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Winter Garden, FL 55+ active adult communities & homes for sale - Page 38
110 communities near Winter Garden
3,654 homes near Winter Garden
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4 rating (17 reviews)
![The Villages®]()
$100ks
- $1Ms
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]()
$100ks
- $800ks
Sun City Center, Sun City Center, FL
Resale Only
|
55+ age-restricted
|
Built 1961 - 2018
|
9,500 homes
4.2 rating (10 reviews)
![Stone Creek]()
$200ks
- $500ks
Stone Creek, Ocala, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
3,800 homes
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$100ks
- $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
4.1 rating (29 reviews)
![Oak Run]()
$100ks
- $300ks
Oak Run, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 2007
|
3,509 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.
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300ks
- $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 homes
4.6 rating (5 reviews)
![Ocala Preserve]()
$100ks
- $500ks
Ocala Preserve, Ocala, FL
New and Resale
|
55+ age-restricted
|
Built 2014 - present
|
1,800 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
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5 rating (1 reviews)
![Ocala Palms]()
$200ks
- $300ks
Ocala Palms, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1994 - 1997
|
1,076 homes
3.8 rating (4 reviews)
![Spruce Creek South]()
$100ks
- $200ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (5 reviews)
![SummerGlen]()
$200ks
- $400ks
SummerGlen, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
1,024 homes
$200ks
- $500ks
Southshore Bay, Wimauma, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
655 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.
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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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4 rating (7 reviews)
![Tampa Bay Golf and Countr...]()
$200ks
- $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only
|
55+ age-restricted
|
Built 1994 - 2015
|
1,336 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200ks
- $500ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 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
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 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.
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
2.3 rating (6 reviews)
![Cherrywood]()
$100ks
- $800ks
Cherrywood, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2003
|
700 homes
4 rating (2 reviews)
![Harbor Hills Country Club]()
$300ks
- $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
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Questions? Call us:
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1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200ks
- $400ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
$100ks
- $200ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
$300ks
- $500ks
Mirada, San Antonio, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
858 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 (1 reviews)
![Palm Cay]()
$100ks
- $200ks
Palm Cay, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1992
|
795 homes
$400ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
Sun City Center
![1021 AUGUSTA DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573]()
3 beds
|2 baths
|1,757 sq ft
|House
1021 AUGUSTA DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
MLS TB8476104 • AMERICAN HOMES REALTY GROUP, Davi...
Heritage Hills
![3538 FAIRWATERS CT B, CLERMONT, FL, 3471..., Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3538 FAIRWATERS CT B, CLERMONT, FL, 3471...
Community: Heritage Hills
MLS G5107747 • KELLER WILLIAMS ELITE PARTNERS III...
Sun City Center
![1102 HAREFIELD CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,390 sq ft
|Condo
1102 HAREFIELD CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS TB8469408 • KELLER WILLIAMS SOUTH SHORE, Cole...
Valencia Ridge
![32623 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543]()
3 beds
|3 baths
|2,209 sq ft
|House
32623 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
MLS TB8472937 • BEACH PLACE ONE REAL ESTATE, Debb...
SummerGlen
![15050 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473]()
3 beds
|2 baths
|2,324 sq ft
|House
15050 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
MLS OM718651 • SOUTHERN ASSOCIATES REALTY LLC, Cy...
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
Royal Highlands
![4741 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,902 sq ft
|House
4741 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
MLS S5143859 • NONA LEGACY POWERED BY LA ROSA, Vi...
Foxwood Lake Estates
![1631 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
3 beds
|2 baths
|1,680 sq ft
|Manufactured Home
1631 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5143840 • THE PROPERTY FIRM, Savina Delgado ...
The Villages®
![670 WOODBRIDGE WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|2,299 sq ft
|House
670 WOODBRIDGE WAY, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5108131 • RE/MAX PREMIER REALTY, Tammy Freil...
The Villages®
![1020 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,240 sq ft
|Manufactured Home
1020 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6382426 • KELLER WILLIAMS CLASSIC, Francis Z...
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.
Valencia Ridge
![32616 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543]()
3 beds
|3 baths
|2,450 sq ft
|House
32616 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
MLS TB8471882 • BEACH PLACE ONE REAL ESTATE, Debb...
Kings Ridge
![2302 EDMONTON CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6382577 • CENTURY 21 CARIOTI, Angelica Tomli...
Foxwood Lake Estates
![1679 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
1679 FOXWAY DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS L4959368 • COLDWELL BANKER REALTY, Kelley Bla...
Lake Jovita Golf and Country Club
![13235 LEGENDS TRL, DADE CITY, FL, 33525, Dade City, FL 33525]()
4 beds
|3 baths
|1,945 sq ft
|House
13235 LEGENDS TRL, DADE CITY, FL, 33525
Community: Lake Jovita Golf and Country Club
MLS W7883013 • F I GREY & SON RESIDENTIAL, Lau...
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Questions? Call us:
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Oak Run
![5706 SW 71ST AVE, OCALA, FL, 34474, Ocala, FL 34474]()
MLS OM718519 • ON TOP OF THE WORLD REAL EST, Jaso...
Palm Cay
![8172 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM718831 • FONTANA REALTY, Donna Sloan
Pelican Bay Daytona Beach
![636 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,484 sq ft
|Townhouse
636 BROWN PELICAN DR, DAYTONA BEACH, FL,...
Community: Pelican Bay Daytona Beach
MLS 1223010 • Simply Real Estate, Deana Frechette
Sun City Center
![2035 HAMPSTEAD CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,378 sq ft
|Condo
2035 HAMPSTEAD CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS TB8476292 • CENTURY 21 BEGGINS ENTERPRISES, S...
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
![2226 BROOKFIELD GREENS CIR, SUN CITY CEN..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,450 sq ft
|Condo
2226 BROOKFIELD GREENS CIR, SUN CITY CEN...
Community: Sun City Center
MLS TB8475986 • KELLER WILLIAMS SOUTH SHORE, Cath...
Pennbrooke Fairways
![32747 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,192 sq ft
|House
32747 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5108173 • MAXREV LLC, Jayne Marvin
Solivita
![246 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6381333 • WEMERT GROUP REALTY LLC, Jenny Wem...
On Top of the World
![9368 SW 82ND TER D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,411 sq ft
|Villa
9368 SW 82ND TER D, OCALA, FL, 34481
Community: On Top of the World
MLS TB8475880 • FLAT FEE MLS REALTY, Stephen Hach...
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Questions? Call us:
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Mirada
![31510 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576]()
2 beds
|3 baths
|2,231 sq ft
|House
31510 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
MLS TB8474523 • AGILE GROUP REALTY, Maria Pasotti
The Villages®
![752 BAISLEY TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,978 sq ft
|House
752 BAISLEY TRL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107748 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Sun City Center
![405 GRAND CHATEAUX WAY, SUN CITY CENTER,..., Sun City Center, FL 33573]()
3 beds
|2 baths
|1,775 sq ft
|House
405 GRAND CHATEAUX WAY, SUN CITY CENTER,...
Community: Sun City Center
MLS TB8475522 • RE/MAX REALTY UNLIMITED, Bonnie V...
Spruce Creek Country Club
![9333 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|2,148 sq ft
|House
9333 SE 124TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS O6381935 • GAILEY ENTERPRISES REAL ESTATE, Ri...
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 Villages®
![933 OLEANDER ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,388 sq ft
|Modular
933 OLEANDER ST, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108064 • RE/MAX FOXFIRE - SUMMERFIELD, Shar...
Royal Harbor
![6002 ARMADA ST, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5107804 • LPT REALTY, LLC, Kathy Tucker
Spruce Creek Preserve
![11335 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
2 beds
|2 baths
|1,452 sq ft
|House
11335 SW 138TH LN, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM718414 • HOMERUN REALTY, Leigh Ann Venable
Lakes of Mount Dora
![8064 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,625 sq ft
|House
8064 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS O6382333 • RE/MAX ASSURED, Vilmari Caraballo
The Villages®
![721 TANGERINE DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
721 TANGERINE DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5108159 • SELLSTATE SUPERIOR REALTY, Willi M...
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
Trilogy® Orlando
![152 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|2,295 sq ft
|House
152 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5107887 • OLYMPUS EXECUTIVE REALTY INC, Lee ...
Twin Lakes
![5043 VANTAGE CT, ST. CLOUD, FL, 34772, St. Cloud, FL 34772]()
MLS 1069272 • Blue Marlin Real Estate, Kimberly C...
The Villages®
![103 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,560 sq ft
|Manufactured Home
103 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5108063 • DOWN HOME REALTY, LLLP, Britney He...
Twin Lakes
![5043 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6382007 • BLUE MARLIN REAL ESTATE, Kimberly ...
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.
Southshore Bay
![17403 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,128 sq ft
|House
17403 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8474720 • EATON REALTY, Leah Johnson
Oak Run
![11534 SW 74TH CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM718752 • REAL BROKER, LLC, Jenni Kennedy
Spruce Creek North
![10720 SW 62ND TER, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,526 sq ft
|House
10720 SW 62ND TER, OCALA, FL, 34476
Community: Spruce Creek North
MLS OM718663 • KELLER WILLIAMS CORNERSTONE RE, Ch...
SummerGlen
![16339 SW 14TH AVE RD, OCALA, FL, 34473, Ocala, FL 34473]()
MLS OM718741 • ON TOP OF THE WORLD REAL EST, Mart...
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
Royal Highlands
![21821 KING JOHN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,694 sq ft
|House
21821 KING JOHN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS O6382093 • CENTURY 21 CARIOTI, Kristi Matthew
Sun City Center
![2110 W VIEW DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573]()
3 beds
|3 baths
|2,327 sq ft
|House
2110 W VIEW DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
MLS TB8474897 • KELLER WILLIAMS SOUTH SHORE, Greg...
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?
3,654
homes
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© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
