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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
Sun City Center 810 BLUEWATER DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$269,990

2 beds

|

2 baths

|

1,756 sq ft

|

Villa

810 BLUEWATER DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Highland Lakes 26032 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$199,900

2 beds

|

2 baths

|

1,120 sq ft

|

Villa

26032 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Highland Lakes 6410 TILDON CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$287,500

3 beds

|

2 baths

|

1,957 sq ft

|

House

6410 TILDON CT, LEESBURG, FL, 34748
Community: Highland Lakes
Arlington Ridge 4223 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748
$329,000

2 beds

|

2 baths

|

1,524 sq ft

|

House

4223 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
Ocala Preserve 5430 NW 46TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$299,000

3 beds

|

2 baths

|

1,504 sq ft

|

House

5430 NW 46TH LANE RD, 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
Sun City Center 2405 NEW HAVEN CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$150,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2405 NEW HAVEN CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Solivita 100 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$315,000

2 beds

|

2 baths

|

1,739 sq ft

|

House

100 VENTANA DR, KISSIMMEE, FL, 34759
Community: Solivita
Sun City Center 1901 CANTERBURY LN 14, SUN CITY CENTER, ..., Sun City Center, FL 33573
$150,000

2 beds

|

2 baths

|

1,120 sq ft

|

Condo

1901 CANTERBURY LN 14, SUN CITY CENTER, ...
Community: Sun City Center
Gatherings of Lake Nona 7517 LAUREATE BLVD UNIT 4206, ORLANDO, F..., Orlando, FL 32827
$370,000

2 beds

|

2 baths

|

1,549 sq ft

|

Condo

7517 LAUREATE BLVD UNIT 4206, ORLANDO, F...
The Villages® 819 HIBISCUS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$124,900

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

819 HIBISCUS DR, THE VILLAGES, FL, 32159
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.
On Top of the World 9662 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$243,900

3 beds

|

2 baths

|

1,742 sq ft

|

House

9662 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Summit Greens 2366 PRAIRIE DUNES, CLERMONT, FL, 34711, Clermont, FL 34711
$407,000

3 beds

|

2 baths

|

1,725 sq ft

|

House

2366 PRAIRIE DUNES, CLERMONT, FL, 34711
Community: Summit Greens
Solivita 573 LAGO MATISSE ST, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$305,000

2 beds

|

2 baths

|

1,274 sq ft

|

House

573 LAGO MATISSE ST, KISSIMMEE, FL, 3475...
Community: Solivita
The Villages® 2518 FOXBRIDGE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,887 sq ft

|

House

2518 FOXBRIDGE TER, THE VILLAGES, FL, 32...
Community: The Villages®
Stone Creek 8875 SW 58TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$560,000

3 beds

|

2 baths

|

2,088 sq ft

|

House

8875 SW 58TH STREET 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
Spruce Creek Country Club 13828 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,315 sq ft

|

House

13828 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Kings Ridge 4020 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$365,000

3 beds

|

2 baths

|

1,572 sq ft

|

House

4020 CAPLAND AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Heritage Hills 3801 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$399,899

3 beds

|

2 baths

|

1,672 sq ft

|

House

3801 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
On Top of the World 9691 SW 95TH CT D, OCALA, FL, 34481, Ocala, FL 34481
$168,900

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9691 SW 95TH CT D, OCALA, FL, 34481
Community: On Top of the World
Valencia Lakes 4961 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598
$369,000

3 beds

|

2 baths

|

1,710 sq ft

|

Villa

4961 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia 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 9693 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481
$355,000

3 beds

|

2 baths

|

2,330 sq ft

|

House

9693 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
Lake Jovita Golf and Country Club 14174 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$600,000

3 beds

|

3 baths

|

2,133 sq ft

|

House

14174 THOROUGHBRED DR, DADE CITY, FL, 33...
Harbor Hills Country Club 6106 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$595,000

3 beds

|

2 baths

|

2,497 sq ft

|

House

6106 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Kings Ridge 2065 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$329,000

2 beds

|

2 baths

|

1,150 sq ft

|

House

2065 BRAXTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
Royal Highlands 21837 ROYAL ST GEORGES LN, LEESBURG, FL,..., Leesburg, FL 34748
$289,900

2 beds

|

2 baths

|

1,481 sq ft

|

House

21837 ROYAL ST GEORGES LN, LEESBURG, FL,...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 8534 SW 59TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$560,000

2 beds

|

3 baths

|

2,409 sq ft

|

House

8534 SW 59TH LANE RD, OCALA, FL, 34481
Community: Stone Creek
Spruce Creek Country Club 9450 SE 130TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$415,000

3 beds

|

3 baths

|

2,252 sq ft

|

House

9450 SE 130TH PLACE RD, SUMMERFIELD, FL,...
On Top of the World 9452 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$339,900

2 beds

|

2 baths

|

1,947 sq ft

|

House

9452 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1335 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$189,000

2 beds

|

2 baths

|

1,342 sq ft

|

Manufactured Home

1335 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
The Villages® 1842 LAKE RIDGE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$875,000

3 beds

|

2 baths

|

2,364 sq ft

|

House

1842 LAKE RIDGE DR, 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.
Pelican Bay Daytona Beach 129 GOLDEN EYE DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$239,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

129 GOLDEN EYE DR C, DAYTONA BEACH, FL, ...
Ocala Preserve 5430 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$685,000

3 beds

|

3 baths

|

2,694 sq ft

|

House

5430 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Oak Run 7692 SW 117TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$350,000

3 beds

|

2 baths

|

2,253 sq ft

|

House

7692 SW 117TH STREET RD, OCALA, FL, 3447...
Community: Oak Run
High Vista at Ridgewood Lakes 725 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$310,000

3 beds

|

2 baths

|

1,594 sq ft

|

House

725 HIGH VISTA DR, DAVENPORT, FL, 33837
On Top of the World 9764 SW 100TH AVENUE RD, OCALA, FL, 3448..., Ocala, FL 34481
$309,900

2 beds

|

2 baths

|

1,579 sq ft

|

House

9764 SW 100TH AVENUE RD, OCALA, FL, 3448...
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
Lakes of Mount Dora 3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$549,990

3 beds

|

2 baths

|

2,180 sq ft

|

House

3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Highlands Ridge 5056 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$320,000

2 beds

|

2 baths

|

1,888 sq ft

|

Villa

5056 BIRKDALE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Sun City Center 1102 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$395,000

2 beds

|

2 baths

|

1,936 sq ft

|

House

1102 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Valencia Lakes 5004 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$450,000

3 beds

|

3 baths

|

2,409 sq ft

|

House

5004 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Twin Lakes 4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$524,999

3 beds

|

3 baths

|

2,365 sq ft

|

House

4909 W FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes

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3,958 homes near Winter Garden
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