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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]()
<$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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(689) 407-5757
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
Ocala Preserve
![3568 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS V4944181 • RE/MAX SIGNATURE, Stephanie Cathey
Solivita
![1001 UMBRIA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5127188 • WEICHERT REALTORS HALLMARK PRO, Om...
Venetian Bay
![3375 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,968 sq ft
|House
3375 BELLINO BLVD, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS O6300640 • BENCHMARK REAL ESTATE GRP INC, Tor...
Twin Lakes
![2301 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2301 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS O6309251 • KELLER WILLIAMS REALTY AT THE PARK...
On Top of the World
![8433 SW 98TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|3 baths
|2,373 sq ft
|House
8433 SW 98TH TERRACE RD, OCALA, FL, 3448...
Community: On Top of the World
MLS G5095116 • CENTURY 21 CARIOTI, Lori Walker
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On Top of the World
![9764 SW 81ST LN, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,309 sq ft
|House
9764 SW 81ST LN, OCALA, FL, 34481
Community: On Top of the World
MLS OM699749 • ON TOP OF THE WORLD REAL EST, Shel...
The Villages®
![17567 SE 81ST PARNASSUS CT, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,922 sq ft
|House
17567 SE 81ST PARNASSUS CT, THE VILLAGES...
Community: The Villages®
MLS TB8395118 • ALTRU REALTY, Keith Gordon
Carillon Lakes
![3999 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,758 sq ft
|House
3999 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
MLS L4954380 • SERHANT, Elizabeth Willers
Harbor Hills Country Club
![5195 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,696 sq ft
|House
5195 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5095402 • NEXTHOME SALLY LOVE REAL ESTATE, C...
Royal Highlands
![20806 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,939 sq ft
|House
20806 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS O6330029 • KELLER WILLIAMS REALTY AT THE PARK...
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.
Summer Trees
![71 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,415 sq ft
|Townhouse
71 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS V4943055 • LPT REALTY LLC, Farrah Thacker
Solivita
![124 MERIDIAN AVE, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS O6286904 • KELLER WILLIAMS ADVANTAGE 2 REALTY...
Heritage Hills
![3632 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3632 SOLANA CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6282838 • BHHS FLORIDA REALTY, Patti Kincaid
On Top of the World
![9491 SW 98TH CT, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,737 sq ft
|House
9491 SW 98TH CT, OCALA, FL, 34481
Community: On Top of the World
MLS O6289299 • GAILEY ENTERPRISES REAL ESTATE, Ri...
Spruce Creek Country Club
![12150 SE 91ST TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,870 sq ft
|House
12150 SE 91ST TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5100462 • RE/MAX PREMIER REALTY LADY LK, Rob...
Want to learn more about 55+ communities in Winter Garden?
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Sun City Center
![205 KINGS BLVD 55, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
1 beds
|2 baths
|800 sq ft
|Condo
205 KINGS BLVD 55, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS TB8417718 • CENTURY 21 BEGGINS ENTERPRISES, D...
Spruce Creek Country Club
![12896 SE 91ST TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,935 sq ft
|House
12896 SE 91ST TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM707637 • RE/MAX PREMIER REALTY LADY LK, Jay...
Oak Run
![8368 SW 109TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM707609 • DECCA REAL ESTATE, Thomas Reeves
Pennbrooke Fairways
![32537 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,927 sq ft
|House
32537 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS S5132745 • SUNSHINE REAL ESTATE PROS LLC, Lou...
Trilogy® Orlando
![363 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,568 sq ft
|House
363 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS O6335931 • MARK SPAIN REAL ESTATE, Christine ...
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.
Kings Ridge
![3443 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5100806 • WHEATLEY REALTY GROUP, Heather Ale...
The Villages®
![1606 TANGO ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,107 sq ft
|House
1606 TANGO ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS V4944335 • SOUTHERN EXCLUSIVE REALTY CORP, Jo...
Spruce Creek Country Club
![9029 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,809 sq ft
|House
9029 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS O6335599 • KELLER WILLIAMS ADVANTAGE REALTY, ...
Sun City Center
![626 TREMONT GREENS LN # 626, SUN CITY CE..., Sun City Center, FL 33573]()
2 beds
|2 baths
|974 sq ft
|Condo
626 TREMONT GREENS LN # 626, SUN CITY CE...
Community: Sun City Center
MLS TB8416640 • KELLER WILLIAMS SOUTH TAMPA, Mich...
Spruce Creek Country Club
![9031 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,346 sq ft
|House
9031 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5100650 • RE/MAX PREMIER REALTY LADY LK, Rob...
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(689) 407-5757
Venetian Bay
![3186 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,890 sq ft
|House
3186 TIGER PALM WAY, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS W7874383 • MALTBIE REALTY GROUP, Bill Maltbie
Lake Jovita Golf and Country Club
![13141 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525]()
2 beds
|2 baths
|2,019 sq ft
|Villa
13141 PALMILLA CIR, DADE CITY, FL, 33525
Community: Lake Jovita Golf and Country Club
MLS TB8321573 • RE/MAX CHAMPIONS, Frederick Alonz...
On Top of the World
![8890 SW 104TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,651 sq ft
|House
8890 SW 104TH CIR, OCALA, FL, 34481
Community: On Top of the World
MLS TB8374654 • PRIME REAL ESTATE SALES, LLC, Doy...
Solivita
![448 FOUNTAIN VALLEY LN, POINCIANA, FL, 3..., Poinciana, FL 34759]()
3 beds
|3 baths
|2,394 sq ft
|House
448 FOUNTAIN VALLEY LN, POINCIANA, FL, 3...
Community: Solivita
MLS S5131238 • BORCHINI REALTY, Yamile Osorio Var...
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
![9841 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,972 sq ft
|House
9841 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM696171 • RE/MAX FOXFIRE - HWY 40, Bobby Mat...
Solivita
![917 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5092308 • FLORIDA PLUS REALTY, LLC, Christin...
Ocala Palms
![5110 NW 19TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM702719 • WEICHERT REALTORS HALLMARK PRO, Ka...
The Villages®
![3531 RESTON DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
3531 RESTON DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6321681 • WEMERT GROUP REALTY LLC, Jenny Wem...
Plantation at Leesburg
![3909 RIVER CREST CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,690 sq ft
|House
3909 RIVER CREST CIR, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5093974 • FLAMINGO REAL ESTATE & MNGMT, Kody...
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(689) 407-5757
The Villages®
![2609 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,388 sq ft
|House
2609 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5094120 • COLDWELL BANKER VANGUARD EDGE, Mar...
The Villages®
![731 HERNANDEZ DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,094 sq ft
|Villa
731 HERNANDEZ DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5093063 • COLDWELL BANKER VANGUARD EDGE, Mar...
The Villages®
![2708 LA POSADA DR, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,527 sq ft
|House
2708 LA POSADA DR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS O6306335 • MARK SPAIN REAL ESTATE, Jeffery Jo...
Twin Lakes
![5040 GARDENROW DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,322 sq ft
|Villa
5040 GARDENROW DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6331745 • PULTE REALTY OF NORTH FLORIDA LLC,...
Del Webb Minneola
![1324 ORANGE VALLEY RD, MINNEOLA, FL, 347..., Minneola, FL 34715]()
3 beds
|2 baths
|1,655 sq ft
|House
1324 ORANGE VALLEY RD, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS O6332893 • PULTE REALTY OF NORTH FLORIDA LLC,...
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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