Winter Park: A Historical and Cultural Experience

The City of Winter Park is a hub for art and culture. Downtown Winter Park is known for its amazing shopping, dining and cultural experiences. This is most notably present on Park Avenue and Hannibal Square.

Majestic oak trees line picturesque brick roads. The downtown train station and Central Park complete a picture right out of a Norman Rockwell painting. You get a Main Street, USA feel with old Europe undertones as you shop and dine down the pet friendly walkways.

Winter Park is nestled in the middle of everything, just minutes from Downtown Orlando, but is truly in a class of its own. Amazing architecture, cultural events and quality of life are some of the things that make Winter Park such a highly desired place to live.

Hot Winter Park Properties

2721 Salisbury Boulevard, Winter Park image

2721 Salisbury Boulevard, Winter Park $329,900 ▼

Every detail was upgraded! Move right in with complete peace of mind to your new Winter Park home. Beautifully renovated 2 bedroom, 1 bathroom, 2 car garage home located ...

2 Beds
1 Baths
Glencoe Sub SubDv.
32789 Zip Code

Winter Park $350,000

Established neighborhood minutes from downtown. Roof new in 2017 and Electric upgrade in 2022 so there shouldn't be any big expense to a new buyer. This would be a good ...

3 Beds
2 Baths
Lake Bell Terrace SubDv.
32789 Zip Code

601 Ololu Drive, Winter Park $350,000

This 3 bedroom, 1 Bath has room to grow and is a great starter home for the right family who wants to build equity, expand renovate and grow into a home or just an awesom...

3 Beds
1 Baths
Killarney Circle SubDv.
32789 Zip Code

700 Melrose Avenue Unit J, Winter Park image

700 Melrose Avenue Unit J, Winter Park — J $365,900

Amazing Winter Park Lake Front location! This fully remodeled and totally updated one bedroom unit has just been completed. All new paint, porcelain flooring, all new fi...

1 Beds
1 Baths
Winter Park Gardens Condo SubDv.
32789 Zip Code

2164 Crandon Avenue, Winter Park $369,000

In the heart of Winter Park, next to 1-4 between Par and Fairbanks exits. This cute 2/1 house is ready for renovations which will make it a great home or rental. It is on...

2 Beds
1 Baths
Olympia Heights Annex SubDv.
32789 Zip Code

811 W Webster Avenue, Winter Park $379,000

Opportunity Knocks- rare Winter Park block home brimming with ownership and investment potential! Live in the heart of Winter Park while enjoying all WP offers in outsta...

3 Beds
1 Baths
Magnolia Gardens Sub SubDv.
32789 Zip Code

690 Osceola Avenue Unit 410, Winter Park image

690 Osceola Avenue Unit 410, Winter Park — Lake Virginia Condo $399,000 ▼

Lake Virginia Condos | 4th Floor Canal Front Unit | Spacious 2 bedrooms, 2 full baths, 1,148 SF | Offered at $399,000. Open layout with large living room, separate dinin...

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

1871 Barker Drive, Winter Park $399,900 ▼

Agents: This property is being sold in an auction-style format. It is not an absolute auction. Prospective buyers should note that the final sale price may significantly ...

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

926 Fremont Avenue, Winter Park $439,900 ▼

Extensively renovated 4 bedroom/3 bath home in sought-after Winter Park! Huge Added Master Suite. Master bedroom with his and her walking closet, Huge walk-in shower. New...

4 Beds
3 Baths
Albert Lee Ridge First Add SubDv.
32789 Zip Code

700 Melrose Avenue Unit K, Winter Park image

700 Melrose Avenue Unit K, Winter Park — K $449,880

Amazing Winter Park Lake Front location! This fully remodeled and totally updated two bedroom unit has just been completed. All new paint, porcelain flooring, all new fi...

2 Beds
2 Baths
Winter Park Gardens Condo SubDv.
32789 Zip Code

Winter Park Living Starts Here

Address Search