Winter Park, FL 55+ active adult communities & homes for sale - Page 19

2,513 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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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

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

Questions? Call us: (888) 625-4885

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 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)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

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

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 (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (7 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

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 (3 reviews)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

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

Questions? Call us: (888) 625-4885

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $600ks

Cresswind at Victoria Gar..., DeLand, FL

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

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200ks - $300ks

Traditions at Lake Ruby, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 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

4.1 rating (9 reviews)

Indian River Colony Club

$200ks - $400ks

Indian River Colony Club, Melbourne, FL

New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2021 - present | 258 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

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

Questions? Call us: (888) 625-4885

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

225 CUNNINGHAM DR, DAVENPORT, FL, 33837

House

3360 RICHMOND DR, THE VILLAGES, FL, 3216...

House

Community: The Lakes at Harmony

Del Webb at Viera

8969 SHORELINE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940

$829,900

3 beds

4 baths

2,838 sq ft

House

8969 SHORELINE AVE, MELBOURNE, FL, 32940

Community: Del Webb at Viera

Plantation at Leesburg

4517 EAGLEWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$295,000

2 beds

2 baths

1,292 sq ft

House

4517 EAGLEWOOD DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

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

Questions? Call us: (888) 625-4885

The Villages®

$569,900

3 beds

3 baths

2,245 sq ft

House

646 STRATFORD LN, THE VILLAGES, FL, 3216...

Community: The Villages®

Plantation at Leesburg

5024 LONG MEADOW DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$329,900

2 beds

2 baths

1,847 sq ft

House

5024 LONG MEADOW DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Harbor Hills Country Club

39634 GROVE HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$619,000

3 beds

3 baths

2,278 sq ft

House

39634 GROVE HEIGHTS, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

Pelican Bay Daytona Beach

128 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$259,000

2 beds

2 baths

1,377 sq ft

Townhouse

128 BERMUDA PETREL CT, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

VillageWalk at Lake Nona

11818 FIORE DR, ORLANDO, FL, 32827, Orlando, FL 32827

$1,170,000

4 beds

3 baths

4,125 sq ft

House

11818 FIORE DR, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Royal Highlands

4732 ST ANDREWS ARC, LEESBURG, FL, 34748, Leesburg, FL 34748

$235,000

2 beds

2 baths

1,295 sq ft

House

4732 ST ANDREWS ARC, LEESBURG, FL, 34748

Community: Royal Highlands

The Villages®

$615,000

3 beds

2 baths

1,944 sq ft

House

904 MAYNARD PATH, THE VILLAGES, FL, 3216...

Community: The Villages®

Royal Highlands

4921 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$279,999

3 beds

2 baths

1,414 sq ft

House

4921 GLEN COE ST, LEESBURG, FL, 34748

Community: Royal Highlands

The Villages®

816 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$129,900

2 beds

1 baths

672 sq ft

Manufactured Home

816 BEECHWOOD AVE, LADY LAKE, FL, 32159

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Solivita

531 VIA VITALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$484,900

5 beds

3 baths

2,430 sq ft

House

531 VIA VITALE CT, KISSIMMEE, FL, 34759

Community: Solivita

Heritage Hills

3543 FAIRWATERS CT B, CLERMONT, FL, 3471..., Clermont, FL 34711

$299,000

2 beds

2 baths

1,374 sq ft

Villa

3543 FAIRWATERS CT B, CLERMONT, FL, 3471...

Community: Heritage Hills

The Villages®

5255 OXFORD CT, WILDWOOD, FL, 34785, Wildwood, FL 34785

$179,000

3 beds

2 baths

1,352 sq ft

Manufactured Home

5255 OXFORD CT, WILDWOOD, FL, 34785

Community: The Villages®

Spruce Creek Country Club

9036 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$319,900

3 beds

2 baths

1,720 sq ft

House

9036 SE 120TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

The Villages®

$262,000

2 beds

2 baths

1,163 sq ft

Villa

16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...

Community: The Villages®

Del Webb Sunbridge

2732 RUBY ROSE LN, ST CLOUD, FL, 34771, St Cloud, FL 34771

$475,000

2 beds

2 baths

1,919 sq ft

House

2732 RUBY ROSE LN, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

Sandpiper Golf & Country Club

669 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809

$284,500

2 beds

2 baths

1,134 sq ft

House

669 EAGLE RUN, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Spruce Creek Country Club

9302 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$344,000

2 beds

2 baths

1,870 sq ft

House

9302 SE 120TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

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

Questions? Call us: (888) 625-4885

The Villages®

$465,000

3 beds

2 baths

1,661 sq ft

House

2946 DUKE TER, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$209,900

2 beds

2 baths

1,299 sq ft

Manufactured Home

953 ORCHID ST, THE VILLAGES, FL, 32159

Community: The Villages®

1…13 14 15 16 17 18 19 20 21 22 23 24 25…63

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

2,513 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: Apr 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 19

90 communities near Winter Park

2,513 homes near Winter Park

3 beds

2 baths

2,159 sq ft

House

2 beds

2 baths

2,008 sq ft

House

2 beds

2 baths

1,504 sq ft

House

3 beds

2 baths

1,927 sq ft

House

3 beds

2 baths

2,454 sq ft

House

2 beds

2 baths

1,040 sq ft

Manufactured Home

2 beds

2 baths

1,710 sq ft

House

3 beds

2 baths

2,195 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

967 sq ft

Manufactured Home

3 beds

2 baths

1,957 sq ft

House

3 beds

2 baths

1,675 sq ft

House

3 beds

2 baths

1,668 sq ft

House

3 beds

2 baths

2,034 sq ft

House

3 beds

2 baths

1,614 sq ft

House

3 beds

2 baths

1,732 sq ft

House

3 beds

2 baths

1,732 sq ft

House

2 beds

2 baths

1,609 sq ft

House

4 beds

3 baths

2,355 sq ft

House

3 beds