not an image

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

Winter Garden, FL 55+ active adult communities & homes for sale - Page 14

3,218 homes near Winter Garden

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
3.8 rating (14 reviews) Sun City Center
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4 rating (57 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
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $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 - $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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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 (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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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.
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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Lake Jovita Golf and Coun...
$400ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 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.
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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 Garden? 55places can help!
Questions? Call us: (689) 407-5757
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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.
12...3
The Villages® 1506 DELLANO WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$449,900

2 beds

|

2 baths

|

1,782 sq ft

|

House

1506 DELLANO WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
Mirada 10806 GABLE DIG LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$259,900

2 beds

|

2 baths

|

1,625 sq ft

|

Villa

10806 GABLE DIG LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
Solivita 941 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$339,000

3 beds

|

3 baths

|

2,325 sq ft

|

House

941 SHOREHAVEN DR, KISSIMMEE, FL, 34759
Community: Solivita
Del Webb Minneola 2458 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715
$725,000

3 beds

|

3 baths

|

2,260 sq ft

|

House

2458 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
Venetian Bay 3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$459,900

4 beds

|

3 baths

|

2,540 sq ft

|

House

3321 MARSILI AVE, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pennbrooke Fairways 32222 SUMMERTREE CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$289,000

2 beds

|

2 baths

|

1,725 sq ft

|

House

32222 SUMMERTREE CIR, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
Valencia Lakes 5044 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$625,000

4 beds

|

3 baths

|

2,799 sq ft

|

House

5044 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Sun City Center 9731 IVORY DR, RUSKIN, FL, 33573, Ruskin, FL 33573
$425,000

4 beds

|

3 baths

|

2,775 sq ft

|

House

9731 IVORY DR, RUSKIN, FL, 33573
Community: Sun City Center
Stone Creek 8764 SW 58TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$312,312

2 beds

|

2 baths

|

1,406 sq ft

|

House

8764 SW 58TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
Ocala Preserve 5641 NW 37TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$315,000

2 beds

|

2 baths

|

1,392 sq ft

|

House

5641 NW 37TH LANE RD, 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 1414 BLUEWATER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$235,000

2 beds

|

2 baths

|

1,155 sq ft

|

House

1414 BLUEWATER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Spruce Creek Country Club 9119 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$270,000

2 beds

|

2 baths

|

1,488 sq ft

|

House

9119 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Southshore Bay 16805 BANNER SHELL PL, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$585,000

3 beds

|

3 baths

|

2,651 sq ft

|

House

16805 BANNER SHELL PL, WIMAUMA, FL, 3359...
Community: Southshore Bay
The Villages® 1726 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$224,900

2 beds

|

2 baths

|

1,290 sq ft

|

Manufactured Home

1726 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
The Villages® 3394 RANDI RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$495,000

3 beds

|

2 baths

|

1,810 sq ft

|

Villa

3394 RANDI RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1132 MAYNARD PATH, THE VILLAGES, FL, 321..., The Villages, FL 32163
$675,000

3 beds

|

3 baths

|

1,901 sq ft

|

House

1132 MAYNARD PATH, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Vienna Square 2452 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$300,000

2 beds

|

2 baths

|

1,729 sq ft

|

House

2452 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
Stone Creek 9098 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$225,000

2 beds

|

2 baths

|

1,437 sq ft

|

House

9098 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 703 OJAI AVE, SUN CITY CENTER, FL, 33573, Sun City Center, FL 33573
$249,000

2 beds

|

2 baths

|

1,750 sq ft

|

House

703 OJAI AVE, SUN CITY CENTER, FL, 33573
Community: Sun City Center
Sun City Center 1816 GRANVILLE LN, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$299,000

2 beds

|

2 baths

|

1,857 sq ft

|

House

1816 GRANVILLE LN, SUN CITY CENTER, FL, ...
Community: Sun City Center
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.
Venetian Bay 424 LUNA BELLA LN 231, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$375,000

3 beds

|

3 baths

|

1,953 sq ft

|

Condo

424 LUNA BELLA LN 231, NEW SMYRNA BEACH,...
Community: Venetian Bay
Stone Creek 8480 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$342,243

3 beds

|

2 baths

|

1,697 sq ft

|

House

8480 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Solivita 505 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$259,000

2 beds

|

2 baths

|

1,548 sq ft

|

House

505 MILLIFIORA LN, KISSIMMEE, FL, 34759
Community: Solivita
Legacy of Leesburg 27134 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,601 sq ft

|

House

27134 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Scottish Highlands 1 DURNESS CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$182,000

2 beds

|

2 baths

|

1,200 sq ft

|

House

1 DURNESS CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Legacy of Leesburg 5127 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$379,900

3 beds

|

2 baths

|

2,386 sq ft

|

House

5127 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Oak Run 6318 SW 117TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$272,900

3 beds

|

2 baths

|

1,921 sq ft

|

House

6318 SW 117TH LOOP, OCALA, FL, 34476
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Breakaway Trails 9 COQUINA RIDGE WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$679,900

4 beds

|

3 baths

|

2,605 sq ft

|

House

9 COQUINA RIDGE WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
SummerGlen 15771 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$234,900

2 beds

|

2 baths

|

1,558 sq ft

|

House

15771 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Spruce Creek South 17584 SE 105TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$225,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

17584 SE 105TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
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 Jovita Golf and Country Club 12749 GRAND TRAVERSE DR, DADE CITY, FL, ..., Dade City, FL 33525
$949,000

3 beds

|

3 baths

|

3,109 sq ft

|

House

12749 GRAND TRAVERSE DR, DADE CITY, FL, ...
Lake Jovita Golf and Country Club 12215 WOODLANDS CIR, DADE CITY, FL, 3352..., Dade City, FL 33525
$551,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

12215 WOODLANDS CIR, DADE CITY, FL, 3352...
Harbor Hills Country Club 5506 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$647,500

3 beds

|

3 baths

|

2,698 sq ft

|

House

5506 CITATION CT, LADY LAKE, FL, 32159
On Top of the World 8907 SW 84TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$289,900

3 beds

|

2 baths

|

1,705 sq ft

|

House

8907 SW 84TH CIR, OCALA, FL, 34481
Community: On Top of the World
Stonecrest 17719 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$275,000

2 beds

|

2 baths

|

1,704 sq ft

|

Villa

17719 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
On Top of the World 8560 SW 90TH ST E, OCALA, FL, 34481, Ocala, FL 34481
$209,900

2 beds

|

2 baths

|

1,856 sq ft

|

Villa

8560 SW 90TH ST E, OCALA, FL, 34481
Community: On Top of the World
Del Webb Sunbridge 6524 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771
$849,000

3 beds

|

4 baths

|

2,808 sq ft

|

House

6524 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
Ocala Preserve 4530 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$314,515

2 beds

|

2 baths

|

1,816 sq ft

|

House

4530 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage - The Cottages of Sanders Grove 6213 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$332,595

4 beds

|

2 baths

|

1,625 sq ft

|

House

6213 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Heritage - The Cottages of Sanders Grove 6217 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$363,389

4 beds

|

3 baths

|

1,938 sq ft

|

House

6217 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
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.

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
3,218 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: Jul 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