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

3,573 homes near Winter Garden

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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!
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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 - $500Ks
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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $600Ks
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
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
Sun City Center 2227 GRENADIER DR # 140, SUN CITY CENTER..., Sun City Center, FL 33573
$130,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

2227 GRENADIER DR # 140, SUN CITY CENTER...
Community: Sun City Center
The Villages® 1601 PINEHURST DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$244,900

2 beds

|

2 baths

|

1,688 sq ft

|

Manufactured Home

1601 PINEHURST DR, THE VILLAGES, FL, 321...
Community: The Villages®
Lake Jovita Golf and Country Club 33744 AMERICANA AVE, DADE CITY, FL, 3352..., Dade City, FL 33525
$875,000

4 beds

|

3 baths

|

2,717 sq ft

|

House

33744 AMERICANA AVE, DADE CITY, FL, 3352...
Sun City Center 301 ANDOVER PL 175, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$115,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 ANDOVER PL 175, SUN CITY CENTER, FL,...
Community: Sun City Center
The Villages® 867 CASTLEBERRY CIR, THE VILLAGES, FL, 3..., The Villages, FL 32162
$585,000

3 beds

|

2 baths

|

1,993 sq ft

|

House

867 CASTLEBERRY CIR, 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
Lake Ashton 4068 STONE CREEK LOOP, LAKE WALES, FL, 3..., Lake Wales, FL 33859
$550,000

3 beds

|

2 baths

|

2,064 sq ft

|

House

4068 STONE CREEK LOOP, LAKE WALES, FL, 3...
Community: Lake Ashton
The Villages® 1065 BERG CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$399,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

1065 BERG CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 3021 BEARD RD, THE VILLAGES, FL, 32163, The Villages, FL 32163
$340,000

2 beds

|

2 baths

|

1,203 sq ft

|

Villa

3021 BEARD RD, THE VILLAGES, FL, 32163
Community: The Villages®
Colonnades 4965 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$255,000

2 beds

|

2 baths

|

1,350 sq ft

|

House

4965 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Spruce Creek Country Club 8447 SE 137TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$350,000

3 beds

|

2 baths

|

2,387 sq ft

|

House

8447 SE 137TH LOOP, SUMMERFIELD, FL, 344...
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.
Stone Creek 9793 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$477,000

4 beds

|

2 baths

|

2,186 sq ft

|

House

9793 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 10287 SW 96TH LN, OCALA, FL, 34481, Ocala, FL 34481
$489,000

3 beds

|

3 baths

|

2,476 sq ft

|

House

10287 SW 96TH LN, OCALA, FL, 34481
Community: On Top of the World
Pennbrooke Fairways 32712 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$287,900

3 beds

|

2 baths

|

1,909 sq ft

|

House

32712 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
On Top of the World 9047 SW 102ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$225,000

2 beds

|

2 baths

|

1,198 sq ft

|

House

9047 SW 102ND CIR, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 6046 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$328,180

2 beds

|

2 baths

|

1,404 sq ft

|

House

6046 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1228 MARIA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,432 sq ft

|

Manufactured Home

1228 MARIA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Highland Fairways 2234 SEA ISLAND CIR, LAKELAND, FL, 33810, Lakeland, FL 33810
$225,000

2 beds

|

2 baths

|

1,166 sq ft

|

House

2234 SEA ISLAND CIR, LAKELAND, FL, 33810
Community: Highland Fairways
Venetian Bay 3098 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$359,000

2 beds

|

2 baths

|

1,272 sq ft

|

House

3098 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Pennbrooke Fairways 32857 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,000

3 beds

|

2 baths

|

1,674 sq ft

|

House

32857 TIMBERWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Twin Lakes 2302 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$335,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2302 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
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 8334 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$250,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

8334 SW 79TH CIR, OCALA, FL, 34476
Community: On Top of the World
Solivita 3432 FALLBROOK DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$312,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

3432 FALLBROOK DR, POINCIANA, FL, 34759
Community: Solivita
Sun City Center 1908 STERLING GLEN CT, SUN CITY CENTER, ..., Sun City Center, FL 33573
$348,000

2 beds

|

2 baths

|

1,497 sq ft

|

House

1908 STERLING GLEN CT, SUN CITY CENTER, ...
Community: Sun City Center
Solivita 125 PRIMA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$440,000

3 beds

|

3 baths

|

2,325 sq ft

|

House

125 PRIMA DR, POINCIANA, FL, 34759
Community: Solivita
On Top of the World 8111 SW 95TH CT, OCALA, FL, 34481, Ocala, FL 34481
$525,000

3 beds

|

3 baths

|

2,311 sq ft

|

House

8111 SW 95TH CT, OCALA, FL, 34481
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
Solivita 663 IRVINE RANCH RD, POINCIANA, FL, 3475..., Poinciana, FL 34759
$423,000

3 beds

|

3 baths

|

2,307 sq ft

|

House

663 IRVINE RANCH RD, POINCIANA, FL, 3475...
Community: Solivita
Solivita 684 SAN AUGUSTO DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$539,000

3 beds

|

3 baths

|

2,363 sq ft

|

House

684 SAN AUGUSTO DR, POINCIANA, FL, 34759
Community: Solivita
Highlands Ridge 2818 S DOCKSIDE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$76,900

2 beds

|

2 baths

|

1,000 sq ft

|

Mobile Home

2818 S DOCKSIDE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Twin Lakes 5043 VANTAGE CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$574,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

5043 VANTAGE CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes
On Top of the World 9664 SW 94TH TER A, OCALA, FL, 34481, Ocala, FL 34481
$159,999

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9664 SW 94TH TER A, OCALA, FL, 34481
Community: On Top of the World
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 2510 LOCKSLEY ST # 2510, SUN CITY CENTER..., Sun City Center, FL 33573
$255,500

2 beds

|

2 baths

|

1,394 sq ft

|

Condo

2510 LOCKSLEY ST # 2510, SUN CITY CENTER...
Community: Sun City Center
Marco Polo Village 5024 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$539,000

3 beds

|

3 baths

|

2,652 sq ft

|

House

5024 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
Harbor Hills Country Club 5235 ISLAND TERRACE CT, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$625,000

3 beds

|

3 baths

|

2,446 sq ft

|

House

5235 ISLAND TERRACE CT, LADY LAKE, FL, 3...
Thunderbird Hill 3745 CAMRY CT, SEBRING, FL, 33872, Sebring, FL 33872
$199,000

2 beds

|

2 baths

|

950 sq ft

|

Villa

3745 CAMRY CT, SEBRING, FL, 33872
Community: Thunderbird Hill
Sun City Center 2246 SIFIELD GREENS WAY # 36, SUN CITY C..., Sun City Center, FL 33573
$415,000

3 beds

|

3 baths

|

2,214 sq ft

|

Condo

2246 SIFIELD GREENS WAY # 36, SUN CITY C...
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 2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$304,999

2 beds

|

2 baths

|

1,346 sq ft

|

Villa

2555 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Foxwood Lake Estates 1811 SHERWOOD HILL DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$164,900

2 beds

|

2 baths

|

1,316 sq ft

|

Manufactured Home

1811 SHERWOOD HILL DR, LAKELAND, FL, 338...
Trilogy® Orlando 115 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$360,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

115 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Highland Lakes 26901 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$360,000

3 beds

|

2 baths

|

2,144 sq ft

|

House

26901 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Sandpiper Golf & Country Club 5970 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5970 CORMORANT CT, LAKELAND, FL, 33809

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3,573 homes near Winter Garden
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