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Winter Garden, FL 55+ active adult communities & homes for sale - Page 84
109 communities near Winter Garden
3,495 homes near Winter Garden
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5 rating (1 reviews)
![Del Webb Oasis]()
$400Ks
- $900Ks
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
- $700Ks
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
- $500Ks
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
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300Ks
- $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
4.2 rating (10 reviews)
![Stone Creek]()
$200Ks
- $900Ks
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
Download the Ultimate 55+ Homebuying Guide
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5 rating (2 reviews)
![Plantation at Leesburg]()
$100Ks
- $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
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
- $600Ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
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$100Ks
- $400Ks
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
4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $400Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
4.7 rating (11 reviews)
![Valencia Lakes]()
$200Ks
- $600Ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 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)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $800Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
$200Ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
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5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
4 rating (7 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]()
$300Ks
- $1Ms
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
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)
![Pennbrooke Fairways]()
<$100k
- $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$200Ks
- $400Ks
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
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5 rating (5 reviews)
![SummerGlen]()
$100Ks
- $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
$400Ks
- $800Ks
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
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 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
4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $300Ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$300Ks
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
<$100k
- $300Ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
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Questions? Call us:
(689) 407-5757
$300Ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
Venetian Bay
![2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,070 sq ft
|House
2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6353959 • DE VIVO REALTY LLC, Alessandro De ...
Valencia Lakes
![4817 SANDY GLEN WAY, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|2 baths
|2,087 sq ft
|House
4817 SANDY GLEN WAY, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8419331 • DALTON WADE INC, Zoki Mbolekwa
Sun City Center
![721 MASTERPIECE DR # 141, SUN CITY CENTE..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,444 sq ft
|Condo
721 MASTERPIECE DR # 141, SUN CITY CENTE...
Community: Sun City Center
MLS TB8408828 • REAL BROKER, LLC, RACHEL COLVIN
Stone Creek
![7091 SW 91ST CT, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM706271 • REAL BROKER LLC - OCALA, Anthony A...
Ocala Palms
![5599 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM711602 • SHOWCASE PROPERTIES OF CENTRAL, Ka...
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55places can help!
Questions? Call us:
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Lakes at Laurel Highlands
![2778 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,685 sq ft
|House
2778 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Lakes at Laurel Highlands
MLS L4955797 • KELLER WILLIAMS REALTY SMART, Garr...
Heritage Landings
![2778 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,685 sq ft
|House
2778 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Heritage Landings
MLS L4955797 • KELLER WILLIAMS REALTY SMART, Garr...
Pine Run Estates
![8955 SW 104TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,144 sq ft
|House
8955 SW 104TH PL, OCALA, FL, 34481
Community: Pine Run Estates
MLS OM691748 • REAL BROKER LLC - OCALA, Anthony A...
On Top of the World
![8556 SW 90TH LN C, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,687 sq ft
|Villa
8556 SW 90TH LN C, OCALA, FL, 34481
Community: On Top of the World
MLS OM709459 • REAL BROKER LLC - OCALA, Melissa M...
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
![1001 OTTER MILL WAY # 1001, SUN CITY CEN..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,810 sq ft
|Condo
1001 OTTER MILL WAY # 1001, SUN CITY CEN...
Community: Sun City Center
MLS TB8438791 • B.K. WOOLDRIDGE & ASSOCIATES, Kat...
Twin Lakes
![2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Villa
2449 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5130528 • WEICHERT REALTORS HALLMARK PRO, Sh...
Pelican Bay Daytona Beach
![129 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,347 sq ft
|Condo
129 BLUE HERON DR A, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS FC304769 • ADAMS, CAMERON & CO., REALTORS, Jo...
Fountain View
![1324 MORNING WALK DR, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
4 beds
|2 baths
|1,882 sq ft
|House
1324 MORNING WALK DR, ORMOND BEACH, FL, ...
Community: Fountain View
MLS 1217221 • A Realty of Florida, LLC, Amy Regan...
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Highlands Ridge
![3509 E SAINT ANDREWS DR, AVON PARK, FL, ..., Avon Park, FL 33825]()
3 beds
|2 baths
|1,845 sq ft
|House
3509 E SAINT ANDREWS DR, AVON PARK, FL, ...
Community: Highlands Ridge
MLS 314943 • RE/MAX REALTY PLUS, Theresa Ann Beck...
Oak Run
![11159 SW 71ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476]()
3 beds
|2 baths
|2,236 sq ft
|House
11159 SW 71ST TERRACE RD, OCALA, FL, 344...
Community: Oak Run
MLS OM711776 • DECCA REAL ESTATE, Cindy Casco
Royal Harbor
![5837 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5101897 • KELLER WILLIAMS ELITE PARTNERS III...
Pennbrooke Fairways
![32218 SWEET BRIAR CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,272 sq ft
|House
32218 SWEET BRIAR CT, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
MLS G5101998 • CARLINO REAL ESTATE GROUP INC, San...
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
![9823 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,467 sq ft
|House
9823 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM685149 • RE/MAX FOXFIRE - HWY200/103 S, Pa...
Ocala Palms
![1960 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM688343 • RE/MAX FOXFIRE - HWY200/103 S, Sh...
Ocala Palms
![2380 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,674 sq ft
|House
2380 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
MLS OM710775 • PREFERRED PROPERTIES OF CEN/FL, An...
On Top of the World
![9868 SW 100TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481]()
2 beds
|2 baths
|1,469 sq ft
|House
9868 SW 100TH TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
MLS OM707121 • RE/MAX FOXFIRE - HWY200/103 S, Pa...
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Arlington Ridge
![26807 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,962 sq ft
|House
26807 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS O6304952 • COLDWELL BANKER RESIDENTIAL RE, Ke...
On Top of the World
![8665 SW 94TH LN E, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,179 sq ft
|Villa
8665 SW 94TH LN E, OCALA, FL, 34481
Community: On Top of the World
MLS OM709267 • PEGASUS REALTY & ASSOC INC, Sharon...
Solivita
![861 BELLA VIANA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135913 • PELLEGO, LLC, Stan Wilson
Oak Run
![10751 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM711633 • DECCA REAL ESTATE, Thomas Reeves
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.
Carlsberg Estates on Lake Suzanne
![260 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,321 sq ft
|House
260 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS K4903100 • LEGACY REAL ESTATE CENTER INC, Vic...
On Top of the World
![9285 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,756 sq ft
|House
9285 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
MLS O6352989 • LPT REALTY, LLC, Jen Viera
On Top of the World
![8414 SW 90TH CT, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,658 sq ft
|House
8414 SW 90TH CT, OCALA, FL, 34481
Community: On Top of the World
MLS OM711579 • ENGEL & VOLKERS OCALA, Alair Boshe...
Lake Ashton
![4004 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
4 beds
|3 baths
|2,937 sq ft
|House
4004 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4936596 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Colonnades
![4829 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,182 sq ft
|House
4829 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4947890 • REGAL REAL ESTATE LLC, Tammy Stori...
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On Top of the World
![8658 SW 95TH LN B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,179 sq ft
|Villa
8658 SW 95TH LN B, OCALA, FL, 34481
Community: On Top of the World
MLS OM711472 • RE/MAX FOXFIRE - HWY 40, Suzanne A...
Ocala Preserve
![4378 NW 54TH TER, OCALA, FL, 34482, Ocala, FL 34482]()
MLS O6325219 • KELLER WILLIAMS CLASSIC, Cassie La...
Pennbrooke Fairways
![615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
1 beds
|1 baths
|490 sq ft
|Manufactured Home
615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS OM710883 • SUNBURST PROPERTIES, Scott Hutchin...
Ocala Palms
![1913 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM706194 • INVICTUS REAL ESTATE LLC, David Cu...
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
![8334 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,226 sq ft
|House
8334 SW 79TH CIR, OCALA, FL, 34476
Community: On Top of the World
MLS OM711150 • EXP REALTY LLC, Shane Sellers
SummerGlen
![15692 SW 11TH COURT RD, OCALA, FL, 34473, Ocala, FL 34473]()
3 beds
|2 baths
|1,768 sq ft
|House
15692 SW 11TH COURT RD, OCALA, FL, 34473
Community: SummerGlen
MLS O6351795 • KFORTUNA SUNSHINE REALTY INC, Vito...
On Top of the World
![8616 SW 82ND TER, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,283 sq ft
|House
8616 SW 82ND TER, OCALA, FL, 34481
Community: On Top of the World
MLS OM709498 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Southshore Bay
![16840 WHISPER ELM ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,951 sq ft
|House
16840 WHISPER ELM ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8373666 • COLLABORATE REAL ESTATE GROUP LLC...
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Alhambra Villas Condominiums
![201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,090 sq ft
|Condo
201 N HILL AVE 150, DELAND, FL, 32724
Community: Alhambra Villas Condominiums
MLS V4939262 • UNITED REAL ESTATE PREFERRED, Chri...
Spruce Creek Country Club
![13822 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,540 sq ft
|House
13822 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM710156 • REALTY ONE GROUP DAVALLS, David St...
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?
3,495
homes
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REIN updates its listings on a daily basis. Data last updated: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.
