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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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(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
- $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
Latitude Margaritaville
![613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,204 sq ft
|House
613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1215143 • Bob Hodges and Sons Realty, Kelley ...
Venetian Bay
![3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,003 sq ft
|Townhouse
3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1083506 • EXIT REAL ESTATE PROPERTY SOL, Ca...
Venetian Bay
![2931 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,511 sq ft
|House
2931 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
MLS NS1085465 • EXIT REAL ESTATE PROPERTY SOL, Ca...
JB Ranch
![6175 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM704571 • KELLER WILLIAMS CORNERSTONE RE, Cr...
On Top of the World
![8710 SW 91ST ST E, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,480 sq ft
|Villa
8710 SW 91ST ST E, OCALA, FL, 34481
Community: On Top of the World
MLS OM701633 • RE/MAX FOXFIRE - HWY 40, Bobby Mat...
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(689) 407-5757
Highland Lakes
![27022 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,999 sq ft
|House
27022 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5095538 • ERA GRIZZARD REAL ESTATE, Ricky Ha...
Stone Creek
![9498 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM705215 • HOMERUN REALTY, Leigh Ann Venable
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
Lake Ashton
![4056 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4056 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS S5129465 • EXP REALTY LLC, Miluska Parot
SummerGlen
![15782 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473]()
3 beds
|2 baths
|1,676 sq ft
|House
15782 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
MLS OM700125 • SUMMERGLEN REALTY,LLC, Melissa Pow...
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.
Arlington Ridge
![26822 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,599 sq ft
|House
26822 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5097176 • REALTY EXECUTIVES IN THE VILLAGES,...
Stone Creek
![9412 SW 53RD PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM705366 • LANGAN REALTY CO, Amanda Langan
Trilogy® Orlando
![252 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|3 baths
|2,532 sq ft
|House
252 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS TB8361477 • SIGNATURE REALTY ASSOCIATES, Roge...
Stonecrest
![17808 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,758 sq ft
|House
17808 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM686017 • TALLEY ALLISTON REALTY LLC, Cynthi...
Sun City Center
![2129 ACADIA GREENS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,194 sq ft
|Condo
2129 ACADIA GREENS DR, SUN CITY CENTER, ...
Community: Sun City Center
MLS TB8359252 • KELLER WILLIAMS SOUTH SHORE, Jeff...
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(689) 407-5757
Sun City Center
![902 MCDANIEL ST # 1, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,825 sq ft
|Condo
902 MCDANIEL ST # 1, SUN CITY CENTER, FL...
Community: Sun City Center
MLS T3551150 • DALTON WADE INC, Patti Carmel
The Villages®
![2552 MARIEL WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2552 MARIEL WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5091480 • OLYMPUS EXECUTIVE REALTY INC, Paul...
Venetian Bay
![2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,034 sq ft
|House
2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
MLS V4943028 • COLDWELL BANKER COAST REALTY, Ron ...
Spruce Creek Country Club
![13111 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,258 sq ft
|House
13111 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM699042 • COLDWELL BANKER ELLISON REALTY O, ...
Highlands Ridge
![3421 E GLEN EAGLES DR, AVON PARK, FL, 33..., Avon Park, FL 33825]()
3 beds
|2 baths
|2,594 sq ft
|House
3421 E GLEN EAGLES DR, AVON PARK, FL, 33...
Community: Highlands Ridge
MLS 315740 • RE/MAX REALTY PLUS, Kim Best
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.
Lake Jovita Golf and Country Club
![13353 CARNOUSTIE CIR, DADE CITY, FL, 335..., Dade City, FL 33525]()
6 beds
|4 baths
|4,572 sq ft
|House
13353 CARNOUSTIE CIR, DADE CITY, FL, 335...
Community: Lake Jovita Golf and Country Club
MLS TB8403054 • KELLER WILLIAMS RLTY NEW TAMPA, E...
Solivita
![346 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5129606 • ARISTA REALTY GROUP, LLC, Douglas ...
Spruce Creek Preserve
![11263 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
2 beds
|2 baths
|1,664 sq ft
|House
11263 SW 138TH LN, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM698391 • FONTANA REALTY, Javier Rojas
Solivita
![2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5119372 • ARISTA REALTY GROUP, LLC, Steve Lo...
Oak Run
![7692 SW 117TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476]()
3 beds
|2 baths
|2,253 sq ft
|House
7692 SW 117TH STREET RD, OCALA, FL, 3447...
Community: Oak Run
MLS OM699420 • DECCA REAL ESTATE, Cindy Casco
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
Sun City Center
![2411 NEW HAVEN CIR 70, SUN CITY CENTER, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,125 sq ft
|Condo
2411 NEW HAVEN CIR 70, SUN CITY CENTER, ...
Community: Sun City Center
MLS A4656789 • BETTER HOMES AND GARDENS REAL ESTA...
On Top of the World
![9262 SW 102ND AVENUE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|3 baths
|2,703 sq ft
|House
9262 SW 102ND AVENUE RD, OCALA, FL, 3448...
Community: On Top of the World
MLS W7874067 • RE/MAX CHAMPIONS, Christian Bennet...
Arlington Ridge
![27121 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,418 sq ft
|Villa
27121 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5097816 • FLORIDA REALTY INVESTMENTS, Diane ...
Solivita
![2129 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5095758 • FLORIDA PLUS REALTY, LLC, Christin...
Solivita
![328 VESTRELLA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5124822 • BORCHINI REALTY, Valerie Williams
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.
Highland Fairways
![2012 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,661 sq ft
|House
2012 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
MLS L4954415 • COLDWELL BANKER REALTY, Kelley Bla...
Del Webb Sunbridge
![3112 RANGER DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
5 beds
|4 baths
|2,995 sq ft
|House
3112 RANGER DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6324603 • KELLER WILLIAMS ADVANTAGE III, Kat...
Venetian Bay
![2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,131 sq ft
|Townhouse
2840 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS FC306481 • NEXTHOME ENDLESS SUMMER, Garrett D...
Plantation at Leesburg
![24802 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|936 sq ft
|Manufactured Home
24802 PINE HL, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5096281 • COLDWELL BANKER VANGUARD EDGE, Lor...
On Top of the World
![9706 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,504 sq ft
|House
9706 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM704175 • KELLER WILLIAMS CORNERSTONE RE, Si...
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(689) 407-5757
Cherrywood
![10269 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM702669 • CB/ELLISON RLTY WEST, Edward Wise
Highland Lakes
![5500 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5096531 • FLORIDA PLUS REALTY, LLC, Christin...
Solivita
![759 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5125870 • PELLEGO, LLC, Stan Wilson
Tampa Bay Golf and Country Club
![29702 TEE SHOT DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576]()
2 beds
|2 baths
|1,489 sq ft
|House
29702 TEE SHOT DR, SAN ANTONIO, FL, 3357...
Community: Tampa Bay Golf and Country Club
MLS TB8397675 • RE/MAX ALLIANCE GROUP, John Halvo...
Sun City Center
![405 GLADSTONE PL, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,008 sq ft
|Condo
405 GLADSTONE PL, SUN CITY CENTER, FL, 3...
Community: Sun City Center
MLS TB8406561 • FLORIDA'S 1ST CHOICE RLTY LLC, Ro...
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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