not an image

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 27

3,497 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 (56 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
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
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
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 (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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
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
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 (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 - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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
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
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
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
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.
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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.
12...3
Sun City Center 327 CALOOSA WOODS LN, SUN CITY CENTER, F..., Sun City Center, FL 33573
$379,000

2 beds

|

2 baths

|

1,695 sq ft

|

House

327 CALOOSA WOODS LN, SUN CITY CENTER, F...
Community: Sun City Center
On Top of the World 8780 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$499,900

3 beds

|

3 baths

|

2,463 sq ft

|

House

8780 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
Legacy of Leesburg 5401 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

5401 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Spruce Creek Country Club 9333 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$387,900

2 beds

|

2 baths

|

2,148 sq ft

|

House

9333 SE 124TH PL, SUMMERFIELD, FL, 34491
On Top of the World 8677 SW 95TH LN E, OCALA, FL, 34481, Ocala, FL 34481
$157,000

2 beds

|

2 baths

|

1,140 sq ft

|

Villa

8677 SW 95TH LN E, 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® 1605 LYNCHBURG LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$525,000

3 beds

|

3 baths

|

2,043 sq ft

|

House

1605 LYNCHBURG LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 8660 SW 94TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$118,900

2 beds

|

2 baths

|

1,571 sq ft

|

Villa

8660 SW 94TH ST C, OCALA, FL, 34481
Community: On Top of the World
Lakes at Laurel Highlands 2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$355,000

4 beds

|

2 baths

|

1,867 sq ft

|

House

2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Heritage Landings 2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$355,000

4 beds

|

2 baths

|

1,867 sq ft

|

House

2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
On Top of the World 9529 SW 85TH AVE D, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,541 sq ft

|

Villa

9529 SW 85TH AVE D, 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.
The Villages® 2873 CHARLEVOIX ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$562,500

3 beds

|

2 baths

|

1,938 sq ft

|

Villa

2873 CHARLEVOIX ST, THE VILLAGES, FL, 32...
Community: The Villages®
Huntington at Hunter's Ridge 51 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$355,000

2 beds

|

2 baths

|

1,603 sq ft

|

House

51 WRENDALE LOOP, ORMOND BEACH, FL, 3217...
Stone Creek 6208 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$559,580

3 beds

|

4 baths

|

2,808 sq ft

|

House

6208 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
Stone Creek 8319 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$449,080

2 beds

|

2 baths

|

1,943 sq ft

|

House

8319 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8352 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$442,160

2 beds

|

2 baths

|

1,889 sq ft

|

House

8352 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Pennbrooke Fairways 333 RANCHWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$344,900

3 beds

|

2 baths

|

1,840 sq ft

|

House

333 RANCHWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 376 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$350,000

3 beds

|

2 baths

|

1,902 sq ft

|

House

376 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
The Villages® 16967 SE 84TH COLERAIN CIR, THE VILLAGES..., The Villages, FL 32162
$569,000

3 beds

|

2 baths

|

1,929 sq ft

|

House

16967 SE 84TH COLERAIN CIR, THE VILLAGES...
Community: The Villages®
Summer Trees 61 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$209,900

2 beds

|

2 baths

|

1,020 sq ft

|

House

61 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
The Villages® 17412 SE 81ST NEWBERRY CT, THE VILLAGES,..., The Villages, FL 32162
$186,000

1 beds

|

1 baths

|

955 sq ft

|

Villa

17412 SE 81ST NEWBERRY CT, 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.
Del Webb Oasis 13043 SANDCASTLE DR, WINTER GARDEN, FL, ..., Winter Garden, FL 34787
$899,000

3 beds

|

2 baths

|

1,943 sq ft

|

House

13043 SANDCASTLE DR, WINTER GARDEN, FL, ...
Community: Del Webb Oasis
Solivita 1317 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$269,000

2 beds

|

2 baths

|

1,363 sq ft

|

House

1317 LOMBARDI CT, KISSIMMEE, FL, 34759
Community: Solivita
Kings Ridge 2241 KINGSMILL WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$399,900

3 beds

|

2 baths

|

2,124 sq ft

|

House

2241 KINGSMILL WAY, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 100 MERIDIAN AVE, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

100 MERIDIAN AVE, POINCIANA, FL, 34759
Community: Solivita
The Villages® 435 SANTA CLARA CIR, THE VILLAGES, FL, 3..., The Villages, FL 32159
$305,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

435 SANTA CLARA CIR, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 8519 SW 91ST ST C, OCALA, FL, 34481, Ocala, FL 34481
$159,000

2 beds

|

2 baths

|

1,204 sq ft

|

Villa

8519 SW 91ST ST C, OCALA, FL, 34481
Community: On Top of the World
Plantation at Leesburg 5338 TIGERS TAIL, LEESBURG, FL, 34748, Leesburg, FL 34748
$230,000

2 beds

|

2 baths

|

1,050 sq ft

|

House

5338 TIGERS TAIL, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$779,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
The Villages® 501 HERRERA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$319,900

3 beds

|

2 baths

|

1,823 sq ft

|

House

501 HERRERA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Marion Landing 8708 SW 67TH TER, OCALA, FL, 34476, Ocala, FL 34476
$312,985

4 beds

|

3 baths

|

2,083 sq ft

|

House

8708 SW 67TH TER, OCALA, FL, 34476
Community: Marion Landing
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® 17263 SE 93RD DEMOSS CT, THE VILLAGES, F..., The Villages, FL 32162
$239,900

2 beds

|

2 baths

|

1,175 sq ft

|

Villa

17263 SE 93RD DEMOSS CT, THE VILLAGES, F...
Community: The Villages®
Sun City Center 1525 ALLEGHENY DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$249,500

2 beds

|

2 baths

|

1,662 sq ft

|

House

1525 ALLEGHENY DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Sun City Center 381 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$259,900

2 beds

|

2 baths

|

1,681 sq ft

|

House

381 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Latitude Margaritaville 842 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$674,900

2 beds

|

3 baths

|

2,303 sq ft

|

House

842 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Spruce Creek Country Club 12531 SE 93RD COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$389,700

2 beds

|

3 baths

|

2,123 sq ft

|

House

12531 SE 93RD COURT RD, SUMMERFIELD, FL,...
Huntington at Hunter's Ridge 23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$399,900

3 beds

|

3 baths

|

1,853 sq ft

|

House

23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Sun City Center 2312 BROOKFIELD GREENS CIR 61, SUN CITY ..., Sun City Center, FL 33573
$272,000

2 beds

|

2 baths

|

1,362 sq ft

|

Condo

2312 BROOKFIELD GREENS CIR 61, SUN CITY ...
Community: Sun City Center
Trilogy® Orlando 88 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$315,000

2 beds

|

2 baths

|

1,568 sq ft

|

House

88 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Ashton 4179 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$379,900

3 beds

|

2 baths

|

2,229 sq ft

|

House

4179 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
The Villages® 16596 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162
$342,500

3 beds

|

2 baths

|

1,483 sq ft

|

House

16596 SE 77TH NORTHRIDGE CT, THE VILLAGE...
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.

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
3,497 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: May 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