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256 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
$1,875,000
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
$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
$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
$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
$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
$1,049,000
Single Family Home
2702 PARKLAND DR, Winter Park, FL 32789
Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audub...
Listed by Elizabeth Nordquist NORDQUIST & COMPANY INC
$1,649,000
Single Family Home
2501 WINTER PARK RD, Winter Park, FL 32789
PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park i...
Listed by Jill Healey KELLER WILLIAMS WINTER PARK
$820,000
Single Family Home
1927 ELAND AVE, Winter Park, FL 32789
*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale ...
Listed by Ryan Leitter CHARLES RUTENBERG REALTY ORLANDO
$3,975,000
Single Family Home
1150 VIA SALERNO, Winter Park, FL 32789
In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends archit...
Listed by Padgett McCormick 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
$2,699,000
Single Family Home
1597 OAKHURST AVE, Winter Park, FL 32789
A DISTINCTIVE WINTER PARK RESIDENCE IN AN EXCEPTIONAL LOCATION. Set along a quiet brick street in one of Winter Park's m...
Listed by Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS
$1,950,000
Single Family Home
751 PANSY AVE, Winter Park, FL 32789
Set along one of Winter Park's charming brick streets just steps from Park Avenue, this beautifully maintained home pair...
Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC
$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
$3,200
Single Family Home
450 W CANTON AVE, Winter Park, FL 32789
450 Canton Avenue — Winter Park, FL | $3,200/mo <br> <br>Charming and spacious, this beautifully located rental sits jus...
Listed by Kelly Price KELLY PRICE & COMPANY LLC
$1,995
Single Family Home
937 ARAGON AVE, Winter Park, FL 32789
Beautiful home located on a quaint, tree lined, brick street in desirable Winter Park. You will walk in a large family r...
Listed by Vivian Lippi LIPPI REALTY LLC
$3,600,000
Single Family Home
276 DETMAR DR, Winter Park, FL 32789
Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of...
Listed by Melanie Johnston CALL IT CLOSED INTL REALTY
$245,000
Condo
1250 S DENNING DR #Unit 233, Winter Park, FL 32789
Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a...
Listed by Samuel Kingsford STOCKWORTH REALTY GROUP
$285,000
Condo
283 SANDLEWOOD TRL #3, Winter Park, FL 32789
Virtually Staged. MOVE IN READY in Winter Park with nearly $30,000 in recent upgrades and improvements! This beautifully...
Listed by Crystal Adams RE/MAX INNOVATION
$660,000
Multi-Family
1016 ARAGON AVE, Winter Park, FL 32789
This "Investment Opportunity" Duplex is centrally located on a quiet tree lined, brick street, close to shopping, restau...
Listed by Pam Stewart PALMANO GROUP RE BROKERAGE LLC
$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
$1,050,000
Condo
311 E MORSE BLVD #4-5, Winter Park, FL 32789
Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated al...
Listed by Kim Garcia KELLER WILLIAMS ADVANTAGE REALTY
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