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 41

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
Cindy Certified
436 HENNEPIN LOOP, LAKE WALES, FL, 33898, Lake Wales, FL 33898
$319,500

3 beds

|

2 baths

|

1,427 sq ft

|

House

436 HENNEPIN LOOP, LAKE WALES, FL, 33898
Palms at Serenoa 17718 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

17718 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Valencia Ridge 32630 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$639,900

2 beds

|

3 baths

|

2,276 sq ft

|

House

32630 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
Spruce Creek Country Club 9203 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$309,000

3 beds

|

2 baths

|

1,721 sq ft

|

House

9203 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Plantation at Leesburg 25243 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$330,000

3 beds

|

3 baths

|

2,512 sq ft

|

House

25243 RIVER CREST DR, LEESBURG, FL, 3474...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Harbor 2852 CAPE HORN CT, TAVARES, FL, 32778, Tavares, FL 32778
$329,000

2 beds

|

3 baths

|

2,163 sq ft

|

House

2852 CAPE HORN CT, TAVARES, FL, 32778
Community: Royal Harbor
Solivita 157 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$320,000

2 beds

|

2 baths

|

1,703 sq ft

|

House

157 PALAZZO LN, KISSIMMEE, FL, 34759
Community: Solivita
Cindy Certified
2016 ROSEWOOD CIR, LAKELAND, FL, 33810, Lakeland, FL 33810
$449,900

4 beds

|

3 baths

|

2,106 sq ft

|

House

2016 ROSEWOOD CIR, LAKELAND, FL, 33810
Scottish Highlands 2107 GREENLAW CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$245,000

2 beds

|

2 baths

|

1,438 sq ft

|

House

2107 GREENLAW CT, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 16815 SE 85TH BELKNAP AVE, THE VILLAGES,..., The Villages, FL 32162
$599,500

3 beds

|

2 baths

|

2,044 sq ft

|

House

16815 SE 85TH BELKNAP AVE, THE VILLAGES,...
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 518 DAVINCI PASS, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$346,000

2 beds

|

2 baths

|

1,491 sq ft

|

House

518 DAVINCI PASS, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 16933 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

16933 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
Cindy Certified
5515 ESTERO LOOP, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$399,000

3 beds

|

2 baths

|

1,896 sq ft

|

House

5515 ESTERO LOOP, PORT ORANGE, FL, 32128
Highlands Ridge 5116 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$298,000

2 beds

|

2 baths

|

1,462 sq ft

|

House

5116 BIRKDALE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Sandpiper Golf & Country Club 6121 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$244,000

2 beds

|

2 baths

|

1,135 sq ft

|

House

6121 KITTIWAKE DR, LAKELAND, FL, 33809
Ocala Preserve 4003 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$250,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4003 NW 44TH CIR, 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
Twin Lakes 2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772
$549,700

3 beds

|

3 baths

|

2,362 sq ft

|

House

2665 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
Ocala Preserve 5329 NW 34TH ST, OCALA, FL, 34482, Ocala, FL 34482
$278,000

2 beds

|

2 baths

|

1,318 sq ft

|

Villa

5329 NW 34TH ST, OCALA, FL, 34482
Community: Ocala Preserve
Spruce Creek South 10358 SE 178 PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$214,900

2 beds

|

2 baths

|

1,260 sq ft

|

House

10358 SE 178 PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Gatherings of Lake Nona 7505 LAUREATE BLVD 2206, ORLANDO, FL, 32..., Orlando, FL 32827
$420,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7505 LAUREATE BLVD 2206, ORLANDO, FL, 32...
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 10280 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$182,000

2 beds

|

2 baths

|

1,320 sq ft

|

House

10280 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Southshore Bay 5309 KELPER HOOK CT, WIMAUMA, FL, 33598, Wimauma, FL 33598
$275,000

2 beds

|

3 baths

|

1,747 sq ft

|

Villa

5309 KELPER HOOK CT, WIMAUMA, FL, 33598
Community: Southshore Bay
Cindy Certified
16852 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$294,900

2 beds

|

2 baths

|

1,683 sq ft

|

House

16852 SCUBA CREST ST, WIMAUMA, FL, 33598
VillageWalk at Lake Nona 12077 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$899,000

5 beds

|

4 baths

|

4,036 sq ft

|

House

12077 ULETA LN, ORLANDO, FL, 32827
Gatherings of Lake Nona 7521 LAUREATE BLVD 5307, ORLANDO, FL, 32..., Orlando, FL 32827
$524,900

3 beds

|

2 baths

|

1,799 sq ft

|

Condo

7521 LAUREATE BLVD 5307, ORLANDO, FL, 32...
Silver Lakes 6353 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$280,000

3 beds

|

2 baths

|

1,735 sq ft

|

House

6353 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
The Villages® 3463 LEELANAU CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$535,066

3 beds

|

2 baths

|

1,938 sq ft

|

House

3463 LEELANAU CT, 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
Del Webb Sunbridge 6261 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$510,000

2 beds

|

2 baths

|

1,919 sq ft

|

House

6261 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
Spruce Creek Country Club 9082 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$328,900

3 beds

|

2 baths

|

2,223 sq ft

|

House

9082 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Huntington at Hunter's Ridge 46 HERON WING DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$299,000

2 beds

|

2 baths

|

1,594 sq ft

|

House

46 HERON WING DR, ORMOND BEACH, FL, 3217...
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.
Tohoqua Reserve 1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$447,000

3 beds

|

3 baths

|

2,175 sq ft

|

House

1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Foxwood Lake Estates 1802 SHERWOOD HILL DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$147,000

2 beds

|

2 baths

|

864 sq ft

|

Manufactured Home

1802 SHERWOOD HILL DR, LAKELAND, FL, 338...
Esplanade Of Tampa 8335 ALBERATA VISTA DR, TAMPA, FL, 33647, Tampa, FL 33647
$430,000

3 beds

|

2 baths

|

1,700 sq ft

|

House

8335 ALBERATA VISTA DR, TAMPA, FL, 33647
Community: Esplanade Of Tampa
Cindy Certified
13506 CIRCA CROSSING DR, LITHIA, FL, 335..., Lithia, FL 33547
$354,900

2 beds

|

2 baths

|

1,525 sq ft

|

Villa

13506 CIRCA CROSSING DR, LITHIA, FL, 335...
Palm Cay 10957 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476
$164,500

3 beds

|

2 baths

|

1,060 sq ft

|

House

10957 SW 79TH TER, OCALA, FL, 34476
Community: Palm Cay
The Villages® 649 TERNBERRY FOREST DR, THE VILLAGES, F..., The Villages, FL 32162
$1,650,000

4 beds

|

3 baths

|

3,682 sq ft

|

House

649 TERNBERRY FOREST DR, THE VILLAGES, F...
Community: The Villages®
Cresswind Lakewood Ranch 17831 CHERISHED LOOP, LAKEWOOD RANCH, FL..., Lakewood Ranch, FL 34211
$400,000

2 beds

|

2 baths

|

1,672 sq ft

|

Villa

17831 CHERISHED LOOP, LAKEWOOD RANCH, FL...
Sun City Center 106 SILVERBELL CT, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$238,000

2 beds

|

2 baths

|

1,796 sq ft

|

House

106 SILVERBELL CT, 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
Stonecrest 10990 SE 170TH STREET RD, SUMMERFIELD, F..., Summerfield, FL 34491
$439,000

3 beds

|

3 baths

|

2,043 sq ft

|

House

10990 SE 170TH STREET RD, SUMMERFIELD, F...
Community: Stonecrest
Harbor Hills Country Club 4044 PINNACLE PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$649,900

3 beds

|

3 baths

|

2,532 sq ft

|

House

4044 PINNACLE PL, 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.

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