Winter Park, FL Homes

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  /28

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,517 Sq Ft

  5547 Garden Grove Cir, Winter Park, FL 32792

  Winter Park, beautifully maintained 3-bedroom, 2-bathroom home nestled in the desirable Garden Grove neighborhood. Designed with an open floor plan and filled with natural light, this home offers versatile spaces perfect for both everyday living and entertaining.Step into the spacious Great Room which can be used for mulitple purposes like game room, home office or gym . The adjoining Kitchen

  Steve Dalton ROYALTY R E BOUTIQUE INC

  5547 Garden Grove Cir, Winter Park, FL 32792
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  /2

  $535,000 Sold May 28, 2025

  • 1,945 Sq Ft
  • $275/SF
  • 35 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  4200 Bear Gully Rd, Winter Park, FL 32792

  ACCEPTING BACK-UP OFFERS.....This is the one you've been waiting for! Located in Winter Park and on OVER HALF AN ACRE this lovely home is awaiting new owners. Step inside and notice the welcoming feeling, with NEW FLOORING throughout, TALL BASEBOARDS, built ins and appealing floor plan. The eat-in kitchen has been updated to include STAINLESS APPLIANCES, GRANITE COUNTERTOPS, backsplash, BREAKFAST

  Renee Killiri RED BIRD REALTY OF FLORIDA INC

  4200 Bear Gully Rd, Winter Park, FL 32792
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  /23

  Est $465,747 Not Listed For Sale

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

  2965 Clever Ln, Winter Park, FL 32792

  2965 Clever Ln, Winter Park, FL 32792
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  /70

  $479,900

  • 4 Beds
  • 2.5 Baths
  • 2,616 Sq Ft

  7679 Bent Bow Trail, Winter Park, FL 32792

  Spacious 4 bedroom 2.5 bath 2600+ Sq. Ft. Winter Park home within the desirable Arrowhead Cove subdivision. As you enter the home, you are greeted by a large living room / dining room area, with engineered hardwood floors, and a beautiful stacked stone electric fireplace at the center. The fully updated kitchen is complete with granite counters, wood cabinets, stainless steel appliances, and a

  Jason Gilkey GILKEY REAL ESTATE

  7679 Bent Bow Trail, Winter Park, FL 32792
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  /22

  $397,500 Sold May 28, 2025

  • 1,327 Sq Ft
  • $300/SF
  • 82 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  927 Mare Bello Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. LOCATION, LOCATION! Welcome to 927 Mare Bello Drive in Winter Park, Florida's highly desirable Eastbrook neighborhood. This peaceful and family-friendly community is renowned for its quiet streets and welcoming atmosphere. TOP-RATED SCHOOLS: Families will appreciate access to excellent educational institutions, including Winter Park High School.

  Susana Moor LA ROSA REALTY KISSIMMEE

  927 Mare Bello Dr, Winter Park, FL 32792
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  /31

  Est $499,380 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  1564 Little Wren Ln, Winter Park, FL 32792

  1564 Little Wren Ln, Winter Park, FL 32792
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  /15

  $179,900

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  1250 S Denning Dr Unit 108, Winter Park, FL 32789

  This move-in-ready, first-floor condo has been completely updated and is ready for its new owner. Enjoy newer flooring, fresh paint, an in unit washer/dryer, and modern fixtures throughout! Located in a well-maintained community with great amenities, including a pool. Conveniently situated in desirable Winter Park, close to shopping, dining, and major roadways. A great opportunity for homeowners

  Cleve Loveland LOVELAND PROPERTIES

  1250 S Denning Dr Unit 108, Winter Park, FL 32789
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  /2

  $190,000 Sold May 28, 2025

  • 1,117 Sq Ft
  • $170/SF
  • 163 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  7317 Forest Hill Ct Unit 235, Winter Park, FL 32792

  Reduced for a quick sell! Step into this captivating 3-bedroom, 2-bathroom second-floor end unit, nestled in a beatiful community. Spanning 1,117 square feet, this nicely upgraded home seamlessly blends style and comfort.Modern Upgrades: Enjoy a beautifully remodeled kitchen and bathrooms, featuring sleek finishes and high-quality materials.Open Concept Living: The spacious living and dining

  GOKHAN YILHAN COLDWELL BANKER RESIDENTIAL RE

  7317 Forest Hill Ct Unit 235, Winter Park, FL 32792
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  /31

  Est $461,050 Not Listed For Sale

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

  1868 Erudite Way, Winter Park, FL 32792

  1868 Erudite Way, Winter Park, FL 32792
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  /23

  $429,900

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft

  1842 Puritan Ave, Winter Park, FL 32792

  Step into this beautifully 2024 REMODELED 4-bedroom, 2-bathroom home located in a newly Re-Urbanized area of Winter Park, FL. Fully renovated in 2024, this 1,836-square-foot residence offers modern design, high-end finishes, and peace of mind with major system updates, including a 2022 roof, 2024 water heater, 2024 HVAC, 2024 plumbing, and 2024 electrical system.The interior features a

  Marissa Crawford COMPASS FLORIDA LLC

  1842 Puritan Ave, Winter Park, FL 32792
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  /2

  $1,340,000 Sold May 28, 2025

  • 5,500 Sq Ft
  • $244/SF
  • 293 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  571 Lakefront Blvd, Winter Park, FL 32789

  Welcome to Winter Park lakefront living at its finest. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  571 Lakefront Blvd, Winter Park, FL 32789
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  /29

  Est $440,784 Not Listed For Sale

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

  1860 Erudite Way, Winter Park, FL 32792

  1860 Erudite Way, Winter Park, FL 32792
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  /43

  $2,195,000

  • 5 Beds
  • 3.5 Baths
  • 3,558 Sq Ft

  1361 Palmer Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 1361 Palmer Avenue, a beautifully updated five-bedroom, 3.5-bath residence in the heart of Winter Park, Florida, 32789. This exceptional home has been meticulously maintained and extensively renovated, blending classic charm with modern design. Inside, you'll find a reimagined designer kitchen with premium finishes, ideal for everyday

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1361 Palmer Ave, Winter Park, FL 32789
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  /2

  $4,750,000 Sold May 27, 2025

  • 4,913 Sq Ft
  • $967/SF
  • 0 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1925

  984 Mayfield Ave, Winter Park, FL 32789

  Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  984 Mayfield Ave, Winter Park, FL 32789
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  /28

  Est $447,247 Not Listed For Sale

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

  1856 Erudite Way, Winter Park, FL 32792

  1856 Erudite Way, Winter Park, FL 32792
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  /26

  $332,000

  • 2 Beds
  • 2.5 Baths
  • 1,133 Sq Ft

  184 Sandlewood Trail Unit 2, Winter Park, FL 32789

  Welcome to Your Turnkey Retreat in Winter Park!Nestled just minutes from the charming boutiques and award-winning restaurants of Park Avenue, this beautifully updated 2-bedroom, 2.5-bathroom condo offers the perfect blend of style, comfort, and location. Zoned for the highly sought-after Dommerich Elementary School, this two-story home is ideal for anyone looking to enjoy the best of

  TOM NOELKE EXP REALTY LLC

  184 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  /2

  $575,000 Sold May 27, 2025

  • 972 Sq Ft
  • $592/SF
  • 24 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  1230 N Denning Dr, Winter Park, FL 32789

  This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original

  Ed Klein FANNIE HILLMAN & ASSOCIATES

  1230 N Denning Dr, Winter Park, FL 32789
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  /35

  Est $339,581 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3220 Crown Jewel Ct, Winter Park, FL 32792

  3220 Crown Jewel Ct, Winter Park, FL 32792
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  /55

  $1,514,950

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

  952 Moss Ln, Winter Park, FL 32789

  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 refined details and creating a luminous, welcoming atmosphere. Step inside to find

  Terry Connors THE SHOP REAL ESTATE CO.

  952 Moss Ln, Winter Park, FL 32789
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  /2

  $2,935,000 Sold May 27, 2025

  • 4,088 Sq Ft
  • $718/SF
  • 30 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1930

  266 Chase Ave, Winter Park, FL 32789

  One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  266 Chase Ave, Winter Park, FL 32789

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