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Winter Park Homes for Sale

Winter Park, Florida, is a suburban city found in Orange County and part of the Orlando-Kissimmee-Sanford metro area. With a rich historic history, Winter Park was founded as a resort community in the early 20th century. Winter Park has grown and is now known for its vibrant main street, luxury communities, museums, galleries, parks and an incredible chain of lakes popular for skiing, boating, fishing and general recreation.

One of the most popular and renowned areas of the City is Park Avenue, a traditional bricked street which provides an amazing variety of fine and casual dining, boutique shopping, entertainment, a central park and museums. The City is home to a public golf club, historic cemetery, train station, art galleries and a famous boating tour. Additional popular activities include visiting the Winter Park Village mall, Annie Russell Theatre, Rollins College, Charles Hosmer Morse Museum of American Art, Cornell Fine Arts Museum, Hannibal Square, Mead Botanical Gardens, Kraft Azalea Park and the Winter Park Historical Museum. The scenic boat tours also provide a great way to see the beautiful luxury homes and natural beauty found throughout the City. Winter Park is also host to the world-famous Winter Park Sidewalk Art Festival, which is the largest and oldest of the art festivals found in the country today.

Winter Park is part of the Orange County Public School system and also boasts great schools from public elementary schools to well-known colleges. Some of the top-ranked schools in Winter Park include: Aloma Elementary School, The Geneva School, The Parke House Academy, Full Sail University, Lakemont Elementary, St. Margaret Mary Catholic School, Trinity Preparatory, Winter Park High, Rollins College, Valencia Community College and the Crealde School of Art.

Winter Park offers many forms of housing including luxury, waterfront, golf front, single-family homes, townhomes, condos, and villas. However, most are single-family homes and tend to be larger with four or more bedrooms. A significant number of the single-family homes have been custom built and target buyers looking for luxurious amenities. A significant number of large estate homes are waterfront and located on the Winter Park Chain of Lakes. The average home listed on the market in Winter Park is about $856K; however, prices can easily range into the multi-millions for some of the larger estate homes.

Some of the most desirable communities in Central Florida are located in Winter Park including Bear Gully Bay, Bear Gully Pointe, Bengerts Bend, Brookshire Heights, Camwood, Charmont, Comstock Park, Conwill Estates, Dixie Terrace, Dubsdread Heights, Ellno Willo, Forest Hills, Fountainhead, Glencoe, Golfview Terrace, Green Oaks, Green Terrace, J Kronenberger, Kenilworth Shores, Killarney Circle, Lake Howell, Lake Howell Lane, Lake Knowles Terrace, Lake Virginia, Maitland Shores, Osceola Place, Park Grove, Sevilla, Shores Lake Killarney, Sicilian Shores, Sylvan Lake Shores, Sylvan Park, Timberlane Shores, Tuscany Place, Tuscany Terrace, Twelve Oaks, Virginia Heights, Windsong and many more.

Looking to sell your home in Winter Park? Follow this link to get an "Instant" Home Value Report

Newest Winter Park Homes for Sale

554 Fitzwalter Drive, Winter Park $649,990

Updated and spacious (5/6) bedroom 3 bath in the city of Winter Park’s Brookshire Heights. Conveniently located steps away from Cady Way bike trail and close to Brookshir...

5 Beds
3 Baths
Brookshire Heights 1st Add SubDv.
32792 Zip Code

267 N Ranger Boulevard, Winter Park image

267 N Ranger Boulevard, Winter Park $330,000

Great three bedroom, two bath Winter Park Pines POOL home with 2 car Garage. Tile floors throughout the public areas and beautiful laminate flooring in the bedrooms. Op...

3 Beds
2 Baths
Winter Park Pines Merrie Oaks SubDv.
32792 Zip Code

2007 S Prince Court, Winter Park $385,000

Discover this quiet subdivision that is close to major roadways, retail and parks. This home finds itself in one of the most desirable school districts in the area. Thi...

4 Beds
3 Baths
Kings Cove SubDv.
32792 Zip Code

1750 Oakhurst Avenue, Winter Park $569,900

Winter Park Beauty! Completely remodeled, this stunning 3 bedroom, 2 bath, 2-car garage property offers a serene ambiance you'll never want to leave. Plentiful sunlit win...

3 Beds
2 Baths
Jenkins Second Add SubDv.
32789 Zip Code

611 Genius Drive, Winter Park $915,000

Lowest price in Windsong! Timeless SINGLE STORY- 3 bedroom plus office, pool home in highly desirable North Shore Windsong. Spectacular open floorplan family, yet keeping...

3 Beds
3 Baths
Windsong North Shore 43/74 SubDv.
32789 Zip Code

2345 Middleton Avenue, Winter Park image

2345 Middleton Avenue, Winter Park $365,000

Welcome home to this beautiful 3 bed/2 bath Winter Park family home. Amazing location, modern charm, and updates throughout. NEW ROOF, NEW PLUMBING, NEW SOD W/IRRIGATION,...

3 Beds
2 Baths
Brookshire Heights SubDv.
32792 Zip Code

665 Ololu Drive, Winter Park $330,000

IN THE EXCLUSIVE CITY OF WINTERPARK, YOU WON'T FIND ANOTHER LIKE THIS ONE. COMPLETELY REMODELED FROM THE GRASS TO THE ROOF, NEW KITCHEN, NEW BATHROOMS, BEAUTIFUL NEW PORC...

3 Beds
2 Baths
Killarney Circle SubDv.
32789 Zip Code

1907 Japonica Road, Winter Park $300,000

Your new home awaits, located in the established Winter Park community of Winter Woods. With it’s SPLIT BEDROOM plan, sizeable rooms, large lot, and plentiful upgrades, t...

4 Beds
2 Baths
Winter Woods Unit 04 SubDv.
32792 Zip Code

690 Osceola Avenue Unit 410, Winter Park image

690 Osceola Avenue Unit 410, Winter Park — Lake Virginia Condo $365,000

Situated in Lake Virginia Condo, this corner unit with two bedrooms, two full baths fully renovated condominium offers Winter Park living at it’s best. Elegant travertin...

2 Beds
2 Baths
Lake Virginia Condo SubDv.
32789 Zip Code

1770 Oakhurst Avenue, Winter Park $1,395,000

Under Construction. Brand new one story with estimated completion date of June 2019. A gorgeous 5 bed, 4 1/2 bath home, with pool, summer kitchen, 2 car garage. The open...

5 Beds
4.5 Baths
Jenkins Second Add SubDv.
32789 Zip Code

1920 Laurel Road, Winter Park $369,000

Highly desirable Winter Park location within the new k-8 Audubon Park School District. Don't miss your opportunity to buy at today's price. Build new or fix up or add on...

2 Beds
1 Baths
Charmont SubDv.
32789 Zip Code

311 E Morse Boulevard Unit 6-19, Winter Park image

311 E Morse Boulevard Unit 6-19, Winter Park — Building 6 Unit 19 $775,000

Enjoy living in the heart of downtown Winter Park in this unique, one story penthouse condo. This 2140 sq ft unit occupies half of the fifth floor with 234 sq ft of scre...

2 Beds
2 Baths
Phillips Circle Rep SubDv.
32789 Zip Code

1792 Mondrian Circle Unit 18, Winter Park image

1792 Mondrian Circle Unit 18, Winter Park — 6 $1,100,000

Under Construction. The art of Modern Style. This luxury lakefront town home, located on Lake Killarney, offers a stunning view. The property includes a private boat slip...

3 Beds
3.5 Baths
The Mondrian Winter Park SubDv.
32789 Zip Code

375 Virginia Drive, Winter Park $3,895,000

Lakefront, Location, Luxury. Move right into this beautiful lakefront custom home on cul-de-sac with views of Rollins College. Located on desirable Lake Virginia. 5 bedro...

5 Beds
4.5 Baths
Shadow Hill SubDv.
32789 Zip Code

Winter Park $995,000

This Mediterranean style home is on a large lot close to Lake Knowles, in the heart of Winter Park. This four bedroom nearly 3,500 square foot home, with upstairs loft, h...

4 Beds
2.5 Baths
32789 Zip Code

315 E New England Avenue Unit 27, Winter Park image

315 E New England Avenue Unit 27, Winter Park — Villa Siena $1,795,000

A RARE OPPORTUNITY! STUNNING PENTHOUSE WITH SWEEPING VIEWS OF THE ICONIC ALFOND INN! This three bedroom, three and a half bath plus media room offers tons of natural ligh...

3 Beds
3.5 Baths
Villa Siena SubDv.
32789 Zip Code

4264 Steed Terrace, Winter Park $375,000

Welcome to King's Cove! One of the most desired communities of Tuskawilla, CORNER LOT, FRESHLY PAINTED IN AND OUT. OPEN PLAN, SPACIOUS home with tile floors in the common...

4 Beds
2 Baths
Kings Cove SubDv.
32792 Zip Code

1660 Palmer Avenue, Winter Park $539,900 ▼

Value is in the Land. 0.36 Acres (15,758 sqft). Come build your dream home. Walking distance to Phelps Park and Lakemont Elementary. A very short distance to Park Ave...

Comstock Park SubDv.
32789 Zip Code

1831 Laurelton Hall Lane, Winter Park image

1831 Laurelton Hall Lane, Winter Park $1,165,000

***Enjoy this ELEGANT Family sized over 4000 square foot, 2- story Mediterranean home with 4 LARGE bedrooms/4.5 baths PLUS home office, large loft AND large bonus room/ho...

4 Beds
4.5 Baths
Windsong - Knowles Place SubDv.
32789 Zip Code

1020 Minnesota Avenue Unit 7, Winter Park image

1020 Minnesota Avenue Unit 7, Winter Park — 7 $325,000

Beautiful Mediterranean style three bedroom, three and a half bath condominium, located in Winter Parks Casa Cielo. On the first level there is a large family room with t...

3 Beds
3.5 Baths
Casa Cielo Condo SubDv.
32789 Zip Code

1276 S Pennsylvania Avenue Unit 12, Winter Park image

1276 S Pennsylvania Avenue Unit 12, Winter Park — 1276 $795,000

If you are looking for a carefree lifestyle within walking distance to Park Avenue, Rollins College and Hannibal Square then this Elegant Townhome is for you! From the mi...

3 Beds
2.5 Baths
Casa Jardin Condo SubDv.
32789 Zip Code

2845 Summerfield Road, Winter Park image

2845 Summerfield Road, Winter Park $475,000

Gorgeous completely updated 4 bedroom Winter Park pool home on corner lot within the City and less than 1/2 block from Winter Pines Golf Course. Lovely front porch with S...

4 Beds
2 Baths
Golfside /Winter Park Pines SubDv.
32792 Zip Code

2703 Ambergate Road, Winter Park $300,000

Must See Pool home with Top Rated Schools. Have you been looking for a while but just can't find a pool home with 4 bedrooms and a 2 car garage? If so, this may be the ...

4 Beds
3 Baths
Winter Park Estates SubDv.
32792 Zip Code

1712 Arbor Park Drive, Winter Park image

1712 Arbor Park Drive, Winter Park $499,700 ▼

Beautiful Charming and Newly Remodeled 4/2 home in well Desired area in winter park. This property boasts new tiles floors , new hard wood flooring in bedrooms, newly ren...

4 Beds
2 Baths
Conwill Estates SubDv.
32789 Zip Code

1660 Mizell Avenue, Winter Park $1,295,000

Custom Windsong Mediterranean pool home built in 2004 - beautifully designed by Winter Park Designs and built by IBK Construction. Upon entering the home you will be gree...

4 Beds
3.5 Baths
Windsong Lakeside Sec 01 43/70 SubDv.
32789 Zip Code

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