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 70

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
Kings Ridge 2535 NEW CASTLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$359,000

2 beds

|

2 baths

|

1,930 sq ft

|

House

2535 NEW CASTLE CT, CLERMONT, FL, 34711
Community: Kings Ridge
Highlands Ridge 2832 S DRIFTWOOD CT, AVON PARK, FL, 3382..., Avon Park, FL 33825
$123,000

2 beds

|

2 baths

|

1,378 sq ft

|

Mobile Home

2832 S DRIFTWOOD CT, AVON PARK, FL, 3382...
Community: Highlands Ridge
Lakes at Laurel Highlands 2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$380,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Heritage Landings 2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$380,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
Spruce Creek Preserve 13834 SW 114TH AVE, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$305,000

3 beds

|

2 baths

|

1,760 sq ft

|

House

13834 SW 114TH AVE, DUNNELLON, FL, 34432
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8868 SW 97TH LANE RD G, OCALA, FL, 34481, Ocala, FL 34481
$162,900

2 beds

|

2 baths

|

1,314 sq ft

|

Condo

8868 SW 97TH LANE RD G, OCALA, FL, 34481
Community: On Top of the World
The Villages® 631 ENCONTO ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$319,000

2 beds

|

2 baths

|

1,128 sq ft

|

Villa

631 ENCONTO ST, THE VILLAGES, FL, 32159
Community: The Villages®
Heritage Hills 3557 BELLAND CIR D, CLERMONT, FL, 34711, Clermont, FL 34711
$240,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3557 BELLAND CIR D, CLERMONT, FL, 34711
Community: Heritage Hills
Venetian Bay 354 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$339,000

3 beds

|

2 baths

|

1,520 sq ft

|

House

354 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Solivita 677 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$449,900

3 beds

|

3 baths

|

2,235 sq ft

|

House

677 VIA CORSO CT, KISSIMMEE, FL, 34759
Community: Solivita
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.
Harbor Hills Country Club 39819 GROVE HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$499,990

3 beds

|

2 baths

|

2,504 sq ft

|

House

39819 GROVE HEIGHTS, LADY LAKE, FL, 3215...
The Villages® 1568 BLACK LAKE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$2,195,000

4 beds

|

5 baths

|

4,654 sq ft

|

House

1568 BLACK LAKE DR, THE VILLAGES, FL, 32...
Community: The Villages®
Ocala Preserve 5341 NW 48TH PL, OCALA, FL, 34482, Ocala, FL 34482
$285,000

3 beds

|

2 baths

|

1,552 sq ft

|

Villa

5341 NW 48TH PL, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 5565 NW 43RD LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$554,900

3 beds

|

3 baths

|

2,348 sq ft

|

House

5565 NW 43RD LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Solivita 2472 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$289,900

3 beds

|

2 baths

|

1,539 sq ft

|

Villa

2472 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 3499 AUBURNDALE AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$315,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

3499 AUBURNDALE AVE, THE VILLAGES, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Tohoqua Reserve 1881 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$355,000

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

1881 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Heritage Hills 3550 FAIRWATERS CT C, CLERMONT, FL, 3471..., Clermont, FL 34711
$289,990

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3550 FAIRWATERS CT C, CLERMONT, FL, 3471...
Community: Heritage Hills
Stonecrest 11351 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$269,500

3 beds

|

2 baths

|

1,717 sq ft

|

House

11351 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek Country Club 8955 SE 118TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$318,500

2 beds

|

2 baths

|

2,270 sq ft

|

House

8955 SE 118TH LN, SUMMERFIELD, FL, 34491
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 13324 SE 91ST COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$342,000

2 beds

|

2 baths

|

1,870 sq ft

|

House

13324 SE 91ST COURT RD, SUMMERFIELD, FL,...
Stonecrest 17187 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$479,900

3 beds

|

3 baths

|

2,026 sq ft

|

House

17187 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
Stone Creek 5472 SW 85TH AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481
$285,000

2 beds

|

2 baths

|

1,433 sq ft

|

House

5472 SW 85TH AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
Alhambra Villas Condominiums 249 N HILL AVE 30, DELAND, FL, 32724, Deland, FL 32724
$186,500

2 beds

|

2 baths

|

1,043 sq ft

|

Condo

249 N HILL AVE 30, DELAND, FL, 32724
Traditions at Lake Ruby 2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$284,500

3 beds

|

2 baths

|

2,109 sq ft

|

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884
Pelican Bay Daytona Beach 196 GRAY DOVE CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119
$264,000

3 beds

|

3 baths

|

1,833 sq ft

|

Townhouse

196 GRAY DOVE CT, DAYTONA BEACH, FL, 321...
Heritage Hills 3201 SONESTA CT A, CLERMONT, FL, 34711, Clermont, FL 34711
$279,500

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3201 SONESTA CT A, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 8516 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,296 sq ft

|

House

8516 SE 137TH LOOP, SUMMERFIELD, FL, 344...
The Villages® 304 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$299,000

2 beds

|

2 baths

|

1,360 sq ft

|

House

304 SAN MARINO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Four Seasons at Orlando 7661 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747
$424,900

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

7661 SAND PIERRE CT, KISSIMMEE, FL, 3474...
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 4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34..., St Cloud, FL 34772
$450,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4909 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...
Community: Twin Lakes
Spruce Creek Country Club 9685 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$299,000

2 beds

|

2 baths

|

1,873 sq ft

|

House

9685 SE 136TH PL, SUMMERFIELD, FL, 34491
Tampa Bay Golf and Country Club 29636 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$305,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

29636 TEE SHOT DR, SAN ANTONIO, FL, 3357...
Lake Ashton 5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$340,000

2 beds

|

2 baths

|

1,677 sq ft

|

House

5197 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Sun City Center 2608 NEWCOMB CT 2608, SUN CITY CENTER, F..., Sun City Center, FL 33573
$180,000

2 beds

|

2 baths

|

1,645 sq ft

|

Condo

2608 NEWCOMB CT 2608, SUN CITY CENTER, F...
Community: Sun City Center
Sandpiper Golf & Country Club 664 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$249,900

2 beds

|

2 baths

|

1,456 sq ft

|

House

664 EAGLE RUN, LAKELAND, FL, 33809
On Top of the World 9972 SW 106TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$463,555

2 beds

|

2 baths

|

2,019 sq ft

|

House

9972 SW 106TH CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9714 SW 108TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481
$324,320

2 beds

|

2 baths

|

1,343 sq ft

|

House

9714 SW 108TH TERRACE RD, OCALA, FL, 344...
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
Trilogy® Orlando 189 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736
$369,900

3 beds

|

2 baths

|

1,820 sq ft

|

House

189 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
VillageWalk at Lake Nona 11932 LORENZA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

11932 LORENZA LN, ORLANDO, FL, 32827
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