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64 Properties for Sale In Winter Park
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$285,000
Condo
1920 WOODCREST DR #15, Winter Park, FL 32792
Gorgeous, fully renovated 2-bedroom / 2-bathroom condominium nestled in the heart of Winter Park along a beautiful and q...
Listed by COLDWELL BANKER RESIDENTIAL RE
$840,000
Condo
100 S INTERLACHEN AVE #204D, Winter Park, FL 32789
Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned bet...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,695,000
Single Family Home
1780 MIZELL AVE., Winter Park, FL 32789
Experience the height of modern luxury in this newly constructed home, masterfully designed by esteemed architect Gary H...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,899,900
Single Family Home
1521 CHESTNUT AVE, Winter Park, FL 32789
Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, built in 2023, located in one of W...
Listed by COMPASS FLORIDA LLC
$1,499,000
Single Family Home
1429 CHAPMAN CIR, Winter Park, FL 32789
Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophistica...
Listed by CORCORAN PREMIER REALTY
$689,900
Single Family Home
3759 KINSLEY PL, Winter Park, FL 32792
EXPECT TO BE IMPRESSED! Tucked away in a quaint and quiet Winter Park neighborhood, this beautifully maintained two-stor...
Listed by COMPASS FLORIDA LLC
$765,000
Single Family Home
620 DARCEY DR, Winter Park, FL 32792
New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heig...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$670,777
Single Family Home
3115 HEARTLEAF PL, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park, FL! This stunning 4-bedroom, ...
Listed by EXP REALTY LLC
$275,000
Townhouse
2318 INAGUA WAY, Winter Park, FL 32792
Discover One of Winter Park's Best Kept Secrets Windward Square! <br> <br>Welcome home to this completely renovated 2-be...
Listed by REAL BROKER, LLC
$399,000
Condo
311 E MORSE BLVD #7-5, Winter Park, FL 32789
Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio apartment in Whispering Waters...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$658,900
Single Family Home
3110 HEARTLEAF PL, Winter Park, FL 32792
Beautiful pool home with an open great room plan with high vaulted ceilings and master on the first floor situated on on...
Listed by RE/MAX PRIME PROPERTIES
$360,000
Single Family Home
1921 DARTMOUTH AVE, Winter Park, FL 32789
Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that make...
Listed by THOMAS LYNNE REALTY GROUP LLC
$410,000
Condo
240 KILLARNEY BAY CT #4, Winter Park, FL 32789
Welcome to Killarney Bay—Winter Park's best-kept secret for tranquil lakeside living, and just steps from the city's fin...
Listed by KELLER WILLIAMS WINTER PARK
$450,000
Single Family Home
2151 CONIFER AVE, Winter Park, FL 32792
Under contract-accepting backup offers. This POOL home is amazing in every way and is truly a must see! Original Owner w...
Listed by KORR REALTY CORP
$1,850,000
Single Family Home
1355 HIBISCUS AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-f...
Listed by PALMANO GROUP RE BROKERAGE LLC
$1,750,000
Single Family Home
446 ALBERTA DR, Winter Park, FL 32789
Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits ...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$649,900
Single Family Home
1926 NATALEN RD, Winter Park, FL 32792
*** MUST SEE WINTER PARK POOL HOME *** <br>Explore the virtual tours to fully appreciate the beauty of this completely r...
Listed by EXP REALTY LLC
$499,999
Single Family Home
1924 SUMMERFIELD RD, Winter Park, FL 32792
**This property qualifies for a closing cost credit up to $7,700 through the Seller's preferred lender.** Welcome to a l...
Listed by KELLER WILLIAMS REALTY AT THE PARKS
$375,000
Single Family Home
3430 ARBUTUS LN, Winter Park, FL 32792
Charming Winter Park Pool Home with Mother-In-Law Suite. Welcome to your own slice of paradise in the heart of Winter Pa...
Listed by URBAN NEST CLUB INC
$410,000
Single Family Home
4959 ARDMORE DR, Winter Park, FL 32792
Tucked away at the end of a quiet cul-de-sac with no HOA, this home sits on an oversized lot that offers exceptional spa...
Listed by COMPASS FLORIDA LLC
$500,000
Single Family Home
Winter Park, FL 32792
Welcome to this beautifully maintained 4-bedroom, 2.5-bath pool home nestled in a peaceful neighborhood. This two-story ...
Listed by TREASURE COAST REALTY GROUP, LLC
$198,000
Condo
4768 TANGERINE AVE #4768, Winter Park, FL 32792
Price adjusted! Fully Renovated 1-Bedroom First-Floor Condo – Stylish & Convenient Living. Move-in ready! Gorgeous new f...
Listed by PROPERTY OUTLET INTERNATIONAL
$3,190,000
Single Family Home
1820 ENGLEWOOD RD, Winter Park, FL 32789
Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Pa...
Listed by KELLER WILLIAMS ADVANTAGE III
$130,000
Condo
7449 DANIEL WEBSTER DR #3, Winter Park, FL 32792
Discover this 2-bedroom, 2-bathroom condo located in The Colonies community in Winter Park. Situated near UCF, Valencia ...
Listed by CREEGAN GROUP