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 38

3,769 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
$100ks - $400ks
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 - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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.
4.6 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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 (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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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
5 rating (1 reviews) Cresswind at Victoria Gar...
$300ks - $500ks
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.
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Cresswind Lakewood Ranch
$400ks - $700ks
Cresswind Lakewood Ranch, Lakewood Ranch, FL
New and Resale | 55+ age-restricted | Built 2018 - present | 648 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
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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.
123...4
The Villages® 911 MEDIRA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$317,900

2 beds

|

2 baths

|

1,268 sq ft

|

Villa

911 MEDIRA DR, LADY LAKE, FL, 32159
Community: The Villages®
Trilogy® Orlando 228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$400,000

2 beds

|

2 baths

|

2,197 sq ft

|

House

228 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Pelican Bay Daytona Beach 144 HERRING GULL CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$335,000

3 beds

|

2 baths

|

1,702 sq ft

|

House

144 HERRING GULL CT, DAYTONA BEACH, FL, ...
Stone Creek 7732 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$234,900

2 beds

|

2 baths

|

1,423 sq ft

|

House

7732 SW 94TH CIR, OCALA, FL, 34481
Community: Stone Creek
Cindy Certified
8906 SW 46TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$299,295

3 beds

|

2 baths

|

1,672 sq ft

|

House

8906 SW 46TH AVE, OCALA, FL, 34476
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 5852 ABNEY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$625,000

3 beds

|

3 baths

|

1,909 sq ft

|

House

5852 ABNEY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 4540 BROOKE LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$419,900

3 beds

|

2 baths

|

1,579 sq ft

|

House

4540 BROOKE LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 6080 ALLEN AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$315,000

2 beds

|

2 baths

|

1,266 sq ft

|

Villa

6080 ALLEN AVE, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 646 MURPHYS ESTATE DR, THE VILLAGES, FL,..., The Villages, FL 32162
$474,900

3 beds

|

3 baths

|

2,171 sq ft

|

House

646 MURPHYS ESTATE DR, THE VILLAGES, FL,...
Community: The Villages®
Stone Creek 6248 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$462,330

2 beds

|

2 baths

|

1,943 sq ft

|

House

6248 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
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.
Cherrywood 6046 SW 98 LOOP, OCALA, FL, 34476, Ocala, FL 34476
$215,000

3 beds

|

2 baths

|

1,384 sq ft

|

House

6046 SW 98 LOOP, OCALA, FL, 34476
Community: Cherrywood
Oak Run 11262 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$259,999

3 beds

|

2 baths

|

1,574 sq ft

|

House

11262 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run
Pine Run Estates 9095 SW 104TH LN, OCALA, FL, 34481, Ocala, FL 34481
$150,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

9095 SW 104TH LN, OCALA, FL, 34481
Community: Pine Run Estates
Cindy Certified
806 GRAND PARK CT, DELAND, FL, 32724, Deland, FL 32724
$339,900

4 beds

|

2 baths

|

1,830 sq ft

|

House

806 GRAND PARK CT, DELAND, FL, 32724
Cindy Certified
5557 PALMER CIR 202, BRADENTON, FL, 3421..., Bradenton, FL 34211
$439,000

2 beds

|

2 baths

|

1,329 sq ft

|

Condo

5557 PALMER CIR 202, BRADENTON, FL, 3421...
The Villages® 595 RANDALL RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$570,000

3 beds

|

2 baths

|

2,033 sq ft

|

House

595 RANDALL RD, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15526 SW 11TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473
$359,957

3 beds

|

2 baths

|

1,647 sq ft

|

House

15526 SW 11TH TERRACE RD, OCALA, FL, 344...
Community: SummerGlen
Majestic Oaks Ocala 5419 SW 84TH PL, OCALA, FL, 34476, Ocala, FL 34476
$280,000

3 beds

|

2 baths

|

1,926 sq ft

|

House

5419 SW 84TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Silver Lakes 6323 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$414,990

3 beds

|

3 baths

|

1,902 sq ft

|

House

6323 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
Cindy Certified
3864 IMMACOLATA WAY, WESLEY CHAPEL, FL, ..., Wesley Chapel, FL 33543
$417,999

2 beds

|

2 baths

|

1,689 sq ft

|

House

3864 IMMACOLATA WAY, WESLEY CHAPEL, FL, ...
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.
Royal Highlands 4808 KILT CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$305,000

2 beds

|

2 baths

|

2,213 sq ft

|

House

4808 KILT CT, LEESBURG, FL, 34748
Community: Royal Highlands
Southshore Bay 17228 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$339,000

2 beds

|

2 baths

|

1,761 sq ft

|

House

17228 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Summit Chase Villas 12520 ORANGEWOOD CT, TAVARES, FL, 32778, Tavares, FL 32778
$185,000

2 beds

|

2 baths

|

918 sq ft

|

Villa

12520 ORANGEWOOD CT, TAVARES, FL, 32778
Community: Summit Chase Villas
Cindy Certified
6087 SW 97TH PL, OCALA, FL, 34476, Ocala, FL 34476
$297,999

2 beds

|

2 baths

|

1,810 sq ft

|

House

6087 SW 97TH PL, OCALA, FL, 34476
The Villages® 542 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$599,900

3 beds

|

2 baths

|

2,666 sq ft

|

House

542 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2007 YEARLING WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$359,900

3 beds

|

2 baths

|

1,559 sq ft

|

House

2007 YEARLING WAY, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 8481 SE 168TH KITTREDGE LOOP, THE VILLAG..., The Villages, FL 32162
$864,000

3 beds

|

2 baths

|

2,523 sq ft

|

House

8481 SE 168TH KITTREDGE LOOP, THE VILLAG...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 3701 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$305,000

3 beds

|

2 baths

|

1,802 sq ft

|

House

3701 PLANTATION BLVD, LEESBURG, FL, 3474...
Highland Fairways 3250 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$249,900

2 beds

|

2 baths

|

1,092 sq ft

|

House

3250 PEBBLE BEND DR, LAKELAND, FL, 33810
Community: Highland Fairways
Highland Fairways 3448 GLEN ABBEY LN, LAKELAND, FL, 33810, Lakeland, FL 33810
$319,900

3 beds

|

2 baths

|

1,709 sq ft

|

House

3448 GLEN ABBEY LN, LAKELAND, FL, 33810
Community: Highland Fairways
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.
Royal Harbor 3354 SAINT LUCIA CT, TAVARES, FL, 32778, Tavares, FL 32778
$384,900

2 beds

|

2 baths

|

1,925 sq ft

|

House

3354 SAINT LUCIA CT, TAVARES, FL, 32778
Community: Royal Harbor
Cindy Certified
14907 IMPERIAL PURPLE LN, WIMAUMA, FL, 3..., Wimauma, FL 33598
$300,000

4 beds

|

2 baths

|

1,817 sq ft

|

House

14907 IMPERIAL PURPLE LN, WIMAUMA, FL, 3...
Stone Creek 5778 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$464,380

2 beds

|

3 baths

|

2,080 sq ft

|

House

5778 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
The Villages® 721 SHARON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$155,000

2 beds

|

2 baths

|

768 sq ft

|

Manufactured Home

721 SHARON DR, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 723 HEATHROW AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$317,500

2 beds

|

2 baths

|

1,352 sq ft

|

House

723 HEATHROW AVE, LADY LAKE, FL, 32159
Community: The Villages®
Latitude Margaritaville 252 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$462,900

2 beds

|

2 baths

|

1,558 sq ft

|

House

252 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Cindy Certified
3124 REPOSE DR, CLERMONT, FL, 34714, Clermont, FL 34714
$245,990

2 beds

|

2 baths

|

1,421 sq ft

|

Villa

3124 REPOSE DR, CLERMONT, FL, 34714
The Villages® 522 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$535,000

3 beds

|

2 baths

|

1,959 sq ft

|

House

522 LOMA PASEO DR, 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
Cindy Certified
5203 HAVEN VIEW DR, CLERMONT, FL, 34714, Clermont, FL 34714
$359,490

2 beds

|

2 baths

|

1,580 sq ft

|

House

5203 HAVEN VIEW DR, CLERMONT, FL, 34714
The Villages® 1911 DEL NORTE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$325,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1911 DEL NORTE DR, 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.

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 optout@55places.com. 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
3,769 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: Aug 25, 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