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Winter Garden, FL 55+ active adult communities & homes for sale - Page 4
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
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
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5 rating (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 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
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
$100ks
- $200ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
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
$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
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 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
New
Sun City Center
![1007 CHELSEA GREENS CT 36, SUN CITY CENT..., Sun City Center, FL 33573]()
3 beds
|2 baths
|1,630 sq ft
|Condo
1007 CHELSEA GREENS CT 36, SUN CITY CENT...
Community: Sun City Center
MLS TB8479942 • KELLER WILLIAMS SOUTH SHORE, Dawn...
New
Sandpiper Golf & Country Club
![6136 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,378 sq ft
|House
6136 MAGPIE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS R4911003 • DYW LLC, Yvonne Wherrett
New
Marion Landing
![6620 SW 85TH ST, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,370 sq ft
|Manufactured Home
6620 SW 85TH ST, OCALA, FL, 34476
Community: Marion Landing
MLS OM720897 • BRICKS & MORTAR REAL ESTATE, Debor...
New
Solivita
![2340 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6395972 • REAL BROKER, LLC, Brian Batiz Sala...
New
On Top of the World
![10345 SW 82ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,145 sq ft
|House
10345 SW 82ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM722123 • ON TOP OF THE WORLD REAL EST, Jaso...
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Questions? Call us:
(689) 407-5757
New
Sun City Center
![431 GLOUCESTER BLVD 87, SUN CITY CENTER,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|960 sq ft
|Condo
431 GLOUCESTER BLVD 87, SUN CITY CENTER,...
Community: Sun City Center
MLS TB8494215 • BHHS FLORIDA REALTY, Trudy Provin...
New
The Villages®
![930 CAMINO DEL REY DR, THE VILLAGES, FL,..., The Villages, FL 32159]()
3 beds
|2 baths
|1,558 sq ft
|House
930 CAMINO DEL REY DR, THE VILLAGES, FL,...
Community: The Villages®
MLS G5110447 • RE/MAX PREMIER REALTY, Guy William...
New
SummerGlen
![15831 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473]()
3 beds
|2 baths
|1,647 sq ft
|House
15831 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
MLS OM722242 • RE/MAX PREMIER REALTY, Mary Johnso...
New
Stone Creek
![5693 SW 90TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|3 baths
|2,110 sq ft
|House
5693 SW 90TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
MLS OM722248 • REAL BROKER LLC - OCALA, Anthony A...
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.
New
The Villages®
![1929 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|2,693 sq ft
|House
1929 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
MLS TB8494065 • HOMECOIN.COM, Jonathan Minerick
New
Kings Ridge
![2246 BELSFIELD CIR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,985 sq ft
|House
2246 BELSFIELD CIR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5110402 • COLDWELL BANKER HUBBARD HANSEN, Je...
New
Cresswind at Victoria Gardens
![1177 AVERY MEADOWS WAY, DELAND, FL, 3272..., Deland, FL 32724]()
3 beds
|3 baths
|2,191 sq ft
|House
1177 AVERY MEADOWS WAY, DELAND, FL, 3272...
Community: Cresswind at Victoria Gardens
MLS O6395605 • BETTER HOMES AND GARDENS REAL ESTA...
New
Stone Creek
![5886 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM722216 • REAL BROKER LLC - OCALA, Anthony A...
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
New
Stone Creek
![9637 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM722227 • SALLY LOVE REAL ESTATE, Melissa Gi...
New
Lakes at Laurel Highlands
![2826 VAN AMBER CT, LAKELAND, FL, 33811, Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
2826 VAN AMBER CT, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS TB8494252 • PROPERTY HOLDINGS REALTY GROUP, L...
New
Highlands Ridge
![3965 PUMA DR, AVON PARK, FL, 33825, Avon Park, FL 33825]()
2 beds
|2 baths
|1,797 sq ft
|House
3965 PUMA DR, AVON PARK, FL, 33825
Community: Highlands Ridge
MLS 324438 • RE/MAX REALTY PLUS, Eric Rhoades
New
Palms at Serenoa
![3449 TWIN FLOWER CT, CLERMONT, FL, 34714, Clermont, FL 34714]()
2 beds
|2 baths
|1,627 sq ft
|House
3449 TWIN FLOWER CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
MLS O6394746 • SOVERA REALTY GROUP, LLC, Gennifer...
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.
New
Marion Landing
![5021 SW 88TH ST, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM710852 • COMPASS FLORIDA LLC, Clayton Wagne...
New
On Top of the World
![8841 SW 91ST ST B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,530 sq ft
|Villa
8841 SW 91ST ST B, OCALA, FL, 34481
Community: On Top of the World
MLS OM722187 • HOMERUN REALTY, Melissa Gary
New
On Top of the World
![8819 SW 91ST PL D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,688 sq ft
|Villa
8819 SW 91ST PL D, OCALA, FL, 34481
Community: On Top of the World
MLS OM721851 • LEGACY REALTY & ASSOCIATES, Theres...
New
The Villages®
![2418 HOPESPRING LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,611 sq ft
|House
2418 HOPESPRING LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS OM722166 • LPT REALTY, LLC, Brian Williams
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
New
Sun City Center
![1203 HADDINGTON CIR, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,085 sq ft
|Condo
1203 HADDINGTON CIR, SUN CITY CENTER, FL...
Community: Sun City Center
MLS TB8494241 • PEOPLE'S TRUST REALTY, Patrick De...
New
The Villages®
![5548 MILLICAN AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,633 sq ft
|Villa
5548 MILLICAN AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110603 • JACOBS PREMIER PROPERTIES, Daniel ...
New
The Country Club of Mount Dora
![3022 ANDOVER CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
2 beds
|2 baths
|1,444 sq ft
|House
3022 ANDOVER CT, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5110593 • FLORIDA LIFESTYLE REALTY GROUP, Ka...
New
The Villages®
![1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,388 sq ft
|House
1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS R4911000 • BLACK TIE REAL ESTATE PROFESSIONAL...
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.
New
Cherrywood
![9840 SW 63 CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM722197 • FONTANA REALTY, Julia McPherson
New
Majestic Oaks Ocala
![8160 SW 53RD CT, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|2,150 sq ft
|House
8160 SW 53RD CT, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS GC539164 • REALTY HUB, Roderick Waisome
New
The Villages®
![1424 WALNUT WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,337 sq ft
|House
1424 WALNUT WAY, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5110581 • SOUNDINGS, LLC, Lili Whittington
New
Plantation at Leesburg
![5225 CHANTICLEER DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,413 sq ft
|House
5225 CHANTICLEER DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6396046 • WATSON REALTY CORP, Beth Stoothoff
New
The Villages®
![1147 ELIZABETH CT, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,602 sq ft
|Villa
1147 ELIZABETH CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110344 • VISIONARY PROPERTIES INC, Judy Blu...
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
New
Solivita
![545 GENOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6395202 • FLORIDA PLUS REALTY, LLC, Sarah Bo...
New
The Lakes at Harmony
![3273 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|3 baths
|1,955 sq ft
|House
3273 SONGBIRD CIR, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6396010 • DALTON WADE INC, Maleisa Remsberg
New
The Villages®
![3984 MCDOWELL DR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,926 sq ft
|House
3984 MCDOWELL DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5110543 • WORTH CLARK REALTY, Chris Day
New
Traditions at Lake Ruby
![4040 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,599 sq ft
|House
4040 CARTERET DR, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS B4902225 • KLINE REAL ESTATE SERVICES, Scott ...
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.
New
Pelican Bay Daytona Beach
![151 GREY WIDGEON CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,850 sq ft
|Townhouse
151 GREY WIDGEON CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS V4948241 • TOWN AND COUNTRY REALTY, Deborah D...
New
Sandpiper Golf & Country Club
![6357 EGRET DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,121 sq ft
|House
6357 EGRET DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS R4910996 • DYW LLC, Yvonne Wherrett
New
Spruce Creek South
![17309 SE 98TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,536 sq ft
|House
17309 SE 98TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS OM722095 • EXP REALTY LLC, Garrett Huffman
New
Oak Run
![7319 SW 115TH PL, OCALA, FL, 34476, Ocala, FL 34476]()
MLS O6396383 • MARK SPAIN REAL ESTATE, Jeff Jones
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
New
Stone Creek
![8359 SW 54TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS O6396372 • MARK SPAIN REAL ESTATE, Jeff Jones
New
On Top of the World
![7771 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,495 sq ft
|House
7771 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
MLS OM721834 • NEXT GENERATION REALTY OF MARION C...
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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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.
