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 77

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
Cindy Certified
2920 MARLBERRY LN, CLERMONT, FL, 34714, Clermont, FL 34714
$450,000

4 beds

|

3 baths

|

2,184 sq ft

|

House

2920 MARLBERRY LN, CLERMONT, FL, 34714
Stone Creek 9221 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$379,000

2 beds

|

2 baths

|

2,147 sq ft

|

House

9221 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Legacy of Leesburg 27111 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,000

3 beds

|

2 baths

|

1,477 sq ft

|

House

27111 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 1809 DAFFODIL LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$170,000

2 beds

|

1 baths

|

936 sq ft

|

Manufactured Home

1809 DAFFODIL LN, LADY LAKE, FL, 32159
Community: The Villages®
Trilogy® Orlando 119 FALLING ACORN AVE, GROVELAND, FL, 34..., Groveland, FL 34736
$338,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

119 FALLING ACORN AVE, GROVELAND, FL, 34...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
17070 OVAL RUM DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$304,000

3 beds

|

2 baths

|

1,516 sq ft

|

House

17070 OVAL RUM DR, WIMAUMA, FL, 33598
Sun City Center 700 RUTGERS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$195,000

2 beds

|

2 baths

|

1,141 sq ft

|

House

700 RUTGERS PL, SUN CITY CENTER, FL, 335...
Community: Sun City Center
The Villages® 732 ROYAL PALM AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159
$219,900

3 beds

|

2 baths

|

1,100 sq ft

|

Manufactured Home

732 ROYAL PALM AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Carillon Lakes 4149 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$305,000

3 beds

|

2 baths

|

1,745 sq ft

|

House

4149 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
Sun City Center 1368 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$429,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1368 EMERALD DUNES DR, SUN CITY CENTER, ...
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.
Cresswind at Victoria Gardens 1634 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724
$400,000

2 beds

|

2 baths

|

1,928 sq ft

|

House

1634 VICTORIA GARDENS DR, DELAND, FL, 32...
Arlington Ridge 4258 JAMES RIVER CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$464,900

4 beds

|

3 baths

|

2,524 sq ft

|

House

4258 JAMES RIVER CIR, LEESBURG, FL, 3474...
Community: Arlington Ridge
Stonecrest 17440 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$320,000

3 beds

|

2 baths

|

1,794 sq ft

|

House

17440 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Spruce Creek Country Club 9280 SE 126TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$468,000

2 beds

|

3 baths

|

2,368 sq ft

|

House

9280 SE 126TH ST, SUMMERFIELD, FL, 34491
Cindy Certified
17043 OVAL RUM DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$275,000

3 beds

|

2 baths

|

1,516 sq ft

|

House

17043 OVAL RUM DR, WIMAUMA, FL, 33598
Sun City Center 301 ANDOVER PL 175, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$85,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 ANDOVER PL 175, 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
Sun City Center 504 RIMINI VISTA WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$449,950

3 beds

|

2 baths

|

2,012 sq ft

|

House

504 RIMINI VISTA WAY, SUN CITY CENTER, F...
Community: Sun City Center
Pennbrooke Fairways 32676 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,000

3 beds

|

2 baths

|

1,709 sq ft

|

House

32676 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Cindy Certified
707 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$350,734

4 beds

|

3 baths

|

1,988 sq ft

|

House

707 SUNSHOWER DR, LADY LAKE, FL, 32159
Ocala Preserve 4355 NW 53RD CT, OCALA, FL, 34482, Ocala, FL 34482
$529,900

3 beds

|

3 baths

|

2,362 sq ft

|

House

4355 NW 53RD CT, 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.
Foxwood Lake Estates 1688 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$169,900

3 beds

|

2 baths

|

1,427 sq ft

|

Manufactured Home

1688 FOXWAY DR, LAKELAND, FL, 33810
Cherrywood 9832 SW 61ST CT, OCALA, FL, 34476, Ocala, FL 34476
$201,500

3 beds

|

2 baths

|

1,370 sq ft

|

House

9832 SW 61ST CT, OCALA, FL, 34476
Community: Cherrywood
Royal Highlands 21630 REGENCY PARK LN, LEESBURG, FL, 347..., Leesburg, FL 34748
$263,900

3 beds

|

2 baths

|

1,438 sq ft

|

House

21630 REGENCY PARK LN, LEESBURG, FL, 347...
Community: Royal Highlands
Oak Run 11416 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$279,000

3 beds

|

2 baths

|

2,123 sq ft

|

House

11416 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Foxwood Lake Estates 1502 LONGBOW DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$212,500

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1502 LONGBOW DR, LAKELAND, FL, 33810
Cindy Certified
6503 FLOWERING SHRUB ST, LAKELAND, FL, 3..., Lakeland, FL 33810
$339,900

3 beds

|

2 baths

|

1,644 sq ft

|

House

6503 FLOWERING SHRUB ST, LAKELAND, FL, 3...
On Top of the World 9958 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$319,000

3 beds

|

2 baths

|

1,953 sq ft

|

House

9958 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2837 GRANT WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$555,777

3 beds

|

2 baths

|

1,923 sq ft

|

House

2837 GRANT WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Cindy Certified
2905 TUPELO LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$519,900

4 beds

|

3 baths

|

1,957 sq ft

|

House

2905 TUPELO LOOP, ST CLOUD, FL, 34772
The Villages® 6231 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$299,900

3 beds

|

2 baths

|

1,426 sq ft

|

House

6231 ATKINSON LN, THE VILLAGES, FL, 3216...
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.
Solivita 537 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$215,000

2 beds

|

2 baths

|

1,071 sq ft

|

House

537 GRAND CANAL DR, POINCIANA, FL, 34759
Community: Solivita
Plantation at Leesburg 4908 CYPRESS HEAD CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$334,900

3 beds

|

2 baths

|

2,087 sq ft

|

House

4908 CYPRESS HEAD CT, LEESBURG, FL, 3474...
The Villages® 1603 COG HILL DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$248,000

2 beds

|

2 baths

|

1,542 sq ft

|

Manufactured Home

1603 COG HILL DR, LADY LAKE, FL, 32159
Community: The Villages®
Cindy Certified
5290 BARNETT CIR, BRADENTON, FL, 34211, Bradenton, FL 34211
$559,990

2 beds

|

2 baths

|

1,852 sq ft

|

House

5290 BARNETT CIR, BRADENTON, FL, 34211
On Top of the World 8515 SW 101ST TER, OCALA, FL, 34481, Ocala, FL 34481
$565,565

3 beds

|

3 baths

|

2,373 sq ft

|

House

8515 SW 101ST TER, OCALA, FL, 34481
Community: On Top of the World
Cindy Certified
4168 SOLAMOR ST, LAKELAND, FL, 33810, Lakeland, FL 33810
$335,000

3 beds

|

2 baths

|

1,584 sq ft

|

Villa

4168 SOLAMOR ST, LAKELAND, FL, 33810
Harbor Hills Country Club 5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$320,000

3 beds

|

2 baths

|

1,954 sq ft

|

House

5013 HARBOR HEIGHTS, LADY LAKE, FL, 3215...
The Villages® 2427 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162
$294,499

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2427 SOUTHERN OAK ST, 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
Spruce Creek Country Club 13828 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,315 sq ft

|

House

13828 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Stone Creek 6276 SW 93RD TER, OCALA, FL, 34481, Ocala, FL 34481
$398,000

2 beds

|

2 baths

|

1,885 sq ft

|

House

6276 SW 93RD TER, OCALA, FL, 34481
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.

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