Winter Park, FL 55+ active adult communities & homes for sale - Page 37

2,259 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

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

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

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 (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)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

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

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.

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

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

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

Questions? Call us: (888) 625-4885

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

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

Questions? Call us: (888) 625-4885

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 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 Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

The Country Club of Mount...

$200ks - $1Ms

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

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

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

Questions? Call us: (888) 625-4885

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

4105 PIUTE LN, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

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

Questions? Call us: (888) 625-4885

The Villages®

508 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159

$253,900

2 beds

2 baths

1,532 sq ft

Manufactured Home

508 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...

Community: The Villages®

The Villages®

$479,900

3 beds

2 baths

1,927 sq ft

House

2028 GLENARDEN PATH, THE VILLAGES, FL, 3...

Community: The Villages®

Highland Lakes

26627 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$235,000

2 beds

2 baths

1,120 sq ft

Villa

26627 RACQUET CIR, LEESBURG, FL, 34748

Community: Highland Lakes

Cresswind at Hammock Oaks

574 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$429,990

3 beds

2 baths

1,724 sq ft

House

574 HAMMOCK OAKS BLVD, LADY LAKE, FL, 32...

Community: Cresswind at Hammock Oaks

The Country Club of Mount Dora

2040 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$730,000

3 beds

3 baths

3,174 sq ft

House

2040 PARK FOREST BLVD, MOUNT DORA, FL, 3...

Community: The Country Club of Mount Dora

Royal Harbor

4913 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778

$322,900

3 beds

2 baths

2,087 sq ft

House

4913 RAINBOW TROUT RD, TAVARES, FL, 3277...

Community: Royal Harbor

Solivita

352 HAMRICK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$540,000

3 beds

3 baths

3,078 sq ft

House

352 HAMRICK DR, KISSIMMEE, FL, 34759

Community: Solivita

Del Webb Orlando

112 CASTELLON CT, DAVENPORT, FL, 33837, Davenport, FL 33837

$429,900

2 beds

2 baths

1,961 sq ft

House

112 CASTELLON CT, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Venetian Bay

3058 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$410,000

2 beds

2 baths

1,003 sq ft

Townhouse

3058 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

The Villages®

4904 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484

$299,990

4 beds

4 baths

1,912 sq ft

House

4904 NE 123RD LN, OXFORD, FL, 34484

Community: The Villages®

The Villages®

807 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$172,000

2 beds

2 baths

1,430 sq ft

Manufactured Home

807 OAK BLVD, WILDWOOD, FL, 34785

House

543 CLUBHILL DR, HAINES CITY, FL, 33844

12371 NE 48TH CIR, OXFORD, FL, 34484

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Del Webb Orlando

1032 SALAMANCA PL, DAVENPORT, FL, 33837, Davenport, FL 33837

$319,900

2 beds

2 baths

1,455 sq ft

House

1032 SALAMANCA PL, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$369,000

2 beds

2 baths

1,196 sq ft

Villa

1041 REIDVILLE RD, THE VILLAGES, FL, 321...

Community: The Villages®

Scottish Highlands

1907 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$215,000

2 beds

2 baths

1,495 sq ft

House

1907 TWEED CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Scottish Highlands

1416 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788

$219,900

3 beds

2 baths

1,736 sq ft

House

1416 ORKNEY DR, LEESBURG, FL, 34788

Community: Scottish Highlands

The Villages®

$265,000

2 beds

2 baths

1,336 sq ft

House

731 CORTEZ AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Plantation Bay Golf & Country Club

513 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$1,499,000

4 beds

3 baths

3,072 sq ft

House

513 WINGSPAN DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Plantation Bay Golf & Country Club

732 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$347,900

2 beds

2 baths

1,510 sq ft

Townhouse

732 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Spruce Creek South

17841 SE 106TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$210,000

2 beds

2 baths

1,446 sq ft

House

17841 SE 106TH CT, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Cresswind at Victoria Gardens

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

$597,000

3 beds

3 baths

2,804 sq ft

House

261 OLD MOSS CIR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Cresswind at Victoria Gardens

1369 HAYTON AVE, DELAND, FL, 32724, Deland, FL 32724

$285,000

2 beds

2 baths

1,512 sq ft

House

1369 HAYTON AVE, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Trilogy® Orlando

184 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736

$519,000

4 beds

3 baths

3,044 sq ft

House

184 CREPE MYRTLE DR, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

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

Questions? Call us: (888) 625-4885

Sullivan Ranch

30215 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$490,000

4 beds

3 baths

2,687 sq ft

House

30215 BRETTON LOOP, MOUNT DORA, FL, 3275...

Community: Sullivan Ranch

The Villages®

$520,500

3 beds

3 baths

1,905 sq ft

House

5791 HENRY LOOP, THE VILLAGES, FL, 32163

Community: The Villages®

1…31 32 33 34 35 36 37 38 39 40 41 42 43…57

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 [email protected]. 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

2,259 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: Jul 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 37

95 communities near Winter Park

2,259 homes near Winter Park

3 beds

2 baths

2,038 sq ft

House

3 beds

2 baths

2,806 sq ft

House

3 beds

2 baths

2,591 sq ft

House

2 beds

2 baths

1,464 sq ft

House

4 beds

4 baths

3,324 sq ft

House

2 beds

2 baths

1,532 sq ft

Manufactured Home

3 beds

2 baths

1,927 sq ft

House

2 beds

2 baths

1,120 sq ft

Villa

3 beds

2 baths

1,724 sq ft

House

3 beds

3 baths

3,174 sq ft

House

3 beds

2 baths

2,087 sq ft

House

3 beds

3 baths

3,078 sq ft

House

2 beds

2 baths

1,961 sq ft

House

2 beds

2 baths

1,003 sq ft

Townhouse

4 beds

4 baths

1,912 sq ft

House

2 beds

2 baths

1,430 sq ft

Manufactured Home

3 beds

2 baths

1,958 sq ft

House

2 beds

2 baths

1,216 sq ft

House

2 beds

2 baths

1,864 sq ft

House

3 beds