Call us at (689) 407-5757 to learn more about active adult communities near Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale

3,648 homes near Winter Garden

Sort by:

Relevance

Relevance

5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 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
3.8 rating (14 reviews) Sun City Center
<$100k - $500Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $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
3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 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
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
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 - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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
<$100k - $500Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $600Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$300Ks - $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 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
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $500Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
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.
5 rating (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
No reviews yet Breakaway Trails
$400Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Stone Creek 9836 SW 75TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$408,888

2 beds

|

2 baths

|

1,904 sq ft

|

House

9836 SW 75TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
SummerGlen 1706 SW 156TH LN, OCALA, FL, 34473, Ocala, FL 34473
$257,900

3 beds

|

2 baths

|

1,676 sq ft

|

House

1706 SW 156TH LN, OCALA, FL, 34473
Community: SummerGlen
Heritage - The Cottages of Sanders Grove 6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$314,900

3 beds

|

2 baths

|

1,788 sq ft

|

House

6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
The Country Club of Mount Dora 9048 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$320,000

2 beds

|

2 baths

|

1,442 sq ft

|

House

9048 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Sun City Center 2504 SAPPHIRE GREENS LN, SUN CITY CENTER..., Sun City Center, FL 33573
$339,000

3 beds

|

2 baths

|

1,568 sq ft

|

Villa

2504 SAPPHIRE GREENS LN, 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
Spruce Creek Country Club 13822 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$267,500

2 beds

|

2 baths

|

1,540 sq ft

|

House

13822 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Spruce Creek South 17810 SE 108TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$209,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

17810 SE 108TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
On Top of the World 8666 SW 92ND LN C, OCALA, FL, 34481, Ocala, FL 34481
$152,000

2 beds

|

2 baths

|

1,394 sq ft

|

Villa

8666 SW 92ND LN C, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1906 CANTERBURY LN UNIT 32, SUN CITY CEN..., Sun City Center, FL 33573
$150,000

2 beds

|

2 baths

|

984 sq ft

|

Condo

1906 CANTERBURY LN UNIT 32, SUN CITY CEN...
Community: Sun City Center
Sandpiper Golf & Country Club 6380 EGRET DR 22, LAKELAND, FL, 33809, Lakeland, FL 33809
$234,900

2 beds

|

2 baths

|

893 sq ft

|

Villa

6380 EGRET DR 22, LAKELAND, FL, 33809
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.
Legacy of Leesburg 26705 WETLANDS WAY, LEESBURG, FL, 34748, Leesburg, FL 34748
$339,000

3 beds

|

2 baths

|

1,615 sq ft

|

House

26705 WETLANDS WAY, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 2378 RIDGEWAY CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,602 sq ft

|

House

2378 RIDGEWAY CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Valencia Lakes 4836 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$347,000

2 beds

|

2 baths

|

1,539 sq ft

|

Villa

4836 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
Tampa Bay Golf and Country Club 9427 ROLLING CIR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$275,000

2 beds

|

2 baths

|

1,480 sq ft

|

Villa

9427 ROLLING CIR, SAN ANTONIO, FL, 33576
Solivita 307 MONTEREY ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$310,000

3 beds

|

2 baths

|

1,629 sq ft

|

House

307 MONTEREY ST, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lakes of Mount Dora 1977 WEYMOUTH CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$785,000

4 beds

|

3 baths

|

2,423 sq ft

|

House

1977 WEYMOUTH CT, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
Ridgehaven 179 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$323,615

3 beds

|

2 baths

|

1,572 sq ft

|

House

179 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
Ocala Palms 5551 NW 25TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$225,000

2 beds

|

2 baths

|

1,673 sq ft

|

House

5551 NW 25TH LOOP, OCALA, FL, 34482
Community: Ocala Palms
The Villages® 1410 NATALIE LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

1410 NATALIE LN, THE VILLAGES, FL, 32162
Community: The Villages®
Arlington Ridge 27018 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748
$250,000

2 beds

|

2 baths

|

1,208 sq ft

|

Villa

27018 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
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.
On Top of the World 10451 SW 98TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$485,000

3 beds

|

3 baths

|

2,288 sq ft

|

House

10451 SW 98TH PLACE RD, OCALA, FL, 34481
Community: On Top of the World
Solivita 159 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$325,000

3 beds

|

2 baths

|

1,813 sq ft

|

House

159 VENTANA DR, KISSIMMEE, FL, 34759
Community: Solivita
SummerGlen 16292 SW 13TH TER, OCALA, FL, 34473, Ocala, FL 34473
$349,000

3 beds

|

2 baths

|

2,297 sq ft

|

House

16292 SW 13TH TER, OCALA, FL, 34473
Community: SummerGlen
On Top of the World 8423 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$349,000

3 beds

|

2 baths

|

2,283 sq ft

|

House

8423 SW 82ND CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8745 SW 92ND ST B, OCALA, FL, 34481, Ocala, FL 34481
$229,000

2 beds

|

2 baths

|

1,652 sq ft

|

Villa

8745 SW 92ND ST B, 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
Legacy of Leesburg 5351 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$489,900

4 beds

|

5 baths

|

3,125 sq ft

|

House

5351 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
The Villages® 3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$415,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ...
Community: The Villages®
Oak Run 11447 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$234,900

2 beds

|

2 baths

|

1,687 sq ft

|

House

11447 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Four Seasons at Orlando 7957 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$499,900

2 beds

|

2 baths

|

2,271 sq ft

|

House

7957 HANSON BAY PL, KISSIMMEE, FL, 34747
Foxwood Lake Estates 4909 FOXWOOD LAKE DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$169,000

2 beds

|

2 baths

|

1,104 sq ft

|

Manufactured Home

4909 FOXWOOD LAKE DR, LAKELAND, FL, 3381...
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 5564 SW 90TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$598,090

3 beds

|

4 baths

|

2,990 sq ft

|

House

5564 SW 90TH AVE, OCALA, FL, 34481
Community: Stone Creek
Summit Greens 1107 EVEREST ST, CLERMONT, FL, 34711, Clermont, FL 34711
$400,000

2 beds

|

2 baths

|

1,881 sq ft

|

House

1107 EVEREST ST, CLERMONT, FL, 34711
Community: Summit Greens
Legacy of Leesburg 27303 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$422,000

3 beds

|

2 baths

|

2,210 sq ft

|

House

27303 STONEY BROOK DR, LEESBURG, FL, 347...
Community: Legacy of Leesburg
Traditions at Lake Ruby 3912 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$295,000

2 beds

|

2 baths

|

1,719 sq ft

|

House

3912 BALDWIN LN, WINTER HAVEN, FL, 33884
The Villages® 5616 BOBCAT TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$364,900

3 beds

|

2 baths

|

1,409 sq ft

|

House

5616 BOBCAT TER, 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
Sun City Center 653 MCDANIEL ST # 178, SUN CITY CENTER, ..., Sun City Center, FL 33573
$212,000

2 beds

|

2 baths

|

1,277 sq ft

|

Condo

653 MCDANIEL ST # 178, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 16946 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$442,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

16946 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
On Top of the World 8580 SW 97TH LANE RD D, OCALA, FL, 34481, Ocala, FL 34481
$135,000

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

8580 SW 97TH LANE RD D, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 7980 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$267,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

7980 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
Lake Ashton 3834 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$599,900

2 beds

|

2 baths

|

1,792 sq ft

|

House

3834 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton

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 [email protected]. 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
3,648 homes near Winter Garden
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.
© 2025 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: Nov 04, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top