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Winter Garden, FL 55+ active adult communities & homes for sale
106 communities near Winter Garden
3,573 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]()
$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
- $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
Want to learn more about 55+ communities in Winter Garden?
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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.
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$300Ks
- $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)
![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
- $900Ks
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?
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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
Pennbrooke Fairways
![651 TIMBERCREST DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,468 sq ft
|House
651 TIMBERCREST DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5099051 • RIGHT REALTY CONNECTION, INC., Bet...
Del Webb Oasis
![12037 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787]()
3 beds
|3 baths
|1,678 sq ft
|House
12037 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
MLS O6327546 • MERITAGE HOMES OF FL REALTY, Tatia...
Oak Run
![10824 SW 90TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM700196 • ROBERT SLACK LLC, Oscar Miranda
On Top of the World
![8034 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,516 sq ft
|House
8034 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM703427 • ROBERT SLACK LLC, Oscar Miranda
Royal Harbor
![5305 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|1,824 sq ft
|House
5305 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS V4941959 • ROUND TABLE REALTY INC., Roxanne L...
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Questions? Call us:
(689) 407-5757
Traditions at Lake Ruby
![3136 LANGDON LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|1,999 sq ft
|House
3136 LANGDON LN, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS L4953050 • KELLER WILLIAMS REALTY SMART 1, Sa...
On Top of the World
![8881 SW 94TH ST E, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,541 sq ft
|Villa
8881 SW 94TH ST E, OCALA, FL, 34481
Community: On Top of the World
MLS OM704083 • ON TOP OF THE WORLD REAL EST, Kath...
Solivita
![657 SHOREHAVEN DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS L4953957 • ELEVATE REAL ESTATE BROKERS, Russ ...
SummerGlen
![16026 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473]()
3 beds
|2 baths
|1,800 sq ft
|House
16026 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
MLS OM678989 • SUMMERGLEN REALTY,LLC, Melissa Pow...
On Top of the World
![8955 SW 86TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,127 sq ft
|House
8955 SW 86TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM699970 • NEXT GENERATION REALTY OF MARION C...
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
![9085 SW 96TH LN B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,709 sq ft
|Villa
9085 SW 96TH LN B, OCALA, FL, 34481
Community: On Top of the World
MLS OM703626 • ON TOP OF THE WORLD REAL EST, Kath...
Pelican Bay Daytona Beach
![102 BOB WHITE CT # 102C, DAYTONA BEACH, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,165 sq ft
|Condo
102 BOB WHITE CT # 102C, DAYTONA BEACH, ...
Community: Pelican Bay Daytona Beach
MLS V4942353 • RE/MAX SIGNATURE, Stephanie Cathey
The Villages®
![1628 BAY MEADOWS LN, THE VILLAGES, FL, 3..., The Villages, FL 32159]()
2 beds
|2 baths
|936 sq ft
|Manufactured Home
1628 BAY MEADOWS LN, THE VILLAGES, FL, 3...
Community: The Villages®
MLS OM692988 • RE/MAX PREMIER REALTY LADY LK, Don...
On Top of the World
![7935 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,344 sq ft
|House
7935 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM696087 • ON TOP OF THE WORLD REAL EST, Kath...
On Top of the World
![7987 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,874 sq ft
|House
7987 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM702419 • ON TOP OF THE WORLD REAL EST, Tamm...
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(689) 407-5757
Stonecrest
![12255 SE 177TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,768 sq ft
|House
12255 SE 177TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
MLS OM700989 • KELLER WILLIAMS CORNERSTONE RE, Ri...
On Top of the World
![9288 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,910 sq ft
|House
9288 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM699768 • RE/MAX FOXFIRE - HWY 40, Mike Kell...
Highlands Ridge
![4032 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825]()
3 beds
|3 baths
|2,808 sq ft
|House
4032 CARTER CREEK DR, AVON PARK, FL, 338...
Community: Highlands Ridge
MLS 315680 • RE/MAX REALTY PLUS, Emily Jones
On Top of the World
![7834 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,469 sq ft
|House
7834 SW 89TH CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM705525 • FLORIDA'S CHOICE REALTY, Stephanie...
Highland Fairways
![3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,529 sq ft
|House
3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS B4901969 • LAND SOUTH REALTY, LLC, Ron Denney
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
![1011 OTTER MILL WAY, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
2 beds
|3 baths
|2,105 sq ft
|Condo
1011 OTTER MILL WAY, SUN CITY CENTER, FL...
Community: Sun City Center
MLS TB8407802 • KELLER WILLIAMS SOUTH SHORE, Davi...
Four Seasons at Orlando
![1987 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1987 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6270026 • KELLER WILLIAMS ADVANTAGE III, Nat...
JB Ranch
![9238 SW 60TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM703888 • EPIQUE REALTY, INC., Noris Roche
The Villages®
![529 DEL MAR DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,539 sq ft
|House
529 DEL MAR DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5096738 • REALTY EXECUTIVES IN THE VILLAGES,...
Heritage Hills
![3677 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,672 sq ft
|House
3677 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5099041 • KELLER WILLIAMS ELITE PARTNERS III...
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
Stone Creek
![5576 SW 88TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM705424 • MEADOWS REALTY, LLC, Jim Sullivan
The Villages®
![1202 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,558 sq ft
|House
1202 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5096826 • ERA GRIZZARD REAL ESTATE, Ann Van ...
Solivita
![1309 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5129926 • PELLEGO, LLC, Claudia Gimenez-Carl...
Baytree
![579 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5096447 • ERA GRIZZARD REAL ESTATE, Jeanne T...
Tohoqua Reserve
![2003 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|1,943 sq ft
|House
2003 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6304939 • THE PARKS REALTY GROUP, Jeena Sanc...
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 Lakes at Harmony
![3184 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,852 sq ft
|House
3184 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5129784 • WEICHERT REALTORS HALLMARK PRO, Ba...
Ocala Palms
![2083 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM697197 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Plantation at Leesburg
![4904 LONG MEADOW DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|3 baths
|2,276 sq ft
|House
4904 LONG MEADOW DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5098556 • CENTURY 21 MYERS REALTY, Mary Jane...
Traditions at Lake Ruby
![3023 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Townhouse
3023 CANEEL ST, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4935116 • CENTURY 21 WOLF'S CROSSING REALTY,...
Plantation at Leesburg
![4520 EAGLEWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,843 sq ft
|House
4520 EAGLEWOOD DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5098683 • FLORIDA PLUS REALTY, LLC, Sandy Tw...
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55places can help!
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(689) 407-5757
The Villages®
![1812 SANIBEL CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,229 sq ft
|House
1812 SANIBEL CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5095690 • HARRISON REAL PROPERTY GROUP, Aman...
Oak Run
![10816 SW 83RD AVE, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM705655 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Sun City Center
![1224 VALLEY FORGE BLVD, SUN CITY CENTER,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,287 sq ft
|House
1224 VALLEY FORGE BLVD, SUN CITY CENTER,...
Community: Sun City Center
MLS TB8407828 • MCPEAK REAL ESTATE FIRM, Jim McPe...
Stone Creek
![9123 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM705457 • NEXT GENERATION REALTY OF MARION C...
The Villages®
![6231 ATKINSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,426 sq ft
|House
6231 ATKINSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6311848 • EXP REALTY LLC, Veronica Figueroa
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?
3,573
homes
near Winter Garden
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