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 46

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.
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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
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) 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 (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
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) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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
2.8 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
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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
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
Trilogy® Orlando 78 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$330,000

2 beds

|

2 baths

|

1,305 sq ft

|

House

78 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Venetian Bay 142 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$950,000

3 beds

|

3 baths

|

2,456 sq ft

|

House

142 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
Lakeside Landings 5336 EDGEWATER WAY 11, OXFORD, FL, 34484, Oxford, FL 34484
$205,000

3 beds

|

2 baths

|

1,291 sq ft

|

Condo

5336 EDGEWATER WAY 11, OXFORD, FL, 34484
Community: Lakeside Landings
On Top of the World 9030 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$424,900

3 beds

|

3 baths

|

2,288 sq ft

|

House

9030 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
Arlington Ridge 4419 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$525,000

2 beds

|

3 baths

|

2,333 sq ft

|

House

4419 BENT CREEK LN, LEESBURG, FL, 34748
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Oak Run 6321 SW 117TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$275,000

2 beds

|

2 baths

|

1,457 sq ft

|

House

6321 SW 117TH LOOP, OCALA, FL, 34476
Community: Oak Run
Esplanade at Westview 5676 NEVIS TER, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$540,000

3 beds

|

3 baths

|

2,296 sq ft

|

House

5676 NEVIS TER, KISSIMMEE, FL, 34758
Cindy Certified
18334 TAVERNSIDE TRL, LAKEWOOD RANCH, FL..., Lakewood Ranch, FL 34211
$379,990

3 beds

|

2 baths

|

1,565 sq ft

|

Villa

18334 TAVERNSIDE TRL, LAKEWOOD RANCH, FL...
Cindy Certified
18330 TAVERNSIDE TRL, LAKEWOOD RANCH, FL..., Lakewood Ranch, FL 34211
$379,990

3 beds

|

2 baths

|

1,565 sq ft

|

Villa

18330 TAVERNSIDE TRL, LAKEWOOD RANCH, FL...
The Villages® 2706 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$309,999

2 beds

|

2 baths

|

1,248 sq ft

|

House

2706 MORVEN PARK WAY, THE VILLAGES, FL, ...
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.
Oak Run 7121 SW 113TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$335,000

2 beds

|

2 baths

|

2,152 sq ft

|

House

7121 SW 113TH LOOP, OCALA, FL, 34476
Community: Oak Run
Esplanade at Westview 4364 CURACAO PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$699,999

3 beds

|

3 baths

|

3,004 sq ft

|

House

4364 CURACAO PL, KISSIMMEE, FL, 34758
Carillon Lakes 3007 BELLFLOWER WAY, LAKELAND, FL, 33811, Lakeland, FL 33811
$379,900

3 beds

|

3 baths

|

1,846 sq ft

|

House

3007 BELLFLOWER WAY, LAKELAND, FL, 33811
Community: Carillon Lakes
Venetian Bay 477 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$625,000

5 beds

|

4 baths

|

3,002 sq ft

|

House

477 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
Four Seasons at Orlando 1667 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$339,500

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1667 KEY BAY TRL, KISSIMMEE, FL, 34747
On Top of the World 8034 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$249,900

3 beds

|

2 baths

|

1,516 sq ft

|

House

8034 SW 81ST LOOP, OCALA, FL, 34476
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
Lake Henry Estates 477 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844
$274,900

3 beds

|

2 baths

|

1,835 sq ft

|

House

477 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
On Top of the World 9200 SW 85TH PL, OCALA, FL, 34481, Ocala, FL 34481
$448,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

9200 SW 85TH PL, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 2437 NANTUCKET HARBOR LOOP 2437, SUN CIT..., Sun City Center, FL 33573
$157,500

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2437 NANTUCKET HARBOR LOOP 2437, SUN CIT...
Community: Sun City Center
The Villages® 112 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785
$197,000

2 beds

|

2 baths

|

1,664 sq ft

|

Manufactured Home

112 LYONIA LN, WILDWOOD, FL, 34785
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.
Stone Creek 9793 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$498,900

4 beds

|

2 baths

|

2,186 sq ft

|

House

9793 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Spruce Creek Preserve 11675 SW 140TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432
$279,000

2 beds

|

2 baths

|

1,926 sq ft

|

House

11675 SW 140TH LOOP, DUNNELLON, FL, 3443...
Royal Harbor 3204 ANTIGUA BAY LN, TAVARES, FL, 32778, Tavares, FL 32778
$334,900

3 beds

|

2 baths

|

1,785 sq ft

|

House

3204 ANTIGUA BAY LN, TAVARES, FL, 32778
Community: Royal Harbor
Carillon Lakes 3833 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$325,000

3 beds

|

2 baths

|

1,706 sq ft

|

House

3833 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
Kings Ridge 4075 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$334,900

3 beds

|

2 baths

|

1,782 sq ft

|

House

4075 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Cindy Certified
1362 CORK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$345,000

3 beds

|

2 baths

|

1,373 sq ft

|

House

1362 CORK DR, ORMOND BEACH, FL, 32174
Pelican Bay Daytona Beach 168 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$210,000

2 beds

|

2 baths

|

1,260 sq ft

|

House

168 BERMUDA PETREL CT, DAYTONA BEACH, FL...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Esplanade at Westview 4536 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$269,900

3 beds

|

2 baths

|

1,553 sq ft

|

House

4536 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Del Webb Orlando 519 VIGO ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$439,900

3 beds

|

2 baths

|

2,320 sq ft

|

House

519 VIGO ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
JB Ranch 6365 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$289,999

2 beds

|

2 baths

|

1,811 sq ft

|

House

6365 SW 88TH LOOP, OCALA, FL, 34476
Community: JB Ranch
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® 16970 SE 94TH SUNNYBROOK CIR, THE VILLAG..., The Villages, FL 32162
$248,000

2 beds

|

2 baths

|

1,198 sq ft

|

House

16970 SE 94TH SUNNYBROOK CIR, THE VILLAG...
Community: The Villages®
SummerGlen 3553 & 3555 SW 158TH LN, OCALA, FL, 3447..., Ocala, FL 34473
$349,900

4 beds

|

4 baths

|

2,216 sq ft

|

Duplex

3553 & 3555 SW 158TH LN, OCALA, FL, 3447...
Community: SummerGlen
Spruce Creek South 10298 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$185,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

10298 SE 176TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Plantation at Leesburg 25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$249,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

25333 RIVER CREST DR, LEESBURG, FL, 3474...
Stonecrest 10982 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$395,000

3 beds

|

2 baths

|

1,727 sq ft

|

House

10982 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 483 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$234,000

2 beds

|

1 baths

|

1,034 sq ft

|

Villa

483 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Cindy Certified
16158 SW 19TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$303,000

4 beds

|

3 baths

|

1,896 sq ft

|

House

16158 SW 19TH AVENUE RD, OCALA, FL, 3447...
The Wellington 689 LAKE HOWARD DR 213, WINTER HAVEN, FL..., Winter Haven, FL 33880
$145,000

2 beds

|

2 baths

|

1,072 sq ft

|

Condo

689 LAKE HOWARD DR 213, WINTER HAVEN, FL...
Community: The Wellington
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15862 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473
$394,900

3 beds

|

2 baths

|

2,283 sq ft

|

House

15862 SW 13TH CIR, OCALA, FL, 34473
Community: SummerGlen
Cindy Certified
3018 ROYAL TERN DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$269,900

3 beds

|

2 baths

|

1,690 sq ft

|

House

3018 ROYAL TERN DR, WINTER HAVEN, FL, 33...
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