Winter Park, FL Homes

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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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  /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

  $186,000

  • 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

  $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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  /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

  $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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  /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

  $685,000 Sold May 27, 2025

  • 2,446 Sq Ft
  • $280/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1321 Medinah Ct, Winter Park, FL 32792

  This incredible home has only ever had one owner! It's your opportunity to own .34 acres on a Winter Park cul-de-sac, complete with mature landscaping and backyard access to the Cady Way Trail. The oversized backyard has endless potential -- bring your ideas for a pool, an addition, or an amazing garden. Inside the home, you'll find a 4 bedroom, 2 bath split floor plan with multiple living space

  Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792
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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

  $660,000 Sold May 23, 2025

  • 1,975 Sq Ft
  • $334/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  2732 Lion Heart Rd, Winter Park, FL 32792

  Welcome to the sought after Winter Park Pines. A neighborhood where children are always riding bikes and playing outside, neighbors look out for one another and neighborhood gatherings are a regular event. When entering the home, you find yourself drawn to the open floor plan and natural light. Beautiful, restored terrazzo floors throughout the house. The eat in kitchen with its great layout has

  Sue Grafton FANNIE HILLMAN & ASSOCIATES

  2732 Lion Heart Rd, Winter Park, FL 32792
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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

  $565,000 Sold May 23, 2025

  • 2,309 Sq Ft
  • $245/SF
  • 40 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  230 S Ranger Blvd, Winter Park, FL 32792

  Beautifully updated and FURNISHED (upon negotiation) 3-bedroom, 2-bath home in the desirable Winter Park Pines neighborhood is truly move-in ready! Fully renovated in 2019, the home boasts a range of high-end features, including hardwood flooring, designer fixtures, custom crown molding, and 5.25” baseboards throughout the majority of the home. Open floor plan is an inviting space for both living

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  230 S Ranger Blvd, Winter Park, FL 32792
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  /38

  Est $205,749 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  7320 Forest Hill Ct Unit 236, Winter Park, FL 32792

  7320 Forest Hill Ct Unit 236, Winter Park, FL 32792
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  /4

  $299,999

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
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  /2

  $284,000 Sold May 23, 2025

  • 1,140 Sq Ft
  • $249/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  2539 Antilles Dr, Winter Park, FL 32792

  Motivated seller! We encourage all offers! Welcome to 2539 Antilles Dr, Winter Park, FL – a beautiful corner unit townhouse in the highly desirable Windward Square. As you step inside, you’re welcomed by a cozy living room that seamlessly leads into the kitchen, featuring a new dishwasher and plenty of cabinet space. As you continue walking through the house you will notice the 3 spacious

  Allie George CORCORAN PREMIER REALTY

  2539 Antilles Dr, Winter Park, FL 32792
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  /31

  Est $668,494 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft

  775 Mcintyre Ave Unit 9, Winter Park, FL 32789

  775 Mcintyre Ave Unit 9, Winter Park, FL 32789

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