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

3,584 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
<$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
$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.
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) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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 - $900Ks
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...
$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
Summer Trees 6068 SPRUCE POINT CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$639,900

4 beds

|

3 baths

|

2,438 sq ft

|

House

6068 SPRUCE POINT CIR, PORT ORANGE, FL, ...
Community: Summer Trees
Southshore Bay 17322 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$270,000

2 beds

|

2 baths

|

1,406 sq ft

|

Villa

17322 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Lakes at Laurel Highlands 1823 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811
$330,000

3 beds

|

2 baths

|

1,711 sq ft

|

House

1823 PRISTINE LOOP, LAKELAND, FL, 33811
Spruce Creek Preserve 11335 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$249,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

11335 SW 138TH LN, DUNNELLON, FL, 34432
Oak Run 11631 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476
$229,888

2 beds

|

2 baths

|

1,218 sq ft

|

House

11631 SW 71ST CIR, OCALA, FL, 34476
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1725 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$174,000

2 beds

|

2 baths

|

1,092 sq ft

|

Manufactured Home

1725 HILTON HEAD BLVD, LADY LAKE, FL, 32...
Community: The Villages®
Sun City Center 226 GLOUCESTER BLVD # 400, SUN CITY CENT..., Sun City Center, FL 33573
$149,900

1 beds

|

2 baths

|

800 sq ft

|

Condo

226 GLOUCESTER BLVD # 400, SUN CITY CENT...
Community: Sun City Center
Cherrywood 9981 SW 59TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$220,000

3 beds

|

2 baths

|

1,837 sq ft

|

House

9981 SW 59TH CIR, OCALA, FL, 34476
Community: Cherrywood
Traditions at Lake Ruby 2733 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$370,000

3 beds

|

3 baths

|

2,032 sq ft

|

House

2733 ATTWATER LOOP, WINTER HAVEN, FL, 33...
The Villages® 514 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$157,000

2 beds

|

2 baths

|

1,352 sq ft

|

Manufactured Home

514 S TIMBER TRL, WILDWOOD, FL, 34785
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.
Foxwood Lake Estates 1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$210,000

3 beds

|

2 baths

|

1,176 sq ft

|

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810
Ocala Preserve 4232 NW 56TH CT, OCALA, FL, 34482, Ocala, FL 34482
$399,000

2 beds

|

2 baths

|

1,938 sq ft

|

House

4232 NW 56TH CT, OCALA, FL, 34482
Community: Ocala Preserve
Lake Ashton 4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$225,000

2 beds

|

2 baths

|

1,083 sq ft

|

House

4488 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Trilogy® Orlando 111 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$425,000

3 beds

|

2 baths

|

1,661 sq ft

|

House

111 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Sun City Center 1507 N LAKE DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$200,000

2 beds

|

1 baths

|

1,264 sq ft

|

House

1507 N LAKE DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 333 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$424,999

2 beds

|

2 baths

|

1,308 sq ft

|

House

333 POP TOP LN, DAYTONA BEACH, FL, 32124
On Top of the World 10394 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$321,000

2 beds

|

2 baths

|

1,462 sq ft

|

House

10394 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 2507 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$157,000

2 beds

|

2 baths

|

1,203 sq ft

|

Condo

2507 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Pelican Bay Daytona Beach 108 GRAY DOVE CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32119
$209,000

2 beds

|

2 baths

|

1,183 sq ft

|

House

108 GRAY DOVE CT, DAYTONA BEACH, FL, 321...
Lake Henry Estates 543 CLUBHILL DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$278,000

2 beds

|

2 baths

|

1,868 sq ft

|

House

543 CLUBHILL DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
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.
Lakes of Mount Dora 8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$795,000

4 beds

|

3 baths

|

3,156 sq ft

|

House

8348 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Sun City Center 1034 MCDANIEL ST # 1034, SUN CITY CENTER..., Sun City Center, FL 33573
$287,000

2 beds

|

2 baths

|

1,887 sq ft

|

Condo

1034 MCDANIEL ST # 1034, SUN CITY CENTER...
Community: Sun City Center
Mirada 31665 MAGNA GULF LOOP, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$340,000

2 beds

|

2 baths

|

1,683 sq ft

|

House

31665 MAGNA GULF LOOP, SAN ANTONIO, FL, ...
Community: Mirada
Colonnades 4854 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$219,000

2 beds

|

2 baths

|

1,078 sq ft

|

House

4854 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
On Top of the World 9025 SW 94TH LN C, OCALA, FL, 34481, Ocala, FL 34481
$174,900

2 beds

|

2 baths

|

1,709 sq ft

|

Villa

9025 SW 94TH LN C, 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
The Villages® 1105 SAN REMO LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$349,900

2 beds

|

2 baths

|

1,610 sq ft

|

House

1105 SAN REMO LN, THE VILLAGES, FL, 3215...
Community: The Villages®
Sun City Center 332 CLUB MANOR DR # 10, SUN CITY CENTER,..., Sun City Center, FL 33573
$190,000

2 beds

|

2 baths

|

1,516 sq ft

|

House

332 CLUB MANOR DR # 10, SUN CITY CENTER,...
Community: Sun City Center
Lake Ashton 4063 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$300,000

2 beds

|

2 baths

|

1,530 sq ft

|

House

4063 BIRKDALE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Highland Lakes 5648 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,458 sq ft

|

House

5648 LAVER ST, LEESBURG, FL, 34748
Community: Highland Lakes
Lake Ashton 5325 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$284,900

2 beds

|

2 baths

|

1,319 sq ft

|

House

5325 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
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® 747 LOUISE LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$274,500

2 beds

|

2 baths

|

961 sq ft

|

Villa

747 LOUISE LN, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 889 ALLAGASH AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

889 ALLAGASH AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
Sun City Center 1211 PERIDOT LN, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$445,900

3 beds

|

2 baths

|

2,072 sq ft

|

House

1211 PERIDOT LN, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Ocala Preserve 4086 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$242,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4086 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Ocala Preserve 4067 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$242,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4067 NW 44TH CIR, 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
Valencia Lakes 16116 CEDAR KEY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$415,000

2 beds

|

2 baths

|

1,939 sq ft

|

House

16116 CEDAR KEY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Heritage - The Cottages of Sanders Grove 6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$319,900

3 beds

|

2 baths

|

1,788 sq ft

|

House

6342 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Highland Fairways 2085 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$219,000

2 beds

|

2 baths

|

1,512 sq ft

|

House

2085 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
Pine Run Estates 10210 SW 93RD AVE, OCALA, FL, 34481, Ocala, FL 34481
$195,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10210 SW 93RD AVE, OCALA, FL, 34481
Community: Pine Run Estates
Highland Lakes 26030 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$244,900

2 beds

|

2 baths

|

1,293 sq ft

|

Villa

26030 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes

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3,584 homes near Winter Garden
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