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

3,631 homes near Winter Garden

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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 - $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 (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
$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
$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
$200Ks - $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 - $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 - $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
Royal Highlands 5137 LINKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$389,999

3 beds

|

2 baths

|

2,189 sq ft

|

House

5137 LINKS LN, LEESBURG, FL, 34748
Community: Royal Highlands
Venetian Bay 3589 GRANDE TUSCANY WAY, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$2,100,000

6 beds

|

10 baths

|

8,260 sq ft

|

House

3589 GRANDE TUSCANY WAY, NEW SMYRNA BEAC...
Community: Venetian Bay
Venetian Bay 347 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$599,000

3 beds

|

2 baths

|

2,006 sq ft

|

House

347 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Royal Highlands 20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$349,900

2 beds

|

2 baths

|

1,722 sq ft

|

House

20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Royal Highlands 21650 STIRLING PASS, LEESBURG, FL, 34748, Leesburg, FL 34748
$300,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

21650 STIRLING PASS, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 17641 SE 90TH CLEMSON CIR, THE VILLAGES,..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,937 sq ft

|

House

17641 SE 90TH CLEMSON CIR, THE VILLAGES,...
Community: The Villages®
The Villages® 16820 SE 74 SOULLIERE AVE, THE VILLAGES,..., The Villages, FL 32162
$384,000

3 beds

|

2 baths

|

1,635 sq ft

|

Villa

16820 SE 74 SOULLIERE AVE, THE VILLAGES,...
Community: The Villages®
Solivita 189 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$240,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

189 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 2074 HARSTON TRL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$424,900

3 beds

|

2 baths

|

1,572 sq ft

|

House

2074 HARSTON TRL, THE VILLAGES, FL, 3216...
Community: The Villages®
Royal Highlands 21325 ROYAL TROON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$395,000

3 beds

|

2 baths

|

2,333 sq ft

|

House

21325 ROYAL TROON DR, LEESBURG, FL, 3474...
Community: Royal Highlands
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® 741 RICHFIELD ST, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$334,900

2 beds

|

2 baths

|

1,220 sq ft

|

Villa

741 RICHFIELD ST, THE VILLAGES, FL, 3216...
Community: The Villages®
VillageWalk at Lake Nona 12004 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$1,200,000

4 beds

|

4 baths

|

4,114 sq ft

|

House

12004 ULETA LN, ORLANDO, FL, 32827
The Villages® 1724 MADERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$500,000

2 beds

|

3 baths

|

1,969 sq ft

|

House

1724 MADERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 7177 SE 172ND HAZELWOOD LOOP, THE VILLAG..., The Villages, FL 32162
$455,000

3 beds

|

2 baths

|

1,918 sq ft

|

House

7177 SE 172ND HAZELWOOD LOOP, THE VILLAG...
Community: The Villages®
The Villages® 502 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$310,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

502 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 9539 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481
$489,900

3 beds

|

2 baths

|

2,413 sq ft

|

House

9539 SW 71ST LOOP, OCALA, FL, 34481
Community: Stone Creek
The Villages® 290 JEFFERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$350,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

290 JEFFERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Cherrywood 6084 SW 105TH PL, OCALA, FL, 34476, Ocala, FL 34476
$275,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

6084 SW 105TH PL, OCALA, FL, 34476
Community: Cherrywood
The Villages® 2260 BARRET LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$549,000

3 beds

|

2 baths

|

1,930 sq ft

|

House

2260 BARRET LN, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 7980 SW 87TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$289,000

2 beds

|

2 baths

|

1,224 sq ft

|

House

7980 SW 87TH LOOP, OCALA, FL, 34476
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 401 DORCHESTER PL APT 69, SUN CITY CENTE..., Sun City Center, FL 33573
$130,000

1 beds

|

2 baths

|

820 sq ft

|

Condo

401 DORCHESTER PL APT 69, SUN CITY CENTE...
Community: Sun City Center
The Villages® 1252 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

1,905 sq ft

|

House

1252 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
Heritage Hills 4016 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$449,000

3 beds

|

2 baths

|

2,130 sq ft

|

House

4016 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
The Villages® 720 ORCHID ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$279,900

2 beds

|

2 baths

|

1,641 sq ft

|

Manufactured Home

720 ORCHID ST, LADY LAKE, FL, 32159
Community: The Villages®
The Villages® 9231 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$394,500

3 beds

|

2 baths

|

1,850 sq ft

|

House

9231 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 4429 WATER OAK BND, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,708 sq ft

|

House

4429 WATER OAK BND, LEESBURG, FL, 34748
Spruce Creek Preserve 11282 SW 138TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$217,500

2 beds

|

2 baths

|

1,158 sq ft

|

House

11282 SW 138TH PL, DUNNELLON, FL, 34432
The Villages® 1717 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$280,000

2 beds

|

2 baths

|

1,143 sq ft

|

Villa

1717 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 2310 GAINESBOROUGH LOOP, SUN CITY CENTER..., Sun City Center, FL 33573
$165,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

2310 GAINESBOROUGH LOOP, SUN CITY CENTER...
Community: Sun City Center
On Top of the World 7819 SW 84TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$369,900

3 beds

|

2 baths

|

2,118 sq ft

|

House

7819 SW 84TH LOOP, OCALA, FL, 34476
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.
The Villages® 1089 ISLE OF PALMS PATH, THE VILLAGES, F..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

1,532 sq ft

|

House

1089 ISLE OF PALMS PATH, THE VILLAGES, F...
Community: The Villages®
Ocala Preserve 5670 NW 39TH LN, OCALA, FL, 34482, Ocala, FL 34482
$407,500

3 beds

|

2 baths

|

1,854 sq ft

|

House

5670 NW 39TH LN, OCALA, FL, 34482
Community: Ocala Preserve
On Top of the World 8675 SW 96TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$157,000

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

8675 SW 96TH ST C, OCALA, FL, 34481
Community: On Top of the World
The Villages® 752 MAYBANK LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

1,953 sq ft

|

House

752 MAYBANK LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 9089 SE 177TH BELMONT PL, THE VILLAGES, ..., The Villages, FL 32162
$315,000

2 beds

|

2 baths

|

1,283 sq ft

|

Villa

9089 SE 177TH BELMONT PL, THE VILLAGES, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ridgehaven 179 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$323,615

3 beds

|

2 baths

|

1,572 sq ft

|

House

179 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
Summer Trees 112 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$233,000

2 beds

|

2 baths

|

1,354 sq ft

|

House

112 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
Palms at Serenoa 3700 BEAUTYBERRY WAY, CLERMONT, FL, 3471..., Clermont, FL 34714
$399,900

3 beds

|

2 baths

|

1,701 sq ft

|

House

3700 BEAUTYBERRY WAY, CLERMONT, FL, 3471...
Community: Palms at Serenoa
The Villages® 16850 SE 86TH DEPTFORD CT, THE VILLAGES,..., The Villages, FL 32162
$365,900

3 beds

|

2 baths

|

1,475 sq ft

|

House

16850 SE 86TH DEPTFORD CT, THE VILLAGES,...
Community: The Villages®
Marion Landing 8478 SW 60TH CT, OCALA, FL, 34476, Ocala, FL 34476
$208,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

8478 SW 60TH CT, OCALA, FL, 34476
Community: Marion Landing

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3,631 homes near Winter Garden
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