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

3,958 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 - $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
<$100k - $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
$200Ks - $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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
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
$200Ks - $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 - $900Ks
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
$200Ks - $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) VillageWalk at Lake Nona
$400Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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
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...
$100Ks - $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
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet 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
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
On Top of the World 9708 SW 97TH ST, OCALA, FL, 34481, Ocala, FL 34481
$244,900

2 beds

|

2 baths

|

1,904 sq ft

|

House

9708 SW 97TH ST, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 104 CARSWELL CIR # 10, SUN CITY CENTER, ..., Sun City Center, FL 33573
$180,000

2 beds

|

2 baths

|

1,180 sq ft

|

Villa

104 CARSWELL CIR # 10, SUN CITY CENTER, ...
Community: Sun City Center
Gatherings of Lake Nona 7557 LAUREATE BLVD UNIT 6208, ORLANDO, F..., Orlando, FL 32827
$410,300

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7557 LAUREATE BLVD UNIT 6208, ORLANDO, F...
Gatherings of Lake Nona 7545 LAUREATE BLVD UNIT 7203, ORLANDO, F..., Orlando, FL 32827
$489,990

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7545 LAUREATE BLVD UNIT 7203, ORLANDO, F...
Gatherings of Lake Nona 7545 LAUREATE BLVD UNIT 7202, ORLANDO, F..., Orlando, FL 32827
$523,990

3 beds

|

2 baths

|

1,805 sq ft

|

Condo

7545 LAUREATE BLVD UNIT 7202, ORLANDO, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1007 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$370,000

2 beds

|

2 baths

|

1,929 sq ft

|

House

1007 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 773 ARTESIA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$299,900

3 beds

|

2 baths

|

1,210 sq ft

|

House

773 ARTESIA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 17913 SE 88TH CASCADE CT, THE VILLAGES, ..., The Villages, FL 32162
$329,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17913 SE 88TH CASCADE CT, THE VILLAGES, ...
Community: The Villages®
New The Villages® 1626 CYPRESS PT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$186,000

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1626 CYPRESS PT, LADY LAKE, FL, 32159
Community: The Villages®
Harbor Hills Country Club 39320 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$484,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

39320 HARBOR HILLS BLVD, LADY LAKE, FL, ...
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 1426 INGRAM DR # 1426, SUN CITY CENTER, ..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

1426 INGRAM DR # 1426, SUN CITY CENTER, ...
Community: Sun City Center
The Villages® 1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$235,000

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

1336 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
Highland Fairways 2085 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$229,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

2085 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
New The Villages® 851 EVELYNTON LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$265,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

851 EVELYNTON LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
New The Villages® 2317 WHISPER ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$239,000

1 beds

|

1 baths

|

991 sq ft

|

Villa

2317 WHISPER ST, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 8450 SE 177TH ROLESON LN, THE VILLAGES, ..., The Villages, FL 32162
$310,000

3 beds

|

2 baths

|

1,430 sq ft

|

Villa

8450 SE 177TH ROLESON LN, THE VILLAGES, ...
Community: The Villages®
The Villages® 1724 MADERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$525,000

2 beds

|

3 baths

|

1,969 sq ft

|

House

1724 MADERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 857 ENISGROVE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$495,000

3 beds

|

2 baths

|

1,965 sq ft

|

House

857 ENISGROVE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1202 SAN BERNARDO RD, THE VILLAGES, FL, ..., The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,146 sq ft

|

Villa

1202 SAN BERNARDO RD, THE VILLAGES, FL, ...
Community: The Villages®
Ocala Preserve 4749 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$273,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4749 NW 39TH STREET RD, 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.
Ocala Preserve 4755 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$278,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4755 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
New Heritage Hills 3547 FAIRWATERS CT F, CLERMONT, FL, 3471..., Clermont, FL 34711
$330,000

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3547 FAIRWATERS CT F, CLERMONT, FL, 3471...
Community: Heritage Hills
Ocala Preserve 4737 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$257,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4737 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4086 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$267,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4086 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4743 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$257,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4743 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4067 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$259,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4067 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4082 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$272,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

4082 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4742 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$262,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4742 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4748 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$266,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4748 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4072 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$278,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

4072 NW 44TH CIR, 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.
Ocala Preserve 4736 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$262,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4736 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4056 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$279,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

4056 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4754 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$266,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4754 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4760 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$268,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4760 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4766 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$268,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4766 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4083 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$267,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

4083 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 5339 NW 46TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$259,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

5339 NW 46TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4767 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$268,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4767 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4761 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$268,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4761 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
JB Ranch 4723 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$315,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4723 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch

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3,958 homes near Winter Garden
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