Winter Park

Upscale, modern, and with too many gorgeous homes for sale, Winter Park is a stunning city with lots to offer just minutes from Orlando making it ideal for any family or investor looking for the delights of suburbia with upscale living. Park Ave. or downtown is a beautiful historic area lined with gourmet restaurants, art galleries, wine bars, and a plethora of shopping options.

 

Fine institutions like Rollins College, the Albin Polasek Museum and Sculpture Garden, and theaters like The Winter Park Playhouse and Enzian provide plenty of excellent entertainment options. The area has a home for every type of buyer whether an investor, flipper, family, or individual.  

 

Located along the I-4 corridor, the town is conveniently located. Although a quiet area but with only a brief drive you have the bright lights and bars of Downtown Orlando. Winter Park is growing and property values are going one way, up.  Come explore this fantastic city today.

 

Homes for Sale in Winter Park

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2036 VIA TUSCANY

WINTER PARK, Florida 32789

Mark Medei
3Bedroom(s)
2Bathroom(s)
22Picture(s)
2,148Sqft
WINTER PARK VIA’S!!! Incredible Oversized Lot is located in the “Heart” of Winter Park. Very Unique opportunity in Winter Park for a high-quality custom build. The brick lined lighted street with sidewalks is located across from the Winter Park Racquet Club. This location is a wonderful opportunity to build your Estate Home.
$1,695,000

1760 OAKHURST AVENUE

WINTER PARK, Florida 32789

Valda Branch-Duncan
3Bedroom(s)
3Bathroom(s)
2Picture(s)
1,989Sqft
Stroll through the giant oak trees on the shady streets of Old Winter Park. This is the perfect lot to build your dream home. This desirable Winter Park location is minutes away from top restaurants, Winter Park hospital, Baldwin Park, Rollins College, YMCA, restaurants and exquisite Park Avenue. Sold "As Is" The value is in the lot and location - build your dream home on Millionaire's Row.
$750,000

502 GENIUS DRIVE

WINTER PARK, Florida 32789

Juliana Hughes
6Bedroom(s)
5Bathroom(s)
34Picture(s)
4,735Sqft
Location, location location! Stately yet friendly, classic yet modern, one-of-a-kind property in highly sought-after Windsong, the only upscale true neighborhood in Winter Park, with access to the historic Winter Park Chain of Lakes. Precious nearly half-acre lot with extremely valuable unobstructed lake view and rarely seen privacy both front and back.
$3,150,000

699 OSCEOLA AVENUE

WINTER PARK, Florida 32789

Nahid Moradi
5Bedroom(s)
3Bathroom(s)
65Picture(s)
5,062Sqft
Pristine custom Mediterranean Lakefront estate, with 5 bedrooms, 3.5 bathrooms, sandy beach (one of a kind) and 127’ on lake Osceola. Enjoy captivating views of lake Osceola, part of winter park chain of lakes. Professionally updated to today’s standards and modern technologies with the authentic character maintained to keep the original charm and elegance.
$4,495,000

910 POINCIANA LANE

WINTER PARK, Florida 32789

Erin Freeman
4Bedroom(s)
3Bathroom(s)
19Picture(s)
2,008Sqft
A fantastic waterfront opportunity in Winter Park on the Lake Maitland Lagoon awaits. This 0.62-acre lot features 100 feet of frontage on Lake Maitland’s quiet lagoon and easy access to the Winter Park Chain of Lakes. A new boat dock with a 10,000-pound lift capacity was completed in 2022. The lagoon is easily navigable and opens up to Lake Maitland.
$1,387,000

231 CHELTON CIRCLE

WINTER PARK, Florida 32789

Dan Haber
5Bedroom(s)
5Bathroom(s)
84Picture(s)
5,754Sqft
Improved Price!! Contemporary living in the heart of Winter Park. This Phil Kean designed/built home is sure to be at the top of your list. Phil Kean’s distinctive signature style features clean lines and extraordinary attention to design detail. A hallmark to their design are walls of glass that open to extensive indoor-outdoor living spaces.
$5,200,000

234 DETMAR DRIVE

WINTER PARK, Florida 32789

Kelly Price
4Bedroom(s)
4Bathroom(s)
47Picture(s)
3,609Sqft
Beautiful 1930’s Winter Park Character Home on Oversized 0.42 acre lot with privacy gate, detached mother-in law apartment, screened pool, and so much more. Originally built in 1935 this charming farmhouse offers a brand-new roof, updated plumbing and electrical, and newer AC units.
$1,625,000

2412 CHANTILLY AVENUE

WINTER PARK, Florida 32789

Sandra Cuba
5Bedroom(s)
6Bathroom(s)
4Picture(s)
4,500Sqft
Under Construction. Under construction. Well on its way to be one of Winter Park’s newest homes, 2412 Chantilly Aveune with its perfect blend of textures and clean finishes, and numerous added features, will be ready for you to move in early 2023. No detail was spared throughout its 4,500 square feet of interiors.
$2,331,000

603 ELLEN DRIVE

WINTER PARK, Florida 32789

Tom Lightsey, Jr
4Bedroom(s)
4Bathroom(s)
5Picture(s)
2,830Sqft
Pre-Construction. To be built. Take advantage of one of the last chances to live in Lake Killarney Shores, one of Winter Park's newest communities - a collection of 30 custom homes convenient to Winter Park Village & The "Golden Mile". Enjoy access to the Lake via a community boat ramp. Ziur Construction's Contemporary Home is 2,830 SF with 4 Bedrooms, 4.
$1,250,000

151 ORLANDO AVENUE

WINTER PARK, Florida 32789

Kim Wood
3Bedroom(s)
2Bathroom(s)
28Picture(s)
1,875Sqft
PRICE REDUCED TO $598,000 !!!! "OWNER FINANCING AVAILABLE" A modern, European condo that has combined two 940 sf lakefront units into a sprawling 1875 sf 2br/2ba luxury second floor condominium, just an easy walk to Trader Joes, our new WP Library and Hillstone Restaurant - all within the heart of Winter Park. This unit has all new plumbing, wiring and a new HVAC system.
$598,000

249 SCOTTSDALE SQUARE

WINTER PARK, Florida 32792

Shariff Manekia
1Bedroom(s)
1Bathroom(s)
12Picture(s)
756Sqft
Stunning and completely renovated 1 bedroom, 1 bath, 756 sqft. modern condo in Winter Park. The amazing kitchen features new cabinetry, granite counter tops, mosaic white marble finish throughout the kitchen walls, new s/steel upgraded appliances. Brand new bathroom, lighted led mirror with hardwood white vanity with carrera marble top.
$124,786

172 SCOTTSDALE SQUARE

WINTER PARK, Florida 32792

Shariff Manekia
2Bedroom(s)
1Bathroom(s)
15Picture(s)
1,085Sqft
Stunning and completely renovated 2 bedroom, 1.5 bath, 1085 sq ft. modern condo in Winter Park. The amazing kitchen features new cabinetry, granite counter tops, mosaic white marble finish throughout the kitchen walls, new s/steel upgraded appliances. Brand new bathroom, lighted led mirror with hardwood white vanity with Carrera marble top.
$244,786
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