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

2245 Nairn Drive, Winter Park — 2245 $415,000

No HOA! Welcome home to an updated and recently modeled modern 3 bedroom, 2.5 bath townhouse in the heart of Winter Park! This townhouse features an updated kitchen with ...

3 Beds
2 Baths
Aloma Sec 1 SubDv.
32792 Zip Code

1851 Via Tuscany, Winter Park $2,650,000

Distinguished, Phil Kean Design, award-winning "NEMO," a warm, inviting contemporary masterpiece nestled among some of the more notable homes in Winter Park in the heart ...

4 Beds
6 Baths
Sicilian Shores Rep 02 SubDv.
32789 Zip Code

1507 Indiana Avenue, Winter Park — Na $499,900

One or more photo(s) has been virtually staged. Newly constructed Winter Park townhome- turn key, lock and leave. Gorgeous light and bright 3 bed / 2.5 bath end unit is m...

3 Beds
2 Baths
Lawndale SubDv.
32789 Zip Code

436 W Swoope Avenue, Winter Park — N/A $589,000

One or more photo(s) has been virtually staged. Enjoy living in the heart of charming downtown Winter Park in this gorgeous contemporary townhome. You will find luxury un...

4 Beds
3 Baths
Swoope Park SubDv.
32789 Zip Code

1570 Bryan Avenue, Winter Park $2,750,000

Pre-Construction. To be built. To be built. This stunning Modern Dutch Masterpiece is being crafted by none other than, Floridian Custom Homes of Winter Park. This timele...

6 Beds
6 Baths
Sylvan Park SubDv.
32789 Zip Code

1048 S Kentucky Avenue, Winter Park image

1048 S Kentucky Avenue, Winter Park — 1048 $525,000

Located minutes from downtown Winter Park and Rollins College, this spacious 3 bed/ 3 bath, 1,983 sq ft end unit town home is a rare gem. Light and bright with volume ce...

3 Beds
3 Baths
Oak Crest SubDv.
32789 Zip Code

1397 Heavenly Cove, Winter Park $599,000

Amazing opportunity to own this Taylor Morrison custom home in a gated community of Eden Point in Winter Park. The exterior features paver driveway to a 3-car garage and ...

5 Beds
4 Baths
Eden Point SubDv.
32792 Zip Code

1263 Michigan Avenue, Winter Park — Na $475,000

Stunning new townhome community in the Heart of Winter Park. These gorgeous 3 bedroom, 2.5 bath units by award-winning builder Osprey Homes are selling fast. Each unit is...

3 Beds
2 Baths
Park Shore SubDv.
32789 Zip Code

1271 Michigan Avenue, Winter Park — Na $475,000

Stunning new townhome community in the Heart of Winter Park. These gorgeous 3 bedroom, 2.5 bath units by award-winning builder Osprey Homes are selling fast. Each unit is...

3 Beds
2 Baths
Park Shore SubDv.
32789 Zip Code

1760 Sunset Drive, Winter Park $1,799,000

Stunning, custom-built, corner-lot pool home with a three-car garage is available in the heart of Winter Park. This traditional style home offers four to five bedrooms, f...

5 Beds
4 Baths
Lake Knowles Terrace Add 02 SubDv.
32789 Zip Code

631 W Swoope Avenue, Winter Park $805,000

Opportunity knocks! Just blocks off Park Ave in downtown Winter Park and within walking distance to Winter Park Village, is this 2019 built, gorgeous, modern home. 4 be...

3 Beds
2 Baths
Carver Town SubDv.
32789 Zip Code

2560 Passamonte Drive Unit 9F, Winter Park image

2560 Passamonte Drive Unit 9F, Winter Park — N/A $311,900 ▼

Location, Location, Location! This well kept townhouse is located within a gated community with excellent schools in the area. This 2 story townhouse offers 3 bedrooms, 2...

3 Beds
2 Baths
Via Lago At Hanging Moss Condominiums SubDv.
32792 Zip Code

4482 Tuscany Island Court, Winter Park image

4482 Tuscany Island Court, Winter Park $1,295,000

LUXURIOUS MEDITERRANEAN ELEGANCE! Impeccably maintained STUNNING custom home in an intimate gated community of only 5 luxury homes ideally situated within close proximity...

5 Beds
4 Baths
Tuscany Island SubDv.
32792 Zip Code

511 W Canton Avenue, Winter Park $3,500,000

Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge ...

5 Beds
6 Baths
Winter Park SubDv.
32789 Zip Code

2407 Lafayette Avenue, Winter Park image

2407 Lafayette Avenue, Winter Park $1,395,000

Immaculate Contemporary Custom Home with charm, located in historic Winter Park. Beautiful design elements throughout with wonderful LED lighting and accents. The home ha...

5 Beds
4 Baths
Fontainebleau SubDv.
32789 Zip Code

315 E New England Avenue Unit 11, Winter Park image

315 E New England Avenue Unit 11, Winter Park — 315 $1,380,000

Centrally located 2-blocks from Park Avenue with easy access to shops, restaurants and Central Park. This stylish condo offers 3-bedrooms with an open floor plan full of ...

3 Beds
2 Baths
Villa Siena SubDv.
32789 Zip Code

780 Pinetree Road, Winter Park $1,995,000

New Listing in The Vias. Custom built, this 4 bedroom, 5 full bath pool home sits within Winter Park’s most sought-after neighborhood. Surrounded by multi-million dollar ...

4 Beds
5 Baths
Sicilian Shores Rep 02 SubDv.
32789 Zip Code

1180 Tom Gurney Drive, Winter Park image

1180 Tom Gurney Drive, Winter Park $2,750,000

Your dream home awaits with this beautiful 4 bedroom, 4.5 bath custom-built pool home nestled in the neighborhood of the Vias. Sophisticated design details and finishes p...

4 Beds
4 Baths
Tuscania SubDv.
32789 Zip Code

350 Carolina Avenue Unit 306, Winter Park image

350 Carolina Avenue Unit 306, Winter Park — 350 $459,000

Beautiful 2 Bedroom 2 Bath corner unit in sought after Park West Condominiums. Newly updated and move-in condition in the heart of Winter Park. This one of a kind communi...

2 Beds
2 Baths
Park West Condo SubDv.
32789 Zip Code

200 Oakwood Way, Winter Park $2,500,000

Pre-Construction. To be built. Excellent opportunity to purchase this new construction modern farmhouse built by Rare Builders. This home features 4,370 square feet of l...

5 Beds
5 Baths
Charmont SubDv.
32789 Zip Code

2550 Temple Drive, Winter Park $1,290,000 ▼

Gorgeous, immaculate, well appointed Winter Park Home. This modern floor plan with an open concept and spacious layout is conveniently located in the heart of Winter Park...

4 Beds
3 Baths
Via Merano SubDv.
32789 Zip Code

1003 S Kentucky Avenue, Winter Park image

1003 S Kentucky Avenue, Winter Park — - $599,000

Granite counter tops/Stainless steel appliances with natural gas burners. Living area features gas fireplace,bamboo hardwood floors and surround sound speakers. Priva...

3 Beds
2 Baths
Fairbanks Park SubDv.
32789 Zip Code

690 N New York Avenue, Winter Park image

690 N New York Avenue, Winter Park $3,850,000

Pre-Construction. To be built. Greens at Park. This address says it all…690 N. New York Avenue, where unparalleled luxury meets quintessential Winter Park lifestyle. Icon...

4 Beds
4 Baths
The Greens At Park SubDv.
32789 Zip Code

1118 Schultz Avenue, Winter Park — Townhomes At Harper Place $419,000 ▲

Winter Park 3 bed/2.5 bath 1661sf townhome with private rear terrace and 2 stall garage. Well lit living spaces complimented by plantation shutters, wood or tile floori...

3 Beds
2 Baths
Townhomes/Harper Place SubDv.
32789 Zip Code

125 S Interlachen Avenue Unit 2, Winter Park image

125 S Interlachen Avenue Unit 2, Winter Park — South Interlachen Place, #2 $2,250,000

Welcome to South Interlachen Place, an exquisite townhome community, boasting turn-key living at its finest. Showcasing the perfect blend of privacy and accessibility, wi...

3 Beds
3 Baths
South Interlachen Place SubDv.
32789 Zip Code

2739 Riddle Drive, Winter Park $559,000

Under Construction. Enjoy Winter Park Lifestyle with this beautiful new home. Built by Davila Homes an award winner custom builder, this home offer modern finishes, open ...

4 Beds
2 Baths
Glencoe Sub SubDv.
32789 Zip Code

1071 Aragon Avenue, Winter Park — Na $475,000

Conveniently located between downtown Winter Park and College Park with easy access to shopping, restaurants and highways. All the amenities one could want in this luxur...

2 Beds
2 Baths
Seville Park SubDv.
32789 Zip Code

2034 East End Avenue, Winter Park $1,135,000

New listing! Check out this amazing, newly built home by Barefoot Brothers, just steps from the East End Market. Built in 2019, this 3-bedroom, 3.5 bath home features an ...

3 Beds
3 Baths
Edgewood Sub SubDv.
32789 Zip Code

171 Genius Drive, Winter Park $4,095,000 ▼

An exquisite Chain of Lakes offering awaits the most discerning of lakefront homebuyers in the heart of Winter Park. Being presented for the first time on the market, thi...

4 Beds
4 Baths
Ardmore SubDv.
32789 Zip Code

2550 Venetian Way, Winter Park $2,400,000

"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic...

4 Beds
3 Baths
Maitland Shores First Add SubDv.
32789 Zip Code

1816 Mondrian Circle, Winter Park — 2 $654,500 ▼

Owner Motivated! Centrally located Lake Killarney Townhomes feature lake access to Lake Killarney, exquisite finishings and resort-like spaces, the perfect balance of lif...

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

125 S Interlachen Avenue Unit 6, Winter Park image

125 S Interlachen Avenue Unit 6, Winter Park — South Interlachen Place, #6 $2,990,000

Life doesn’t get more luxurious or convenient than at South Interlachen Place! This prestigious community consists of six exquisitely built townhomes, boasting turn-key l...

3 Beds
3 Baths
South Interlachen Place SubDv.
32789 Zip Code

777 Halifax Avenue, Winter Park $919,000 ▲

Under Construction. Location, location, location! Nestled in Winter Park, this home is convenient to the best in shopping, dining and entertainment! The two-story Easterl...

4 Beds
4 Baths
Park Manor First Add SubDv.
32792 Zip Code

1786 Mondrian Circle Unit 15, Winter Park image

1786 Mondrian Circle Unit 15, Winter Park — 1786 $825,000

Lakefront Living in Winter Park! Welcome to this fantastic interior unit townhome located on beautiful Lake Killarney. These residences are truly an unparalleled opportun...

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

865 W Canton Avenue, Winter Park $1,000,000 ▼

Coastal inspired, newly built, 2-story POOL home exceeds your expectations and is desirably located just minutes away from the Park Avenue fine dining and retail shopping...

4 Beds
3 Baths
Canton Residences SubDv.
32789 Zip Code

315 E New England Avenue E Unit 8, Winter Park image

315 E New England Avenue E Unit 8, Winter Park — Villa Siena $985,000

Known as the Jewel of Winter Park, Villa Siena is located 2 blocks off Park Avenue and is directly across from the chic Alfond Inn. Amenities include assigned garage park...

2 Beds
2 Baths
Villa Siena SubDv.
32789 Zip Code

7145 Aloma Avenue, Winter Park $825,000

Under Construction. Location! Location! Location! These professional Office suites are awaiting for someone to transform them into a successful business. It offers shell ...

32792 Zip Code

100 S Virginia Avenue Unit 403, Winter Park image

100 S Virginia Avenue Unit 403, Winter Park — Douglas Grand $950,000

One story unit at the Douglas Grand building in downtown Winter Park. High-end appliances and fixtures, granite counter tops in the kitchen and all baths. Oversized wal...

3 Beds
3 Baths
Winter Park Residential 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 Unit 18, Winter Park image

1792 Mondrian Circle Unit 18, 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