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 15

3,654 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
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
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 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
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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 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.
3.6 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
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
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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.
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 (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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 (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
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
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
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
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
12...3
The Villages® 2056 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$650,000

3 beds

|

2 baths

|

2,477 sq ft

|

House

2056 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Solivita 144 SORRENTO RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$270,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

144 SORRENTO RD, POINCIANA, FL, 34759
Community: Solivita
SummerGlen 1429 SW 160TH LN, OCALA, FL, 34473, Ocala, FL 34473
$425,000

4 beds

|

3 baths

|

2,864 sq ft

|

House

1429 SW 160TH LN, OCALA, FL, 34473
Community: SummerGlen
Venetian Bay 3011 ARECA AVE, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$675,000

4 beds

|

2 baths

|

2,003 sq ft

|

House

3011 ARECA AVE, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 2415 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$449,500

3 beds

|

2 baths

|

1,979 sq ft

|

House

2415 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2983 SAINT THOMAS LN, THE VILLAGES, FL, ..., The Villages, FL 32162
$675,000

3 beds

|

2 baths

|

2,228 sq ft

|

House

2983 SAINT THOMAS LN, THE VILLAGES, FL, ...
Community: The Villages®
Del Webb Sunbridge 2904 VOYAGER AVE, ST CLOUD, FL, 34771, St Cloud, FL 34771
$357,990

3 beds

|

3 baths

|

1,744 sq ft

|

Townhouse

2904 VOYAGER AVE, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Oak Run 10898 SW 88TH CT, OCALA, FL, 34481, Ocala, FL 34481
$180,000

2 beds

|

2 baths

|

1,140 sq ft

|

House

10898 SW 88TH CT, OCALA, FL, 34481
Community: Oak Run
Latitude Margaritaville 737 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$639,900

2 beds

|

2 baths

|

1,937 sq ft

|

House

737 LANDSHARK BLVD, DAYTONA BEACH, 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.
Lake Ashton 1347 OAKMONT DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$384,900

3 beds

|

2 baths

|

1,712 sq ft

|

House

1347 OAKMONT DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
Scottish Highlands 1144 BEN MORE DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$210,000

2 beds

|

2 baths

|

1,213 sq ft

|

House

1144 BEN MORE DR, LEESBURG, FL, 34788
Community: Scottish Highlands
Arlington Ridge 26657 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$430,000

3 beds

|

2 baths

|

1,832 sq ft

|

House

26657 MANASSAS DR, LEESBURG, FL, 34748
Community: Arlington Ridge
The Villages® 2005 CLAUDIO LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$324,800

2 beds

|

2 baths

|

1,389 sq ft

|

House

2005 CLAUDIO LN, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 21811 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748
$339,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

21811 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
Valencia Lakes 16122 CEDAR KEY DR DRIVE, WIMAUMA, FL, 3..., Wimauma, FL 33598
$570,000

3 beds

|

3 baths

|

2,191 sq ft

|

House

16122 CEDAR KEY DR DRIVE, WIMAUMA, FL, 3...
Community: Valencia Lakes
Trilogy® Orlando 329 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$425,000

2 beds

|

2 baths

|

1,808 sq ft

|

House

329 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
On Top of the World 9077 SW 95TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,701 sq ft

|

House

9077 SW 95TH AVE, OCALA, FL, 34481
Community: On Top of the World
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.
Traditions at Lake Ruby 3473 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$215,000

2 beds

|

2 baths

|

1,118 sq ft

|

House

3473 RALEIGH DR, WINTER HAVEN, FL, 33884
Oak Run 11171 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476
$299,888

3 beds

|

2 baths

|

1,594 sq ft

|

House

11171 SW 73RD CT, OCALA, FL, 34476
Community: Oak Run
Highland Lakes 6501 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,900

3 beds

|

2 baths

|

2,260 sq ft

|

House

6501 BORG ST, LEESBURG, FL, 34748
Community: Highland Lakes
Highland Fairways 3502 INNISBROOK DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$279,000

3 beds

|

2 baths

|

1,928 sq ft

|

House

3502 INNISBROOK DR, LAKELAND, FL, 33810
Community: Highland Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1134 FIELDBROOK WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163
$485,500

3 beds

|

2 baths

|

1,860 sq ft

|

House

1134 FIELDBROOK WAY, THE VILLAGES, FL, 3...
Community: The Villages®
Harbor Hills Country Club 5340 SADDLEBACK CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$425,000

3 beds

|

2 baths

|

2,347 sq ft

|

House

5340 SADDLEBACK CT, LADY LAKE, FL, 32159
Sun City Center 401 DORCHESTER PL 61, SUN CITY CENTER, F..., Sun City Center, FL 33573
$115,000

1 beds

|

2 baths

|

820 sq ft

|

Condo

401 DORCHESTER PL 61, SUN CITY CENTER, F...
Community: Sun City Center
The Villages® 510 BONITA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$180,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

510 BONITA DR, THE VILLAGES, FL, 32159
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.
Latitude Margaritaville 128 RED LIGHTHOUSE PT, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$619,500

2 beds

|

2 baths

|

1,922 sq ft

|

House

128 RED LIGHTHOUSE PT, DAYTONA BEACH, FL...
The Villages® 1449 MURRELLS INLET LOOP, THE VILLAGES, ..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1449 MURRELLS INLET LOOP, THE VILLAGES, ...
Community: The Villages®
Twin Lakes 2388 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$315,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

2388 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Liberty Village 7381 SW 78TH TER, OCALA, FL, 34481, Ocala, FL 34481
$299,900

3 beds

|

2 baths

|

1,755 sq ft

|

House

7381 SW 78TH TER, OCALA, FL, 34481
Community: Liberty Village
The Villages® 1565 LAKEWOOD DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$354,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

1565 LAKEWOOD DR, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 112 SEVILLA CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$465,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

112 SEVILLA CT, KISSIMMEE, FL, 34759
Community: Solivita
Royal Highlands 5729 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$469,900

3 beds

|

3 baths

|

2,402 sq ft

|

House

5729 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 17385 SE 78TH DRAUGHTON CT, THE VILLAGES..., The Villages, FL 32162
$259,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17385 SE 78TH DRAUGHTON CT, THE VILLAGES...
Community: The Villages®
The Villages® 5719 SPARTINA TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$279,000

2 beds

|

2 baths

|

1,258 sq ft

|

Villa

5719 SPARTINA TER, THE VILLAGES, FL, 321...
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® 1615 SNELLING AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$634,700

3 beds

|

2 baths

|

1,887 sq ft

|

House

1615 SNELLING AVE, THE VILLAGES, FL, 321...
Community: The Villages®
On Top of the World 8954 SW 75TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$348,900

3 beds

|

2 baths

|

1,874 sq ft

|

House

8954 SW 75TH LOOP, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8954 SW 75TH LP LP, OCALA, FL, 34481, Ocala, FL 34481
$348,900

3 beds

|

2 baths

|

1,874 sq ft

|

House

8954 SW 75TH LP LP, OCALA, FL, 34481
Community: On Top of the World
Marion Landing 6740 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476
$190,000

3 beds

|

2 baths

|

1,187 sq ft

|

Manufactured Home

6740 SW 84TH ST, OCALA, FL, 34476
Community: Marion Landing
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 3552 GROUBY RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$324,900

2 beds

|

2 baths

|

1,203 sq ft

|

House

3552 GROUBY RD, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 2129 ZARAGOZA PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$385,000

3 beds

|

2 baths

|

1,669 sq ft

|

House

2129 ZARAGOZA PL, THE VILLAGES, FL, 3215...
Community: The Villages®

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
3,654 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