Call us at (689) 407-5757 to learn more about active adult communities near Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale

3,703 homes near Winter Garden

Sort by:

Relevance

Relevance

5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $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
<$100k - $500Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $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 - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 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
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
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 - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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) Stonecrest
<$100k - $500Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 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 (3 reviews) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$300Ks - $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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) Sandpiper Golf & Coun...
$200Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $500Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
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.
5 rating (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
No reviews yet Breakaway Trails
$400Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
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
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Traditions at Lake Ruby 2733 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$369,000

3 beds

|

3 baths

|

2,032 sq ft

|

House

2733 ATTWATER LOOP, WINTER HAVEN, FL, 33...
On Top of the World 8530 SW 90TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$150,000

2 beds

|

2 baths

|

1,375 sq ft

|

Villa

8530 SW 90TH ST C, OCALA, FL, 34481
Community: On Top of the World
Pennbrooke Fairways 32901 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$246,000

2 beds

|

2 baths

|

1,331 sq ft

|

House

32901 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Venetian Bay 3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$600,000

3 beds

|

2 baths

|

2,214 sq ft

|

House

3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
SummerGlen 1429 SW 160TH LN, OCALA, FL, 34473, Ocala, FL 34473
$525,000

4 beds

|

3 baths

|

2,864 sq ft

|

House

1429 SW 160TH LN, OCALA, FL, 34473
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2403 NANTUCKET GREEN CT, SUN CITY CENTER..., Sun City Center, FL 33573
$200,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2403 NANTUCKET GREEN CT, SUN CITY CENTER...
Community: Sun City Center
The Villages® 5647 KEY DEER PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163
$799,900

3 beds

|

2 baths

|

1,971 sq ft

|

House

5647 KEY DEER PATH, THE VILLAGES, FL, 32...
Community: The Villages®
On Top of the World 8885 SW 90TH LN, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

1,688 sq ft

|

Villa

8885 SW 90TH LN, OCALA, FL, 34481
Community: On Top of the World
Gatherings of Lake Nona 7565 LAUREATE BLVD UNIT 3308, ORLANDO, F..., Orlando, FL 32827
$379,000

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7565 LAUREATE BLVD UNIT 3308, ORLANDO, F...
Sun City Center 1420 EMERALD DUNES DR # 7, SUN CITY CENT..., Sun City Center, FL 33573
$445,000

3 beds

|

2 baths

|

2,482 sq ft

|

Condo

1420 EMERALD DUNES DR # 7, SUN CITY CENT...
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 1503 COUNCIL DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$250,000

2 beds

|

2 baths

|

1,346 sq ft

|

House

1503 COUNCIL DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
The Villages® 1717 LILLY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$259,000

2 beds

|

2 baths

|

1,856 sq ft

|

Manufactured Home

1717 LILLY LN, LADY LAKE, FL, 32159
Community: The Villages®
Sun City Center 1901 CANTERBURY LN 19, SUN CITY CENTER, ..., Sun City Center, FL 33573
$122,500

2 beds

|

2 baths

|

960 sq ft

|

Condo

1901 CANTERBURY LN 19, SUN CITY CENTER, ...
Community: Sun City Center
Twin Lakes 2768 BUCKEYE LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$335,000

2 beds

|

2 baths

|

1,321 sq ft

|

Villa

2768 BUCKEYE LN, SAINT CLOUD, FL, 34772
Community: Twin Lakes
Sun City Center 1226 HUNTINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$260,000

2 beds

|

2 baths

|

1,195 sq ft

|

Condo

1226 HUNTINGTON GREENS DR, SUN CITY CENT...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 335 LOGAN ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$319,900

2 beds

|

2 baths

|

1,266 sq ft

|

House

335 LOGAN ST, THE VILLAGES, FL, 32163
Community: The Villages®
Pelican Bay Daytona Beach 289 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$389,000

3 beds

|

4 baths

|

2,196 sq ft

|

House

289 GULL DR, DAYTONA BEACH, FL, 32119
Four Seasons at Orlando 2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$379,990

2 beds

|

2 baths

|

1,778 sq ft

|

House

2160 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Twin Lakes 2717 GREENLANDS ST, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34772
$515,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

2717 GREENLANDS ST, SAINT CLOUD, FL, 347...
Community: Twin Lakes
Trilogy® Orlando 112 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$313,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

112 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
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.
Lake Ashton 4276 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$625,000

2 beds

|

2 baths

|

2,328 sq ft

|

House

4276 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
SummerGlen 15692 SW 16TH TER, OCALA, FL, 34473, Ocala, FL 34473
$245,000

3 beds

|

2 baths

|

1,647 sq ft

|

House

15692 SW 16TH TER, OCALA, FL, 34473
Community: SummerGlen
Spruce Creek South 17747 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$249,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

17747 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Stonecrest 17520 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$329,000

2 beds

|

2 baths

|

1,402 sq ft

|

House

17520 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Highland Lakes 26740 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$225,000

2 beds

|

2 baths

|

1,293 sq ft

|

Villa

26740 CASH CT, LEESBURG, FL, 34748
Community: Highland Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Four Seasons at Orlando 1855 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$350,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1855 FLORA PASS PL, KISSIMMEE, FL, 34747
Solivita 572 SIENNA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

572 SIENNA DR, POINCIANA, FL, 34759
Community: Solivita
Tarawood 10494 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436
$269,900

3 beds

|

2 baths

|

1,185 sq ft

|

House

10494 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
Valencia Lakes 4963 SAPPHIRE SOUND DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$475,000

3 beds

|

3 baths

|

2,437 sq ft

|

House

4963 SAPPHIRE SOUND DR, WIMAUMA, FL, 335...
Community: Valencia Lakes
Ocala Preserve 3637 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$470,000

3 beds

|

4 baths

|

2,341 sq ft

|

House

3637 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
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 703 RUTGERS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$290,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

703 RUTGERS PL, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Pine Run Estates 10161 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$169,500

3 beds

|

2 baths

|

1,456 sq ft

|

House

10161 SW 87TH TER, OCALA, FL, 34481
Community: Pine Run Estates
Tampa Bay Golf and Country Club 29405 COCHITI LAKE DR, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$349,900

3 beds

|

2 baths

|

1,731 sq ft

|

House

29405 COCHITI LAKE DR, SAN ANTONIO, FL, ...
SummerGlen 1690 SW 158TH LN, OCALA, FL, 34473, Ocala, FL 34473
$279,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

1690 SW 158TH LN, OCALA, FL, 34473
Community: SummerGlen
Sun City Center 2035 HAMPSTEAD CIR # 275, SUN CITY CENTE..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,378 sq ft

|

Condo

2035 HAMPSTEAD CIR # 275, SUN CITY CENTE...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 217 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$463,000

3 beds

|

3 baths

|

2,319 sq ft

|

House

217 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Highlands Ridge 3218 E ANGLERS STRM, AVON PARK, FL, 3382..., Avon Park, FL 33825
$262,000

2 beds

|

2 baths

|

1,315 sq ft

|

House

3218 E ANGLERS STRM, AVON PARK, FL, 3382...
Community: Highlands Ridge
Sullivan Ranch 30308 LIPIZZAN TER, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$310,000

3 beds

|

2 baths

|

1,769 sq ft

|

Villa

30308 LIPIZZAN TER, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
The Villages® 879 ASTOR WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$409,900

3 beds

|

2 baths

|

1,861 sq ft

|

House

879 ASTOR WAY, THE VILLAGES, FL, 32162
Community: The Villages®
Stone Creek 9395 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$477,000

3 beds

|

3 baths

|

2,280 sq ft

|

House

9395 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek

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
3,703 homes near Winter Garden
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.
© 2025 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: Nov 02, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top