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

3,584 homes near Winter Garden

Sort by:

Relevance

Relevance

No reviews yet Del Webb Oasis
$400Ks - $1Ms
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $2Ms
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 - $600Ks
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 (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $500Ks
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 - $400Ks
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
$200Ks - $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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $600Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $1Ms
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.
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 - $900Ks
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
$100Ks - $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 - $400Ks
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 - $400Ks
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
$300Ks - $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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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
The Villages® 2136 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$305,000

2 beds

|

2 baths

|

1,135 sq ft

|

Villa

2136 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Solivita 164 TORINO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$639,000

2 beds

|

3 baths

|

2,343 sq ft

|

House

164 TORINO LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 145 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$245,999

2 beds

|

2 baths

|

1,102 sq ft

|

House

145 PALAZZO LN, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 3218 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$674,900

4 beds

|

2 baths

|

2,239 sq ft

|

House

3218 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Sun City Center 1808 MILFORD CIR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$283,900

3 beds

|

2 baths

|

1,662 sq ft

|

House

1808 MILFORD CIR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$479,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
Sun City Center 1207 HUNTINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$274,900

2 beds

|

2 baths

|

1,318 sq ft

|

Condo

1207 HUNTINGTON GREENS DR, SUN CITY CENT...
Community: Sun City Center
Colonnades 4865 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$189,500

2 beds

|

2 baths

|

1,170 sq ft

|

Manufactured Home

4865 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Pelican Bay Daytona Beach 128 GOLDEN EYE DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$249,900

3 beds

|

2 baths

|

1,376 sq ft

|

Condo

128 GOLDEN EYE DR B, DAYTONA BEACH, FL, ...
Marion Landing 6548 SW 84TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$225,000

2 beds

|

2 baths

|

1,721 sq ft

|

House

6548 SW 84TH PLACE RD, OCALA, FL, 34476
Community: Marion Landing
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 8738 SW 95TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$164,900

2 beds

|

2 baths

|

1,644 sq ft

|

Villa

8738 SW 95TH LN B, OCALA, FL, 34481
Community: On Top of the World
The Country Club of Mount Dora 1022 SAINT IVES CT, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$329,000

2 beds

|

2 baths

|

1,442 sq ft

|

House

1022 SAINT IVES CT, MOUNT DORA, FL, 3275...
The Country Club of Mount Dora 8051 SAINT JAMES WAY, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$400,000

3 beds

|

2 baths

|

2,562 sq ft

|

House

8051 SAINT JAMES WAY, MOUNT DORA, FL, 32...
Lakes of Mount Dora 8492 HARTFORD WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$599,999

3 beds

|

2 baths

|

2,384 sq ft

|

House

8492 HARTFORD WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
The Villages® 2573 CARRINGTON CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,188 sq ft

|

House

2573 CARRINGTON CT, THE VILLAGES, FL, 32...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1257 CORINTH GREENS DR # 1257, SUN CITY ..., Sun City Center, FL 33573
$229,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

1257 CORINTH GREENS DR # 1257, SUN CITY ...
Community: Sun City Center
Tampa Bay Golf and Country Club 29636 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$375,000

3 beds

|

2 baths

|

1,762 sq ft

|

House

29636 TEE SHOT DR, SAN ANTONIO, FL, 3357...
The Villages® 5638 CEDAR WAXWING DR, THE VILLAGES, FL,..., The Villages, FL 32163
$380,000

4 beds

|

2 baths

|

2,001 sq ft

|

House

5638 CEDAR WAXWING DR, THE VILLAGES, FL,...
Community: The Villages®
Tampa Bay Golf and Country Club 10026 GAP WEDGE DR, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$329,000

3 beds

|

2 baths

|

1,731 sq ft

|

House

10026 GAP WEDGE DR, SAN ANTONIO, FL, 335...
Del Webb Orlando 406 TORTOSA CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$284,900

2 beds

|

2 baths

|

1,289 sq ft

|

House

406 TORTOSA CT, DAVENPORT, FL, 33837
Community: Del Webb 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.
Valencia del Sol 5013 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$574,900

3 beds

|

2 baths

|

2,074 sq ft

|

House

5013 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
Valencia del Sol 4914 SIENNA ISLES AVE, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$384,900

3 beds

|

3 baths

|

2,040 sq ft

|

Villa

4914 SIENNA ISLES AVE, WIMAUMA, FL, 3359...
Community: Valencia del Sol
Venetian Bay 3110 ARECA AVE, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$365,000

3 beds

|

2 baths

|

1,650 sq ft

|

House

3110 ARECA AVE, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 3358 CASTLEGATE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163
$295,000

2 beds

|

2 baths

|

1,188 sq ft

|

House

3358 CASTLEGATE CT, THE VILLAGES, FL, 32...
Community: The Villages®
High Vista at Ridgewood Lakes 206 GOLF VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$315,000

2 beds

|

2 baths

|

1,485 sq ft

|

House

206 GOLF VISTA DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Harbor Hills Country Club 5312 MEADOW HILL LOOP, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$589,000

4 beds

|

3 baths

|

2,532 sq ft

|

House

5312 MEADOW HILL LOOP, LADY LAKE, FL, 32...
Southshore Bay 16810 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$470,000

2 beds

|

3 baths

|

2,239 sq ft

|

House

16810 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Sun City Center 1119 VILLEROY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$499,999

3 beds

|

2 baths

|

1,924 sq ft

|

House

1119 VILLEROY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Sun City Center 719 WINTERBROOKE WAY, SUN CITY CENTER, F..., Sun City Center, FL 33573
$300,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

719 WINTERBROOKE WAY, SUN CITY CENTER, F...
Community: Sun City Center
Venetian Bay 711 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$549,990

3 beds

|

3 baths

|

2,796 sq ft

|

House

711 JUNONIA 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.
The Villages® 2102 ESTEVEZ DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$275,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

2102 ESTEVEZ DR, THE VILLAGES, FL, 32159
Community: The Villages®
Stone Creek 5307 SW 86TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$341,700

2 beds

|

2 baths

|

1,405 sq ft

|

House

5307 SW 86TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8435 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$532,670

3 beds

|

3 baths

|

2,483 sq ft

|

House

8435 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8335 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$350,110

3 beds

|

2 baths

|

1,662 sq ft

|

House

8335 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
The Villages® 521 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$269,500

2 beds

|

2 baths

|

1,192 sq ft

|

House

521 SAN MARINO DR, 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 8163 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$374,130

3 beds

|

2 baths

|

1,662 sq ft

|

House

8163 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Majestic Oaks Ocala 5461 SW 87TH PL, OCALA, FL, 34476, Ocala, FL 34476
$509,100

2 beds

|

3 baths

|

2,269 sq ft

|

House

5461 SW 87TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
The Villages® 9621 SE 168TH MAPLESONG LN, THE VILLAGES..., The Villages, FL 32162
$309,500

3 beds

|

2 baths

|

1,392 sq ft

|

House

9621 SE 168TH MAPLESONG LN, THE VILLAGES...
Community: The Villages®
Stone Creek 8206 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$351,630

3 beds

|

2 baths

|

1,662 sq ft

|

House

8206 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Venetian Bay 703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$489,990

3 beds

|

3 baths

|

2,226 sq ft

|

House

703 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay

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
3,584 homes near Winter Garden
Remove Boundaries ×
Map Satellite

Call Us Call Us
Scroll to Top