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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? 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? 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) VillageWalk at Lake Nona
$400Ks - $1Ms
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...
$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? 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
Summer Trees 111 GREY BRANCH RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$278,401

3 beds

|

2 baths

|

1,316 sq ft

|

House

111 GREY BRANCH RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Solivita 1029 UMBRIA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$310,000

2 beds

|

2 baths

|

1,365 sq ft

|

House

1029 UMBRIA DR, POINCIANA, FL, 34759
Community: Solivita
The Villages® 750 EDEN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$499,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

750 EDEN PL, THE VILLAGES, FL, 32162
Community: The Villages®
Foxwood Lake Estates 1742 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$175,000

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

1742 FOX HILL DR, LAKELAND, FL, 33810
Lakeside Landings 5437 COMPASS PT # 00, OXFORD, FL, 34484, Oxford, FL 34484
$225,000

2 beds

|

2 baths

|

1,400 sq ft

|

Condo

5437 COMPASS PT # 00, OXFORD, FL, 34484
Community: Lakeside Landings
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8712 SW 92ND ST C, OCALA, FL, 34481, Ocala, FL 34481
$165,000

2 beds

|

2 baths

|

1,366 sq ft

|

Villa

8712 SW 92ND ST C, OCALA, FL, 34481
Community: On Top of the World
Lake Jovita Golf and Country Club 12333 WOODLANDS CIR, DADE CITY, FL, 3352..., Dade City, FL 33525
$524,900

3 beds

|

3 baths

|

2,292 sq ft

|

House

12333 WOODLANDS CIR, DADE CITY, FL, 3352...
New The Villages® 2608 CASSO CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

2,192 sq ft

|

House

2608 CASSO CT, THE VILLAGES, FL, 32162
Community: The Villages®
VillageWalk at Lake Nona 11953 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

2 beds

|

2 baths

|

1,708 sq ft

|

Halfplex

11953 DELFINA LN, ORLANDO, FL, 32827
On Top of the World 8712 SW 92ND PL D, OCALA, FL, 34481, Ocala, FL 34481
$157,999

2 beds

|

2 baths

|

1,322 sq ft

|

Villa

8712 SW 92ND PL D, OCALA, FL, 34481
Community: On Top of the World
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.
Arlington Ridge 3641 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$468,800

3 beds

|

2 baths

|

1,728 sq ft

|

House

3641 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
The Villages® 1904 DE HOYOS PL, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$295,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

1904 DE HOYOS PL, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 1913 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$365,000

3 beds

|

2 baths

|

1,451 sq ft

|

House

1913 AUGUSTINE DR, THE VILLAGES, FL, 321...
Community: The Villages®
New Latitude Margaritaville 342 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$409,900

2 beds

|

2 baths

|

1,461 sq ft

|

House

342 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
The Villages® 1923 GREELEYVILLE TER, THE VILLAGES, FL,..., The Villages, FL 32162
$434,900

3 beds

|

2 baths

|

1,685 sq ft

|

Villa

1923 GREELEYVILLE TER, THE VILLAGES, FL,...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Foxwood Lake Estates 5002 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$169,500

2 beds

|

2 baths

|

1,104 sq ft

|

Manufactured Home

5002 LODGEWOOD DR, LAKELAND, FL, 33810
Spruce Creek South 10173 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$219,900

2 beds

|

2 baths

|

1,296 sq ft

|

House

10173 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 5557 HAWKINS DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$875,000

3 beds

|

2 baths

|

2,070 sq ft

|

House

5557 HAWKINS DR, THE VILLAGES, FL, 32163
Community: The Villages®
JB Ranch 4754 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$289,990

3 beds

|

2 baths

|

1,672 sq ft

|

House

4754 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
High Vista at Ridgewood Lakes 220 LEWIS DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$315,000

2 beds

|

2 baths

|

1,796 sq ft

|

House

220 LEWIS DR, DAVENPORT, FL, 33837
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.
On Top of the World 4831 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$216,440

3 beds

|

3 baths

|

1,707 sq ft

|

Townhouse

4831 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Foxwood Lake Estates 1622 TALLY HO DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$189,900

2 beds

|

2 baths

|

1,392 sq ft

|

Manufactured Home

1622 TALLY HO DR, LAKELAND, FL, 33810
The Villages® 1639 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$234,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

1639 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 17930 SE 83RD MELODY AVE, THE VILLAGES, ..., The Villages, FL 32162
$299,000

3 beds

|

2 baths

|

1,262 sq ft

|

House

17930 SE 83RD MELODY AVE, THE VILLAGES, ...
Community: The Villages®
Solivita 1001 UMBRIA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$340,000

3 beds

|

2 baths

|

1,724 sq ft

|

House

1001 UMBRIA DR, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marion Landing 8478 SW 60TH CT, OCALA, FL, 34476, Ocala, FL 34476
$229,900

3 beds

|

2 baths

|

1,863 sq ft

|

House

8478 SW 60TH CT, OCALA, FL, 34476
Community: Marion Landing
Oak Run 8237 108TH SW STREET RD, OCALA, FL, 3448..., Ocala, FL 34481
$209,788

2 beds

|

2 baths

|

1,344 sq ft

|

House

8237 108TH SW STREET RD, OCALA, FL, 3448...
Community: Oak Run
Sun City Center 2403 NANTUCKET FIELD WAY # 27, SUN CITY ..., Sun City Center, FL 33573
$210,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2403 NANTUCKET FIELD WAY # 27, SUN CITY ...
Community: Sun City Center
JB Ranch 4770 SW 88TH LN, OCALA, FL, 34476, Ocala, FL 34476
$310,990

4 beds

|

2 baths

|

1,828 sq ft

|

House

4770 SW 88TH LN, OCALA, FL, 34476
Community: JB Ranch
Ocala Preserve 4379 NW 56TH CT, OCALA, FL, 34482, Ocala, FL 34482
$437,900

2 beds

|

3 baths

|

2,024 sq ft

|

House

4379 NW 56TH CT, OCALA, FL, 34482
Community: Ocala Preserve
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® 1323 BALBOA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$244,990

1 beds

|

1 baths

|

935 sq ft

|

Villa

1323 BALBOA CT, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 411 LOMA PASEO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$375,900

3 beds

|

2 baths

|

1,632 sq ft

|

House

411 LOMA PASEO DR, THE VILLAGES, FL, 321...
Community: The Villages®
Spruce Creek South 9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$319,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

9645 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Sun City Center 1016 MCDANIEL ST, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$220,000

2 beds

|

2 baths

|

1,810 sq ft

|

Condo

1016 MCDANIEL ST, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Vienna Square 1674 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$242,999

2 beds

|

2 baths

|

1,350 sq ft

|

House

1674 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Palms 2260 NW 51ST TER, OCALA, FL, 34482, Ocala, FL 34482
$380,000

3 beds

|

2 baths

|

1,950 sq ft

|

House

2260 NW 51ST TER, OCALA, FL, 34482
Community: Ocala Palms
High Vista at Ridgewood Lakes 705 ASHTON DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$299,900

2 beds

|

2 baths

|

1,814 sq ft

|

House

705 ASHTON DR, DAVENPORT, FL, 33837
High Vista at Ridgewood Lakes 100 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$429,000

3 beds

|

2 baths

|

2,051 sq ft

|

House

100 MOSS LN, DAVENPORT, FL, 33837
High Vista at Ridgewood Lakes 106 MOSSY OAK DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$380,000

3 beds

|

2 baths

|

1,797 sq ft

|

House

106 MOSSY OAK DR, DAVENPORT, FL, 33837
Kings Ridge 4087 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$349,900

2 beds

|

2 baths

|

1,792 sq ft

|

House

4087 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge

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3,958 homes near Winter Garden
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