not an image

Call us at (888) 625-4885 to learn more about active adult communities in Winter Park

Winter Park, FL 55+ active adult communities & homes for sale - Page 36

2,513 homes near Winter Park

Sort by:

Relevance

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 (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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
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 (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
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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 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) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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
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
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
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
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 (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
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
12...3
Solivita 217 LAKE CASSIDY DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$420,000

3 beds

|

2 baths

|

2,201 sq ft

|

House

217 LAKE CASSIDY DR, KISSIMMEE, FL, 3475...
Community: Solivita
Venetian Bay 553 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$415,000

3 beds

|

3 baths

|

1,916 sq ft

|

House

553 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
The Villages® 1587 HARTSVILLE TRL, THE VILLAGES, FL, 3..., The Villages, FL 32162
$987,000

3 beds

|

3 baths

|

3,128 sq ft

|

House

1587 HARTSVILLE TRL, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 3436 COUNTRYSIDE PATH, THE VILLAGES, FL,..., The Villages, FL 32163
$675,000

3 beds

|

2 baths

|

2,013 sq ft

|

House

3436 COUNTRYSIDE PATH, THE VILLAGES, FL,...
Community: The Villages®
Plantation at Leesburg 24805 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748
$194,000

2 beds

|

2 baths

|

1,432 sq ft

|

Manufactured Home

24805 PINE HL, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Kings Ridge 3554 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711
$307,000

3 beds

|

2 baths

|

1,334 sq ft

|

House

3554 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
Twin Lakes 2437 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$289,500

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2437 YELLOW BRICK RD, ST CLOUD, FL, 3477...
Community: Twin Lakes
Latitude Margaritaville 361 PARROT LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$359,900

2 beds

|

2 baths

|

1,204 sq ft

|

House

361 PARROT LN, DAYTONA BEACH, FL, 32124
Venetian Bay 3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$310,000

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3014 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
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.
Lake Ashton 1209 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$439,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

1209 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
The Villages® 17662 SE 93RD BUTLER CT, THE VILLAGES, F..., The Villages, FL 32162
$269,900

3 beds

|

2 baths

|

1,400 sq ft

|

House

17662 SE 93RD BUTLER CT, THE VILLAGES, F...
Community: The Villages®
The Villages® 2938 CHIMBORAZO WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$419,999

3 beds

|

2 baths

|

1,459 sq ft

|

House

2938 CHIMBORAZO WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Trilogy® Orlando 422 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$349,000

2 beds

|

2 baths

|

1,568 sq ft

|

House

422 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 2711 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$278,900

2 beds

|

2 baths

|

1,507 sq ft

|

Villa

2711 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
Pelican Bay Daytona Beach 233 BOB WHITE CT 233, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119
$184,900

2 beds

|

2 baths

|

1,189 sq ft

|

Villa

233 BOB WHITE CT 233, DAYTONA BEACH, FL,...
Spruce Creek South 10835 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$224,900

2 beds

|

2 baths

|

1,296 sq ft

|

House

10835 SE 176TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 1402 CONCHAS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$359,900

2 beds

|

2 baths

|

1,146 sq ft

|

Villa

1402 CONCHAS DR, THE VILLAGES, FL, 32162
Community: The Villages®
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.
The Villages® 2611 JUPITER WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$824,900

3 beds

|

2 baths

|

2,109 sq ft

|

House

2611 JUPITER WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 2584 ACOSTA CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$295,000

2 beds

|

2 baths

|

1,390 sq ft

|

Villa

2584 ACOSTA CT, THE VILLAGES, FL, 32162
Community: The Villages®
Del Webb Sunbridge 6491 CYRILS DR, ST CLOUD, FL, 34771, St Cloud, FL 34771
$355,000

3 beds

|

3 baths

|

1,855 sq ft

|

Townhouse

6491 CYRILS DR, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
The Villages® 1988 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$690,000

3 beds

|

2 baths

|

2,594 sq ft

|

House

1988 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation at Leesburg 5089 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

3 beds

|

2 baths

|

1,706 sq ft

|

House

5089 EL DESTINO DR, LEESBURG, FL, 34748
Archers Mill 338 E MERIMONT LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$374,500

4 beds

|

2 baths

|

2,034 sq ft

|

House

338 E MERIMONT LN, ORMOND BEACH, FL, 321...
Community: Archers Mill
Plantation at Leesburg 25527 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$185,000

2 beds

|

2 baths

|

1,120 sq ft

|

Manufactured Home

25527 BELLE HELENE, LEESBURG, FL, 34748
The Villages® 17656 SE 80TH ALTAMAHA CT, THE VILLAGES,..., The Villages, FL 32162
$329,900

3 beds

|

2 baths

|

1,511 sq ft

|

House

17656 SE 80TH ALTAMAHA CT, THE VILLAGES,...
Community: The Villages®
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.
The Villages® 675 KENDALL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$304,890

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

675 KENDALL CT, THE VILLAGES, FL, 32162
Community: The Villages®
Cresswind at Victoria Gardens 1353 RED CLOVER LN, DELAND, FL, 32724, Deland, FL 32724
$340,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

1353 RED CLOVER LN, DELAND, FL, 32724
Solivita 251 ROCK SPRINGS DR, POINCIANA, FL, 3475..., Poinciana, FL 34759
$325,000

2 beds

|

2 baths

|

2,085 sq ft

|

House

251 ROCK SPRINGS DR, POINCIANA, FL, 3475...
Community: Solivita
Spruce Creek Country Club 9495 SE 130TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

2,003 sq ft

|

House

9495 SE 130TH PLACE RD, SUMMERFIELD, FL,...
Latitude Margaritaville 600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$619,900

2 beds

|

3 baths

|

2,158 sq ft

|

House

600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 801 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$574,000

3 beds

|

2 baths

|

2,719 sq ft

|

House

801 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
Vienna Square 2349 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$314,900

3 beds

|

3 baths

|

1,724 sq ft

|

House

2349 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
Grand Haven 14 IBIS CT N, PALM COAST, FL, 32137, Palm Coast, FL 32137
$465,000

3 beds

|

2 baths

|

2,043 sq ft

|

House

14 IBIS CT N, PALM COAST, FL, 32137
Community: Grand Haven
The Villages® 1473 STRATON WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$749,000

3 beds

|

2 baths

|

2,044 sq ft

|

House

1473 STRATON WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
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.
The Villages® 5092 NE 81ST BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$970,000

3 beds

|

3 baths

|

3,407 sq ft

|

House

5092 NE 81ST BLVD, WILDWOOD, FL, 34785
Community: The Villages®
Del Webb Orlando 799 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$281,900

2 beds

|

2 baths

|

1,281 sq ft

|

House

799 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Del Webb Minneola 1596 EVENING SUMMIT CIR, MINNEOLA, FL, 3..., Minneola, FL 34715
$895,000

3 beds

|

4 baths

|

2,844 sq ft

|

House

1596 EVENING SUMMIT CIR, MINNEOLA, FL, 3...
Community: Del Webb Minneola
Royal Harbor 6002 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$275,000

3 beds

|

2 baths

|

1,615 sq ft

|

House

6002 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2437 TATUM TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$449,900

3 beds

|

2 baths

|

1,845 sq ft

|

House

2437 TATUM TER, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 2454 YOUNGMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$419,999

3 beds

|

2 baths

|

1,569 sq ft

|

House

2454 YOUNGMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®

Want more information about active adult communities around Winter Park?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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

Reinmlsx

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
Scroll to Top