Call us at (689) 407-5757 to learn more about active adult communities near Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale

3,703 homes near Winter Garden

Sort by:

Relevance

Relevance

5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 reviews) On Top of the World
$100Ks - $600Ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
3.8 rating (14 reviews) Sun City Center
<$100k - $500Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $700Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $300Ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
5 rating (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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 (3 reviews) Stonecrest
<$100k - $500Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$300Ks - $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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 (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $500Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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 (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
No reviews yet Breakaway Trails
$400Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
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 Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Carillon Lakes 3870 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$429,500

3 beds

|

2 baths

|

2,121 sq ft

|

House

3870 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
Venetian Bay 118 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$409,990

3 beds

|

2 baths

|

1,900 sq ft

|

House

118 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Tampa Bay Golf and Country Club 9936 CLEGHORN DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$359,900

3 beds

|

2 baths

|

1,772 sq ft

|

House

9936 CLEGHORN DR, SAN ANTONIO, FL, 33576
Spruce Creek Country Club 13876 SE 94TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$273,000

2 beds

|

2 baths

|

1,575 sq ft

|

House

13876 SE 94TH AVE, SUMMERFIELD, FL, 3449...
Latitude Margaritaville 479 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$617,900

3 beds

|

2 baths

|

1,922 sq ft

|

House

479 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 780 MYSTIC HILL CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$409,900

2 beds

|

3 baths

|

2,053 sq ft

|

House

780 MYSTIC HILL CT, POINCIANA, FL, 34759
Community: Solivita
Sun City Center 401 DORCHESTER PL APT 62, SUN CITY CENTE..., Sun City Center, FL 33573
$125,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

401 DORCHESTER PL APT 62, SUN CITY CENTE...
Community: Sun City Center
Plantation at Leesburg 4826 SABLE RIDGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$330,000

3 beds

|

2 baths

|

1,882 sq ft

|

House

4826 SABLE RIDGE CT, LEESBURG, FL, 34748
Legacy of Leesburg 27123 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$318,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

27123 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Oak Run 8059 SW 116TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$182,000

2 beds

|

2 baths

|

1,243 sq ft

|

House

8059 SW 116TH LOOP, OCALA, FL, 34481
Community: Oak Run
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.
Solivita 2502 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$329,000

2 beds

|

2 baths

|

1,539 sq ft

|

Townhouse

2502 PALM TREE DR, POINCIANA, FL, 34759
Community: Solivita
Plantation at Leesburg 5413 BARNWELL CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$409,000

2 beds

|

2 baths

|

2,383 sq ft

|

House

5413 BARNWELL CT, LEESBURG, FL, 34748
Sun City Center 412 S PEBBLE BEACH BLVD, SUN CITY CENTER..., Sun City Center, FL 33573
$190,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

412 S PEBBLE BEACH BLVD, SUN CITY CENTER...
Community: Sun City Center
On Top of the World 8980 SW 93RD LN B, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,288 sq ft

|

Villa

8980 SW 93RD LN B, OCALA, FL, 34481
Community: On Top of the World
Cresswind at Victoria Gardens 419 TISBURY CT, DELAND, FL, 32724, Deland, FL 32724
$359,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

419 TISBURY CT, DELAND, FL, 32724
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 11246 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$250,000

2 beds

|

2 baths

|

1,312 sq ft

|

House

11246 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Stonecrest 17808 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$429,000

3 beds

|

3 baths

|

2,758 sq ft

|

House

17808 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Solivita 3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$524,900

4 beds

|

3 baths

|

2,495 sq ft

|

House

3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475...
Community: Solivita
Plantation at Leesburg 4634 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748
$349,000

3 beds

|

2 baths

|

2,005 sq ft

|

House

4634 SUMMERBRIDGE CIR, LEESBURG, FL, 347...
Majestic Oaks Ocala 5659 SW 89TH PL, OCALA, FL, 34476, Ocala, FL 34476
$405,000

4 beds

|

3 baths

|

2,574 sq ft

|

House

5659 SW 89TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
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.
On Top of the World 8180 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476
$283,900

3 beds

|

2 baths

|

1,576 sq ft

|

House

8180 SW 80TH TER, OCALA, FL, 34476
Community: On Top of the World
Highlands Ridge 3541 E GLEN EAGLES DR, AVON PARK, FL, 33..., Avon Park, FL 33825
$435,000

2 beds

|

3 baths

|

2,092 sq ft

|

House

3541 E GLEN EAGLES DR, AVON PARK, FL, 33...
Community: Highlands Ridge
Twin Lakes 2410 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$369,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2410 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Solivita 729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$514,900

4 beds

|

4 baths

|

2,616 sq ft

|

House

729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759
Community: Solivita
Highlands Ridge 4298 NORTH COURSE LN, AVON PARK, FL, 338..., Avon Park, FL 33825
$459,000

3 beds

|

2 baths

|

1,832 sq ft

|

House

4298 NORTH COURSE LN, AVON PARK, FL, 338...
Community: Highlands Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Traditions at Lake Ruby 3565 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$305,000

3 beds

|

2 baths

|

1,866 sq ft

|

House

3565 RALEIGH DR, WINTER HAVEN, FL, 33884
Huntington at Hunter's Ridge 19 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$399,000

3 beds

|

2 baths

|

1,837 sq ft

|

House

19 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
The Villages® 2071 WESTCHESTER WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$499,950

3 beds

|

2 baths

|

2,060 sq ft

|

House

2071 WESTCHESTER WAY, THE VILLAGES, FL, ...
Community: The Villages®
On Top of the World 8711 SW 96TH LN D, OCALA, FL, 34481, Ocala, FL 34481
$175,500

2 beds

|

2 baths

|

1,341 sq ft

|

Villa

8711 SW 96TH LN D, OCALA, FL, 34481
Community: On Top of the World
Ocala Preserve 5555 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482
$439,000

3 beds

|

2 baths

|

1,854 sq ft

|

House

5555 NW 40TH PL, OCALA, FL, 34482
Community: Ocala Preserve
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.
Sun City Center 2202 CLUBHOUSE DR 174, SUN CITY CENTER, ..., Sun City Center, FL 33573
$128,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

2202 CLUBHOUSE DR 174, SUN CITY CENTER, ...
Community: Sun City Center
Tarawood 10541 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$279,000

3 beds

|

2 baths

|

1,260 sq ft

|

House

10541 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Scottish Highlands 918 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$245,000

2 beds

|

2 baths

|

1,380 sq ft

|

House

918 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
Solivita 504 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$275,000

2 beds

|

2 baths

|

1,543 sq ft

|

House

504 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Spruce Creek Country Club 12896 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$399,500

3 beds

|

2 baths

|

1,935 sq ft

|

House

12896 SE 91ST TERRACE RD, SUMMERFIELD, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 8012 SW 109TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$240,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

8012 SW 109TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
SummerGlen 16405 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$279,870

3 beds

|

2 baths

|

1,676 sq ft

|

House

16405 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Sun City Center 226 GLOUCESTER BLVD # 400, SUN CITY CENT..., Sun City Center, FL 33573
$129,900

1 beds

|

2 baths

|

800 sq ft

|

Condo

226 GLOUCESTER BLVD # 400, SUN CITY CENT...
Community: Sun City Center
Arlington Ridge 26951 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$260,000

2 beds

|

2 baths

|

1,418 sq ft

|

Villa

26951 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
On Top of the World 9371 SW 82ND TER B, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,249 sq ft

|

Villa

9371 SW 82ND TER B, OCALA, FL, 34481
Community: On Top of the World

Frequently Asked Questions


Want more information about active adult communities around Winter Garden?

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 Garden?

Call us: (689) 407-5757
3,703 homes near Winter Garden
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.
© 2025 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: Nov 02, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top