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 47

3,769 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
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
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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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
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
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.
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Cresswind Lakewood Ranch
$400ks - $700ks
Cresswind Lakewood Ranch, Lakewood Ranch, FL
New and Resale | 55+ age-restricted | Built 2018 - present | 648 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
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.
123...4
Cindy Certified
7563 BENT TREE LOOP, ST CLOUD, FL, 34771, St Cloud, FL 34771
$381,900

3 beds

|

2 baths

|

1,515 sq ft

|

House

7563 BENT TREE LOOP, ST CLOUD, FL, 34771
Royal Highlands 5506 PRINCE CHARLES LN, LEESBURG, FL, 34..., Leesburg, FL 34748
$379,000

3 beds

|

2 baths

|

1,895 sq ft

|

House

5506 PRINCE CHARLES LN, LEESBURG, FL, 34...
Community: Royal Highlands
Ocala Palms 2515 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$319,900

3 beds

|

2 baths

|

2,399 sq ft

|

House

2515 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Cresswind at Victoria Gardens 309 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724
$499,800

3 beds

|

2 baths

|

2,240 sq ft

|

House

309 BELLINGRATH TER, DELAND, FL, 32724
The Country Club of Mount Dora 8051 SAINT JAMES WAY, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$385,000

3 beds

|

2 baths

|

2,562 sq ft

|

House

8051 SAINT JAMES WAY, MOUNT DORA, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
1539 ASPEN AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$349,900

4 beds

|

2 baths

|

1,850 sq ft

|

House

1539 ASPEN AVE, DAVENPORT, FL, 33837
Venetian Bay 3354 MONACO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$449,990

3 beds

|

2 baths

|

2,066 sq ft

|

House

3354 MONACO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Stonecrest 11137 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$315,900

3 beds

|

2 baths

|

1,695 sq ft

|

House

11137 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 1942 DETWILER LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$349,111

2 beds

|

2 baths

|

1,299 sq ft

|

Villa

1942 DETWILER LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Venetian Bay 3331 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$649,000

3 beds

|

2 baths

|

1,908 sq ft

|

House

3331 BELLINO BLVD, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
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.
On Top of the World 9042 SW 102ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$235,000

2 beds

|

2 baths

|

1,225 sq ft

|

House

9042 SW 102ND CIR, OCALA, FL, 34481
Community: On Top of the World
Stonecrest 12421 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$425,000

3 beds

|

2 baths

|

1,945 sq ft

|

House

12421 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Latitude Margaritaville 509 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$429,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

509 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Valencia del Sol 4838 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$509,000

3 beds

|

3 baths

|

2,252 sq ft

|

House

4838 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
On Top of the World 10529 SW 96TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$652,240

3 beds

|

2 baths

|

2,678 sq ft

|

House

10529 SW 96TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
Cindy Certified
286 BECKENHAM DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$305,000

4 beds

|

2 baths

|

1,811 sq ft

|

House

286 BECKENHAM DR, KISSIMMEE, FL, 34758
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
280 BECKENHAM DR, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$315,000

4 beds

|

2 baths

|

1,640 sq ft

|

House

280 BECKENHAM DR, KISSIMMEE, FL, 34758
Sun City Center 1050 REGAL MANOR WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$285,000

2 beds

|

2 baths

|

1,412 sq ft

|

House

1050 REGAL MANOR WAY, SUN CITY CENTER, F...
Community: Sun City Center
On Top of the World 7847 SW 82ND PL, OCALA, FL, 34476, Ocala, FL 34476
$310,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

7847 SW 82ND PL, OCALA, FL, 34476
Community: On Top of the World
Sun City Center 2027 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$395,000

3 beds

|

2 baths

|

2,370 sq ft

|

House

2027 NEW BEDFORD 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.
Summit Greens 809 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711
$309,000

3 beds

|

2 baths

|

1,721 sq ft

|

House

809 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
Cindy Certified
4313 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482
$330,000

4 beds

|

2 baths

|

2,034 sq ft

|

House

4313 NW 55TH CT, OCALA, FL, 34482
Majestic Oaks Ocala 8598 SW 56TH AVENUE RD, OCALA, FL, 34476, Ocala, FL 34476
$299,000

4 beds

|

2 baths

|

2,537 sq ft

|

House

8598 SW 56TH AVENUE RD, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Venetian Bay 424 LUNA BELLA LN 330, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$325,000

3 beds

|

3 baths

|

1,953 sq ft

|

Condo

424 LUNA BELLA LN 330, NEW SMYRNA BEACH,...
Community: Venetian Bay
Sun City Center 2611 LANCASTER DR 33, SUN CITY CENTER, F..., Sun City Center, FL 33573
$180,900

2 beds

|

2 baths

|

1,579 sq ft

|

Condo

2611 LANCASTER DR 33, SUN CITY CENTER, F...
Community: Sun City Center
Ocala Palms 5815 NW 21ST ST, OCALA, FL, 34482, Ocala, FL 34482
$334,900

3 beds

|

2 baths

|

1,525 sq ft

|

House

5815 NW 21ST ST, OCALA, FL, 34482
Community: Ocala Palms
Stone Creek 9557 SW 64TH LN, OCALA, FL, 34481, Ocala, FL 34481
$394,400

3 beds

|

2 baths

|

2,179 sq ft

|

House

9557 SW 64TH LN, 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® 716 TRUMAN AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$234,900

2 beds

|

1 baths

|

1,124 sq ft

|

House

716 TRUMAN AVE, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 1388 VIOLA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$279,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1388 VIOLA CT, THE VILLAGES, FL, 32163
Community: The Villages®
Ocala Palms 5450 NW 25TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$299,900

3 beds

|

2 baths

|

2,314 sq ft

|

House

5450 NW 25TH LOOP, 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.
Pine Run Estates 10731 SW 102ND LN, OCALA, FL, 34481, Ocala, FL 34481
$464,845

2 beds

|

2 baths

|

2,019 sq ft

|

House

10731 SW 102ND LN, OCALA, FL, 34481
Community: Pine Run Estates
Cindy Certified
16491 GLASSY LOCH LOOP, CLERMONT, FL, 34..., Clermont, FL 34714
$404,990

4 beds

|

2 baths

|

1,936 sq ft

|

House

16491 GLASSY LOCH LOOP, CLERMONT, FL, 34...
Pine Run Estates 8972 SW 103RD LN, OCALA, FL, 34481, Ocala, FL 34481
$159,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

8972 SW 103RD LN, OCALA, FL, 34481
Community: Pine Run Estates
Del Webb Lakehaven 6838 CREEK FALLS ALY, CLERMONT, FL, 3471..., Clermont, FL 34714
$494,610

5 beds

|

3 baths

|

2,231 sq ft

|

House

6838 CREEK FALLS ALY, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Del Webb Lakehaven 6834 CREEK FALLS ALY, CLERMONT, FL, 3471..., Clermont, FL 34714
$476,590

4 beds

|

3 baths

|

1,896 sq ft

|

House

6834 CREEK FALLS ALY, CLERMONT, FL, 3471...
Community: Del Webb Lakehaven
Cindy Certified
3184 ROYAL TERN DR, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$286,900

3 beds

|

2 baths

|

1,725 sq ft

|

House

3184 ROYAL TERN DR, WINTER HAVEN, FL, 33...
Cresswind at Victoria Gardens 1365 BRAYFORD PT, DELAND, FL, 32724, Deland, FL 32724
$420,000

3 beds

|

2 baths

|

1,820 sq ft

|

House

1365 BRAYFORD PT, DELAND, FL, 32724
Gatherings of Lake Nona 7521 LAUREATE BLVD 5403, ORLANDO, FL, 32..., Orlando, FL 32827
$425,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7521 LAUREATE BLVD 5403, ORLANDO, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
2456 BATES AVE SW, WINTER HAVEN, FL, 338..., Winter Haven, FL 33880
$249,900

3 beds

|

2 baths

|

1,232 sq ft

|

House

2456 BATES AVE SW, WINTER HAVEN, FL, 338...
On Top of the World 7981 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$299,000

3 beds

|

2 baths

|

2,062 sq ft

|

House

7981 SW 81ST LOOP, OCALA, FL, 34476
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.

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
3,769 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: Aug 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