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 11

3,495 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) VillageWalk at Lake Nona
$300Ks - $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
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
Ocala Palms 2083 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482
$259,000

2 beds

|

2 baths

|

1,731 sq ft

|

House

2083 NW 57TH CT, OCALA, FL, 34482
Community: Ocala Palms
New Solivita 461 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759
$263,000

2 beds

|

2 baths

|

1,548 sq ft

|

House

461 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
Latitude Margaritaville 233 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$519,900

2 beds

|

2 baths

|

1,768 sq ft

|

House

233 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Plantation at Leesburg 5712 SUMMERBROOKE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$525,000

3 beds

|

3 baths

|

2,961 sq ft

|

House

5712 SUMMERBROOKE CT, LEESBURG, FL, 3474...
Latitude Margaritaville 765 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$939,900

3 beds

|

3 baths

|

2,493 sq ft

|

House

765 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 3862 NW 49TH CT, OCALA, FL, 34482, Ocala, FL 34482
$550,000

3 beds

|

3 baths

|

2,455 sq ft

|

House

3862 NW 49TH CT, OCALA, FL, 34482
Community: Ocala Preserve
New The Villages® 3017 BATALLY CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$435,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

3017 BATALLY CT, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 501 HEARTWELL DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$315,000

2 beds

|

2 baths

|

1,574 sq ft

|

House

501 HEARTWELL DR, POINCIANA, FL, 34759
Community: Solivita
On Top of the World 9436 SW 97TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$320,000

2 beds

|

2 baths

|

1,716 sq ft

|

House

9436 SW 97TH AVE, 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.
Solivita 2009 LAZIO LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759
$259,900

2 beds

|

2 baths

|

1,658 sq ft

|

House

2009 LAZIO LOOP, POINCIANA, FL, 34759
Community: Solivita
Sun City Center 906 HACIENDA DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$249,900

2 beds

|

1 baths

|

1,344 sq ft

|

House

906 HACIENDA DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
The Villages® 1057 CARVER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$329,900

2 beds

|

2 baths

|

1,270 sq ft

|

Villa

1057 CARVER CT, THE VILLAGES, FL, 32163
Community: The Villages®
New Harbor Hills Country Club 38912 HARBORWOODS PL, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$599,000

3 beds

|

3 baths

|

2,457 sq ft

|

House

38912 HARBORWOODS PL, LADY LAKE, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New Esplanade at Wiregrass Ranch 4739 GAROFALO RD, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543
$484,900

2 beds

|

2 baths

|

1,689 sq ft

|

House

4739 GAROFALO RD, WESLEY CHAPEL, FL, 335...
Palm Cay 8449 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$172,000

2 beds

|

2 baths

|

1,114 sq ft

|

House

8449 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Palm Cay 8326 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481
$205,000

3 beds

|

2 baths

|

1,404 sq ft

|

House

8326 SW 107TH PL, OCALA, FL, 34481
Community: Palm Cay
New Palm Cay 8305 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481
$249,000

3 beds

|

2 baths

|

1,404 sq ft

|

House

8305 SW 107TH PL, OCALA, FL, 34481
Community: Palm Cay
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 8329 SW 106TH ST, OCALA, FL, 34481, Ocala, FL 34481
$169,000

2 beds

|

2 baths

|

864 sq ft

|

House

8329 SW 106TH ST, OCALA, FL, 34481
Community: Palm Cay
Palm Cay 8274 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$161,000

2 beds

|

1 baths

|

768 sq ft

|

House

8274 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Spruce Creek Country Club 9369 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$349,000

2 beds

|

2 baths

|

1,649 sq ft

|

House

9369 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Pennbrooke Fairways 651 TIMBERCREST DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$198,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

651 TIMBERCREST 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
New Highlands Ridge 2701 E WATERVIEW DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$147,900

2 beds

|

2 baths

|

1,600 sq ft

|

Mobile Home

2701 E WATERVIEW DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
New Sandpiper Golf & Country Club 6380 EGRET DR 19, LAKELAND, FL, 33809, Lakeland, FL 33809
$229,900

2 beds

|

2 baths

|

1,228 sq ft

|

House

6380 EGRET DR 19, LAKELAND, FL, 33809
Majestic Oaks Ocala 8895 SW 57TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$288,800

3 beds

|

2 baths

|

1,864 sq ft

|

House

8895 SW 57TH COURT RD, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Ocala Palms 5063 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$209,000

2 beds

|

2 baths

|

1,207 sq ft

|

House

5063 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
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.
Twin Lakes 2410 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$369,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2410 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
On Top of the World 7980 SW 87TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$259,900

2 beds

|

2 baths

|

1,224 sq ft

|

House

7980 SW 87TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Four Seasons at Orlando 1598 WHITEWOOD CT, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$490,000

3 beds

|

2 baths

|

2,066 sq ft

|

House

1598 WHITEWOOD CT, KISSIMMEE, FL, 34747
Stonecrest 10952 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$340,000

3 beds

|

2 baths

|

1,476 sq ft

|

House

10952 SE 169TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
New Stone Creek 9652 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$243,342

2 beds

|

2 baths

|

1,367 sq ft

|

House

9652 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 9653 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162
$337,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9653 SE 171ST ARGYLL ST, THE VILLAGES, F...
Community: The Villages®
The Villages® 2630 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$365,000

3 beds

|

2 baths

|

1,674 sq ft

|

House

2630 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 923 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159
$339,900

3 beds

|

2 baths

|

1,527 sq ft

|

House

923 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
The Villages® 2940 GULLEY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$459,900

3 beds

|

2 baths

|

1,525 sq ft

|

Villa

2940 GULLEY LN, THE VILLAGES, FL, 32163
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.
The Villages® 849 YEMASSEE LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$389,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

849 YEMASSEE LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 2921 EVINSTON CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$600,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

2921 EVINSTON CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Del Webb Sunbridge 2479 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771
$575,000

3 beds

|

2 baths

|

2,054 sq ft

|

House

2479 PINE PRESERVE CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
Spruce Creek Country Club 9573 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$319,000

2 beds

|

2 baths

|

1,708 sq ft

|

House

9573 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Heritage Hills 3808 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$380,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

3808 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Spruce Creek North 6468 SW 107TH PL, OCALA, FL, 34476, Ocala, FL 34476
$179,900

2 beds

|

2 baths

|

1,095 sq ft

|

House

6468 SW 107TH PL, OCALA, FL, 34476
Community: Spruce Creek North

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
3,495 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 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