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60 Properties Available
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$1,565,000
Single Family Home
341 E READING WAY, Winter Park, FL 32789
Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. B...
Listed by Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES
$1,399,000
Single Family Home
1473 BERKSHIRE AVE, Winter Park, FL 32789
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this s...
Listed by Gilson Rodrigues KARDOSH REALTY
$350,000
Condo
700 MELROSE AVE #J24, Winter Park, FL 32789
Fully updated ..Amazing modern Winter Park Lake Front location! This is a DELUXE corner unit fully remodeled and totally...
Listed by Scott Butts KIMBRIDGE REALTY, LLC
$1,795,000
Condo
106 S INTERLACHEN AVE #518, Winter Park, FL 32789
Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to ...
Listed by Mary Colton FANNIE HILLMAN & ASSOCIATES
$649,000
Single Family Home
1409 SUNSET DR, Winter Park, FL 32789
LOCATION. LIFESTYLE. TIMELESS WINTER PARK CHARM. Discover an exceptional opportunity in Lake Knowles Terrace, where clas...
Listed by TJ Tuzzeo KONA REALTY SERVICES LLC
$499,000
Single Family Home
1652 BERKSHIRE AVE, Winter Park, FL 32789
Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner...
Listed by Brian Teach COLDWELL BANKER REALTY
$425,000
Single Family Home
1955 ELAND AVE, Winter Park, FL 32789
Nestled in Winter Park's Lake Bell Terrace neighborhood, this 3 bedroom, 2 bathroom home is located close to everything ...
Listed by Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$2,295
Single Family Home
2028 ALBERT LEE Pkwy, Winter Park, FL 32789
This charming 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy the best of Downtown Winter Park,...
Listed by Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$4,295
Single Family Home
1625 TIOGA TRL, Winter Park, FL 32789
A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD. <br> <br>Welcome home to this beautifu...
Listed by Andrew Musashe SUN PROPERTIES, INC.
$1,350
Single Family Home
1600 INDIANA AVE, Winter Park, FL 32789
This 1 bedroom, 1 bathroom home is located in the heart of Winter Park. Enjoy the best of Downtown Winter Park, Park Ave...
Listed by Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$6,000
Townhouse
1136 S PENNSYLVANIA AVE, Winter Park, FL 32789
Welcome home to this beautifully appointed end-unit Georgetown townhome in the highly desirable Virginia Heights communi...
Listed by Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC
$4,595,000
Single Family Home
1525 GRANVILLE DR, Winter Park, FL 32789
There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vim...
Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC
$6,300
Single Family Home
835 W CANTON AVE, Winter Park, FL 32789
Now available for lease in the highly desirable Gardens at Park West, this beautifully completed home offers luxury livi...
Listed by Brian Hyser THE AGENCY FL
$3,050
Single Family Home
2401 ALBERT LEE Pkwy, Winter Park, FL 32789
Gorgeous 3/2 Mid-century Modern Style Home with a Covered Patio and a Large Backyard in the Desirable Albert Lee Ridge C...
Listed by Rebeca Lima VERANDAH PROPERTIES INC
$1,590,000
Single Family Home
708 BALMORAL RD, Winter Park, FL 32789
A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and s...
Listed by Caitlin De Oliveira EXP REALTY LLC
$729,000
Single Family Home
1850 BRYAN AVE, Winter Park, FL 32789
This well-cared-for immaculate home features quality workmanship inside and out! In addition to the three bedroom two ba...
Listed by Vanessa Winters CENTRAL FLORIDA REAL ESTATE CE
$7,995
Single Family Home
2234 HOWARD DR, Winter Park, FL 32789
Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-...
Listed by Raquel Elliott COLDWELL BANKER REALTY
$1,999
Single Family Home
1261 RICHMOND RD, Winter Park, FL 32789
Available on July 29th 2026!! CHARMING AND UNIQUE two bedrooms /one bath home in the heart of Winter Park down street fr...
Listed by Steven Simpson 407 PROPERTIES
$699,000
Townhouse
436 W SWOOPE AVE, Winter Park, FL 32789
Virtually Staged. Don't miss the best priced townhome in Winter Park!! Welcome to this virtually staged contemporary tow...
Listed by Kim Griffin RE/MAX EXCLUSIVE COLLECTION
$549,900
Single Family Home
2803 RIDDLE DR, Winter Park, FL 32789
Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle...
Listed by Allie George CORCORAN PREMIER REALTY
$549,900
Single Family Home
1003 LAKE BELL DR, Winter Park, FL 32789
Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offerin...
Listed by Bryan Douglas KELLER WILLIAMS REALTY AT THE PARKS
$439,900
Single Family Home
2041 JEWELL AVE, Winter Park, FL 32789
Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful hom...
Listed by Martha Coronel IAD REAL ESTATE
$88,999
Condo
1695 LEE RD #B108, Winter Park, FL 32789
This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desir...
Listed by Brandy Ray LOKATION
$1,500
Condo
Winter Park, FL 32789
2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, a...
Listed by Kirsten Cantello TRUSTHOME PROPERTIES INC
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