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 41

3,654 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
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
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 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
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.
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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
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) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 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.
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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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.
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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.
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
12...3
Del Webb Sunbridge 2707 RIVER CREEK LN, ST CLOUD, FL, 34769, St Cloud, FL 34769
$529,000

2 beds

|

2 baths

|

1,670 sq ft

|

House

2707 RIVER CREEK LN, ST CLOUD, FL, 34769
Community: Del Webb Sunbridge
On Top of the World 9936 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$430,765

2 beds

|

2 baths

|

1,718 sq ft

|

House

9936 SW 106TH CIR, OCALA, FL, 34481
Community: On Top of the World
Valencia del Sol 15452 SANTA POLA DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$374,900

2 beds

|

2 baths

|

1,599 sq ft

|

House

15452 SANTA POLA DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
On Top of the World 9918 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$508,000

2 beds

|

3 baths

|

2,493 sq ft

|

House

9918 SW 106TH CIR, OCALA, FL, 34481
Community: On Top of the World
Thunderbird Hill 3810 THUNDERBIRD HILL CIR, SEBRING, FL, ..., Sebring, FL 33872
$174,900

2 beds

|

2 baths

|

1,242 sq ft

|

Villa

3810 THUNDERBIRD HILL CIR, SEBRING, FL, ...
Community: Thunderbird Hill
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates 10634 SW 101ST LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$445,525

2 beds

|

2 baths

|

2,019 sq ft

|

House

10634 SW 101ST LANE RD, OCALA, FL, 34481
Community: Pine Run Estates
Pine Run Estates 10563 SW 101ST LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$451,465

2 beds

|

2 baths

|

2,142 sq ft

|

House

10563 SW 101ST LANE RD, OCALA, FL, 34481
Community: Pine Run Estates
Cherrywood 9958 SW 59TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$214,000

3 beds

|

2 baths

|

1,363 sq ft

|

House

9958 SW 59TH CIR, OCALA, FL, 34476
Community: Cherrywood
Carillon Lakes 3891 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$310,000

3 beds

|

2 baths

|

1,758 sq ft

|

House

3891 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
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.
Pine Run Estates 10602 SW 101ST LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$463,645

2 beds

|

2 baths

|

2,142 sq ft

|

House

10602 SW 101ST LANE RD, OCALA, FL, 34481
Community: Pine Run Estates
Traditions at Lake Ruby 3588 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$274,995

2 beds

|

2 baths

|

1,719 sq ft

|

House

3588 RALEIGH DR, WINTER HAVEN, FL, 33884
Arlington Ridge 4506 SHENANDOAH RIVER TRL, LEESBURG, FL,..., Leesburg, FL 34748
$354,900

3 beds

|

2 baths

|

1,711 sq ft

|

House

4506 SHENANDOAH RIVER TRL, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 2610 LINDEWOOD ST, THE VILLAGES, FL, 321..., The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,620 sq ft

|

Villa

2610 LINDEWOOD ST, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 5375 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$284,900

3 beds

|

2 baths

|

1,514 sq ft

|

House

5375 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
Stonecrest 11266 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$409,999

3 beds

|

2 baths

|

1,987 sq ft

|

House

11266 SE 170TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Ocala Palms 5888 NW 21ST ST, OCALA, FL, 34482, Ocala, FL 34482
$264,900

2 beds

|

2 baths

|

1,697 sq ft

|

House

5888 NW 21ST ST, OCALA, FL, 34482
Community: Ocala Palms
On Top of the World 9325 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$314,900

2 beds

|

2 baths

|

1,342 sq ft

|

House

9325 SW 106TH 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.
Palms at Serenoa 17718 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

2 beds

|

2 baths

|

1,816 sq ft

|

House

17718 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Sullivan Ranch 22019 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$270,000

3 beds

|

2 baths

|

1,663 sq ft

|

Villa

22019 BELGIAN CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Palm Cay 7561 SW 76TH TER, OCALA, FL, 34481, Ocala, FL 34481
$318,900

4 beds

|

3 baths

|

2,039 sq ft

|

House

7561 SW 76TH TER, OCALA, FL, 34481
Community: Palm Cay
Stone Creek 9256 SW 66TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$399,000

3 beds

|

2 baths

|

1,736 sq ft

|

House

9256 SW 66TH 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
Highland Fairways 3542 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810
$247,000

2 beds

|

2 baths

|

1,420 sq ft

|

House

3542 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
The Villages® 5685 ZEBRA LONGWING PATH, THE VILLAGES, ..., The Villages, FL 32163
$500,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

5685 ZEBRA LONGWING PATH, THE VILLAGES, ...
Community: The Villages®
Ocala Palms 1870 NW 56TH TER, OCALA, FL, 34482, Ocala, FL 34482
$325,000

3 beds

|

2 baths

|

1,957 sq ft

|

House

1870 NW 56TH TER, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 2531 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$261,900

2 beds

|

2 baths

|

1,579 sq ft

|

Condo

2531 LANCASTER 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.
Sun City Center 1723 WOLF LAUREL DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$332,000

2 beds

|

2 baths

|

2,031 sq ft

|

House

1723 WOLF LAUREL DR, SUN CITY CENTER, FL...
Community: Sun City Center
The Villages® 1270 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

1270 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3508 RIDGEWOOD PATH, THE VILLAGES, FL, 3..., The Villages, FL 32163
$375,000

3 beds

|

2 baths

|

1,561 sq ft

|

House

3508 RIDGEWOOD PATH, THE VILLAGES, FL, 3...
Community: The Villages®
Sun City Center 908 HENDON CT 129, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$139,000

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

908 HENDON CT 129, SUN CITY CENTER, FL, ...
Community: Sun City Center
On Top of the World 8889 SW 96TH ST E, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8889 SW 96TH ST 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
Southshore Bay 16810 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$459,999

2 beds

|

3 baths

|

2,239 sq ft

|

House

16810 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
The Villages® 3024 MACON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$285,000

2 beds

|

2 baths

|

1,270 sq ft

|

Villa

3024 MACON CT, THE VILLAGES, FL, 32162
Community: The Villages®
Sandpiper Golf & Country Club 6140 SEAGULL LN, LAKELAND, FL, 33809, Lakeland, FL 33809
$339,999

3 beds

|

3 baths

|

1,982 sq ft

|

House

6140 SEAGULL LN, LAKELAND, FL, 33809
Sun City Center 2203 OAKLEY GREEN DR 45, SUN CITY CENTER..., Sun City Center, FL 33573
$359,900

2 beds

|

2 baths

|

1,854 sq ft

|

Condo

2203 OAKLEY GREEN DR 45, SUN CITY CENTER...
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.
The Villages® 1120 AVENIDA DE LAS CASAS, THE VILLAGES,..., The Villages, FL 32159
$399,999

2 beds

|

3 baths

|

1,575 sq ft

|

Villa

1120 AVENIDA DE LAS CASAS, THE VILLAGES,...
Community: The Villages®
The Villages® 3698 ROBERTSON WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163
$559,000

3 beds

|

2 baths

|

1,695 sq ft

|

Villa

3698 ROBERTSON WAY, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 7370 SE 167TH ZINA LN, THE VILLAGES, FL,..., The Villages, FL 32162
$368,900

3 beds

|

2 baths

|

1,661 sq ft

|

Villa

7370 SE 167TH ZINA LN, THE VILLAGES, FL,...
Community: The Villages®
Arlington Ridge 3637 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$434,000

3 beds

|

2 baths

|

2,226 sq ft

|

House

3637 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 350 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$659,000

3 beds

|

3 baths

|

2,067 sq ft

|

House

350 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
The Villages® 17340 SE 70TH ROYAL PINE CT, THE VILLAGE..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

17340 SE 70TH ROYAL PINE CT, THE VILLAGE...
Community: The Villages®

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
3,654 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: Apr 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