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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
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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
On Top of the World 9463 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$254,900

2 beds

|

2 baths

|

1,462 sq ft

|

House

9463 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek North 6180 SW 110TH ST, OCALA, FL, 34476, Ocala, FL 34476
$224,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

6180 SW 110TH ST, OCALA, FL, 34476
Community: Spruce Creek North
Plantation at Leesburg 24112 ROBINWOOD ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

2 beds

|

2 baths

|

2,071 sq ft

|

House

24112 ROBINWOOD ST, LEESBURG, FL, 34748
Ocala Palms 2550 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$279,900

3 beds

|

2 baths

|

1,548 sq ft

|

House

2550 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Tampa Bay Golf and Country Club 10216 MOSHIE LN, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$475,000

3 beds

|

2 baths

|

2,470 sq ft

|

House

10216 MOSHIE LN, SAN ANTONIO, FL, 33576
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 5470 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$279,900

2 beds

|

2 baths

|

1,569 sq ft

|

House

5470 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
Sun City Center 104 GLOUCESTER BLVD 340, SUN CITY CENTER..., Sun City Center, FL 33573
$155,000

1 beds

|

2 baths

|

928 sq ft

|

Condo

104 GLOUCESTER BLVD 340, SUN CITY CENTER...
Community: Sun City Center
The Lakes at Harmony 3378 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$448,990

3 beds

|

3 baths

|

1,953 sq ft

|

House

3378 SAGEBRUSH ST, HARMONY, FL, 34773
Plantation at Leesburg 24104 ROBINWOOD ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$358,000

2 beds

|

2 baths

|

2,447 sq ft

|

House

24104 ROBINWOOD ST, LEESBURG, FL, 34748
Venetian Bay 3053 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$425,000

2 beds

|

2 baths

|

1,096 sq ft

|

Townhouse

3053 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
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.
Oak Run 8968 SW 116TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$217,500

2 beds

|

2 baths

|

1,238 sq ft

|

House

8968 SW 116TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
The Villages® 3017 MOULTRIE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162
$319,900

2 beds

|

2 baths

|

1,278 sq ft

|

Villa

3017 MOULTRIE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Stone Creek 8843 SW 57TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$699,500

3 beds

|

3 baths

|

2,522 sq ft

|

House

8843 SW 57TH PLACE RD, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 322 NORTHWAY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$350,000

3 beds

|

2 baths

|

1,939 sq ft

|

House

322 NORTHWAY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Plantation at Leesburg 25102 MERIWEATHER RD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$364,900

2 beds

|

2 baths

|

2,271 sq ft

|

House

25102 MERIWEATHER RD, LEESBURG, FL, 3474...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1004 YELLOWBIRD PL, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$305,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

1004 YELLOWBIRD PL, SUN CITY CENTER, FL,...
Community: Sun City Center
The Villages® 2388 BRANCHVILLE TER, THE VILLAGES, FL, ..., The Villages, FL 32162
$285,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2388 BRANCHVILLE TER, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 1541 DORAL CIR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$227,500

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1541 DORAL CIR, LADY LAKE, FL, 32159
Community: The Villages®
Kings Ridge 3507 TENBY CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$319,900

2 beds

|

2 baths

|

1,716 sq ft

|

House

3507 TENBY CIR, CLERMONT, FL, 34711
Community: Kings Ridge
Traditions at Lake Ruby 2825 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$233,000

2 beds

|

2 baths

|

1,385 sq ft

|

Villa

2825 ATTWATER LOOP, WINTER HAVEN, FL, 33...
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.
Pelican Bay Daytona Beach 102 BOB WHITE CT C, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$205,000

2 beds

|

2 baths

|

1,165 sq ft

|

Condo

102 BOB WHITE CT C, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$619,900

2 beds

|

2 baths

|

1,922 sq ft

|

House

664 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 914 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$470,000

2 beds

|

2 baths

|

1,563 sq ft

|

House

914 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Ormond Renaissance 799 STERTHAUS DR 207, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$465,500

3 beds

|

2 baths

|

1,523 sq ft

|

Condo

799 STERTHAUS DR 207, ORMOND BEACH, FL, ...
Community: Ormond Renaissance
Latitude Margaritaville 216 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$389,900

2 beds

|

2 baths

|

1,321 sq ft

|

House

216 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$439,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Breakaway Trails 5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$568,000

3 beds

|

3 baths

|

2,204 sq ft

|

House

5 LAKE ISLE WAY, ORMOND BEACH, FL, 32174
Community: Breakaway Trails
Latitude Margaritaville 227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$507,900

2 beds

|

2 baths

|

1,786 sq ft

|

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 623 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$389,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

623 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Latitude Margaritaville 600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$619,900

2 beds

|

3 baths

|

2,158 sq ft

|

House

600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
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.
Pelican Bay Daytona Beach 102 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$220,000

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

102 BLUE HERON DR A, DAYTONA BEACH, FL, ...
Latitude Margaritaville 378 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$439,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

378 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Breakaway Trails 4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$500,000

3 beds

|

2 baths

|

2,575 sq ft

|

House

4 CREEK BLUFF WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Pelican Bay Daytona Beach 149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$229,770

2 beds

|

2 baths

|

1,075 sq ft

|

House

149 BLACK DUCK CIR, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 786 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$729,900

3 beds

|

3 baths

|

2,392 sq ft

|

House

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 500 BAREFOOT LIFE LN, DAYTONA BEACH, FL,..., Daytona Beach, FL 32124
$749,900

3 beds

|

4 baths

|

2,542 sq ft

|

House

500 BAREFOOT LIFE LN, DAYTONA BEACH, FL,...
Latitude Margaritaville 899 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$499,500

3 beds

|

2 baths

|

1,768 sq ft

|

House

899 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Summer Trees 6017 HICKORY GROVE LN, PORT ORANGE, FL, ..., Port Orange, FL 32128
$489,000

4 beds

|

2 baths

|

1,808 sq ft

|

House

6017 HICKORY GROVE LN, PORT ORANGE, FL, ...
Community: Summer Trees
Latitude Margaritaville 281 COMPASS ROSE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$675,000

2 beds

|

3 baths

|

2,067 sq ft

|

House

281 COMPASS ROSE DR, DAYTONA BEACH, FL, ...
Breakaway Trails 10 CARRIAGE CREEK WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$379,900

3 beds

|

2 baths

|

1,896 sq ft

|

House

10 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails

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3,573 homes near Winter Garden
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