52 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$2,299,000
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
$4,900
Single Family Home
2227 HOWARD DR, Winter Park, FL 32789
Zoned for Audubon K-8 and Winter Park High. Move in just in time for the school year!! Single-story LAKEFRONT gem in Win...
Listed by REALTY ONE GROUP MAGIC CITY
$599,000
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
$2,700
Single Family Home
648 W SWOOPE AVE, Winter Park, FL 32789
FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professio...
Listed by KELLY PRICE & COMPANY LLC
$535,000
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
$2,900
Condo
644 N KNOWLES AVE #8, Winter Park, FL 32789
Welcome to your private retreat in the heart of Downtown Winter Park. This exclusive address affords views of the world ...
Listed by BELMONT 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
$409,988
Single Family Home
920 GLORIOSA AVE, Winter Park, FL 32789
Charming Move-In Ready Home in the Heart of Winter Park! <br> <br>Discover this beautifully maintained 3-bedroom, 2-bath...
Listed by EXP REALTY LLC
$1,650,000
Condo
101 S NEW YORK AVE #311, Winter Park, FL 32789
Discover luxury living in this exquisite two-story condominium, located on the third floor of the highly sought-after Do...
Listed by KELLY PRICE & COMPANY LLC
$1,449,000
Single Family Home
1644 HIBISCUS AVE, Winter Park, FL 32789
Charming, Well-Maintained Home on a Prime Lot in Winter Park's Coveted Tree Streets <br> <br>Don't miss this rare opport...
Listed by COLDWELL BANKER RESIDENTIAL RE
$479,000
Single Family Home
3601 MIDIRON DR, Winter Park, FL 32789
BUILD YOUR DREAM HOME IN WINTER PARK! <br>Nestled directly across from the historic Dubsdread Golf Course, this property...
Listed by EMPIRE NETWORK REALTY
$185,000
Condo
1695 LEE RD #E215, Winter Park, FL 32789
Move-in Ready Renovated Condo – Prime Location! <br>This beautifully renovated condo offers both style and convenience, ...
Listed by LA ROSA REALTY CENTRAL FLORIDA
$2,100,000
Single Family Home
2614 PARKLAND DR, Winter Park, FL 32789
Welcome to 2614 Parkland Drive—an exquisite, fully renovated luxury residence nestled in the heart of Winter Park, Flori...
Listed by JW GASTON LLC
$2,700
Single Family Home
850 W CANTON AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. This charming single-family home comes with 3 bedrooms, 2 full bathrooms...
Listed by FLORIDA REALTY INVESTMENTS
$459,000
Single Family Home
1564 CAVENDISH RD, Winter Park, FL 32789
Charming 3BR bungalow in sought-after Orwin Manor with a true bungalow vibe and tons of potential. Updated throughout w...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$960,000
Single Family Home
250 CORTLAND AVE, Winter Park, FL 32789
Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of th...
Listed by EXP REALTY LLC
$1,299,000
Single Family Home
1600 BARCELONA WAY, Winter Park, FL 32789
Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the...
Listed by LPT REALTY, LLC
$1,475,000
Condo
690 OSCEOLA AVE #604, Winter Park, FL 32789
Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder's unit with panoramic views of Lake Virginia from almos...
Listed by COLDWELL BANKER RESIDENTIAL RE
$629,000
Single Family Home
2812 MULFORD AVE, Winter Park, FL 32789
Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking dist...
Listed by SYNCHRONICITY REAL ESTATE SOLUTIONS
$4,950,000
Single Family Home
1660 PALMER AVE, Winter Park, FL 32789
New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening t...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$249,000
Condo
2500 LEE RD #202, Winter Park, FL 32789
2/2 * 956 SQ FT * LAKE KILLARNEY * CLOSE TO PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NE...
Listed by THE ANDERSON GROUP & CO PL
$1,290,000
Single Family Home
1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. <br>You will...
Listed by JACK KELLER INC
$4,650,000
Single Family Home
2161 SHARON RD, Winter Park, FL 32789
New Home Nestled in the esteemed The Vias area and near the WPRC. Situated on a secluded street, it occupies an approxim...
Listed by LA ROSA REALTY HORIZONS LLC
$179,900
Condo
1250 S DENNING DR #122, Winter Park, FL 32789
One or more photo(s) has been virtually staged. **MAJOR PRICE DROP – UNBEATABLE VALUE IN WINTER PARK!** <br>Don't miss t...
Listed by ORLANDO HOME DEALER LLC
