Recently Sold Winter Park, FL Homes

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  $230,000 Sold Apr 15, 2025

  • 1,295 Sq Ft
  • $178/SF
  • 52 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  2498 Timberline Dr Unit 2498, Winter Park, FL 32792

  Cedarwood Village-Affordable living in a great location in Winter Park. This 2 bedroom, 2 bath, 1295 SF condominium offers an open floor plan with vaulted ceilings and sky lights in the living and dining areas and a wood burning fireplace in the living room. The Kitchen overlooks a private courtyard with sliding glass doors. There is room for a quaint breakfast table, additional storage cabinets

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  2498 Timberline Dr Unit 2498, Winter Park, FL 32792
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  /2

  $2,100,000 Sold Apr 15, 2025

  • 2,894 Sq Ft
  • $726/SF
  • 35 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  1032 Early Ave, Winter Park, FL 32789

  Discover your own slice of paradise on this extraordinary property spanning nearly five acres, perfectly nestled between two serene lakes in Winter Park. Offering unmatched privacy and tranquility, this retreat is ideal for those who value seclusion, natural beauty, and convenience—all within city limits, yet feeling a world away. With motorized boats allowed on both lakes, you can spend

  Teresa Corbett KINCAID REALTY

  1032 Early Ave, Winter Park, FL 32789
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  /2

  $439,900 Sold Apr 14, 2025

  • 1,708 Sq Ft
  • $258/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  1751 Meadowgold Ln, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home with a loft in the highly sought-after Autumn Glen community, located in the heart of Winter Park and within a top-rated school district.This home offers a new roof installed in 2020 and a Goodman 2-stage A/C system from 2018, ensuring both comfort and energy efficiency. Freshly updated with new stucco and paint in 2022, it

  Vi Mateo KELLER WILLIAMS WINTER PARK

  1751 Meadowgold Ln, Winter Park, FL 32792
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  /2

  $649,000 Sold Apr 14, 2025

  • 1,545 Sq Ft
  • $420/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  721 Glenridge Way, Winter Park, FL 32789

  Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  721 Glenridge Way, Winter Park, FL 32789
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  /2

  $660,000 Sold Apr 14, 2025

  • 2,145 Sq Ft
  • $308/SF
  • 29 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1978

  1037 Fairway Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Elegant 3-Bedroom, 3-Bathroom Home With New Roof and NO HOA on Winter Park Pines Golf Course!Step into this beautifully updated single-story home, perfectly situated on the scenic Winter Park Pines Golf Course. Offering a seamless blend of modern design and cozy charm, this property boasts 3 spacious bedrooms, each with its own en suite

  Skip Juma LEGACY REALTY & BROKERS LLC

  1037 Fairway Dr, Winter Park, FL 32792
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  /2

  $315,000 Sold Apr 14, 2025

  • 1,148 Sq Ft
  • $274/SF
  • 35 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  690 Osceola Ave Unit 308, Winter Park, FL 32789

  Seller motivated!!! **Prime Location & Endless Potential!** Fantastic opportunity to make it your own Oasis with some updating. Transform this condo with your personal design. Situated in Winter Park's most sought-after zip code, this spacious 2-bedroom, 2-bath lakefront condo is an incredible opportunity to create your perfect retreat. Enjoy your dock—ideal for a boat or paddle board—and unwind

  Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

  690 Osceola Ave Unit 308, Winter Park, FL 32789
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  /2

  $90,250 Sold Apr 14, 2025

  • 1,108 Sq Ft
  • $81/SF
  • 58 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1974

  3000 George Mason Ave Unit 1, Winter Park, FL 32792

  Back on the Market. Don’t miss the opportunity to live in fabulous Winter Park just minutes from shopping, amazing restaurants and easy access to the airport and 417 Expressway. This beautiful two-level condo is in the heart of it all. With Spanish Tile throughout the bottom floor. Kitchen with beautiful granite counter tops. Gorgeous staircase that leads you up to two bedrooms. The master

  Nathalie Charles PREMIUM PROPERTIES REAL ESTATE

  3000 George Mason Ave Unit 1, Winter Park, FL 32792
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  /2

  $140,000 Sold Apr 14, 2025

  • 582 Sq Ft
  • $241/SF
  • 152 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1960

  151 N Orlando Ave Unit 142, Winter Park, FL 32789

  Introducing a charming 1 bed, 1 bath condo located on the serene shores of Lake Killarney in Winter Park Florida. Enjoy the perfect balance of lakeside tranquility, urban convenience, with a stunning sunset and being just a short walk to Trader Joe's, movie theaters, restaurants, and coffee shops. This home is ideal for someone seeking a peaceful retreat with all the benefits of a vibrant

  TOM NOELKE EXP REALTY LLC

  151 N Orlando Ave Unit 142, Winter Park, FL 32789
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  /2

  $1,885,000 Sold Apr 11, 2025

  • 3,499 Sq Ft
  • $539/SF
  • 0 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2024

  2144 Sycamore Dr, Winter Park, FL 32789

  Stunning new Winter Park residence.

  Christopher Christensen COMPASS FLORIDA LLC

  2144 Sycamore Dr, Winter Park, FL 32789
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  /2

  $675,000 Sold Apr 11, 2025

  • 2,258 Sq Ft
  • $299/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  604 Darcey Dr, Winter Park, FL 32792

  Welcome to this desirable 4 bedroom, 2 bathroom gem situated on a coveted corner lot in the heart of Brookshire Heights. With more than 2,200 SF of living space, this home offers a welcoming atmosphere with its spacious formal living and dining areas. Beautiful plantation shutters enhance the interior, providing both elegance and privacy. The kitchen features convenient eat-in space, a closet

  Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  604 Darcey Dr, Winter Park, FL 32792
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  /2

  $500,000 Sold Apr 11, 2025

  • 2,204 Sq Ft
  • $227/SF
  • 23 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1985

  4309 Enright Ct, Winter Park, FL 32792

  Welcome home! This inviting two-story pool home offers the perfect blend of modern features and classic 1980s charm on a large, 0.25-acre lot. Driving up to the property, you immediately notice its quaint, cul-de-sac location and warm curb appeal enhanced by its warm brick facade. At the front door, high ceilings and a cozy fireplace greet you in the living room and lead you into the heart of the

  Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  4309 Enright Ct, Winter Park, FL 32792
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  /2

  $175,000 Sold Apr 11, 2025

  • 730 Sq Ft
  • $240/SF
  • 230 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1964

  700 Melrose Ave Unit E6, Winter Park, FL 32789

  Welcome to this charming first-floor, one-bedroom, one-bathroom condo in the highly sought-after Winter Park Gardens community, exclusive 55+. This bright and airy home features an open floor plan with a spacious living area and a versatile sunroom, perfect for an additional living space or home office. The sunroom offers stunning views of the tranquil pond and lush garden, creating a serene

  Milton James COLDWELL BANKER RESIDENTIAL RE

  700 Melrose Ave Unit E6, Winter Park, FL 32789
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  /2

  $600,000 Sold Apr 10, 2025

  • 2,141 Sq Ft
  • $280/SF
  • 20 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  7531 Lodge Pole Trail, Winter Park, FL 32792

  Welcome to this beautifully renovated 4-bedroom, 2.5-bathroom block home located on a serene, over one-third acre lot in desirable Winter Park. The private, fully fenced yard offers peace and quiet, making it the perfect retreat for families and those who love to entertain. With 2,141 square feet of living space and 3,175 total square feet under the roof, including porches and a large garage,

  Austin Cummings NEXTDWELL

  7531 Lodge Pole Trail, Winter Park, FL 32792
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  /2

  $1,100,000 Sold Apr 10, 2025

  • 2,432 Sq Ft
  • $452/SF
  • 44 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  1932 Temple Dr, Winter Park, FL 32789

  Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street is full of natural light, clean lines and crisp open spaces. Three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and beckons the green of an outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1932 Temple Dr, Winter Park, FL 32789
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  /2

  $365,000 Sold Apr 10, 2025

  • 1,452 Sq Ft
  • $251/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  5102 Lake Howell Rd, Winter Park, FL 32792

  Live the perfect suburban lifestyle. Minutes to historic downtown Winter Park, this 3 bedroom 2 Bath Mid Century Modern home has an ideal location. The nearly quarter acre lot backs up to the Interlachen Country Club Conservation area, so it feels very private. Yet, you are close to every convenience, shopping, restaurants, hospitals. Walking distance to YMCA. From the minute you step in, you

  Rosye Chowanski COLDWELL BANKER REALTY

  5102 Lake Howell Rd, Winter Park, FL 32792
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  /2

  $551,000 Sold Apr 10, 2025

  • 1,906 Sq Ft
  • $289/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  7884 Broken Arrow Trail, Winter Park, FL 32792

  **The MOST discerning buyers must come see this home in person!** Have you been dreaming of cul-de-sac life? Take a long look at this better-than-new home. The many improvements will impress the most particular buyer and are too lengthy to fit in this description, so please reach out for a full list of updates and to schedule a tour! This is the last home sitting at the end of a beautiful

  Stacy Bucek CHARLES RUTENBERG REALTY ORLANDO

  7884 Broken Arrow Trail, Winter Park, FL 32792
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  /2

  $1,250,000 Sold Apr 10, 2025

  • 2,334 Sq Ft
  • $536/SF
  • 267 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  858 Douglas Ave, Winter Park, FL 32789

  Stunning residence in Winter Park! Experience luxury and convenience in this highly sought-after location, so close to everything, you can walk to Winter Park Village (.5 miles), Hannibal Square (.3 miles) and Park Avenue (.6 miles), and less than a block to the beautiful Lake Island Park. You will be the envy of all who visit.This home features a gourmet kitchen with waterfall island

  Greta Bost SUMMER WIND REALTY CENTRAL FL

  858 Douglas Ave, Winter Park, FL 32789
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  /2

  $385,000 Sold Apr 09, 2025

  • 1,600 Sq Ft
  • $241/SF
  • 100 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  3607 Datura Ct, Winter Park, FL 32792

  Recently reduced for quick sale! Three bedroom/2 bath pool home located in a much sought after neighborhood in Winter Park. Located on large corner lot. Many recent updates including luxury vinyl flooring, new hot water heater, new HVAC system, new pool pump, and roof replaced 1 year ago. Centrally located to all major highways, shopping, Altamonte Springs, and downtown Orlando. Ready for

  Dana Stanley PREMIUM PROPERTIES R.E SERVICE

  3607 Datura Ct, Winter Park, FL 32792
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  /2

  $799,000 Sold Apr 08, 2025

  • 2,331 Sq Ft
  • $343/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1952

  Unlisted Address

  A pristine location to build the home of your dreams in the heart of the Tree Streets of Winter Park. Elm is a quiet tree-lined street providing tranquility while providing the lifestyle Winter Park is known for. Elm is a block from Phelps Park, a short walk to YMCA, Interlachen Country Club and Winter Park Racquet Club. The lot is roughly 75 by 122 feet and among multimillion-dollar homes. Home

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  Unlisted Address
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  /2

  $288,000 Sold Apr 08, 2025

  • 1,187 Sq Ft
  • $243/SF
  • 204 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  1811 Winter Green Blvd, Winter Park, FL 32792

  Welcome to this charming property with a soothing neutral color scheme that exudes elegance. The kitchen features equipped with all stainless steel appliances. Fresh interior paint throughout gives it a brand-new feel. Outside, the patio is ideal for relaxation or entertaining. Inside, updated flooring adds a modern touch and durability. With these features, this property is more than just a

  GREGORY BLACKALL VERANDA REALTY GROUP

  1811 Winter Green Blvd, Winter Park, FL 32792
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  /2

  $1,850,000 Sold Apr 07, 2025

  • 3,505 Sq Ft
  • $528/SF
  • 10 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2025

  2248 Middleton Ave, Winter Park, FL 32792

  Step into the coastal lifestyle you've always dreamed of with this one-of-a-kind, luxurious home that has everything you could ever want—and more. From the moment you enter, you’ll be greeted with positive vibes and a seamless flow that combines elegance with practicality. The spacious open floor plan, complemented by beautiful wood flooring, creates a bright and airy atmosphere perfect for both

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  2248 Middleton Ave, Winter Park, FL 32792
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  /2

  $425,000 Sold Apr 07, 2025

  • 1,715 Sq Ft
  • $248/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  2642 Tierra Cir, Winter Park, FL 32792

  Charming home in a convenient Winter Park location, with a brand-new roof, enormous yard, and spacious living areas. A brick paver walkway leads to a welcoming front foyer. The living and dining room combination features newer windows, complemented by wood shutters and parquet floors. The updated kitchen has stainless steel appliances, granite countertops, beautiful cream-colored cabinets, and an

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  2642 Tierra Cir, Winter Park, FL 32792
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  /2

  $585,000 Sold Apr 07, 2025

  • 1,132 Sq Ft
  • $517/SF
  • 38 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1949

  1424 Cavendish Rd, Winter Park, FL 32789

  Welcome to 1424 Cavendish Road. This Beautiful 1940’s Pool Home is tucked between the tree-lined streets of highly desired, Orwin Manor, offering the perfect blend of classic appeal and modern convenience.Step into this charming home and experience its warm and inviting ambiance. The living room is bathed in natural light, with a cozy wood-burning fireplace that adds timeless character and

  Lisa Grey KEYSEEKERS REAL ESTATE

  1424 Cavendish Rd, Winter Park, FL 32789
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  /2

  $270,000 Sold Apr 04, 2025

  • 929 Sq Ft
  • $291/SF
  • 12 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  609 Gallery Dr Unit 2, Winter Park, FL 32792

  Welcome home to Winter Park! This corner, end unit is located on the second floor with a cozy fireplace and vaulted ceilings to create an open feeling. Tons of natural light fill the space. The large primary bedroom has a pool view, ensuite bath and walk-in closet. The split bedroom plan offers privacy and there is indoor laundry. This unit has eating space in the kitchen and solid countertops.

  Kim Oliver NONA LEGACY POWERED BY LA ROSA

  609 Gallery Dr Unit 2, Winter Park, FL 32792
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  /2

  $410,000 Sold Apr 04, 2025

  • 1,245 Sq Ft
  • $329/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  7549 Dockside St, Winter Park, FL 32792

  Completely renovated cute and cozy home in Winter Park is available for sale on a quiet street with low traffic.

  Marina Baranska COLDWELL BANKER REALTY

  7549 Dockside St, Winter Park, FL 32792
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  /2

  $410,000 Sold Apr 04, 2025

  • 1,292 Sq Ft
  • $317/SF
  • 45 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1954

  2111 Staunton Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to a delightful property that boasts a modern, neutral-colored paint scheme throughout. The kitchen is a chef's dream, equipped with all stainless steel appliances. The outdoor area is perfect for entertaining, featuring a deck and covered patio in the backyard. The property also includes a fenced-in backyard, providing privacy and security.

  GREGORY BLACKALL VERANDA REALTY GROUP

  2111 Staunton Ave, Winter Park, FL 32789
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  /2

  $600,000 Sold Apr 04, 2025

  • 1,751 Sq Ft
  • $343/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  631 Callahan St, Winter Park, FL 32789

  **PRICED TO SELL** Welcome to this beautifully remodeled ranch-style home, where modern elegance meets timeless charm. Located less than half a mile from the vibrant heart of Park Avenue, this home has 1,750 square feet of living space, presenting the perfect blend of contemporary functionality. Remodeled in 2022, Roof replaced in 2023. New Paver Patio and Turf. Step inside to discover

  Yousef Zeidan CORCORAN PREMIER REALTY

  631 Callahan St, Winter Park, FL 32789
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  /2

  $527,500 Sold Apr 04, 2025

  • 1,735 Sq Ft
  • $304/SF
  • 55 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  513 Cornwall Rd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Location, Location, Location! Don’t miss this opportunity to own a charming single-story home in the well-established Winter Park Pines neighborhood, known for its great schools and quiet streets. The exterior boasts tidy landscaping and an inviting front porch. Step inside to discover a spacious and bright living room, highlighted by an attractive

  Michelle Deleon BHHS FLORIDA REALTY

  513 Cornwall Rd, Winter Park, FL 32792
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  /2

  $1,000,000 Sold Apr 04, 2025

  • 2,458 Sq Ft
  • $407/SF
  • 141 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1001 Tuscany Place, Winter Park, FL 32789

  Located in the Tuscany Place neighborhood in the heart of Winter Park, this home offers endless potential for those looking to create their dream residence. With its classic ranch architecture and original features, this property is a blank canvas awaiting your personal touch, or provides a great opportunity to build new on its 0.39-acre corner lot. The home includes 3 bedrooms and 2 bathrooms, a

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
• 

  /2

  $1,290,000 Sold Apr 04, 2025

  • 2,350 Sq Ft
  • $549/SF
  • 173 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  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 amongst the lush landscape. Once inside the arched entry door you will be transported to an open floor plan with lots of natural light adorned with oversized windows, showcasing flora at every turn,

  Elizabeth Hall CHARLES RUTENBERG REALTY ORLANDO

  840 W Comstock Ave, Winter Park, FL 32789
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  /2

  $385,000 Sold Apr 03, 2025

  • 1,904 Sq Ft
  • $202/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1970

  1873 Poinciana Rd, Winter Park, FL 32792

  Discover a rare investment opportunity tucked away in the heart of Winter Park, this 4-bedroom, 3-bathroom home is brimming with potential. Overlooking a green scenic golf course, this property offers a prime location, spacious layout, and endless possibilities. Whether you're looking for a home with character or a rewarding renovation project, this is a golden opportunity you don’t want to miss!

  Benondre Cerezo COLDWELL BANKER REALTY

  1873 Poinciana Rd, Winter Park, FL 32792
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  /2

  $415,000 Sold Apr 03, 2025

  • 1,755 Sq Ft
  • $236/SF
  • 52 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2021

  1496 Broad Wing Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This gorgeous townhome offers the luxury and modern touches you've been seeking. As you step inside this home, you'll be greeted by high ceilings and neutral colors which enhance the abundance of natural light. The expansive great room is perfect for entertaining, and the kitchen features sleek espresso cabinets, stunning granite countertops, and

  Michelle Deleon BHHS FLORIDA REALTY

  1496 Broad Wing Ln, Winter Park, FL 32792
• 

  /2

  $850,000 Sold Apr 03, 2025

  • 2,066 Sq Ft
  • $411/SF
  • 251 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1905 S Lakemont Ave, Winter Park, FL 32792

  Special financing or closing cost credits available for qualified buyers!Introducing the 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! This exceptional, move-in ready residence is perfectly situated between the serene shores of Lake Spier and Lake Compton in the exclusive Lake Spier Crossing community of Winter Park.Discover modern luxury with 10 impeccably designed two-story townhomes,

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1905 S Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $372,000 Sold Apr 02, 2025

  • 1,782 Sq Ft
  • $209/SF
  • 19 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1975

  5339 Cypress Dr, Winter Park, FL 32792

  Great Opportunity in Prime Winter Park Location. Single-story, 4-bedroom, 2-bath home with a split floor plan, featuring separate living, dining, and family rooms. Original owner, with most features still in original condition—ideal for a renovation project. Loads of potential for investors or buyers looking to customize their dream home. Great location with easy access to top-rated Seminole

  JASON CRAWFORD FUTURE HOME REALTY INC

  5339 Cypress Dr, Winter Park, FL 32792
• 

  /2

  $2,495,000 Sold Apr 01, 2025

  • 4,168 Sq Ft
  • $599/SF
  • 4 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1926

  140 Cortland Ave, Winter Park, FL 32789

  Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom,

  Stephen Hachey FLAT FEE MLS REALTY

  140 Cortland Ave, Winter Park, FL 32789
• 

  /2

  $1,877,500 Sold Apr 01, 2025

  • 4,612 Sq Ft
  • $407/SF
  • 5 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 1925

  1446 Berkshire Ave, Winter Park, FL 32789

  Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads

  Jimmy Hendrickson SERHANT

  1446 Berkshire Ave, Winter Park, FL 32789
• 

  /2

  $449,000 Sold Apr 01, 2025

  • 1,964 Sq Ft
  • $229/SF
  • 98 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2021

  1323 Merrydale Way, Winter Park, FL 32792

  Welcome to 1323 Merrydale Way, Winter Park! Located in the esteemed Hawks Crest gated community, this beautifully maintained 3-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern design and everyday comfort. As you step inside, you’ll find an open-concept floor plan that’s ideal for entertaining and relaxation.The spacious master suite is a highlight, featuring an oversized

  Melissa Johnson EXP REALTY LLC

  1323 Merrydale Way, Winter Park, FL 32792
• 

  /2

  $375,000 Sold Apr 01, 2025

  • 1,512 Sq Ft
  • $248/SF
  • 320 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1967

  565 Heritage Blvd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Located in the established, well-maintained subdivision of Georgetown Estates in beautiful Winter Park, this 4 bedroom, 2 bathroom split plan home is ready for you to move in and make it your very own! Walking into the home you are welcomed into a spacious foyer, and beyond that is an open concept

  Bethanne Baer BEAR TEAM REAL ESTATE

  565 Heritage Blvd, Winter Park, FL 32792
• 

  /2

  $719,000 Sold Mar 31, 2025

  • 1,734 Sq Ft
  • $415/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1961

  2003 Woodcrest Dr, Winter Park, FL 32792

  Renovated and ready for MOVE IN! Top location in Kenilworth Estates! Top Schools - Brookshire, Glenridge, WP High! Walk, bike, scooter or quick drive to schools, Baldwin Park, East End/Corrine, Lake Baldwin Dog Park, VA Clinic and tons of Shopping and Dining! Light and bright open floor plan w/split bedrooms, easy care and stylish porcelain wood tile flooring, recessed lighting. Wood burning

  Lisa Gould KELLER WILLIAMS WINTER PARK

  2003 Woodcrest Dr, Winter Park, FL 32792
• 

  /2

  $685,000 Sold Mar 31, 2025

  • 1,267 Sq Ft
  • $541/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1971

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

  Experience a lifestyle of refined sophistication and effortless tranquility at The Cloisters Condominium, ideally between Park Avenue and the serene shores of Lake Osceola. This exquisitely remodeled residence offers a seamless blend of timeless elegance and thoughtful design. Set on the second floor, this sun-drenched retreat is bathed in natural light from its northeast-facing sunroom, where

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

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