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258 Properties Available
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$340,000
Single Family Home
1941 OGLESBY AVE, Winter Park, FL 32789
Welcome home to this charming 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. This charm...
Listed by KaLeena Laubach LPT REALTY, LLC
$1,598,000
Single Family Home
2430 CHANTILLY AVE, Winter Park, FL 32789
Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed...
Listed by Kelly Price KELLY PRICE & COMPANY LLC
$3,265,000
Single Family Home
1761 LEGION DR, Winter Park, FL 32789
One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combi...
Listed by Harry Pool, III COLDWELL BANKER REALTY
$425,000
Single Family Home
2126 ALBERT LEE Pkwy, Winter Park, FL 32789
Welcome home to this adorable and beautifully updated 3-bedroom, 2-bathroom home in the heart of Winter Park! From the m...
Listed by Ross Pino, LLC COMPASS FLORIDA LLC
$1,875,000
Single Family Home
1661 LAUREL RD, Winter Park, FL 32789
Set along the brick-lined streets of Charmont, one of Winter Park's most coveted and established neighborhoods, 1661 Lau...
Listed by Caroline Van Den Berg VAN DEN BERG REAL ESTATE GROUP
$689,000
Single Family Home
900 CARVER ST, Winter Park, FL 32789
Completely Remodeled 2026 | Single-Story | Prime Location | Dual Suites | The redesigned kitchen features 42" shaker cab...
Listed by Farhad Haniff EXP REALTY LLC
$589,900
Single Family Home
1313 S DENNING DR, Winter Park, FL 32789
Welcome to a beautifully renovated 3-bedroom, 2-bath residence offering approximately 1,700 square feet of thoughtfully ...
Listed by Elizabeth Sanchez THE AGENCY FL
$664,900
Single Family Home
2333 WESTMINSTER CT, Winter Park, FL 32789
Welcome to 2333 Westminster Court, a stunningly reimagined residence that perfectly captures the effortless elegance of ...
Listed by Steven Luppert COMPASS FLORIDA LLC
$1,350,000
Single Family Home
720 PANSY AVE, Winter Park, FL 32789
Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and ...
Listed by Nick McKee KELLER WILLIAMS WINTER PARK
$635,000
Condo
565 HUNTINGTON AVE #565, Winter Park, FL 32789
Private, no-through-traffic street in one of Winter Park's most desirable locations. Just a short walk from downtown Win...
Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
$850,000
Single Family Home
1431 PALM AVE, Winter Park, FL 32789
Welcome to this beautifully maintained 1960s home nestled in one of Winter Park's desirable neighborhoods, where classic...
Listed by Kelsey Payton ALL REAL ESTATE & INVESTMENTS
$4,595,000
Single Family Home
1525 GRANVILLE DR, Winter Park, FL 32789
There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vim...
Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC
$3,245,000
Single Family Home
1836 WHITEHALL DR, Winter Park, FL 32789
Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil i...
Listed by Bianca Khoury PREMIER SOTHEBY'S INTL. REALTY
$2,050,000
Single Family Home
240 N PHELPS AVE, Winter Park, FL 32789
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designe...
Listed by Nick McKee KELLER WILLIAMS WINTER PARK
$810,000
Townhouse
1265 ARLINGTON PL, Winter Park, FL 32789
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park'...
Listed by Erika Beerbower FANNIE HILLMAN & ASSOCIATES
$1,399,000
Single Family Home
1473 BERKSHIRE AVE, Winter Park, FL 32789
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this s...
Listed by Gilson Rodrigues KARDOSH REALTY
$1,599,000
Single Family Home
641 NORTHWOOD CIRCLE, Winter Park, FL 32789
Virtually Staged. 641 Northwood Circle is a rare opportunity to own newer construction in the heart of Winter Park at a ...
Listed by Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY
$550,000
Townhouse
1250 FORMOSA AVE, Winter Park, FL 32789
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after...
Listed by Jeanine Louis, LLC EXP REALTY LLC
$699,900
Single Family Home
860 N DENNING DR, Winter Park, FL 32789
**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** <br> <br>This is not a remodel — it's a comple...
Listed by LaDarrius Sanders OUTLET REALTY
$840,000
Single Family Home
338 BLUE HERON DR, Winter Park, FL 32789
Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in th...
Listed by Samuel Kingsford STOCKWORTH REALTY GROUP
$1,079,000
Single Family Home
1120 WISCONSIN AVE, Winter Park, FL 32789
Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Win...
Listed by Kelly Price KELLY PRICE & COMPANY LLC
$350,000
Condo
700 MELROSE AVE #J24, Winter Park, FL 32789
Fully updated ..Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally...
Listed by Scott Butts KIMBRIDGE REALTY, LLC
$995,000
Single Family Home
1611 CHESTNUT AVE, Winter Park, FL 32789
HUGE PRICE IMPROVEMENT!! BRING ALL OFFERS!! Situated on arguably the finest brick street in Winter Park, beneath a canop...
Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
$1,795,000
Condo
106 S INTERLACHEN AVE #518, Winter Park, FL 32789
Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to ...
Listed by Mary Colton FANNIE HILLMAN & ASSOCIATES
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