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

3,703 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 - $500Ks
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
<$100k - $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
$300Ks - $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 - $500Ks
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
Sun City Center 1803 PINEAPPLE PALM CT, SUN CITY CENTER,..., Sun City Center, FL 33573
$249,000

2 beds

|

2 baths

|

1,506 sq ft

|

House

1803 PINEAPPLE PALM CT, SUN CITY CENTER,...
Community: Sun City Center
Spruce Creek Country Club 9009 SE 136TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$319,500

3 beds

|

2 baths

|

2,106 sq ft

|

House

9009 SE 136TH LOOP, SUMMERFIELD, FL, 344...
Ocala Preserve 5403 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$223,000

2 beds

|

2 baths

|

1,318 sq ft

|

Villa

5403 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
Stone Creek 7646 SW 100TH CT, OCALA, FL, 34481, Ocala, FL 34481
$519,900

3 beds

|

3 baths

|

2,539 sq ft

|

House

7646 SW 100TH CT, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8491 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$355,750

3 beds

|

2 baths

|

1,697 sq ft

|

House

8491 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sullivan Ranch 30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$397,900

3 beds

|

2 baths

|

1,851 sq ft

|

House

30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Scottish Highlands 1416 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$199,900

2 beds

|

2 baths

|

1,736 sq ft

|

House

1416 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
Lakes of Mount Dora 3969 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$394,990

2 beds

|

2 baths

|

1,402 sq ft

|

House

3969 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Lakes of Mount Dora 3974 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$454,990

2 beds

|

2 baths

|

1,816 sq ft

|

House

3974 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Sun City Center 404 FULHAM CT A, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$153,900

2 beds

|

2 baths

|

1,100 sq ft

|

Condo

404 FULHAM CT A, SUN CITY CENTER, FL, 33...
Community: Sun City Center
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.
Solivita 1388 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$285,000

2 beds

|

2 baths

|

1,366 sq ft

|

House

1388 LOMBARDI CT, KISSIMMEE, FL, 34759
Community: Solivita
Windermere 806 WINDERMERE BLVD, INVERNESS, FL, 3445..., Inverness, FL 34453
$209,000

2 beds

|

2 baths

|

1,193 sq ft

|

Condo

806 WINDERMERE BLVD, INVERNESS, FL, 3445...
Community: Windermere
VillageWalk at Lake Nona 11938 KIPPER DR, ORLANDO, FL, 32827, Orlando, FL 32827
$469,000

4 beds

|

3 baths

|

1,810 sq ft

|

Townhouse

11938 KIPPER DR, ORLANDO, FL, 32827
Huntington at Hunter's Ridge 15 SHEAR WATER TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$394,000

3 beds

|

2 baths

|

2,105 sq ft

|

House

15 SHEAR WATER TRL, ORMOND BEACH, FL, 32...
Highlands Ridge 2835 S MAINSAIL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$119,000

2 beds

|

2 baths

|

1,200 sq ft

|

Mobile Home

2835 S MAINSAIL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 5087 NE 121ST AVE, OXFORD, FL, 34484, Oxford, FL 34484
$429,900

3 beds

|

2 baths

|

1,839 sq ft

|

House

5087 NE 121ST AVE, OXFORD, FL, 34484
Community: The Villages®
Venetian Bay 349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$394,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Venetian Bay 3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$347,000

3 beds

|

3 baths

|

1,672 sq ft

|

House

3039 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Lakes of Mount Dora 3972 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$481,990

3 beds

|

2 baths

|

2,034 sq ft

|

House

3972 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Sun City Center 832 KING LEON WAY, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$340,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

832 KING LEON WAY, SUN CITY CENTER, FL, ...
Community: Sun City Center
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.
Latitude Margaritaville 203 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$548,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

203 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Oak Run 8968 SW 116TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$205,000

2 beds

|

2 baths

|

1,238 sq ft

|

House

8968 SW 116TH PLACE RD, OCALA, FL, 34481
Community: Oak Run
Lakes of Mount Dora 3973 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$404,990

2 beds

|

2 baths

|

1,614 sq ft

|

House

3973 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Lakes of Mount Dora 3975 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$396,990

2 beds

|

2 baths

|

1,402 sq ft

|

House

3975 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
The Villages® 471 GASKIN LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$439,900

3 beds

|

2 baths

|

1,732 sq ft

|

House

471 GASKIN LN, 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
Liberty Village 7707 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$364,900

3 beds

|

3 baths

|

2,039 sq ft

|

House

7707 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
Stone Creek 9423 SW 60TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$434,900

2 beds

|

2 baths

|

1,891 sq ft

|

House

9423 SW 60TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
Solivita 136 VERONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$314,000

3 beds

|

3 baths

|

1,946 sq ft

|

House

136 VERONA DR, KISSIMMEE, FL, 34759
Community: Solivita
Stonecrest 11961 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$369,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

11961 SE 176TH PLACE RD, SUMMERFIELD, FL...
Community: Stonecrest
Cresswind at Victoria Gardens 1208 EGGLESTON DR, DELAND, FL, 32724, Deland, FL 32724
$525,000

2 beds

|

2 baths

|

1,843 sq ft

|

House

1208 EGGLESTON DR, DELAND, FL, 32724
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.
Lake Ashton 6301 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$479,900

3 beds

|

2 baths

|

2,057 sq ft

|

House

6301 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
Latitude Margaritaville 613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$367,000

2 beds

|

2 baths

|

1,204 sq ft

|

House

613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Latitude Margaritaville 443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$429,000

3 beds

|

2 baths

|

1,563 sq ft

|

House

443 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Cresswind at Victoria Gardens 1079 LINCOLNSHIRE DR, DELAND, FL, 32724, Deland, FL 32724
$379,900

2 beds

|

2 baths

|

1,651 sq ft

|

House

1079 LINCOLNSHIRE DR, DELAND, FL, 32724
High Vista at Ridgewood Lakes 105 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$280,000

2 beds

|

2 baths

|

1,542 sq ft

|

House

105 RIDGE VIEW DR, DAVENPORT, FL, 33837
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Ashton 4115 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$325,000

2 beds

|

2 baths

|

1,688 sq ft

|

House

4115 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Cherrywood 10274 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$179,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

10274 SW 61ST TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
On Top of the World 7942 SW 86TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$361,000

2 beds

|

2 baths

|

1,747 sq ft

|

House

7942 SW 86TH TERRACE RD, OCALA, FL, 3448...
Community: On Top of the World
Cherrywood 10086 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$240,000

3 beds

|

2 baths

|

1,487 sq ft

|

House

10086 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Venetian Bay 3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$579,000

3 beds

|

2 baths

|

1,712 sq ft

|

House

3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay

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3,703 homes near Winter Garden
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