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

3,958 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 - $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
<$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
$200Ks - $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, FL? 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 - $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 - $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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
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, FL? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$200Ks - $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 - $900Ks
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
$200Ks - $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 - $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, FL? 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...
$100Ks - $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
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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 - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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, FL? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Latitude Margaritaville 1024 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$448,999

2 beds

|

2 baths

|

1,563 sq ft

|

House

1024 SEA SHELL CT, DAYTONA BEACH, FL, 32...
Pennbrooke Fairways 533 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$315,000

3 beds

|

2 baths

|

1,701 sq ft

|

House

533 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Lake Ashton 1104 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$439,500

3 beds

|

2 baths

|

2,045 sq ft

|

House

1104 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Pine Run Estates 8879 SW 104TH LN, OCALA, FL, 34481, Ocala, FL 34481
$219,900

2 beds

|

2 baths

|

1,347 sq ft

|

House

8879 SW 104TH LN, OCALA, FL, 34481
Community: Pine Run Estates
Latitude Margaritaville 191 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$411,111

2 beds

|

2 baths

|

1,205 sq ft

|

House

191 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Windermere 751 INVERIE DR, INVERNESS, FL, 34453, Inverness, FL 34453
$239,000

3 beds

|

3 baths

|

1,912 sq ft

|

Townhouse

751 INVERIE DR, INVERNESS, FL, 34453
Community: Windermere
Valencia Lakes 16232 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598
$285,000

3 beds

|

2 baths

|

1,517 sq ft

|

Villa

16232 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
Solivita 672 SAN JOAQUIN RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$435,000

3 beds

|

3 baths

|

2,190 sq ft

|

House

672 SAN JOAQUIN RD, KISSIMMEE, FL, 34759
Community: Solivita
Marco Polo Village 5323 SW 111TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$449,000

4 beds

|

3 baths

|

2,592 sq ft

|

House

5323 SW 111TH LANE RD, OCALA, FL, 34476
Community: Marco Polo Village
The Villages® 960 PICKERING PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163
$829,000

3 beds

|

2 baths

|

2,575 sq ft

|

House

960 PICKERING PATH, THE VILLAGES, FL, 32...
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.
The Villages® 965 EASTMONT CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$329,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

965 EASTMONT CT, THE VILLAGES, FL, 32162
Community: The Villages®
New JB Ranch 6318 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$249,988

3 beds

|

2 baths

|

1,505 sq ft

|

House

6318 SW 89TH LANE RD, OCALA, FL, 34476
Community: JB Ranch
Pennbrooke Fairways 701 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$175,000

2 beds

|

1 baths

|

636 sq ft

|

House

701 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 3219 ORANGEDALE TER, THE VILLAGES, FL, 3..., The Villages, FL 32163
$799,000

3 beds

|

3 baths

|

2,019 sq ft

|

House

3219 ORANGEDALE TER, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 2738 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$425,000

3 beds

|

2 baths

|

2,175 sq ft

|

House

2738 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 9818 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$329,900

3 beds

|

2 baths

|

1,938 sq ft

|

House

9818 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
Stonecrest 17490 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$330,000

3 beds

|

2 baths

|

1,471 sq ft

|

House

17490 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 1721 SUNSET RIDGE DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$1,530,000

4 beds

|

3 baths

|

3,897 sq ft

|

House

1721 SUNSET RIDGE DR, THE VILLAGES, FL, ...
Community: The Villages®
New Tampa Bay Golf and Country Club 10232 BUNCOMBE WAY, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$375,000

3 beds

|

2 baths

|

1,397 sq ft

|

House

10232 BUNCOMBE WAY, SAN ANTONIO, FL, 335...
Esplanade at Wiregrass Ranch 4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543
$909,900

3 beds

|

3 baths

|

3,087 sq ft

|

House

4795 FRECCIA LOOP, WESLEY CHAPEL, 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.
Palms at Serenoa 3371 YELLOWTOP LOOP, CLERMONT, FL, 34714, Clermont, FL 34714
$392,990

2 beds

|

2 baths

|

1,700 sq ft

|

House

3371 YELLOWTOP LOOP, CLERMONT, FL, 34714
Community: Palms at Serenoa
The Villages® 5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484
$418,000

4 beds

|

3 baths

|

2,180 sq ft

|

House

5107 NE 122ND BLVD, OXFORD, FL, 34484
Community: The Villages®
Venetian Bay 266 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$459,000

5 beds

|

3 baths

|

2,508 sq ft

|

House

266 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
On Top of the World 8166 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476
$265,000

3 beds

|

2 baths

|

1,487 sq ft

|

House

8166 SW 80TH TER, OCALA, FL, 34476
Community: On Top of the World
Venetian Bay 610 MURA CT, NEW SMYRNA BEACH, FL, 32168, New Smyrna Beach, FL 32168
$987,900

5 beds

|

5 baths

|

3,535 sq ft

|

House

610 MURA CT, NEW SMYRNA BEACH, FL, 32168
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 2192 KERWOOD LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32162
$309,000

2 beds

|

2 baths

|

1,142 sq ft

|

House

2192 KERWOOD LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
Spruce Creek Country Club 9417 SE 132ND LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,147 sq ft

|

House

9417 SE 132ND LOOP, SUMMERFIELD, FL, 344...
VillageWalk at Lake Nona 11754 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$624,900

4 beds

|

2 baths

|

2,211 sq ft

|

House

11754 BARLETTA DR, ORLANDO, FL, 32827
Four Seasons at Orlando 7928 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$590,000

3 beds

|

2 baths

|

2,066 sq ft

|

House

7928 HANSON BAY PL, KISSIMMEE, FL, 34747
The Villages® 1727 HILTON HEAD BLVD, LADY LAKE, FL, 32..., Lady Lake, FL 32159
$210,000

2 beds

|

2 baths

|

1,180 sq ft

|

Manufactured Home

1727 HILTON HEAD BLVD, LADY LAKE, FL, 32...
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.
Lakes of Mount Dora 8780 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$539,000

3 beds

|

2 baths

|

1,682 sq ft

|

House

8780 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
The Villages® 16967 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$345,000

3 beds

|

2 baths

|

1,514 sq ft

|

House

16967 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
Trilogy® Orlando 119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$359,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Solivita 806 VIA COMO ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$360,000

2 beds

|

2 baths

|

1,652 sq ft

|

House

806 VIA COMO ST, POINCIANA, FL, 34759
Community: Solivita
The Villages® 17848 SE 87TH BOURNE AVE, THE VILLAGES, ..., The Villages, FL 32162
$295,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

17848 SE 87TH BOURNE AVE, THE VILLAGES, ...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Lakeside Landings 4987 BELTED KINGFISHER DR, OXFORD, FL, 3..., Oxford, FL 34484
$355,900

3 beds

|

2 baths

|

1,916 sq ft

|

House

4987 BELTED KINGFISHER DR, OXFORD, FL, 3...
Community: Lakeside Landings
The Villages® 1007 ALOHA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$163,900

2 beds

|

2 baths

|

1,152 sq ft

|

Mobile Home

1007 ALOHA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 2096 CALLAWAY DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$489,000

3 beds

|

2 baths

|

2,215 sq ft

|

House

2096 CALLAWAY DR, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 1912 ARMONDO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$389,900

3 beds

|

2 baths

|

1,894 sq ft

|

House

1912 ARMONDO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3810 COSMOS WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$379,900

3 beds

|

2 baths

|

1,501 sq ft

|

House

3810 COSMOS WAY, THE VILLAGES, FL, 32163
Community: The Villages®

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3,958 homes near Winter Garden
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