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 7

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
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 (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 (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) 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 (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
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 655 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) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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
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
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
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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 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
Valencia del Sol 15479 SANTA POLA DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$379,900

2 beds

|

2 baths

|

1,686 sq ft

|

House

15479 SANTA POLA DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
Latitude Margaritaville 1103 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$889,900

2 beds

|

3 baths

|

2,339 sq ft

|

House

1103 SEA SHELL CT, DAYTONA BEACH, FL, 32...
SummerGlen 1376 SW 161ST PL, OCALA, FL, 34473, Ocala, FL 34473
$299,900

3 beds

|

2 baths

|

1,810 sq ft

|

House

1376 SW 161ST PL, OCALA, FL, 34473
Community: SummerGlen
Lake Jovita Golf and Country Club 13303 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525
$825,000

4 beds

|

3 baths

|

2,555 sq ft

|

House

13303 TRAILING MOSS DR, DADE CITY, FL, 3...
Summit Chase Villas 12441 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778
$198,500

2 beds

|

2 baths

|

986 sq ft

|

House

12441 ORANGEWOOD CIR, TAVARES, FL, 32778
Community: Summit Chase Villas
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 124 VENTANA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$310,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

124 VENTANA DR, POINCIANA, FL, 34759
Community: Solivita
Solivita 173 BELL TOWER XING, POINCIANA, FL, 3475..., Poinciana, FL 34759
$249,900

2 beds

|

2 baths

|

1,317 sq ft

|

House

173 BELL TOWER XING, POINCIANA, FL, 3475...
Community: Solivita
Stonecrest 10957 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$289,900

3 beds

|

2 baths

|

1,381 sq ft

|

House

10957 SE 170TH LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Solivita 1120 VIA GALUPPI ST, POINCIANA, FL, 3475..., Poinciana, FL 34759
$320,000

2 beds

|

2 baths

|

1,367 sq ft

|

House

1120 VIA GALUPPI ST, POINCIANA, FL, 3475...
Community: Solivita
Plantation at Leesburg 25419 CRESTWATER DRIVE DR, LEESBURG, FL,..., Leesburg, FL 34748
$245,000

2 beds

|

2 baths

|

1,581 sq ft

|

House

25419 CRESTWATER DRIVE DR, LEESBURG, FL,...
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.
Lakeside Landings 10150 MAINSAIL DR, OXFORD, FL, 34484, Oxford, FL 34484
$267,500

3 beds

|

2 baths

|

1,592 sq ft

|

House

10150 MAINSAIL DR, OXFORD, FL, 34484
Community: Lakeside Landings
Pelican Bay Daytona Beach 132 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$249,000

3 beds

|

3 baths

|

2,008 sq ft

|

Townhouse

132 BERMUDA PETREL CT, DAYTONA BEACH, FL...
Sun City Center 2020 HULLHOUSE DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$169,900

2 beds

|

2 baths

|

1,448 sq ft

|

Condo

2020 HULLHOUSE DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
The Villages® 2265 HACKNEY WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$399,900

3 beds

|

2 baths

|

1,715 sq ft

|

House

2265 HACKNEY WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
Del Webb Orlando 123 MAGELLAN CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$514,900

3 beds

|

3 baths

|

2,186 sq ft

|

House

123 MAGELLAN CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Solivita 219 KNOLL WOOD DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$255,000

2 beds

|

2 baths

|

1,467 sq ft

|

House

219 KNOLL WOOD DR, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Trilogy® Orlando 771 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736
$539,990

2 beds

|

3 baths

|

2,087 sq ft

|

House

771 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 3001 GLENWOOD PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$347,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3001 GLENWOOD PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 180 TALL PINES PASS, POINCIANA, FL, 3475..., Poinciana, FL 34759
$249,000

2 beds

|

2 baths

|

1,595 sq ft

|

House

180 TALL PINES PASS, POINCIANA, FL, 3475...
Community: Solivita
Latitude Margaritaville 130 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$899,900

2 beds

|

3 baths

|

2,339 sq ft

|

House

130 CORAL REEF WAY, DAYTONA BEACH, 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.
Lake Jovita Golf and Country Club 13823 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$915,000

4 beds

|

4 baths

|

3,156 sq ft

|

House

13823 THOROUGHBRED DR, DADE CITY, FL, 33...
The Villages® 12166 NE 51ST CIR, OXFORD, FL, 34484, Oxford, FL 34484
$299,900

3 beds

|

2 baths

|

1,536 sq ft

|

House

12166 NE 51ST CIR, OXFORD, FL, 34484
Community: The Villages®
Stone Creek 8187 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$434,900

3 beds

|

2 baths

|

1,697 sq ft

|

House

8187 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Ocala Preserve 3461 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$585,000

3 beds

|

3 baths

|

2,290 sq ft

|

House

3461 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
Lakeside Landings 10331 ADDISON SHORE WAY, OXFORD, FL, 344..., Oxford, FL 34484
$423,500

3 beds

|

2 baths

|

2,003 sq ft

|

House

10331 ADDISON SHORE WAY, OXFORD, FL, 344...
Community: Lakeside Landings
Marion Landing 8641 SW 62ND TER, OCALA, FL, 34476, Ocala, FL 34476
$179,900

2 beds

|

2 baths

|

1,184 sq ft

|

Manufactured Home

8641 SW 62ND TER, OCALA, FL, 34476
Community: Marion Landing
Ocala Palms 5216 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482
$249,900

2 beds

|

2 baths

|

1,212 sq ft

|

House

5216 NW 21ST LOOP, OCALA, FL, 34482
Community: Ocala Palms
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Scottish Highlands 1409 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$219,900

2 beds

|

2 baths

|

1,674 sq ft

|

House

1409 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
Twin Lakes 2327 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772
$340,000

2 beds

|

2 baths

|

1,469 sq ft

|

Villa

2327 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
Del Webb Orlando 336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$424,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

336 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
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.
Latitude Margaritaville 290 LAST MANGO DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$389,500

2 beds

|

2 baths

|

1,308 sq ft

|

House

290 LAST MANGO DR, DAYTONA BEACH, FL, 32...
Cindy Certified
476 MARION OAKS LN, OCALA, FL, 34473, Ocala, FL 34473
$269,000

3 beds

|

2 baths

|

1,390 sq ft

|

House

476 MARION OAKS LN, OCALA, FL, 34473
The Villages® 720 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$318,000

2 beds

|

2 baths

|

1,613 sq ft

|

House

720 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Harbor Hills Country Club 39622 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$410,000

3 beds

|

2 baths

|

2,175 sq ft

|

House

39622 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Plantation at Leesburg 5336 TIDEWATER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

2 beds

|

2 baths

|

1,918 sq ft

|

House

5336 TIDEWATER ST, LEESBURG, FL, 34748
Spruce Creek Country Club 13932 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$589,000

3 beds

|

2 baths

|

2,413 sq ft

|

House

13932 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Traditions at Lake Ruby 4035 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$249,900

2 beds

|

2 baths

|

1,719 sq ft

|

House

4035 CARTERET DR, WINTER HAVEN, FL, 3388...
Cindy Certified
5369 TEMPEST WAY, CLERMONT, FL, 34714, Clermont, FL 34714
$283,490

2 beds

|

2 baths

|

1,421 sq ft

|

Villa

5369 TEMPEST WAY, CLERMONT, FL, 34714
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Country Club of Mount Dora 3022 ANDOVER CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$325,000

2 beds

|

2 baths

|

1,444 sq ft

|

House

3022 ANDOVER CT, MOUNT DORA, FL, 32757
Cindy Certified
2676 GIARDINO LOOP, KISSIMMEE, FL, 34741, Kissimmee, FL 34741
$349,000

3 beds

|

3 baths

|

1,700 sq ft

|

Townhouse

2676 GIARDINO LOOP, KISSIMMEE, FL, 34741
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