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238 Properties Available
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$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
$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
$1,200,000
Single Family Home
835 ANTONETTE AVE, Winter Park, FL 32789
Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter. <br>Nestled in the heart of...
Listed by FANNIE HILLMAN & ASSOCIATES
$610,000
Condo
151 N ORLANDO AVE #212, Winter Park, FL 32789
Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom second-floor condo. This expa...
Listed by THE AGENCY ORLANDO
$2,495
Single Family Home
1955 ELAND AVE, Winter Park, FL 32789
This charming 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy all Downtown Winter Park has, Par...
Listed by REAL PROPERTY MANAGEMENT AND REALTY
$950,000
Single Family Home
1018 TURNER RD, Winter Park, FL 32789
Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Pa...
Listed by WEMERT GROUP REALTY LLC
$1,180,000
Single Family Home
2607 LAFAYETTE AVE, Winter Park, FL 32789
Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park's most desirable neig...
Listed by FORTUNE INTERNATIONAL REALTY
$775,000
Single Family Home
1840 LAUREL RD, Winter Park, FL 32789
Unlock the potential of this charming 3-bedroom, 2-bathroom home—ideal for renovation or building your custom dream resi...
Listed by KEYSEEKERS REAL ESTATE
$1,300,000
Single Family Home
171 CORTLAND AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Come see this outstanding 15,000 sqft lot surrounded by multi-million dollar hom...
Listed by FANNIE HILLMAN & ASSOCIATES
$975,000
Townhouse
1760 MONDRIAN CIR, Winter Park, FL 32789
Don't miss out on the final new construction unit available - act fast! Discover unparalleled luxury at Mondrian Winter ...
Listed by COLDWELL BANKER RESIDENTIAL RE
$355,000
Condo
700 MELROSE AVE #C22, Winter Park, FL 32789
CLICK ON VIRTUAL TOUR to get an overview of the complex. <br>Discover a RARE opportunity to own a 3 BEDROOM 2.5 BATH uni...
Listed by FANNIE HILLMAN & ASSOCIATES
$3,040
Single Family Home
333 CAMBRIDGE BLVD, Winter Park, FL 32789
Welcome to your dream home in Winter Park, Florida! Nestled in the heart of sunshine and sophistication, this charming 3...
Listed by KELLER WILLIAMS REALTY AT THE PARKS
$4,600
Single Family Home
336 BLUE HERON DR, Winter Park, FL 32789
AVAILABLE NOW!!! Charming Waterfront home in Winter Park's established community featuring 3 bedrooms, 2 full bathrooms ...
Listed by LPT REALTY, LLC
$1,599,000
Single Family Home
1327 BRIDGEPORT DR, Winter Park, FL 32789
This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, do...
Listed by RE/MAX TOWN & COUNTRY REALTY
$1,495,000
Single Family Home
1420 PALMER AVE, Winter Park, FL 32789
Luxurious Retreat in the Heart of Winter Park's Premier Neighborhood – Minutes from Park Ave! <br>Discover timeless eleg...
Listed by KELLER WILLIAMS WINTER PARK
$675,000
Single Family Home
1511 CHESTNUT AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Attention builders and investors! Here's your chance to own a prime property in ...
Listed by FANNIE HILLMAN & ASSOCIATES
$569,000
Single Family Home
240 CAMBRIDGE BLVD, Winter Park, FL 32789
3-Bed, 2-Bath Home in Prime Winter Park Location! Steps away from paddleboarding, kayaking or fishing on beautiful Lake ...
Listed by REAL BROKER, LLC
$530,000
Single Family Home
2525 LAFAYETTE AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Investor / Builder special!! Prime land opportunity located just minutes from Pa...
Listed by KELLER WILLIAMS WINTER PARK
$4,175,000
Single Family Home
1581 FOREST AVE, Winter Park, FL 32789
Oak trees line the brick street as you arrive at this exquisite Hollywood Regency style home. Situated on a double lot ...
Listed by BHHS FLORIDA REALTY