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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!
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 - $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
Venetian Bay 219 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$549,900

4 beds

|

3 baths

|

2,196 sq ft

|

House

219 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Majestic Oaks Ocala 5327 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476
$264,900

3 beds

|

2 baths

|

1,661 sq ft

|

House

5327 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Venetian Bay 3331 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$424,900

3 beds

|

2 baths

|

2,002 sq ft

|

Halfplex

3331 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Lake James 7929 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$568,000

3 beds

|

2 baths

|

2,653 sq ft

|

House

7929 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Pennbrooke Fairways 751 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

3 beds

|

2 baths

|

1,753 sq ft

|

House

751 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 594 MARISOL DR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$580,000

3 beds

|

3 baths

|

2,409 sq ft

|

House

594 MARISOL DR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Pine Run Estates 9940 SW 103RD PL, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

9940 SW 103RD PL, OCALA, FL, 34481
Community: Pine Run Estates
Ocala Palms 5551 NW 25TH LOOP, OCALA, FL, 34482, Ocala, FL 34482
$265,000

2 beds

|

2 baths

|

1,673 sq ft

|

House

5551 NW 25TH LOOP, OCALA, FL, 34482
Community: Ocala Palms
Solivita 4624 VIA VENETO CT, KISSIMMEE, FL, 34746, Kissimmee, FL 34746
$475,000

4 beds

|

3 baths

|

1,838 sq ft

|

House

4624 VIA VENETO CT, KISSIMMEE, FL, 34746
Community: Solivita
Spruce Creek Country Club 12508 SE 90TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$349,000

2 beds

|

2 baths

|

1,598 sq ft

|

House

12508 SE 90TH TER, SUMMERFIELD, FL, 3449...
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.
Kings Ridge 3773 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$300,000

2 beds

|

2 baths

|

1,498 sq ft

|

House

3773 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Lake Ashton 4469 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$289,000

3 beds

|

2 baths

|

2,029 sq ft

|

House

4469 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
On Top of the World 8753 SW 91ST ST B, OCALA, FL, 34481, Ocala, FL 34481
$169,000

2 beds

|

2 baths

|

1,375 sq ft

|

Villa

8753 SW 91ST ST B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2882 ADRIENNE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$600,000

3 beds

|

2 baths

|

1,967 sq ft

|

House

2882 ADRIENNE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Spring Lake Towers 700 MIRROR TER 702, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$119,900

2 beds

|

2 baths

|

1,029 sq ft

|

Condo

700 MIRROR TER 702, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4755 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$272,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4755 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Lake Ashton 4568 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884
$349,900

3 beds

|

2 baths

|

2,043 sq ft

|

House

4568 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
Lake Ashton 5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884
$599,000

3 beds

|

2 baths

|

2,354 sq ft

|

House

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL...
Community: Lake Ashton
Oak Run 8720 SW 108TH LN, OCALA, FL, 34481, Ocala, FL 34481
$174,000

2 beds

|

2 baths

|

960 sq ft

|

House

8720 SW 108TH LN, OCALA, FL, 34481
Community: Oak Run
The Lakes at Harmony 3333 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$354,990

3 beds

|

2 baths

|

1,677 sq ft

|

House

3333 SAGEBRUSH ST, HARMONY, FL, 34773
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.
Carlsberg Estates on Lake Suzanne 348 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$259,000

2 beds

|

2 baths

|

1,546 sq ft

|

House

348 LAKE SUZANNE DR, LAKE WALES, FL, 338...
The Villages® 17009 SE 96TH CHAPELWOOD CIR, THE VILLAG..., The Villages, FL 32162
$369,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...
Community: The Villages®
Stone Creek 9586 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$309,900

2 beds

|

2 baths

|

1,756 sq ft

|

Villa

9586 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 101 CAMBRIDGE TRL APT 194, SUN CITY CENT..., Sun City Center, FL 33573
$105,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

101 CAMBRIDGE TRL APT 194, SUN CITY CENT...
Community: Sun City Center
Southshore Bay 16913 ANCHOR ROOT ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$425,000

3 beds

|

2 baths

|

1,761 sq ft

|

House

16913 ANCHOR ROOT ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
SummerGlen 15268 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$325,000

3 beds

|

2 baths

|

2,093 sq ft

|

House

15268 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Ocala Palms 2323 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$305,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

2323 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
Oak Run 7251 SW 115TH PL, OCALA, FL, 34476, Ocala, FL 34476
$190,000

2 beds

|

2 baths

|

1,537 sq ft

|

House

7251 SW 115TH PL, OCALA, FL, 34476
Community: Oak Run
Colonnades 4926 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811
$227,000

2 beds

|

2 baths

|

1,193 sq ft

|

House

4926 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
The Villages® 1502 EL PASO WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$317,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

1502 EL PASO WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
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 4749 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482
$267,990

2 beds

|

2 baths

|

1,565 sq ft

|

Villa

4749 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
Spruce Creek South 17475 SE 107TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$298,900

2 beds

|

2 baths

|

1,678 sq ft

|

House

17475 SE 107TH CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Heritage Hills 3492 LA JOLLA DR, CLERMONT, FL, 34711, Clermont, FL 34711
$550,000

3 beds

|

3 baths

|

2,615 sq ft

|

House

3492 LA JOLLA DR, CLERMONT, FL, 34711
Community: Heritage Hills
Sun City Center 413 LAKE POINT CT # 4B, SUN CITY CENTER,..., Sun City Center, FL 33573
$152,000

2 beds

|

2 baths

|

952 sq ft

|

Condo

413 LAKE POINT CT # 4B, SUN CITY CENTER,...
Community: Sun City Center
Four Seasons at Orlando 1855 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$375,000

2 beds

|

2 baths

|

1,437 sq ft

|

Villa

1855 FLORA PASS PL, KISSIMMEE, FL, 34747
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9175 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$289,900

2 beds

|

2 baths

|

1,488 sq ft

|

House

9175 SE 118TH LOOP, SUMMERFIELD, FL, 344...
On Top of the World 8787 SW 90TH LN E, OCALA, FL, 34481, Ocala, FL 34481
$195,000

2 beds

|

2 baths

|

1,594 sq ft

|

Villa

8787 SW 90TH LN E, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 220 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$529,000

4 beds

|

3 baths

|

2,113 sq ft

|

House

220 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
The Villages® 1618 CYPRESS PT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$220,000

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1618 CYPRESS PT, LADY LAKE, FL, 32159
Community: The Villages®
On Top of the World 9646 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$230,900

2 beds

|

2 baths

|

1,517 sq ft

|

House

9646 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World

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3,573 homes near Winter Garden
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