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 83

3,776 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
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
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
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.
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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) 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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
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 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) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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
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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 655 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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.
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 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) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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
4.4 rating (9 reviews) Spruce Creek Preserve
$100ks - $200ks
Spruce Creek Preserve, Dunnellon, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 810 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 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
Stonecrest 11614 SE 172ND LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$349,000

3 beds

|

2 baths

|

1,919 sq ft

|

House

11614 SE 172ND LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
The Villages® 9230 SE 179TH WESLEY ST, THE VILLAGES, F..., The Villages, FL 32162
$254,900

2 beds

|

2 baths

|

1,148 sq ft

|

House

9230 SE 179TH WESLEY ST, THE VILLAGES, F...
Community: The Villages®
Gatherings of Lake Nona 7545 LAUREATE BLVD 7303, ORLANDO, FL, 32..., Orlando, FL 32827
$464,990

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7545 LAUREATE BLVD 7303, ORLANDO, FL, 32...
Stonecrest 17380 SE 111TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$259,000

2 beds

|

2 baths

|

1,359 sq ft

|

Villa

17380 SE 111TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Sun City Center 2321 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$175,000

2 beds

|

2 baths

|

1,829 sq ft

|

Condo

2321 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
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
$324,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

21811 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
Cindy Certified
15250 MAUDE LANDING LOOP, WIMAUMA, FL, 3..., Wimauma, FL 33598
$350,610

3 beds

|

2 baths

|

1,615 sq ft

|

House

15250 MAUDE LANDING LOOP, WIMAUMA, FL, 3...
Cindy Certified
342 RUSTIC RAIL DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$319,900

4 beds

|

2 baths

|

2,381 sq ft

|

House

342 RUSTIC RAIL DR, LAKE WALES, FL, 3385...
Trilogy® Orlando 329 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$385,900

2 beds

|

2 baths

|

1,808 sq ft

|

House

329 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Cindy Certified
10707 TORCHWOOD SEA WAY, SAN ANTONIO, FL..., San Antonio, FL 33576
$713,350

4 beds

|

4 baths

|

2,387 sq ft

|

House

10707 TORCHWOOD SEA WAY, SAN ANTONIO, 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 5729 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

3 baths

|

2,402 sq ft

|

House

5729 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
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®
Four Seasons at Orlando 7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$675,000

3 beds

|

2 baths

|

1,969 sq ft

|

House

7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
SummerGlen 1706 SW 156TH LN, OCALA, FL, 34473, Ocala, FL 34473
$234,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

1706 SW 156TH LN, OCALA, FL, 34473
Community: SummerGlen
Venetian Bay 3377 CATERINA DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$829,000

4 beds

|

4 baths

|

3,882 sq ft

|

House

3377 CATERINA DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Heritage Hills 4052 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$385,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

4052 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
6870 SW 109TH PL, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,624 sq ft

|

House

6870 SW 109TH PL, OCALA, FL, 34476
JB Ranch 6260 SW 90TH ST, OCALA, FL, 34476, Ocala, FL 34476
$296,500

3 beds

|

2 baths

|

1,826 sq ft

|

House

6260 SW 90TH ST, OCALA, FL, 34476
Community: JB Ranch
Vienna Square 1678 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$245,000

2 beds

|

2 baths

|

1,158 sq ft

|

House

1678 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Palm Cay 13846 SW 79TH AVE, OCALA, FL, 34473, Ocala, FL 34473
$409,900

3 beds

|

2 baths

|

1,934 sq ft

|

House

13846 SW 79TH AVE, OCALA, FL, 34473
Community: Palm Cay
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 2035 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573
$369,900

2 beds

|

2 baths

|

1,487 sq ft

|

House

2035 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
Sandpiper Golf & Country Club 6236 RAVEN RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$230,000

2 beds

|

2 baths

|

1,179 sq ft

|

House

6236 RAVEN RUN, LAKELAND, FL, 33809
Spruce Creek Country Club 9003 SE 118TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$324,900

2 beds

|

2 baths

|

1,850 sq ft

|

House

9003 SE 118TH LN, SUMMERFIELD, FL, 34491
Sun City Center 1511 CLOISTER DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,756 sq ft

|

House

1511 CLOISTER DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Ocala Preserve 5662 NW 40TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$399,999

2 beds

|

2 baths

|

1,938 sq ft

|

House

5662 NW 40TH LOOP, OCALA, FL, 34482
Community: Ocala Preserve
Tampa Bay Golf and Country Club 9916 CLEGHORN DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$330,000

3 beds

|

2 baths

|

1,749 sq ft

|

House

9916 CLEGHORN DR, SAN ANTONIO, FL, 33576
Liberty Village 7934 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$284,900

3 beds

|

2 baths

|

1,755 sq ft

|

House

7934 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 12767 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$329,000

3 beds

|

2 baths

|

1,720 sq ft

|

House

12767 SE 97TH TERRACE RD, SUMMERFIELD, F...
Plantation at Leesburg 3544 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$310,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

3544 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Cindy Certified
902 BUCKEYE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$427,990

4 beds

|

3 baths

|

2,471 sq ft

|

House

902 BUCKEYE DR, LADY LAKE, FL, 32159
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.
Summer Trees 49 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$249,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

49 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
The Villages® 2679 LANTANA AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$499,000

3 beds

|

2 baths

|

1,966 sq ft

|

House

2679 LANTANA AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 258 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$298,000

2 beds

|

2 baths

|

1,130 sq ft

|

House

258 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Cindy Certified
1830 NW 44TH COURT RD, OCALA, FL, 34482, Ocala, FL 34482
$242,000

3 beds

|

2 baths

|

1,548 sq ft

|

House

1830 NW 44TH COURT RD, OCALA, FL, 34482
Cindy Certified
3821 COUNTRY VIEW CT, BRADENTON, FL, 342..., Bradenton, FL 34211
$974,900

4 beds

|

3 baths

|

2,968 sq ft

|

House

3821 COUNTRY VIEW CT, BRADENTON, FL, 342...
Legacy of Leesburg 27106 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

1,541 sq ft

|

House

27106 GREENFLY ORCHID LN, LEESBURG, FL, ...
Community: Legacy of Leesburg
Cindy Certified
4049 PINNACLE PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$579,900

3 beds

|

3 baths

|

2,505 sq ft

|

House

4049 PINNACLE PL, LADY LAKE, FL, 32159
Sun City Center 737 MCCALLISTER AVE 265, SUN CITY CENTER..., Sun City Center, FL 33573
$239,000

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

737 MCCALLISTER AVE 265, SUN CITY CENTER...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Archers Mill 3295 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$549,900

4 beds

|

4 baths

|

2,787 sq ft

|

House

3295 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
On Top of the World 9646 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,517 sq ft

|

House

9646 SW 92ND PLACE RD, 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.

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
3,776 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: Oct 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