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Winter Garden, FL 55+ active adult communities & homes for sale
109 communities near Winter Garden
3,537 homes near Winter Garden
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5 rating (1 reviews)
![Del Webb Oasis]()
$400Ks
- $900Ks
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]()
$100Ks
- $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
- $500Ks
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
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300Ks
- $900Ks
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
- $500Ks
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
- $600Ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
$100Ks
- $400Ks
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
- $400Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
4.7 rating (11 reviews)
![Valencia Lakes]()
$200Ks
- $700Ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 homes
5 rating (1 reviews)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $800Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$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
- $500Ks
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]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 homes
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5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$200Ks
- $400Ks
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
$400Ks
- $800Ks
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, FL?
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4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $300Ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$300Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
$100Ks
- $300Ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
$300Ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
High Vista at Ridgewood Lakes
![322 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,776 sq ft
|House
322 HIGH VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6327698 • CHARLES RUTENBERG REALTY ORLANDO, ...
Pennbrooke Fairways
![543 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|1 baths
|788 sq ft
|House
543 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5102481 • CENTURY 21 MYERS REALTY, Lisa Wolf...
Cherrywood
![9747 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS TB8429790 • CASA FRESCA REALTY, Michael Human
Kings Ridge
![3416 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5098813 • RE/MAX TITANIUM GROUP, Kimberly Jo...
Sun City Center
![401 DORCHESTER PL APT 62, SUN CITY CENTE..., Sun City Center, FL 33573]()
2 beds
|2 baths
|984 sq ft
|Condo
401 DORCHESTER PL APT 62, SUN CITY CENTE...
Community: Sun City Center
MLS TB8345441 • DREAM HOME REALTY GROUP, LLC, Eve...
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Stonecrest
![11246 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,312 sq ft
|House
11246 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5102326 • CHARLES RUTENBERG REALTY ORLANDO, ...
Solivita
![3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
4 beds
|3 baths
|2,495 sq ft
|House
3775 VIA MAZZINI CT, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5134048 • BORCHINI REALTY, Cherie Pontes
On Top of the World
![8180 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,576 sq ft
|House
8180 SW 80TH TER, OCALA, FL, 34476
Community: On Top of the World
MLS V4944952 • RE/MAX SIGNATURE, Stephanie Cathey
Highlands Ridge
![3541 E GLEN EAGLES DR, AVON PARK, FL, 33..., Avon Park, FL 33825]()
2 beds
|3 baths
|2,092 sq ft
|House
3541 E GLEN EAGLES DR, AVON PARK, FL, 33...
Community: Highlands Ridge
MLS B4901842 • COLDWELL BANKER HIGHLAND, Nancy Mc...
Twin Lakes
![2410 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2410 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5103150 • COLDWELL BANKER SOLOMON, Susy Orti...
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
![8711 SW 96TH LN D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,341 sq ft
|Villa
8711 SW 96TH LN D, OCALA, FL, 34481
Community: On Top of the World
MLS OM704771 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Ocala Preserve
![5555 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM705821 • OCALA HORSE PROPERTIES, LLC, Matt ...
Solivita
![504 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135090 • PELLEGO, LLC, Diane Cisek
Arlington Ridge
![26951 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,418 sq ft
|Villa
26951 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5095981 • LOKATION, Steven Simpkins
On Top of the World
![9030 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,288 sq ft
|House
9030 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
MLS OM709702 • ROYAL OAK REALTY LLC, Robyn Wagner
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On Top of the World
![8616 SW 82ND TER, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,283 sq ft
|House
8616 SW 82ND TER, OCALA, FL, 34481
Community: On Top of the World
MLS OM709498 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Foxwood Lake Estates
![5026 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,456 sq ft
|Manufactured Home
5026 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4955800 • KELLER WILLIAMS REALTY SMART, Casa...
Marion Landing
![6126 SW 84TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,595 sq ft
|House
6126 SW 84TH PLACE RD, OCALA, FL, 34476
Community: Marion Landing
MLS TB8426208 • PRISTINE BAY REAL ESTATE SERVICES...
On Top of the World
![7729 SW 85TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,159 sq ft
|House
7729 SW 85TH CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM693348 • EXP REALTY LLC, Della Lazare
Valencia Lakes
![16130 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598]()
2 beds
|2 baths
|1,496 sq ft
|Villa
16130 AMETHYST KEY DR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
MLS TB8416184 • DALTON WADE INC, Zoki Mbolekwa
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.
Sun City Center
![401 DORCHESTER PL 58, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|984 sq ft
|Condo
401 DORCHESTER PL 58, SUN CITY CENTER, F...
Community: Sun City Center
MLS T3553243 • DALTON WADE INC, Kevin McPherson
Ocala Palms
![2310 NW 59TH AVE, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM695123 • RE/MAX FOXFIRE - HWY200/103 S, Sh...
Sullivan Ranch
![30113 JUTLAND CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|4 baths
|3,320 sq ft
|House
30113 JUTLAND CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5101223 • COLDWELL BANKER VANGUARD EDGE, Mic...
The Villages®
![16950 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,687 sq ft
|House
16950 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
MLS O6318915 • CENTURY 21 CARIOTI, Kristi Matthew
Highland Lakes
![6419 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS O6301006 • SAND DOLLAR REALTY GROUP INC, Jeff...
Want to learn more about 55+ communities in Winter Garden, FL?
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(689) 407-5757
Solivita
![541 MILANO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5133852 • PELLEGO, LLC, Stan Wilson
Spruce Creek South
![9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
9645 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5095488 • TEAM WYN REALTY LLC, Gloria Wyning...
On Top of the World
![9686 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,515 sq ft
|House
9686 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM694231 • RE/MAX FOXFIRE - HWY200/103 S, Kr...
Pine Run Estates
![10040 SW 98TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,144 sq ft
|House
10040 SW 98TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
MLS OM696839 • RE/MAX FOXFIRE - HWY200/103 S, Ju...
Valencia Ridge
![32608 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543]()
3 beds
|3 baths
|2,209 sq ft
|House
32608 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
MLS TB8384852 • EXP REALTY LLC, Tamily Abdo
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.
Ocala Preserve
![5333 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,368 sq ft
|Halfplex
5333 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
MLS OM701324 • NEWGATE REALTY, LLC, Hanna Pieri
Pelican Bay Daytona Beach
![149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,192 sq ft
|Condo
149 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS S5123673 • LPT REALTY, LLC, Yomari Ayala
On Top of the World
![9662 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,412 sq ft
|Villa
9662 SW 95TH CT A, OCALA, FL, 34481
Community: On Top of the World
MLS OM693876 • RE/MAX FOXFIRE - HWY 40, Suzanne A...
On Top of the World
![9656 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,702 sq ft
|House
9656 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS O6136944 • MV REALTY PBC LLC, Andres Lizarazo...
On Top of the World
![8635 SW 95TH ST B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,484 sq ft
|Villa
8635 SW 95TH ST B, OCALA, FL, 34481
Community: On Top of the World
MLS OM710092 • ROBERTS REAL ESTATE INC, Diane Tre...
Want to learn more about 55+ communities in Winter Garden, FL?
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Sun City Center
![305 SIENA VISTA PL, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
2 beds
|3 baths
|1,984 sq ft
|House
305 SIENA VISTA PL, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS A4655474 • WAGNER REALTY, Shannon Dodge
New
Stone Creek
![5543 SW 85TH AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481]()
4 beds
|2 baths
|1,583 sq ft
|House
5543 SW 85TH AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
MLS OM715178 • H & H REALTY AND ASSOCIATES, Danie...
The Villages®
![1722 MYRTLE BEACH DR, THE VILLAGES, FL, ..., The Villages, FL 32159]()
2 beds
|1 baths
|832 sq ft
|Manufactured Home
1722 MYRTLE BEACH DR, THE VILLAGES, FL, ...
Community: The Villages®
MLS O6359638 • ERA GRIZZARD REAL ESTATE, Jessica ...
Arlington Ridge
![4719 HERITAGE TRL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,761 sq ft
|House
4719 HERITAGE TRL, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS OM714339 • DISCOVER FLORIDA REALTY GROUP LLC,...
The Villages®
![7168 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,512 sq ft
|House
7168 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
MLS G5103916 • SALLY LOVE REAL ESTATE, Caroline 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?
3,537
homes
near Winter Garden
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REIN updates its listings on a daily basis. Data last updated: Dec 18, 2025.
This application does not include information on all of the properties available for sale at this time.
