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 70

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
Sun City Center 2006 GRANTHAM GREENS DR, SUN CITY CENTER..., Sun City Center, FL 33573
$249,900

2 beds

|

2 baths

|

1,855 sq ft

|

Condo

2006 GRANTHAM GREENS DR, SUN CITY CENTER...
Community: Sun City Center
The Villages® 7809 SE 171ST HARLESTON ST, THE VILLAGES..., The Villages, FL 32162
$477,900

3 beds

|

2 baths

|

2,048 sq ft

|

Villa

7809 SE 171ST HARLESTON ST, THE VILLAGES...
Community: The Villages®
Plantation at Leesburg 4960 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,289 sq ft

|

House

4960 HERON RUN CIR, LEESBURG, FL, 34748
The Villages® 1639 ALLENDALE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162
$285,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1639 ALLENDALE PL, THE VILLAGES, FL, 321...
Community: The Villages®
Cindy Certified
1208 TURTLE ISLAND RD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$299,000

3 beds

|

2 baths

|

1,509 sq ft

|

Villa

1208 TURTLE ISLAND RD, LADY LAKE, FL, 32...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 10323 SW 98TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$274,900

2 beds

|

2 baths

|

1,469 sq ft

|

House

10323 SW 98TH PLACE RD, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2604 ALCADE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$374,990

3 beds

|

2 baths

|

1,654 sq ft

|

House

2604 ALCADE PL, THE VILLAGES, FL, 32163
Community: The Villages®
Lake Ashton 4120 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$799,000

3 beds

|

4 baths

|

2,968 sq ft

|

House

4120 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Sun City Center 718 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$299,900

2 beds

|

2 baths

|

1,493 sq ft

|

Villa

718 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Sun City Center 1802 BEDFORD LN 1, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$119,900

2 beds

|

2 baths

|

960 sq ft

|

Condo

1802 BEDFORD LN 1, 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.
Breakaway Trails 5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$579,000

3 beds

|

3 baths

|

2,204 sq ft

|

House

5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174
Community: Breakaway Trails
Sun City Center 2017 HULLHOUSE DR 351, SUN CITY CENTER, ..., Sun City Center, FL 33573
$137,500

2 beds

|

2 baths

|

1,000 sq ft

|

Condo

2017 HULLHOUSE DR 351, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 2623 ASCOT LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$250,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2623 ASCOT LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 209 GENET CT, SUN CITY CENTER, FL, 33573, Sun City Center, FL 33573
$224,900

2 beds

|

2 baths

|

1,180 sq ft

|

House

209 GENET CT, SUN CITY CENTER, FL, 33573
Community: Sun City Center
Enclave at VillageWalk 8591 ADALINA PL, ORLANDO, FL, 32827, Orlando, FL 32827
$1,399,999

5 beds

|

5 baths

|

4,924 sq ft

|

House

8591 ADALINA PL, ORLANDO, FL, 32827
Sun City Center 2020 NANTUCKET DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$190,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2020 NANTUCKET DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 633 MARISOL DR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$630,000

3 beds

|

2 baths

|

2,335 sq ft

|

House

633 MARISOL DR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Cindy Certified
4432 VERMILLION SKY DR, WESLEY CHAPEL, F..., Wesley Chapel, FL 33544
$468,999

3 beds

|

2 baths

|

2,037 sq ft

|

House

4432 VERMILLION SKY DR, WESLEY CHAPEL, F...
Ocala Palms 5340 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$320,000

3 beds

|

2 baths

|

1,719 sq ft

|

House

5340 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
Kings Ridge 3739 HASTING LN, CLERMONT, FL, 34711, Clermont, FL 34711
$354,900

3 beds

|

2 baths

|

1,844 sq ft

|

House

3739 HASTING LN, CLERMONT, FL, 34711
Community: Kings Ridge
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.
Spruce Creek Country Club 9210 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$269,500

3 beds

|

2 baths

|

1,575 sq ft

|

House

9210 SE 118TH LOOP, SUMMERFIELD, FL, 344...
Thunderbird Hill 3914 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872
$192,000

2 beds

|

2 baths

|

1,242 sq ft

|

Villa

3914 SUNBIRD CIR, SEBRING, FL, 33872
Community: Thunderbird Hill
On Top of the World 10345 SW 82ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$569,790

2 beds

|

2 baths

|

2,145 sq ft

|

House

10345 SW 82ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
SummerGlen 15831 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$279,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

15831 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Highlands Ridge 3965 PUMA DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$330,000

2 beds

|

2 baths

|

1,797 sq ft

|

House

3965 PUMA DR, AVON PARK, FL, 33825
Community: Highlands Ridge
The Villages® 1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$465,000

3 beds

|

2 baths

|

1,388 sq ft

|

House

1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1147 ELIZABETH CT, THE VILLAGES, FL, 321..., The Villages, FL 32162
$499,900

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

1147 ELIZABETH CT, 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
Stone Creek 8359 SW 54TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$253,000

3 beds

|

2 baths

|

1,260 sq ft

|

House

8359 SW 54TH LOOP, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 7771 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$298,888

2 beds

|

2 baths

|

1,495 sq ft

|

House

7771 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
Cherrywood 6121 SW 103RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$184,900

2 beds

|

2 baths

|

1,119 sq ft

|

House

6121 SW 103RD LOOP, OCALA, FL, 34476
Community: Cherrywood
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.
Oak Run 10891 SW 89TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$189,999

2 beds

|

2 baths

|

1,432 sq ft

|

House

10891 SW 89TH AVE, OCALA, FL, 34481
Community: Oak Run
Oak Run 11496 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$247,500

2 beds

|

2 baths

|

1,715 sq ft

|

House

11496 SW 82ND COURT RD, OCALA, FL, 34481
Community: Oak Run
Sun City Center 1905 CANTERBURY LN E-9, SUN CITY CENTER,..., Sun City Center, FL 33573
$129,000

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

1905 CANTERBURY LN E-9, SUN CITY CENTER,...
Community: Sun City Center
Valencia Lakes 15939 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$540,000

3 beds

|

4 baths

|

3,018 sq ft

|

House

15939 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Tampa Bay Golf and Country Club 11204 COREY PAVIN LN, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$250,000

2 beds

|

2 baths

|

1,212 sq ft

|

House

11204 COREY PAVIN LN, SAN ANTONIO, FL, 3...
Sun City Center 1801 BEDFORD LN 30, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$77,500

1 beds

|

2 baths

|

800 sq ft

|

Condo

1801 BEDFORD LN 30, SUN CITY CENTER, FL,...
Community: Sun City Center
Cindy Certified
142 TRANQUIL MIRROR LAKE CT 18, CLERMONT..., Clermont, FL 34711
$1,492,545

4 beds

|

3 baths

|

2,974 sq ft

|

House

142 TRANQUIL MIRROR LAKE CT 18, CLERMONT...
Plantation at Leesburg 25312 GREEN HERON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$220,000

2 beds

|

2 baths

|

1,289 sq ft

|

House

25312 GREEN HERON DR, LEESBURG, FL, 3474...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Southshore Bay 17538 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$299,000

2 beds

|

3 baths

|

1,737 sq ft

|

Townhouse

17538 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Lake Ashton 4152 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$488,900

3 beds

|

2 baths

|

2,255 sq ft

|

House

4152 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
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