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240 Properties Available
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$1,500,000
Single Family Home
2401 LAFAYETTE AVE, Winter Park, FL 32789
Experience the charm and elegance of Winter Park living in this beautifully designed 4-bedroom, 3.5-bath home offering 3...
Listed by DIVINE ESTATES REALTY LLC
$5,900
Single Family Home
2227 HOWARD DR, Winter Park, FL 32789
Single-story LAKEFRONT gem in Winter Park! This beautifully renovated mid-century home sits on an oversized waterfront l...
Listed by REALTY ONE GROUP MAGIC CITY
$349,900
Condo
1308 S PENNSYLVANIA AVE #3, Winter Park, FL 32789
PRICE IMPROVEMENT! WINTER PARK FOR UNDER 350k!!! Sip coffee or tea overlooking lush Mead Gardens from your private deck....
Listed by KELLER WILLIAMS CLASSIC
$2,900,000
Single Family Home
1401 GREEN COVE RD, Winter Park, FL 32789
This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open inte...
Listed by BUCKEYE REALTY LLC
$2,895,000
Single Family Home
940 LINCOLN CIR, Winter Park, FL 32789
This newly adjusted price represents extraordinary value for one of Winter Park's most coveted addresses. Located in the...
Listed by KELLY PRICE & COMPANY LLC
$675,000
Single Family Home
1399 ALOMA AVE, Winter Park, FL 32789
Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on...
Listed by FLORIDA HOMES REALTY & MTG
$1,495,000
Single Family Home
1661 WOODLAND AVE, Winter Park, FL 32789
PRICE IMPROVEMENT! Fabulous Top-to-Bottom Renovation on Coveted Brick Street in Prime Winter Park Location! This excep...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,795,000
Single Family Home
817 ANTONETTE AVE, Winter Park, FL 32789
Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality an...
Listed by FANNIE HILLMAN & ASSOCIATES
$674,000
Single Family Home
2612 LAFAYETTE AVE, Winter Park, FL 32789
***SELLER IS OFFERING $10,000 IN CONCESSIONS TOWARDS CLOSING COSTS***This exquisite residence offers sophistication and ...
Listed by EXP REALTY LLC
$3,599,999
Single Family Home
1761 LEGION DR, Winter Park, FL 32789
One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was complet...
Listed by SCANLON REALTY GROUP LLC
$1,595,000
Single Family Home
1733 HARMON AVE, Winter Park, FL 32789
Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3...
Listed by SOUTH REALTY, INC
$650,000
Single Family Home
1730 ONECO AVE, Winter Park, FL 32789
Vintage house with close proximity to Park Avenue surronded by newely constructed homes on a scenic brick street. A crea...
Listed by THE TEAM REAL ESTATE GROUP INC
$3,650
Single Family Home
2070 SAINT GEORGE AVE, Winter Park, FL 32789
Charming lakefront cottage in the heart of Winter Park! Welcome to this rare gem nestled on Lake Spier in beautiful Wint...
Listed by KELLER WILLIAMS WINTER PARK
$2,749,000
Condo
140 E MORSE BLVD #J, Winter Park, FL 32789
Experience the pinnacle of luxury living in the heart of downtown Winter Park with this stunning penthouse residence at ...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$825,000
Single Family Home
734 MARYLAND AVE, Winter Park, FL 32789
Dreaming of living in an historic home in the much sought-after charming city of Winter Park, north of Orlando? Are you ...
Listed by HOMECOIN.COM
$635,000
Single Family Home
1339 ORCHID AVE, Winter Park, FL 32789
A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office ...
Listed by ABIDE REALTY
$949,900
Single Family Home
609 LANGHOLM DR, Winter Park, FL 32789
Nestled in the heart of Winter Park in one of the area's most sought-after neighborhoods, this professionally designed a...
Listed by JMO REAL ESTATE GROUP
$1,800
Single Family Home
830 HUNTINGTON CT, Winter Park, FL 32789
Welcome to this charming and beautifully updated 1/2 duplex, ideally situated in one of Winter Park's most desirable nei...
Listed by LIVING MANAGEMENT REALTY LLC
$775,000
Single Family Home
1961 WINTER PARK RD, Winter Park, FL 32789
Charming & Updated 3-Bedroom Home in Prime Winter Park Location! <br> <br>Nestled in the highly sought-after Audubon Par...
Listed by THE REAL ESTATE PRINCIPLE, INC
$2,399,000
Single Family Home
922 N PENNSYLVANIA AVE, Winter Park, FL 32789
Experience timeless elegance and modern sophistication in this stunning 3 bedroom, 4 bath Mediterranean home, ideally si...
Listed by FANNIE HILLMAN & ASSOCIATES
$650,000
Condo
300 CAROLINA AVE #205, Winter Park, FL 32789
Live in the heart of Winter Park, just steps from Park Avenue, in this well-maintained 2 bedroom, 2 bathroom corner cond...
Listed by PALMANO GROUP RE BROKERAGE LLC
$3,000
Condo
300 CAROLINA AVE #205, Winter Park, FL 32789
Live in the heart of Winter Park just steps from Park Avenue in this charming and well-maintained 2 bedroom, 2 bathroom ...
Listed by PALMANO GROUP RE BROKERAGE LLC
$3,300,000
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
$2,490,000
Condo
1602 ALABAMA DR #PH404, Winter Park, FL 32789
A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residen...
Listed by KELLY PRICE & COMPANY LLC