave of Winter Park, this captivating residence transcends the ordinary, offering an unparalleled living experience that...
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1546 Minnesota Ave, Winter Park, FL 32789

Welcome to this immaculately remodeled 4-bedroom, 3-bathroom home, ideally situated just minutes from Downtown Winter Park, showcasing exquisite attention to detail and a blend of elegant, luxurious,...
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1135 Lakeview Dr, Winter Park, FL 32789

Amazing opportunity to own a lakefront home on Lake Virginia footsteps from Rollins College, nestled in walking distance to downtown Park Avenue shops and restaurants, and located on the coveted Chai...
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5118 Lake Howell Rd, Winter Park, FL 32792

Short Sale. Discover the perfect gem in Winter Park with no HOA or CDD fees! This fully remodeled home is conveniently located minutes from downtown Winter Park, top-rated restaurants, shopping cente...
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2819 Scarlet Rd, Winter Park, FL 32792

NEW ROOF COMING SOON! Welcome to the Winter Park Pines, with its tree-lined streets and where the mailman still delivers to your door! This is your opportunity to invest in a 2,000+ sq ft home, nestl...
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1210 Via Capri, Winter Park, FL 32789

Under Construction. Welcome to your custom-designed oasis of contemporary living in the esteemed Vias neighborhood of Winter Park, crafted by Z Properties. Scheduled for completion in late 2024, this...