58+ Gated Homes for Sale in Winter Park

× Winter Park × Gated × 1+ beds

Sort By:

1128 Preserve Point Dr, Winter Park, FL 32789

Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150 on the shores of Lake ... View Full Details

5Beds
5Baths
6,179SqFt

Listing Provided By Kelly Price & Company LLC MYFLR

$4,195,000

1830 Gipson Green Ln, Winter Park, FL 32789

Luxury and elegance abound in this private, gated Winter Park Chain of Lakes estate, nestled on almo ... View Full Details

5Beds
7Baths
6,444SqFt

Listing Provided By Fannie Hillman & Associates MYFLR

$2,850,000

1740 Via Palermo, Winter Park, FL 32789

Located in the heart of Winter Park, this exceptional and well appointed estate home sits on an over ... View Full Details

5Beds
6Baths
5,259SqFt

Listing Provided By Kelly Price & Company LLC MYFLR

$2,750,000

1610 Via Tuscany, Winter Park, FL 32789

Welcome to this Exquisite Mizner style Tuscan Estate located in the heart of the Via's of Olde Winte ... View Full Details

5Beds
6Baths
5,980SqFt

Listing Provided By Stockworth Realty Group MYFLR

$2,295,000

1660 Palmer Ave, Winter Park, FL 32789

Pre-Construction. To be built. Pre-Construction. To be built. Modern French country villa, situated ... View Full Details

4Beds
6Baths
5,400SqFt

Listing Provided By Premier Sotheby's Intl. Realty MYFLR

$1,995,000

1237 Via Del Mar, Winter Park, FL 32789

This fabulous custom built gated estate home situated on a quiet street in the exclusive Vias of Win ... View Full Details

4Beds
5Baths
5,479SqFt

Listing Provided By Coldwell Banker Realty MYFLR

$1,750,000

147 S Interlachen Ave Unit 301, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Just completed in downtown Winter Park's distinctive ... View Full Details

3Beds
4Baths
3,272SqFt

Listing Provided By Florida One Real Estate LLC MYFLR

$1,590,000

140 E Morse Blvd C, Winter Park, FL 32789

Luxury living in the Landmark Building - Winter Parks premiere address for privacy and proximity to ... View Full Details

2Beds
3Baths
2,450SqFt

Listing Provided By Keller Williams Winter Park MYFLR

$1,579,000

1731 Via Genoa, Winter Park, FL 32789

Exceptionally beautiful private pool home in the most desirable heart of the Vias. Unmatched curb ap ... View Full Details

4Beds
5Baths
3,795SqFt

Listing Provided By Kelly Price & Company LLC MYFLR

$1,425,000

1731 Palmer Ave, Winter Park, FL 32789

Welcome to 1731 Palmer Avenue, a beautifully appointed Santa Barbara inspired pool home. This gorgeo ... View Full Details

5Beds
6Baths
4,579SqFt

Listing Provided By Corcoran Premier Realty MYFLR

$1,425,000

1760 Lookout Landing Cir, Winter Park, FL 32789

Welcome to this Gorgeous Mediterranean Estate Home, Custom built for the Windsong Street of Dreams. ... View Full Details

5Beds
5Baths
3,931SqFt

Listing Provided By Cogan Realty LLC MYFLR

$1,295,000

4578 Tigua Island Ct, Winter Park, FL 32792

Quiet, gated and family oriented community that is close to top rated schools, excellent shopping an ... View Full Details

5Beds
5Baths
5,990SqFt

MYFLR

1 - 12 of 58 listings

Average Price	$758,177
Avg Bedrooms	2.9 beds
Avg Bathrooms	2.66 baths

1 bedroom	$132,320
2 bedrooms	$379,987
3 bedrooms	$540,536
4 bedrooms	$943,666
5 bedrooms	$1,435,185

Current Search

Winter Park Homes for Sale

Winter Park Open Houses

Winter Park Home Report

Average Home

Average Price by Bedrooms

Quick Searches

Search Options

58+ Gated Homes for Sale in Winter Park

Current Search

Winter Park Homes for Sale

Winter Park Open Houses

Winter Park Home Report

Average Home

Average Price by Bedrooms

Quick Searches

Search Options

58+ Gated Homes for Sale in Winter Park

Accept Terms

Opt-In

Share a Link

Create a Note

Select a Notebook

or make a new notebook

Looks like your phone is invalid.

Would you like to update it?

Create Your Free Account

Create Your Free Account

Create Your Free Account

Have a house to sell?

Almost there!

Log In