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 70

3,517 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 - $2Ms
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 - $700Ks
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 - $600Ks
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 - $900Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $500Ks
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
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 (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes
5 rating (3 reviews) Stonecrest
$200Ks - $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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pelican Bay Daytona Beach
$100Ks - $400Ks
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
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $400Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $600Ks
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.
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
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
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 (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
4 rating (7 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) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 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.
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 - $400Ks
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 - $400Ks
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$100Ks - $400Ks
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
Breakaway Trails
$400Ks - $800Ks
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
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 (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
4.8 rating (6 reviews) Highland Lakes
$100Ks - $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
Pine Run Estates
<$100k - $300Ks
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
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
Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Lakeside Landings 5361 COMPASS PT # 1, OXFORD, FL, 34484, Oxford, FL 34484
$239,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5361 COMPASS PT # 1, OXFORD, FL, 34484
Community: Lakeside Landings
Sun City Center 1305 SPRY CT, SUN CITY CENTER, FL, 33573, Sun City Center, FL 33573
$169,900

2 beds

|

2 baths

|

1,219 sq ft

|

Condo

1305 SPRY CT, SUN CITY CENTER, FL, 33573
Community: Sun City Center
On Top of the World 8885 SW 97TH LANE RD A, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

1,356 sq ft

|

Villa

8885 SW 97TH LANE RD A, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Preserve 13710 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$249,500

2 beds

|

2 baths

|

1,446 sq ft

|

House

13710 SW 112TH CIR, DUNNELLON, FL, 34432
Venetian Bay 3417 GALLIA ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$429,000

4 beds

|

4 baths

|

2,402 sq ft

|

Townhouse

3417 GALLIA ST, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1701 PALM AIRE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$259,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

1701 PALM AIRE DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 4280 GALE LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$329,000

3 beds

|

2 baths

|

1,440 sq ft

|

Villa

4280 GALE LN, THE VILLAGES, FL, 32163
Community: The Villages®
VillageWalk at Lake Nona 11858 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$608,000

3 beds

|

2 baths

|

1,941 sq ft

|

House

11858 BARLETTA DR, ORLANDO, FL, 32827
Spruce Creek South 10337 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,800

3 beds

|

2 baths

|

1,526 sq ft

|

House

10337 SE 176TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
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.
New Palm Cay 10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476
$145,000

2 beds

|

2 baths

|

1,112 sq ft

|

House

10881 SW 79TH TER, OCALA, FL, 34476
Community: Palm Cay
Oak Run 10943 SW 86TH CT, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10943 SW 86TH CT, OCALA, FL, 34481
Community: Oak Run
The Villages® 8065 SE 175TH COLUMBIA PL, THE VILLAGES,..., The Villages, FL 32162
$282,000

2 beds

|

2 baths

|

1,120 sq ft

|

House

8065 SE 175TH COLUMBIA PL, THE VILLAGES,...
Community: The Villages®
New Tampa Bay Golf and Country Club 29318 SNAP HOOK DR, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$335,000

2 beds

|

2 baths

|

1,489 sq ft

|

House

29318 SNAP HOOK DR, SAN ANTONIO, FL, 335...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 504 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$275,000

2 beds

|

2 baths

|

1,543 sq ft

|

House

504 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
Windermere 823 BALMORAL CT, INVERNESS, FL, 34453, Inverness, FL 34453
$330,000

3 beds

|

3 baths

|

2,047 sq ft

|

House

823 BALMORAL CT, INVERNESS, FL, 34453
Community: Windermere
Plantation at Leesburg 24817 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,837 sq ft

|

House

24817 CRANES ROOST CIR, LEESBURG, FL, 34...
Sun City Center 2007 EAST VIEW DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$349,900

3 beds

|

2 baths

|

2,635 sq ft

|

House

2007 EAST VIEW DR, SUN CITY CENTER, FL, ...
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.
Stonecrest 12459 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$309,900

3 beds

|

2 baths

|

1,326 sq ft

|

House

12459 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Stonecrest 12225 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$315,900

3 beds

|

2 baths

|

1,475 sq ft

|

House

12225 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
On Top of the World 8535 SW 90TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

1,089 sq ft

|

Villa

8535 SW 90TH ST C, OCALA, FL, 34481
Community: On Top of the World
Solivita 243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$289,000

2 beds

|

2 baths

|

1,560 sq ft

|

House

243 NEW RIVER DR, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New The Villages® 1780 REEDY CREEK PL, THE VILLAGES, FL, 3..., The Villages, FL 32162
$465,000

3 beds

|

2 baths

|

1,743 sq ft

|

House

1780 REEDY CREEK PL, THE VILLAGES, FL, 3...
Community: The Villages®
New Oak Run 11456 SW 67TH CT, OCALA, FL, 34476, Ocala, FL 34476
$289,900

3 beds

|

2 baths

|

1,831 sq ft

|

House

11456 SW 67TH CT, OCALA, FL, 34476
Community: Oak Run
Heritage Landings 2795 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$319,000

3 beds

|

2 baths

|

1,769 sq ft

|

House

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
Lakes at Laurel Highlands 2795 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$319,000

3 beds

|

2 baths

|

1,769 sq ft

|

House

2795 GRANDBURY GROVE RD, LAKELAND, FL, 3...
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.
Trilogy® Orlando 244 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$425,000

2 beds

|

2 baths

|

1,853 sq ft

|

House

244 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
The Villages® 1052 JACKSON ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$439,900

2 beds

|

2 baths

|

1,258 sq ft

|

House

1052 JACKSON ST, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 418 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$615,000

3 beds

|

3 baths

|

2,427 sq ft

|

House

418 TREVISO DR, KISSIMMEE, FL, 34759
Community: Solivita
New Trilogy® Orlando 383 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$357,000

2 beds

|

2 baths

|

1,568 sq ft

|

Villa

383 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
New Solivita 771 GLENDORA RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$465,000

3 beds

|

3 baths

|

2,450 sq ft

|

House

771 GLENDORA RD, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Solivita 729 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$439,900

3 beds

|

3 baths

|

2,325 sq ft

|

House

729 GLENDORA RD, KISSIMMEE, FL, 34759
Community: Solivita
New The Villages® 550 LITTLE RIVER PATH, THE VILLAGES, FL,..., The Villages, FL 32162
$739,000

3 beds

|

2 baths

|

2,012 sq ft

|

House

550 LITTLE RIVER PATH, THE VILLAGES, FL,...
Community: The Villages®
New The Villages® 782 MILLHORN LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163
$329,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

782 MILLHORN LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
New Scottish Highlands 1507 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$225,000

2 beds

|

2 baths

|

1,478 sq ft

|

House

1507 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
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.
New Valencia del Sol 4715 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$450,000

2 beds

|

3 baths

|

2,040 sq ft

|

Villa

4715 AVILA LAKES DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
New Valencia del Sol 4717 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$375,000

2 beds

|

2 baths

|

1,648 sq ft

|

Villa

4717 AVILA LAKES DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
New On Top of the World 8089 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$240,000

3 beds

|

2 baths

|

2,032 sq ft

|

House

8089 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
New On Top of the World 8670 SW 88TH PL, OCALA, FL, 34481, Ocala, FL 34481
$289,900

3 beds

|

2 baths

|

2,032 sq ft

|

House

8670 SW 88TH PL, 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
New Venetian Bay 3643 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$349,900

2 beds

|

3 baths

|

1,664 sq ft

|

Townhouse

3643 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
New Palm Cay 7670 SW 112TH LN, OCALA, FL, 34476, Ocala, FL 34476
$129,500

2 beds

|

2 baths

|

864 sq ft

|

House

7670 SW 112TH LN, OCALA, FL, 34476
Community: Palm Cay

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
3,517 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: Jan 11, 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