Winter Park, FL 55+ active adult communities & homes for sale - Page 40

2,698 homes near Winter Park

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

5 rating (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

5 rating (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (8 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

5 rating (1 reviews)

Legacy of Leesburg

$200ks - $400ks

Legacy of Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

10 RAINER PL, PALM COAST, FL, 32164

Stonecrest

11193 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$332,750

3 beds

2 baths

1,974 sq ft

House

11193 SE 173RD PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Cresswind at Victoria Gardens

173 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724

$379,000

2 beds

2 baths

1,652 sq ft

House

173 OLD MOSS CIR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Arlington Ridge

4348 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748

$436,415

3 beds

3 baths

2,359 sq ft

House

4348 ANTIETAM CREEK TRL, LEESBURG, FL, 3...

Community: Arlington Ridge

Spruce Creek South

17832 SE 96TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$239,900

2 beds

2 baths

1,248 sq ft

House

17832 SE 96TH AVE, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

The Villages®

$539,500

3 beds

2 baths

2,058 sq ft

Villa

3101 ARCHER AVE, THE VILLAGES, FL, 32162

Community: The Villages®

Four Seasons at Orlando

7964 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$485,000

4 beds

3 baths

2,261 sq ft

House

7964 HANSON BAY PL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Del Webb Sunbridge

6323 DEW DROP LOOP, ST CLOUD, FL, 34771, St Cloud, FL 34771

$579,766

2 beds

2 baths

1,949 sq ft

House

6323 DEW DROP LOOP, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

Spring Lake Towers

700 MIRROR TER 511, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881

$149,900

2 beds

2 baths

1,190 sq ft

Condo

700 MIRROR TER 511, WINTER HAVEN, FL, 33...

Community: Spring Lake Towers

Lake Henry Estates

501 EASTLAKE DR, HAINES CITY, FL, 33844, Haines City, FL 33844

$272,900

2 beds

2 baths

1,724 sq ft

House

501 EASTLAKE DR, HAINES CITY, FL, 33844

Community: Lake Henry Estates

Latitude Margaritaville

237 SAND BAR LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124

$499,900

2 beds

2 baths

1,681 sq ft

House

237 SAND BAR LN, DAYTONA BEACH, FL, 3212...

Community: Latitude Margaritaville

Spruce Creek Country Club

12992 SE 91ST CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$480,000

2 beds

3 baths

2,446 sq ft

House

12992 SE 91ST CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Esplanade at Highland Ranch

2594 STARGRASS CIR, CLERMONT, FL, 34715, Clermont, FL 34715

$395,000

2 beds

2 baths

1,732 sq ft

House

2594 STARGRASS CIR, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

2 baths

1,935 sq ft

House

2470 SALZBURG LOOP, WINTER HAVEN, FL, 33...

House

1514 HAMLIN ST, WINTER HAVEN, FL, 33881

Del Webb at Viera

3103 TIDEPOOL PL, MELBOURNE, FL, 32940, Melbourne, FL 32940

$443,000

3 beds

2 beds

2 baths

1,132 sq ft

Villa

308 ALMERIA ST, THE VILLAGES, FL, 32162

Community: The Villages®

Venetian Bay

3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$575,000

3 beds

3 baths

2,472 sq ft

House

3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Carillon Lakes

3933 SERENADE LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$329,900

3 beds

2 baths

2,048 sq ft

Condo

3933 SERENADE LN, LAKELAND, FL, 33811

Community: Carillon Lakes

The Villages®

$390,000

3 beds

2 baths

1,384 sq ft

Villa

2877 FEUSTEL AVE, THE VILLAGES, FL, 3216...

Community: The Villages®

Cindy Certified

436 LEMONGRASS RD, MINNEOLA, FL, 34715, Minneola, FL 34715

$579,990

4 beds

3 baths

2,105 sq ft

House

436 LEMONGRASS RD, MINNEOLA, FL, 34715

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

The Villages®

$530,000

3 beds

3 baths

2,016 sq ft

House

1967 FLOWERSVILLE PL, THE VILLAGES, FL, ...

Community: The Villages®

Cindy Certified

2110 RAGLAN CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$398,990

3 beds

2 baths

2,139 sq ft

House

2110 RAGLAN CIR, ORMOND BEACH, FL, 32174

1…34 35 36 37 38 39 40 41 42 43 44 45 46…68

Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

Want more information about active adult communities around Winter Park?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting optout@55places.com. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Winter Park?

Call us: (888) 625-4885

2,698 homes

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Winter Park, FL 55+ active adult communities & homes for sale - Page 40

98 communities near Winter Park

2,698 homes near Winter Park

4 beds

2 baths

1,754 sq ft

House

2 beds

2 baths

1,698 sq ft

House

3 beds

2 baths

2,593 sq ft

House

4 beds

2 baths

1,912 sq ft

House

3 beds

2 baths

1,974 sq ft

House

2 beds

2 baths

1,652 sq ft

House

3 beds

3 baths

2,359 sq ft

House

2 beds

2 baths

1,248 sq ft

House

3 beds

2 baths

2,058 sq ft

Villa

4 beds

3 baths

2,261 sq ft

House

2 beds

2 baths

1,949 sq ft

House

2 beds

2 baths

1,190 sq ft

Condo

2 beds

2 baths

1,724 sq ft

House

2 beds

2 baths

1,681 sq ft

House

2 beds

3 baths

2,446 sq ft

House

2 beds

2 baths

1,732 sq ft

House

2 beds

2 baths

1,870 sq ft

House

4 beds

2 baths

1,635 sq ft

House

3 beds

2 baths

1,612 sq ft

House

2 beds