Winter Park Real Estate Winter Park Orlando Florida

Located northeast of Downtown Orlando, Winter Park is a city of beautiful natural scenery and friendly small town villages. Winter Park real estate is populated by approximately 25,000 residents and nearly as many oak trees. Originally a sanctuary for artists and many of the countries most influential families, Winter Park provides its citizens with relaxing, upscale living with the comforts of nature and the nearby excitement of Central Florida's world-class attractions.

Winter Park Homes for Sale

283 Properties Found. Page 1 of 6.
Photo of Listing #O5889106
Reduced 4.1%

1731 Pinetree Rd

$4,695,000
Winter Park
MLS® # O5889106
6 Beds, 8 Baths, 7,654 Sf
Photo of Listing #O5809404
Reduced 1.2%
Winter Park
MLS® # O5809404
10 Beds, 14 Baths, 8,325 Sf
Photo of Listing #O5830109
Reduced 6.7%
Winter Park
MLS® # O5830109
5 Beds, 5 Baths, 6,179 Sf
Photo of Listing #O5902307
New
Winter Park
MLS® # O5902307
5 Beds, 7 Baths, 6,444 Sf
Photo of Listing #O5815144

668 W Morse Blvd

$3,485,000
Winter Park
MLS® # O5815144
4 Beds, 6 Baths, 5,819 Sf
Photo of Listing #V4912283

639 N Park Ave

$3,465,000
Winter Park
MLS® # V4912283
3 Beds, 5 Baths, 4,244 Sf
Photo of Listing #O5863273
Winter Park
MLS® # O5863273
3 Beds, 5 Baths, 4,160 Sf
Photo of Listing #O5808325
Reduced 4.3%

511 W Canton Ave

$3,350,000
Winter Park
MLS® # O5808325
5 Beds, 7 Baths, 8,910 Sf
Photo of Listing #O5509686
Reduced 2.3%

740 Palmer Ave

$3,175,000
Winter Park
MLS® # O5509686
5 Beds, 5 Baths, 4,810 Sf
Photo of Listing #O5845264
Reduced 3.3%

2359 Forrest Rd

$2,895,000
Winter Park
MLS® # O5845264
4 Beds, 5 Baths, 6,344 Sf
Photo of Listing #O5897286

331 Trismen Ter

$2,600,000
Winter Park
MLS® # O5897286
4 Beds, 5 Baths, 5,565 Sf
Photo of Listing #O5869066

1330 N Park Ave

$2,500,000
Winter Park
MLS® # O5869066
6 Beds, 6 Baths, 4,324 Sf
Photo of Listing #O5883546

1246 Alabama Dr

$2,399,000
Winter Park
MLS® # O5883546
5 Beds, 7 Baths, 4,872 Sf
Photo of Listing #O5863271
Winter Park
MLS® # O5863271
2 Beds, 5 Baths, 3,244 Sf
Photo of Listing #O5820463

1760 Via Venetia

$2,385,000
Winter Park
MLS® # O5820463
4 Beds, 6 Baths, 6,242 Sf
Photo of Listing #O5834956
Reduced 1.7%

2218 Via Tuscany

$2,345,000
Winter Park
MLS® # O5834956
5 Beds, 7 Baths, 4,423 Sf
Photo of Listing #O5896286

1660 Palmer Ave

$2,295,000
Winter Park
MLS® # O5896286
4 Beds, 6 Baths, 5,400 Sf
Photo of Listing #O5876945
Reduced 6.1%
Winter Park
MLS® # O5876945
3 Beds, 4 Baths, 5,583 Sf
Photo of Listing #O5876353

2400 Venetian Way

$2,195,000
Winter Park
MLS® # O5876353
5 Beds, 5 Baths, 4,293 Sf
Photo of Listing #O5891439

141 N Virginia Ave

$2,150,000
Winter Park
MLS® # O5891439
5 Beds, 6 Baths, 4,018 Sf
Photo of Listing #O5876425

4245 Bear Gully Rd

$2,150,000
Winter Park
MLS® # O5876425
5 Beds, 5 Baths, 5,528 Sf
Photo of Listing #O5882111

147 N Virginia Ave

$1,999,500
Winter Park
MLS® # O5882111
3 Beds, 6 Baths, 4,512 Sf
Photo of Listing #O5882305
Reduced 4.8%

1237 Via Del Mar

$1,995,000
Winter Park
MLS® # O5882305
4 Beds, 5 Baths, 5,479 Sf
Photo of Listing #O5891473
Reduced 9%

280 Stirling Avenue

$1,950,000
Winter Park
MLS® # O5891473
4 Beds, 4 Baths, 3,428 Sf
Photo of Listing #O5871527
Reduced 1.3%

1560 Cardinal Ct

$1,924,900
Winter Park
MLS® # O5871527
5 Beds, 6 Baths, 4,581 Sf
Photo of Listing #O5888220
Reduced 2.3%

2340 Randall Rd

$1,880,000
Winter Park
MLS® # O5888220
5 Beds, 6 Baths, 4,421 Sf
Photo of Listing #O5846918
Winter Park
MLS® # O5846918
4 Beds, 6 Baths, 4,573 Sf
Photo of Listing #O5882425
Reduced 5.4%
Winter Park
MLS® # O5882425
3 Beds, 4 Baths, 3,272 Sf
Photo of Listing #O5877191
Reduced 0.6%

1341 Place Picardy

$1,749,900
Winter Park
MLS® # O5877191
5 Beds, 6 Baths, 4,469 Sf
Photo of Listing #O5899490

2023 Venetian Way

$1,700,000
Winter Park
MLS® # O5899490
4 Beds, 4 Baths, 3,326 Sf
Photo of Listing #O5889654
Reduced 3%

1730 Greenwich Ave

$1,697,000
Winter Park
MLS® # O5889654
4 Beds, 5 Baths, 4,611 Sf
Photo of Listing #O5891290

570 Country Club Dr

$1,695,000
Winter Park
MLS® # O5891290
5 Beds, 7 Baths, 3,697 Sf
Photo of Listing #O5871398
Winter Park
MLS® # O5871398
5 Beds, 7 Baths, 4,398 Sf
Photo of Listing #O5898157
Reduced 5.3%

1022 Mckean Cir

$1,690,000
Winter Park
MLS® # O5898157
4 Beds, 4 Baths, 4,610 Sf
Photo of Listing #O5845744

444 Shepherd Ave

$1,689,900
Winter Park
MLS® # O5845744
5 Beds, 6 Baths, 4,322 Sf
Photo of Listing #O5899896
Winter Park
MLS® # O5899896
3 Beds, 4 Baths, 3,174 Sf
Photo of Listing #O5880298
Reduced 2.2%

140 E Morse Blvd #c

$1,590,000
Winter Park
MLS® # O5880298
2 Beds, 3 Baths, 2,450 Sf
Photo of Listing #O5889388

1731 Via Genoa

$1,579,000
Winter Park
MLS® # O5889388
4 Beds, 5 Baths, 3,795 Sf
Photo of Listing #O5889672
Reduced 3.2%

1641 Woodland Ave

$1,499,000
Winter Park
MLS® # O5889672
5 Beds, 6 Baths, 4,509 Sf
Photo of Listing #O5902080

1750 Edwin Blvd

$1,495,000
Winter Park
MLS® # O5902080
5 Beds, 5 Baths, 4,108 Sf
Photo of Listing #O5900120
New

1616 Hibiscus Ave

$1,450,000
Winter Park
MLS® # O5900120
4 Beds, 5 Baths, 3,897 Sf
Photo of Listing #O5835530
Reduced 2.7%

135 W Swoope Ave

$1,450,000
Winter Park
MLS® # O5835530
3 Beds, 3 Baths, 2,457 Sf
Photo of Listing #O5888397
Winter Park
MLS® # O5888397
5 Beds, 5 Baths, 3,931 Sf
Photo of Listing #O5851176
Reduced 1.7%

1731 Palmer Ave

$1,425,000
Winter Park
MLS® # O5851176
5 Beds, 6 Baths, 4,579 Sf
Photo of Listing #O5725156
Reduced 3.4%

110 Chelton Cir

$1,425,000
Winter Park
MLS® # O5725156
4 Beds, 4 Baths, 4,225 Sf
Photo of Listing #O5889338

1903 N Park Ave

$1,400,000
Winter Park
MLS® # O5889338
4 Beds, 4 Baths, 2,823 Sf
Photo of Listing #O5870374

1637 Magnolia Ave

$1,400,000
Winter Park
MLS® # O5870374
4 Beds, 5 Baths, 3,616 Sf
Photo of Listing #O5898624

1650 Dale Ave

$1,399,000
Winter Park
MLS® # O5898624
4 Beds, 5 Baths, 4,577 Sf

More about Winter Park

A journey into Winter Park reveals breathtaking luxury homes, gorgeous scenery, and an inviting community of towns with character and old world charm.  Packed with 70 different parks and a beautiful chain of lakes, Winter Park has earned a reputation as a one Central Florida's most relaxing and tranquil cities. Chartered in 1870, Winter Park gets its name from the wealthy northerners who visited the city to escape harsh and cold winters.  Fortunately, Winter Park has retained that aesthetic throughout the years.

Winter Park Luxury Real Estate

Winter Park is famous for its brick lined streets, tall oak trees, and European style thoroughfare. Blocks and blocks of boutique shops, sidewalk cafés, and courtyards populate the city. There is a wide range of fine dining restaurants, local theaters and museums, including the Charles Hosmer Morse Museum of American Art, housing the world's largest collection of Tiffany glass. Being a city rich in culture, residents enjoy year round festivals and events from the Sidewalk Art Festival to the Exotic Car Show to Saturday morning Farmers' markets. It is the city's beauty and sense of community that attracts these celebrations and makes them highly anticipated events.

Downtown Winter Park Orlando Florida

Thanks to the Winter Park Chain of Lakes, residents take advantage of plenty of water recreation from boating and fishing to swimming and water skiing. The shores of Lake Virginia are home to Florida's oldest institution of higher education, Rollins College. Home to the Cornell Fine Art museum and the world renowned Bach Festival Choir, Rollins College is recognized by U.S. News and World Report as one of  "America's Best Colleges." The local schools are considered to be some of Florida's finest, making Winter Park the perfect place to raise a family.

As special and unique as Winter Park is, citizens can easily travel to another one of Florida's most exciting places, Orlando. Just a short drive away, downtown Orlando has world class dining and entertainment, exquisite shopping opportunities, and an elegant night life. World famous theme parks such as Walt Disney World, Universal Studios, and Sea World are perfectly in reach for family getaways. Winter Park is so close to the excitement while remaining far enough away to be sheltered from the hustle and bustle associated with big city living.

Since its inception, Winter Park has been refuge for those looking for a comfortable yet exciting place to live, complete with picturesque parks, rich culture and history, and amazing educational opportunities.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on October 30th, 2020 at 11:30am EDT.