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Winter Garden, FL 55+ active adult communities & homes for sale
106 communities near Winter Garden
3,584 homes near Winter Garden
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![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
- $2Ms
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]()
$100Ks
- $700Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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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
- $500Ks
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
- $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
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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]()
$200Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $500Ks
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]()
$300Ks
- $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)
![VillageWalk at Lake Nona]()
$400Ks
- $900Ks
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
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(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...]()
$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
- $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
- $400Ks
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]()
$300Ks
- $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
4.3 rating (15 reviews)
![Del Webb Orlando]()
$200Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
No reviews yet
![Pine Run Estates]()
<$100k
- $400Ks
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
Liberty Village
![7412 SW 76TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,712 sq ft
|House
7412 SW 76TH TER, OCALA, FL, 34481
Community: Liberty Village
MLS O6286084 • EPIQUE REALTY, INC., Jacqueline Ha...
Sandpiper Golf & Country Club
![6054 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,915 sq ft
|House
6054 CRANE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4955307 • HOMETRUST REAL ESTATE & PTY MGT, D...
Venetian Bay
![711 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,796 sq ft
|House
711 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS TB8408871 • ASHTON WOODS FLORIDA REALTY LLC, ...
Palms at Serenoa
![3798 MYRTLE OAK CT, CLERMONT, FL, 34714, Clermont, FL 34714]()
2 beds
|2 baths
|1,646 sq ft
|Townhouse
3798 MYRTLE OAK CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
MLS O6337520 • WENDY MORRIS REALTY, Wendy Morris
Harbor Hills Country Club
![38634 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159]()
3 beds
|2 baths
|1,701 sq ft
|House
38634 LAKEVIEW WALK, LADY LAKE, FL, 3215...
Community: Harbor Hills Country Club
MLS G5101058 • EXP REALTY LLC, Barbara Cifelli
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
Southshore Bay
![16833 BANNER SHELL PL, WIMAUMA, FL, 3359..., Wimauma, FL 33598]()
3 beds
|3 baths
|2,611 sq ft
|House
16833 BANNER SHELL PL, WIMAUMA, FL, 3359...
Community: Southshore Bay
MLS A4661933 • SAVVY AVENUE, LLC, Moe Mossa
The Villages®
![1276 BENNETT PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|2,439 sq ft
|House
1276 BENNETT PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM705032 • VAUGHT REALTY, Billy Vaught
On Top of the World
![10045 SW 82ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,211 sq ft
|House
10045 SW 82ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM703680 • ON TOP OF THE WORLD REAL EST, Jaso...
Oak Run
![11552 SW 75TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM707310 • DECCA REAL ESTATE, Dawn Williams
The Country Club of Mount Dora
![1775 COUNTRY CLUB BLVD, MOUNT DORA, FL, ..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,252 sq ft
|Halfplex
1775 COUNTRY CLUB BLVD, MOUNT DORA, FL, ...
Community: The Country Club of Mount Dora
MLS G5101093 • MOUNT DORA GOLF AND LAKE RLTY, Joh...
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.
Majestic Oaks Ocala
![5920 SW 88TH PL, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|2,374 sq ft
|House
5920 SW 88TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS OM701787 • FONTANA REALTY, Donna Sloan
On Top of the World
![7881 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,342 sq ft
|House
7881 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM703199 • FLORIDA ADVANTAGE REALTY GROUP, Qu...
Harbor Hills Country Club
![5096 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|2,900 sq ft
|House
5096 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5088771 • RE/MAX FOXFIRE - SUMMERFIELD, Cher...
Solivita
![159 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5120654 • FAIRWAY REALTY OF SOLIVITA, Bonnie...
Venetian Bay
![254 CAPPELLA CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
4 beds
|5 baths
|3,040 sq ft
|House
254 CAPPELLA CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1084912 • EXIT REAL ESTATE PROPERTY SOL, Ca...
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Questions? Call us:
(689) 407-5757
Solivita
![517 MILANO RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5126980 • BORCHINI REALTY, Yamile Osorio Var...
Stone Creek
![5947 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM698332 • COPPOLA REALTY LLC, Bernii Coppola
Esplanade at Wiregrass Ranch
![29492 ZUPETTA LN, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543]()
3 beds
|2 baths
|1,926 sq ft
|House
29492 ZUPETTA LN, WESLEY CHAPEL, FL, 335...
Community: Esplanade at Wiregrass Ranch
MLS TB8413289 • AGILE GROUP REALTY, Mark LaPresti
Four Seasons at Orlando
![1650 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,586 sq ft
|Villa
1650 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6315407 • VIVA ORLANDO REALTY INC., Susan Ri...
Oak Run
![8602 SW 116TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM707595 • DECCA REAL ESTATE, David Tomlin
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.
Marion Landing
![8554 SW 63RD CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM703316 • FONTANA REALTY, Javier Rojas
On Top of the World
![8876 SW 95TH LN E, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,748 sq ft
|Villa
8876 SW 95TH LN E, OCALA, FL, 34481
Community: On Top of the World
MLS OM707716 • RE/MAX FOXFIRE - HWY200/103 S, St...
Solivita
![300 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6332662 • EXP REALTY LLC, Aidelys Hernandez
Legacy of Leesburg
![27123 NOSTALGIA DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,477 sq ft
|House
27123 NOSTALGIA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
MLS G5100026 • WEICHERT REALTORS HALLMARK PRO, Ma...
Cherrywood
![6100 SW 105TH PL, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM707029 • RE/MAX FOXFIRE - HWY200/103 S, Ju...
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Questions? Call us:
(689) 407-5757
Tampa Bay Golf and Country Club
![10118 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576]()
3 beds
|2 baths
|1,799 sq ft
|House
10118 CLEGHORN DR, SAN ANTONIO, FL, 3357...
Community: Tampa Bay Golf and Country Club
MLS TB8369438 • TOOLBOX SISTERS REALTY LLC, Allis...
Stone Creek
![7270 SW 99TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM701543 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Royal Harbor
![5008 ADRIATIC AVE, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|2 baths
|2,101 sq ft
|House
5008 ADRIATIC AVE, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5099454 • BHHS FLORIDA REALTY, Shella Jean O...
Tampa Bay Golf and Country Club
![9936 CLEGHORN DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576]()
3 beds
|2 baths
|1,772 sq ft
|House
9936 CLEGHORN DR, SAN ANTONIO, FL, 33576
Community: Tampa Bay Golf and Country Club
MLS TB8413879 • BHHS FLORIDA PROPERTIES GROUP, Sc...
Lake Ashton
![1202 ASHTON PALMS DR # 6, LAKE WALES, FL..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,436 sq ft
|Condo
1202 ASHTON PALMS DR # 6, LAKE WALES, FL...
Community: Lake Ashton
MLS P4931960 • LAKE ASHTON REALTY INC., Lori Raat...
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
![9865 SW 105TH CT, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,019 sq ft
|House
9865 SW 105TH CT, OCALA, FL, 34481
Community: On Top of the World
MLS OM702810 • ON TOP OF THE WORLD REAL EST, Jaso...
On Top of the World
![10553 SW 98TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,907 sq ft
|House
10553 SW 98TH PL, OCALA, FL, 34481
Community: On Top of the World
MLS OM702634 • ON TOP OF THE WORLD REAL EST, Jaso...
Kings Ridge
![3706 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5097026 • KELLER WILLIAMS ELITE PARTNERS III...
Ocala Preserve
![5339 NW 46TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,565 sq ft
|Villa
5339 NW 46TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
MLS OM699560 • DR HORTON REALTY OF WEST CENTRAL F...
Ocala Preserve
![4743 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,565 sq ft
|Villa
4743 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
MLS OM687697 • DR HORTON REALTY OF WEST CENTRAL F...
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Ocala Preserve
![4737 NW 39TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,565 sq ft
|Villa
4737 NW 39TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
MLS OM687696 • DR HORTON REALTY OF WEST CENTRAL F...
Ocala Preserve
![4062 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM693393 • DR HORTON REALTY OF WEST CENTRAL F...
Stonecrest
![17508 SE 119TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,539 sq ft
|House
17508 SE 119TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM707364 • KELLER WILLIAMS CORNERSTONE RE, Ci...
Twin Lakes
![2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|Villa
2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5130528 • WEICHERT REALTORS HALLMARK PRO, Sh...
JB Ranch
![9358 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM706846 • DR HORTON REALTY OF WEST CENTRAL F...
Frequently Asked Questions
In Winter Garden, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.
The smallest 55+ communities in Winter Garden has 163 homes, the largest has 422 homes, and the average communities consists of 292 homes.
Yes, there are new 55+ homes available in Winter Garden. The most recent communities started in Winter Garden include Overture Hamlin, Del Webb Oasis. There are also 2 communities in Winter Garden that offer new construction homes, including Overture Hamlin, Del Webb Oasis.
Yes, there is gated 55+ communities in Winter Garden. Approximately 50.0% of 55+ communities in the area are gated. For instance, Del Webb Oasis is a gated communities with 422 homes.
Want more information about active adult communities around Winter Garden?
Want to learn more about 55+ communities in Winter Garden?
3,584
homes
near Winter Garden
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