33 Properties Available
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$2,100
Single Family Home
2011 CORNELL AVE, Winter Park, FL 32789
Charming 3-Bedroom Home for Rent in Winter Park <br> <br>This beautiful 3-bedroom, 1-bathroom home has been completely r...
Listed by Andres Ospina Rivera LPT REALTY, LLC
$655,000
Townhouse
1267 MICHIGAN AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Modern Comfort in the Heart of Winter Park! Built in 2019, this 3-bedroo...
Listed by Megan Cross FANNIE HILLMAN & ASSOCIATES
$1,999,000
Single Family Home
1540 PALM AVE, Winter Park, FL 32789
Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park's most desirable neigh...
Listed by John McDade FANNIE HILLMAN & ASSOCIATES
$1,190,000
Single Family Home
1150 KENWOOD AVE, Winter Park, FL 32789
Wonderful opportunity - homes rarely come available on this street! Located in the heart of Winter Park, this elegantly ...
Listed by JJ Mackle PREMIER SOTHEBY'S INTL. REALTY
$1,199,900
Single Family Home
1822 GREENWICH AVE, Winter Park, FL 32789
Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this hi...
Listed by Cliff Glansen FLATFEE.COM
$749,800
Single Family Home
3018 NORTHWOOD BLVD, Winter Park, FL 32789
One or more photo(s) has been virtually staged. "UPDATED & MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH ...
Listed by Joel Bornstein ROCK SPRINGS REALTY, LLC
$499,000
Single Family Home
259 BLOSSOM LN, Winter Park, FL 32789
No HOA! Fully Renovated Home with Deeded Lake Access to Lake Killarney in Prime Winter Park Location! Welcome to this mo...
Listed by Carlinhos Fregonezi TALENT REALTY SOLUTIONS
$359,900
Single Family Home
780 BAFFIE AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Fantastic Opportunity / Dubsdread Heights in Winter Park! Do not miss ou...
Listed by Rachael Klinker DAHLIA REALTY GROUP
$8,900
Single Family Home
1442 PALM AVE, Winter Park, FL 32789
Discover this exquisite property featuring a main house, complemented by a separate guest apartment equipped with one be...
Listed by Bianca Botelho, PA RE/MAX ASSURED
$3,345
Single Family Home
1835 EDWIN BLVD, Winter Park, FL 32789
Welcome to this charming bungalow located near the historic district of Winter Park, FL. This home boasts three spacious...
Listed by Francisco Nieves-Taranto CT HOMES REALTY CORPORATION
$2,049
Single Family Home
770 BAFFIE AVE, Winter Park, FL 32789
Adorable home by Dubsdread Golf Course! This 3 bedroom. 1 bathroom home has been nicely updated throughout. The kitchen ...
Listed by Nicholas Wild GATE PROPERTIES & MANAGEMENT INC
$2,500
Single Family Home
313 GRANADA DR, Winter Park, FL 32789
Four bedroom, two bathroom, single family home with carport and outdoor laundry/utility/storage room. Located in the Fai...
Listed by Rafael Pierluisi ALFANO PROPERTY MANAGEMENT
$1,950
Single Family Home
263 BLOSSOM LN, Winter Park, FL 32789
Located in the heart of Everything that Winter Park has to offer! Access highways with minutes . Short drive to Park Ave...
Listed by Doreen Landi ENGEL & VOLKERS CLERMONT
$2,095
Single Family Home
2828 SALISBURY BLVD, Winter Park, FL 32789
This 3 bedroom, 2 bathroom home is located on a quiet street in Winter Park. Enjoy all Winter Park has, Park Avenue's sh...
Listed by Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$4,750
Single Family Home
2031 TEMPLE DR, Winter Park, FL 32789
Discover Winter Park, a charming suburb that blends historic character with modern convenience, all just minutes from do...
Listed by Summer Hornburg BELMONT REALTY
$260,000
Condo
151 N ORLANDO AVE #101, Winter Park, FL 32789
Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lak...
Listed by Elizabeth Fowler THE FLORIDA PROPERTY SHOP SALE
$3,295,000
Single Family Home
1821 ENGLEWOOD RD, Winter Park, FL 32789
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Developmen...
Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY
$345,000
Single Family Home
917 DUPONT AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to this charming mid-century 3-bedroom, 2-bathroom ranch-style home loca...
Listed by Alex Castillo LPT REALTY, LLC
$3,295
Single Family Home
1641 CHESTNUT AVE, Winter Park, FL 32789
Welcome to your new home nestled along Winter Park's coveted tree-lined Chestnut Avenue. This beautiful 3 bedroom, 3 bat...
Listed by Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$900,000
Single Family Home
915 GARDEN DR, Winter Park, FL 32789
Stunning Mid-Century Modern Home in Prime Winter Park Location – Solar Powered, Pool, No HOA <br> <br>Beautifully mainta...
Listed by Cassie Lamoureux KELLER WILLIAMS CLASSIC
$2,535
Single Family Home
2843 RIDDLE DR, Winter Park, FL 32789
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with fu...
Listed by Daniel Reyes MAIN STREET RENEWAL LLC
$520,000
Single Family Home
240 ORANGE TERRACE DR, Winter Park, FL 32789
WHAT ARE YOU WAITING FOR? THIS IS IT! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated...
Listed by Susan Pinnock A+ REALTY PROFESSIONALS, INC
$430,000
Single Family Home
2464 LOTAFUN AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. A rare gem nestled in one of Winter Park's most secluded subdivisions—ju...
Listed by Irina Paul, LLC FUTURE HOME REALTY INC
$925,000
Single Family Home
208 BREWER AVE, Winter Park, FL 32789
Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thought...
Listed by Cassandra King COMPASS FLORIDA LLC