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 30

3,218 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
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
4.5 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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
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 - $300ks
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
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
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) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
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
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
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
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
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.
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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) 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 (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 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.
12...3
The Villages® 3746 NEW MOON AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163
$478,788

3 beds

|

2 baths

|

1,905 sq ft

|

House

3746 NEW MOON AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Stone Creek 5481 SW 92ND AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481
$604,000

2 beds

|

2 baths

|

2,049 sq ft

|

House

5481 SW 92ND AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
Twin Lakes 2764 GREENLANDS ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$615,500

3 beds

|

3 baths

|

2,208 sq ft

|

House

2764 GREENLANDS ST, ST CLOUD, FL, 34772
Community: Twin Lakes
On Top of the World 10363 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$292,900

2 beds

|

2 baths

|

1,342 sq ft

|

House

10363 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Latitude Margaritaville 408 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$459,777

2 beds

|

2 baths

|

1,509 sq ft

|

House

408 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8386 SW 90TH CT, OCALA, FL, 34481, Ocala, FL 34481
$624,900

4 beds

|

3 baths

|

2,893 sq ft

|

House

8386 SW 90TH CT, OCALA, FL, 34481
Community: On Top of the World
Royal Harbor 4962 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778
$285,000

3 beds

|

2 baths

|

1,489 sq ft

|

House

4962 RAINBOW TROUT RD, TAVARES, FL, 3277...
Community: Royal Harbor
On Top of the World 8350 SW 93RD LN D, OCALA, FL, 34481, Ocala, FL 34481
$195,000

2 beds

|

2 baths

|

1,571 sq ft

|

Villa

8350 SW 93RD LN D, OCALA, FL, 34481
Community: On Top of the World
Oak Run 7296 SW 112TH PL, OCALA, FL, 34476, Ocala, FL 34476
$179,900

2 beds

|

2 baths

|

1,121 sq ft

|

House

7296 SW 112TH PL, OCALA, FL, 34476
Community: Oak Run
Southshore Bay 17415 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$475,000

3 beds

|

3 baths

|

2,651 sq ft

|

House

17415 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore 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.
Solivita 118 VISTA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$359,000

2 beds

|

2 baths

|

2,170 sq ft

|

House

118 VISTA DR, POINCIANA, FL, 34759
Community: Solivita
Latitude Margaritaville 768 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$775,000

2 beds

|

3 baths

|

2,160 sq ft

|

House

768 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Four Seasons at Orlando 1981 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$675,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

1981 FLORA PASS PL, KISSIMMEE, FL, 34747
Ocala Palms 1927 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$465,000

4 beds

|

3 baths

|

2,550 sq ft

|

House

1927 NW 50TH CIR, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 201 KINGS BLVD 5, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$93,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

201 KINGS BLVD 5, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Trilogy® Orlando 187 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736
$447,000

2 beds

|

2 baths

|

2,570 sq ft

|

House

187 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9687 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$389,900

3 beds

|

2 baths

|

2,411 sq ft

|

House

9687 SE 137TH STREET RD, SUMMERFIELD, FL...
Stone Creek 9663 SW 76TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$250,000

2 beds

|

2 baths

|

1,425 sq ft

|

House

9663 SW 76TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
The Villages® 8932 SE 168TH SEDGWICK PL, THE VILLAGES,..., The Villages, FL 32162
$300,000

3 beds

|

2 baths

|

1,483 sq ft

|

Villa

8932 SE 168TH SEDGWICK PL, THE VILLAGES,...
Community: The Villages®
The Villages® 1678 GOVAN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$579,000

3 beds

|

2 baths

|

1,978 sq ft

|

Villa

1678 GOVAN PL, THE VILLAGES, FL, 32162
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® 17115 SE 93RD TELLFIER TER, THE VILLAGES..., The Villages, FL 32162
$499,999

3 beds

|

2 baths

|

2,036 sq ft

|

House

17115 SE 93RD TELLFIER TER, THE VILLAGES...
Community: The Villages®
On Top of the World 9994 SW 96TH ST, OCALA, FL, 34481, Ocala, FL 34481
$319,900

3 beds

|

2 baths

|

1,747 sq ft

|

House

9994 SW 96TH ST, OCALA, FL, 34481
Community: On Top of the World
JB Ranch 6265 SW 88 LOOP, OCALA, FL, 34476, Ocala, FL 34476
$329,500

4 beds

|

2 baths

|

2,039 sq ft

|

House

6265 SW 88 LOOP, OCALA, FL, 34476
Community: JB Ranch
Royal Harbor 3370 SAINT LUCIA CT, TAVARES, FL, 32778, Tavares, FL 32778
$352,900

3 beds

|

2 baths

|

1,893 sq ft

|

House

3370 SAINT LUCIA CT, TAVARES, FL, 32778
Community: Royal Harbor
JB Ranch 9152 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476
$289,900

2 beds

|

2 baths

|

1,815 sq ft

|

Townhouse

9152 SW 60TH COURT RD, OCALA, FL, 34476
Community: JB Ranch
Carlsberg Estates on Lake Suzanne 241 LOURDES ST, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$297,000

2 beds

|

2 baths

|

1,251 sq ft

|

House

241 LOURDES ST, LAKE WALES, FL, 33859
Venetian Bay 424 LUNA BELLA LN 415, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$299,990

2 beds

|

2 baths

|

1,492 sq ft

|

Condo

424 LUNA BELLA LN 415, NEW SMYRNA BEACH,...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 872 WINCHESTER CT, THE VILLAGES, FL, 321..., The Villages, FL 32162
$310,000

2 beds

|

2 baths

|

1,116 sq ft

|

Villa

872 WINCHESTER CT, THE VILLAGES, FL, 321...
Community: The Villages®
Pelican Bay Daytona Beach 100 BLACK CROW CIR 4000, DAYTONA BEACH, ..., Daytona Beach, FL 32119
$289,900

3 beds

|

3 baths

|

1,869 sq ft

|

Condo

100 BLACK CROW CIR 4000, DAYTONA BEACH, ...
Stonecrest 11086 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$250,000

2 beds

|

2 baths

|

1,348 sq ft

|

House

11086 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
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.
Ocala Preserve 4976 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$420,000

2 beds

|

2 baths

|

1,956 sq ft

|

House

4976 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Latitude Margaritaville 616 BEACH BUM BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$714,900

3 beds

|

3 baths

|

2,083 sq ft

|

House

616 BEACH BUM BLVD, DAYTONA BEACH, FL, 3...
Sandpiper Golf & Country Club 5817 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$365,000

3 beds

|

2 baths

|

1,957 sq ft

|

House

5817 SWALLOW DR, LAKELAND, FL, 33809
VillageWalk at Lake Nona 11830 ISELLE DR, ORLANDO, FL, 32827, Orlando, FL 32827
$427,000

2 beds

|

2 baths

|

1,512 sq ft

|

Halfplex

11830 ISELLE DR, ORLANDO, FL, 32827
Latitude Margaritaville 601 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$385,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

601 MARGARITAVILLE AVE, DAYTONA BEACH, F...
SummerGlen 15143 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$265,000

3 beds

|

2 baths

|

1,658 sq ft

|

House

15143 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Plantation at Leesburg 24345 AMBERLEAF CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,900

2 beds

|

2 baths

|

1,898 sq ft

|

House

24345 AMBERLEAF CT, LEESBURG, FL, 34748
The Villages® 17350 SE 77TH SYCAMORE AVE, THE VILLAGES..., The Villages, FL 32162
$249,900

2 beds

|

1 baths

|

1,071 sq ft

|

Villa

17350 SE 77TH SYCAMORE AVE, THE VILLAGES...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 17300 SE 93RD HEYWARD AVE, THE VILLAGES,..., The Villages, FL 32162
$258,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17300 SE 93RD HEYWARD AVE, THE VILLAGES,...
Community: The Villages®
The Villages® 1672 GUMWOOD DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$424,000

3 beds

|

2 baths

|

1,621 sq ft

|

House

1672 GUMWOOD DR, THE VILLAGES, FL, 32162
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.

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
3,218 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: Jul 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