Why Live in Winter Park?

Winter Park is easily the most vibrant community in Orlando. The lively downtown area around Park Avenue is known for nationally ranked art festivals, world-class museums, great entertainment and restaurants with sidewalk seating just like in Miami South Beach. Winter Park was originally almost exclusively a second home and vacation destination for wealthy Northerners. Housing supply consists of high-end properties, waterfront mansions, and estate homes. Median sold price in Winter Park is almost triple that of Central Florida and homes here regularly sell in multi-millions. Beautiful lakes of Winter Park are connected with the system of canals originally built to transport lumber during construction boom in late 19th and early 20th century. You can now take a scenic boat tour through the chain of lakes and experience the jewels of Winter Park real estate from another angle.

Winter Park Neighborhood Guides

Living in Winter Park is a lifestyle choice. While there are many good neighborhoods in Orlando area, Winter Park with it's luxury homes, museums, beautiful restaurants and lakes stands among the top. It is a great place to live or spend an afternoon. Winter Park is the home of Rollins College, the first college established in Florida. The Morse Museum on Park Avenue holds the largest collection of Tiffany.

Winter Park School Data

Winter Park Newest Properties for Sale

8020 Pleasant Pine Circle, Winter Park image

8020 Pleasant Pine Circle, Winter Park $419,900

Wonderful, 4 bedroom home in Winter Park that has been maintained beautifully is waiting for your family to make it their own! Built in 2013 and close to the 417 for easy...

4 Beds
2 Baths
Enclave At Aloma SubDv.
32792 Zip Code

375 W Welbourne Avenue Unit 107, Winter Park image

375 W Welbourne Avenue Unit 107, Winter Park — Douglas Grand $850,000

This is your opportunity to own a two-story, three-bedroom, three and a half bathroom townhome with its own private street entrance in historic downtown Winter Park at th...

3 Beds
3 Baths
Douglas Grand SubDv.
32789 Zip Code

870 Mayfield Avenue, Winter Park $2,295,000

This New England inspired home is located on a large lot (.41 acres), just over a mile from the boutiques and restaurants lining Park Avenue. Almost 6,000 SF of living sp...

6 Beds
6 Baths
J Kronenberger Sub SubDv.
32789 Zip Code

1277 Michigan Avenue, Winter Park — Na $459,900

Stunning new townhome community in the Heart of Winter Park! Multiple units available. Built by award-winning Osprey Custom Home Builders, this 3 bedroom, 2.5 bath interi...

3 Beds
2 Baths
Park Shore SubDv.
32789 Zip Code

1020 Minnesota Avenue Unit 2, Winter Park image

1020 Minnesota Avenue Unit 2, Winter Park — 1020 $389,000

GREAT 3/2.5 THREE STORY MEDITERRANEAN STYLE TOWNHOME LOCATED IN WINTER PARK. ENJOY A GORGEOUS KITCHEN WITH COOK TOP CENTER ISLAND, GAS RANGE, STAINLESS STEEL APPLIANCES,...

3 Beds
2 Baths
Casa Cielo Condo Or 6314 6111 SubDv.
32789 Zip Code

1120 Aragon Avenue, Winter Park — 1120 $475,000

Welcome to your new residence in Winter Park! This home is practically perfect with its oversized owner’s suite (with walk-in closet and jetted tub), guest room (split be...

2 Beds
2 Baths
Seville Park SubDv.
32789 Zip Code

1751 Goodrich Avenue, Winter Park $835,000

STATE-OF-THE-ART technology, TOP-OF-THE-LINE finishes, attention to DETAIL, and centrally LOCATED in historic WINTER PARK is where you will find this 2019 fully renovated...

4 Beds
3 Baths
Sylvan Heights SubDv.
32789 Zip Code

1624 Hibiscus Avenue, Winter Park $1,150,000

Welcome to the heart of Winter Park. This beautiful 2-story, 4-bedroom, 3.5-bath home includes a backyard oasis with pool/spa. A home that was built in 2012 features "wee...

4 Beds
3 Baths
Winter Park SubDv.
32789 Zip Code

2051 Versailles Avenue, Winter Park image

2051 Versailles Avenue, Winter Park $1,549,000

Located on a quiet street in the heart of Winter Park, this beautiful 5 bedroom home is zoned for A+ schools--including Dommerich Elementary, Maitland Middle, and Winter ...

5 Beds
3 Baths
Fontainebleau SubDv.
32789 Zip Code

140 Dana Way, Winter Park $1,395,000

Welcome to this luxurious, one-of-a-kind Posada custom home located on a quiet street in a very desirable Winter Park neighborhood. The classic finishes and open floor pl...

3 Beds
2 Baths
Charmont SubDv.
32789 Zip Code

1762 Elizabeths Walk, Winter Park $1,250,000

Come see this beautiful custom home locate in the Windsong Community in Winter Park built by Keith Groninger of Groninger Custom Homes. This 3,775 sqft 4 bedroom 4 bath h...

4 Beds
4 Baths
Windsong SubDv.
32789 Zip Code

1814 Mondrian Circle, Winter Park — 1 $700,000

The beautiful Lake Killarney Townhomes provide the best in style, location, and value. This fully upgraded smart home features every luxury of the modern era, convenient ...

3 Beds
3 Baths
Lake Killarney Townhomes SubDv.
32789 Zip Code

101 S New York Avenue Unit 304, Winter Park image

101 S New York Avenue Unit 304, Winter Park — Douglas Grand $1,499,000

You'll find one of Central Florida's most distinctive and established in-town living experiences in historic downtown Winter Park. Now is your opportunity to own a two-st...

3 Beds
3 Baths
Winter Park Residential SubDv.
32789 Zip Code

1792 Mondrian Circle, Winter Park — 6 $854,000

The Art of Modern Style in Winter Park. This Luxury Lakefront Town home, located on sparkling Lake Killarney, offers stunning sunset views. This Modern marvel will deligh...

3 Beds
3 Baths
Lake Killarney Townhomes SubDv.
32789 Zip Code

1806 Gipson Green Lane, Winter Park image

1806 Gipson Green Lane, Winter Park $2,350,000

Fabulous Winter Park Custom Builder Rex-Tibbs designed this Winter Park home, is located in one of Winter Park's most beautiful and private neighborhoods. on a Cul-de-sac...

7 Beds
5 Baths
Boiley Green Sub SubDv.
32789 Zip Code

451 W Comstock Avenue, Winter Park image

451 W Comstock Avenue, Winter Park $1,299,000

2019 PARADE OF HOMES Entrant - Come see this lovely pool home with a nice open floor plan located in walking distance to all that Winter Park has to offer. After a long w...

4 Beds
4 Baths
Winter Park SubDv.
32789 Zip Code

811 Hamilton Place Court, Winter Park image

811 Hamilton Place Court, Winter Park $925,000 ▼

Fabulous modern Mediterranean on a quiet cul-de-sac location nearby downtown Winter Park/Park Avenue. The property affords wonderful privacy with a "park-like" backyard. ...

4 Beds
3 Baths
Hamilton Place SubDv.
32789 Zip Code

141 N Virginia Avenue, Winter Park image

141 N Virginia Avenue, Winter Park — 141 $2,150,000

A fantastic opportunity for a discerning buyer to own Oak Tree House, the "Jewel in the Crown" of the Phil Kean designed Brownstones located in downtown Winter Park. Just...

5 Beds
5 Baths
Virginia & Morse Brownstones SubDv.
32789 Zip Code

1001 N Kentucky Avenue, Winter Park image

1001 N Kentucky Avenue, Winter Park $1,297,000

Stunning contemporary new build in the Winter Park Design district. Offering 4 oversized bedrooms, 3.5 elegantly appointed bathrooms, and 3,186sf of gracious living. With...

4 Beds
3 Baths
Fairbanks Park SubDv.
32789 Zip Code

2219 Venetian Way, Winter Park $2,550,000 ▲

Beautifully designed and custom-built by premier Winter Park builder Bill Felkel, this stunning home is situated on an oversized 0.40 acre lot in the distinguished Winter...

6 Beds
6 Baths
Maitland Shores SubDv.
32789 Zip Code

7211 Gardner Street, Winter Park $675,000

Automotive/Body Repair for Sale - 4,500 SF block and metal building. Includes 600 SF office, 3900 SF warehouse with two 160 SF storage containers and semi-down draft pai...

32792 Zip Code

2234 Hawick Lane Unit 2234, Winter Park image

2234 Hawick Lane Unit 2234, Winter Park — N/A $395,000

Your search is over! Come see this beautiful Spanish/Mediterranean three bedroom, two and a half bath condo/townhome located just minutes from downtown Winter Park. Fir...

3 Beds
2 Baths
Corinthean/Winter Park Condo SubDv.
32792 Zip Code

315 E New England Avenue Unit 31, Winter Park image

315 E New England Avenue Unit 31, Winter Park — 315 $2,450,000

BEAUTIFUL WINTER PARK PENTHOUSE oriented in the most private section of the Jewel of Winter Park! Villa Siena is located 2 blocks off Park Avenue and is directly across f...

4 Beds
4 Baths
Villa Siena SubDv.
32789 Zip Code

1433 Chapman Circle, Winter Park $928,500 ▼

Custom built Mediterranean home on secluded cul-de-sac in exclusive Elizabeth's Walk enclave of Windsong. Exterior features include 10' solid mahogany double entry doors...

3 Beds
3 Baths
Windsong Elizabeths Walk 43/81 SubDv.
32789 Zip Code

8021 Pleasant Pine Circle, Winter Park image

8021 Pleasant Pine Circle, Winter Park $625,000 ▼

This is the home you have been looking for! If you have been searching for the perfect move-in ready, like-new home, then this may be the one!! Upon entering, you will ...

5 Beds
4 Baths
Enclave At Aloma SubDv.
32792 Zip Code

1624 Elizabeths Walk, Winter Park $965,000 ▼

Amazing opportunity in the charming Winter Park neighborhood of Windsong. This 5 bedroom/ 5 bath, 3,085 sq ft pool home was fully remodeled in 2015, including flooring, ...

5 Beds
5 Baths
Windsong Elizabeths Walk 43/81 SubDv.
32789 Zip Code

5610 Winterbrook Way, Winter Park $439,900

Winter Park - Nearly new 3 bdrm 2 bath energy efficient home plus flex room, built by Pulte in 2020 in boutique 17 home gated, sold out, community. Quality construction...

3 Beds
2 Baths
Winterbrook SubDv.
32792 Zip Code

2156 Talman Court, Winter Park $1,950,000

Rare opportunity to own a completely multi-generational home in the exclusive neighborhood of Talman Mews on DUAL lots. The statement entrance begins under the portico w...

5 Beds
5 Baths
Talman Mews Ph 2 SubDv.
32792 Zip Code

1211 Preserve Point Drive, Winter Park image

1211 Preserve Point Drive, Winter Park $2,415,000

Tuscan inspired custom built pool home located in Windsong offers five or six bedrooms, an open floor plan, home office, media and game room, and a stunning wrap-around s...

6 Beds
5 Baths
Windsong Lookout Landing 43/79 SubDv.
32789 Zip Code

1671 Chestnut Avenue, Winter Park $1,019,000

Located in the highly coveted tree streets of Winter Park, this traditional two-story home features 5 bedrooms, 3.5 bathrooms, and plenty of entertaining space inside and...

5 Beds
3 Baths
Lake Knowles Terrace SubDv.
32789 Zip Code

1637 Magnolia Avenue, Winter Park $1,399,000 ▼

***Price Improvement*** Welcome to the home of your dreams!! Your brand new 2020 Custom built French Provincial style estate is ready and waiting for your family. The qua...

4 Beds
4 Baths
Flora Park 2nd Add SubDv.
32789 Zip Code

1750 Edwin Boulevard, Winter Park $1,395,000 ▼

Discover an exceptional opportunity in the heart of Winter Park. This beautiful custom-built two-story modern home is very bright with southern exposure on the rear of th...

5 Beds
4 Baths
Campo Bello SubDv.
32789 Zip Code

467 Carolina Avenue, Winter Park $1,195,000

Brand new home. 10 foot ceilings. Front and back porches. Engineered wood floors. Thermidor appliances. Upgraded windows. Huge attic storage. Surrounded by 6 foot block w...

4 Beds
3 Baths
Winter Park SubDv.
32789 Zip Code

1149 S Pennsylvania Street, Winter Park image

1149 S Pennsylvania Street, Winter Park — Na $700,000 ▼

*Price Improvement* Located just minutes from Winter Park’s famed Park Avenue, this beautiful 3 bedroom, 2 1/2 bath designed by the award winning, world-renowned Nasralla...

3 Beds
2 Baths
Cherokee Park SubDv.
32789 Zip Code

2700 Wright Avenue, Winter Park $1,125,000

Under Construction. Your Brand New 2021 Custom Home is almost ready for your family. Rex-Tibbs Construction has been building timeless homes in Winter Park for over 35 ye...

4 Beds
4 Baths
Parklando SubDv.
32789 Zip Code

2409 Firstlight Way, Winter Park — N/A $345,000

Why wait on the builder when YOU can own this beautiful Julian model home built in 2019! This nearly new energy-efficient townhome is located in one of the newest communi...

3 Beds
2 Baths
Enclave At Hawks Crest SubDv.
32792 Zip Code

1420 Chapman Circle, Winter Park $899,900 ▼

Take the virtual tour: https://my.matterport.com/show/?m=ti1mdHMXxU9. This gorgeous custom-built 4 bedroom, 3.5 bathroom home is located in the exclusive Windsong subdivi...

4 Beds
3 Baths
Windsong Elizabeths Walk SubDv.
32789 Zip Code

1807 Barker Drive, Winter Park $1,450,000 ▼

Welcome to 1807 Barker Drive, a lakefront home that includes tranquil views of a natural habitat, with magnificent sunsets off the water. Approximately 40% of the shoreli...

5 Beds
3 Baths
South Lakemont Shores SubDv.
32789 Zip Code

816 Hamilton Place Court, Winter Park image

816 Hamilton Place Court, Winter Park $977,000

Rare Opportunity to live in Winter Park, in a secluded beautiful Cul-de-Sac overlooking a wide open green area with a great privacy. Only a steps away from all the Major ...

5 Beds
3 Baths
Hamilton Place SubDv.
32789 Zip Code

1001 Anchorage Court, Winter Park $5,750,000

Magnificent mew construction Downtown Winter Park estate, built by one of the country’s top builders, this architectural masterpiece is situated just steps from Park Aven...

5 Beds
6 Baths
Chapman & Chase Plan/Town/Wint SubDv.
32789 Zip Code