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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.
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
$200Ks - $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) 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
$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
The Villages® 1307 GALINDO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$389,900

3 beds

|

2 baths

|

1,872 sq ft

|

House

1307 GALINDO PL, THE VILLAGES, FL, 32159
Community: The Villages®
Lake Jovita Golf and Country Club 13805 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,399,000

3 beds

|

4 baths

|

3,201 sq ft

|

House

13805 CARRYBACK DR, DADE CITY, FL, 33525
Sun City Center 2222 MAYFIELD PALMS LN # 322, SUN CITY C..., Sun City Center, FL 33573
$269,900

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

2222 MAYFIELD PALMS LN # 322, SUN CITY C...
Community: Sun City Center
The Villages® 461 TROY LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$455,000

3 beds

|

2 baths

|

1,661 sq ft

|

House

461 TROY LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
Venetian Bay 3396 LEONARDO LN, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$599,888

3 beds

|

2 baths

|

1,658 sq ft

|

House

3396 LEONARDO LN, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 6014 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$299,900

2 beds

|

2 baths

|

1,469 sq ft

|

House

6014 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Heritage Hills 3825 QUAINT LN F, CLERMONT, FL, 34711, Clermont, FL 34711
$333,500

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3825 QUAINT LN F, CLERMONT, FL, 34711
Community: Heritage Hills
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
Solivita 734 VIA COMO ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$308,000

2 beds

|

2 baths

|

1,350 sq ft

|

House

734 VIA COMO ST, POINCIANA, FL, 34759
Community: Solivita
Pine Run Estates 9880 SW 101ST PL, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

9880 SW 101ST PL, OCALA, FL, 34481
Community: Pine Run 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.
The Villages® 2378 RIDGEWAY CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$359,999

3 beds

|

2 baths

|

1,602 sq ft

|

House

2378 RIDGEWAY CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Cherrywood 9896 SW 61ST CT, OCALA, FL, 34476, Ocala, FL 34476
$179,800

2 beds

|

2 baths

|

1,320 sq ft

|

House

9896 SW 61ST CT, OCALA, FL, 34476
Community: Cherrywood
Arlington Ridge 4041 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$327,000

3 beds

|

2 baths

|

1,529 sq ft

|

House

4041 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Quail Meadow 4716 NW 34TH PL, OCALA, FL, 34482, Ocala, FL 34482
$365,000

3 beds

|

2 baths

|

2,112 sq ft

|

House

4716 NW 34TH PL, OCALA, FL, 34482
Community: Quail Meadow
Foxwood Lake Estates 1744 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$182,900

3 beds

|

2 baths

|

1,566 sq ft

|

Manufactured Home

1744 QUAIL HILL DR, LAKELAND, FL, 33810
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Majestic Oaks Ocala 5327 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476
$279,900

3 beds

|

2 baths

|

1,661 sq ft

|

House

5327 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Pelican Bay Daytona Beach 102 BOB WHITE CT # 102C, DAYTONA BEACH, ..., Daytona Beach, FL 32119
$205,000

2 beds

|

2 baths

|

1,165 sq ft

|

Condo

102 BOB WHITE CT # 102C, DAYTONA BEACH, ...
Cresswind at Victoria Gardens 307 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$314,800

2 beds

|

2 baths

|

1,547 sq ft

|

House

307 HERON POINT WAY, DELAND, FL, 32724
Sun City Center 1912 ACADIA GREENS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$319,900

2 beds

|

2 baths

|

1,620 sq ft

|

Condo

1912 ACADIA GREENS DR, SUN CITY CENTER, ...
Community: Sun City Center
Pelican Bay Daytona Beach 102 BOB WHITE CT C, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$205,000

2 beds

|

2 baths

|

1,165 sq ft

|

Condo

102 BOB WHITE CT C, DAYTONA BEACH, FL, 3...
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.
Summit Greens 1063 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$399,999

3 beds

|

2 baths

|

1,900 sq ft

|

House

1063 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
SummerGlen 16026 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$282,900

3 beds

|

2 baths

|

1,800 sq ft

|

House

16026 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Spruce Creek South 10551 SE 179TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$280,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

10551 SE 179TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 8338 SE 178TH DEVEAUX LN, THE VILLAGES, ..., The Villages, FL 32162
$379,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

8338 SE 178TH DEVEAUX LN, THE VILLAGES, ...
Community: The Villages®
Ocala Palms 2083 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482
$286,900

2 beds

|

2 baths

|

1,731 sq ft

|

House

2083 NW 57TH CT, OCALA, FL, 34482
Community: Ocala Palms
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2320 MARKSMEN CT # 205, SUN CITY CENTER,..., Sun City Center, FL 33573
$209,000

2 beds

|

2 baths

|

1,182 sq ft

|

Condo

2320 MARKSMEN CT # 205, SUN CITY CENTER,...
Community: Sun City Center
Kings Ridge 2160 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$299,990

2 beds

|

2 baths

|

1,334 sq ft

|

House

2160 ADDISON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Venetian Bay 3621 CASELLO DR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$389,000

3 beds

|

3 baths

|

1,827 sq ft

|

Townhouse

3621 CASELLO DR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Windermere 819 BALMORAL CT, INVERNESS, FL, 34453, Inverness, FL 34453
$325,000

3 beds

|

2 baths

|

1,988 sq ft

|

House

819 BALMORAL CT, INVERNESS, FL, 34453
Community: Windermere
Carillon Lakes 3323 SONGBIRD LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$312,000

3 beds

|

2 baths

|

1,704 sq ft

|

House

3323 SONGBIRD LN, LAKELAND, FL, 33811
Community: Carillon Lakes
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 9504 SW 97TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$227,900

2 beds

|

2 baths

|

1,360 sq ft

|

Villa

9504 SW 97TH LN B, OCALA, FL, 34481
Community: On Top of the World
The Villages® 3050 GULFPORT CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$379,900

2 beds

|

2 baths

|

1,161 sq ft

|

Villa

3050 GULFPORT CT, THE VILLAGES, FL, 3216...
Community: The Villages®
Sun City Center 2438 SIFIELD GREENS WAY # 44, SUN CITY C..., Sun City Center, FL 33573
$229,000

2 beds

|

2 baths

|

1,183 sq ft

|

Condo

2438 SIFIELD GREENS WAY # 44, SUN CITY C...
Community: Sun City Center
On Top of the World 8747 SW 98TH STREET RD F, OCALA, FL, 344..., Ocala, FL 34481
$149,900

2 beds

|

2 baths

|

1,198 sq ft

|

Villa

8747 SW 98TH STREET RD F, OCALA, FL, 344...
Community: On Top of the World
Sun City Center 2426 SIFIELD GREENS WAY, SUN CITY CENTER..., Sun City Center, FL 33573
$274,000

2 beds

|

2 baths

|

1,188 sq ft

|

Condo

2426 SIFIELD GREENS WAY, SUN CITY CENTER...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Summer Trees 6037 WHISPERING TREES LN, PORT ORANGE, F..., Port Orange, FL 32128
$399,900

3 beds

|

2 baths

|

1,820 sq ft

|

House

6037 WHISPERING TREES LN, PORT ORANGE, F...
Community: Summer Trees
Tohoqua Reserve 1931 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$487,460

2 beds

|

2 baths

|

1,670 sq ft

|

House

1931 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Royal Harbor 6250 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778
$365,000

3 beds

|

3 baths

|

1,827 sq ft

|

House

6250 SAILBOAT AVE, TAVARES, FL, 32778
Community: Royal Harbor
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
Spruce Creek South 9802 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$249,900

3 beds

|

2 baths

|

1,450 sq ft

|

House

9802 SE 178TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South

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3,958 homes near Winter Garden
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