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Winter Garden, FL 55+ active adult communities & homes for sale - Page 85
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
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 (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
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
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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
Want to learn more about 55+ communities in Winter Garden?
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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
SummerGlen
![16292 SW 13TH TER, OCALA, FL, 34473, Ocala, FL 34473]()
MLS OM682147 • FONTANA REALTY, Javier Rojas
Solivita
![159 VENTANA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5120654 • FAIRWAY REALTY OF SOLIVITA, Bonnie...
The Villages®
![3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|2 baths
|1,559 sq ft
|House
3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS OM685882 • RE/MAX PREMIER REALTY LADY LK, Don...
Oak Run
![11447 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS O6254513 • INNOVATIVE REALTY SOLUTIONS GROUP,...
Stone Creek
![5564 SW 90TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM707435 • NEXT GENERATION REALTY OF MARION C...
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55places can help!
Questions? Call us:
(689) 407-5757
Sun City Center
![653 MCDANIEL ST # 178, SUN CITY CENTER, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,277 sq ft
|Condo
653 MCDANIEL ST # 178, SUN CITY CENTER, ...
Community: Sun City Center
MLS TB8436473 • FLORIDA'S 1ST CHOICE RLTY LLC, ch...
Lake Ashton
![3834 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,792 sq ft
|House
3834 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
MLS P4936538 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Sun City Center
![1811 BEDFORD LN APT 163, SUN CITY CENTER..., Sun City Center, FL 33573]()
1 beds
|2 baths
|800 sq ft
|Condo
1811 BEDFORD LN APT 163, SUN CITY CENTER...
Community: Sun City Center
MLS TB8432425 • SUN CITY LIVING REALTY OF FLORIDA...
Stone Creek
![7153 SW 93RD AVE, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM709731 • ROBERTS REAL ESTATE INC, Melissa B...
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®
![4908 NE 123RD LN, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|1,912 sq ft
|House
4908 NE 123RD LN, OXFORD, FL, 34484
Community: The Villages®
MLS G5101496 • BLACK TIE REALTY, INC., Alex Scopi...
Ocala Palms
![1900 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM710431 • REAL PROPERTY MGMT DIVERSIFIED, Le...
Silver Lakes
![6341 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,637 sq ft
|House
6341 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
MLS L4955861 • COLDWELL BANKER REALTY, Kelley Bla...
Lake Ashton
![4489 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4489 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
MLS P4936248 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
On Top of the World
![8981 SW 95TH ST C, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,709 sq ft
|Villa
8981 SW 95TH ST C, OCALA, FL, 34481
Community: On Top of the World
MLS OM711026 • RE/MAX FOXFIRE - HWY200/103 S, Ch...
Cherrywood
![9981 SW 59TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS GC526785 • KELLER WILLIAMS GAINESVILLE REALTY...
Legacy of Leesburg
![27437 DESERT ROSE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,115 sq ft
|House
27437 DESERT ROSE CT, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
MLS O6339748 • COLDWELL BANKER RESIDENTIAL RE, Mi...
On Top of the World
![9274 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,010 sq ft
|House
9274 SW 94TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM695156 • KELLER WILLIAMS CORNERSTONE RE, Cr...
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
![1034 MCDANIEL ST # 1034, SUN CITY CENTER..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,887 sq ft
|Condo
1034 MCDANIEL ST # 1034, SUN CITY CENTER...
Community: Sun City Center
MLS TB8360151 • DALTON WADE INC, Cindy Hurlburt
Sun City Center
![2113 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
3 beds
|3 baths
|2,218 sq ft
|House
2113 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8372693 • DALTON WADE INC, Jaclyn McGregor
The Villages®
![15102 SANDALWOOD DR # 102, WILDWOOD, FL,..., Wildwood, FL 34785]()
3 beds
|2 baths
|1,474 sq ft
|Condo
15102 SANDALWOOD DR # 102, WILDWOOD, FL,...
Community: The Villages®
MLS G5100208 • DOWN HOME REALTY, LLLP, Melanie Mo...
Twin Lakes
![2516 PICKETT AVE, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
2516 PICKETT AVE, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS S5106768 • GODWIN REALTY GROUP, Melissa Godwi...
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(689) 407-5757
SummerGlen
![16193 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473]()
3 beds
|2 baths
|1,647 sq ft
|House
16193 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
MLS OM701506 • RE/MAX FOXFIRE - HWY 40, Robin Ran...
Sun City Center
![811 STAFFORDSHIRE LN 32, SUN CITY CENTER..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,651 sq ft
|Condo
811 STAFFORDSHIRE LN 32, SUN CITY CENTER...
Community: Sun City Center
MLS TB8436092 • COMPASS FLORIDA LLC, Nadia Anac
Ocala Palms
![5232 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM709372 • GOLDEN OCALA REAL ESTATE INC, Ashl...
Plantation at Leesburg
![3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,664 sq ft
|House
3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Community: Plantation at Leesburg
MLS G5102758 • CENTURY 21 MYERS REALTY, Mary Jane...
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®
![13103 SANDALWOOD DR # 13103, WILDWOOD, F..., Wildwood, FL 34785]()
2 beds
|1 baths
|1,000 sq ft
|Condo
13103 SANDALWOOD DR # 13103, WILDWOOD, F...
Community: The Villages®
MLS G5089886 • FLAMINGO REAL ESTATE & MNGMT, Kody...
On Top of the World
![8630 SW 94TH LN A, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,531 sq ft
|Villa
8630 SW 94TH LN A, OCALA, FL, 34481
Community: On Top of the World
MLS OM710679 • FONTANA REALTY, Donna Sloan
The Villages®
![1737 LAUREN LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
1737 LAUREN LN, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5102847 • FLAMINGO REAL ESTATE & MNGMT, Robb...
Stone Creek
![6606 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,706 sq ft
|Townhouse
6606 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
MLS OM705777 • TOUCHSTONE REALTY, LLC, Nicole Pet...
Solivita
![555 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|2 baths
|1,610 sq ft
|House
555 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5121580 • ARISTA REALTY GROUP, LLC, Douglas ...
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(689) 407-5757
On Top of the World
![8876 SW 95TH LN E, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,748 sq ft
|Villa
8876 SW 95TH LN E, OCALA, FL, 34481
Community: On Top of the World
MLS OM707716 • RE/MAX FOXFIRE - HWY200/103 S, St...
The Villages®
![4406 CREIGHTON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|2,061 sq ft
|House
4406 CREIGHTON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5100580 • WORTH CLARK REALTY, Nathan Piotrow...
Stonecrest
![17867 SE 115TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,597 sq ft
|House
17867 SE 115TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS GC532918 • WATSON REALTY CORP, Faylene Welcom...
On Top of the World
![10406 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,432 sq ft
|House
10406 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM692222 • KELLER WILLIAMS CORNERSTONE RE, Ca...
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 Country Club of Mount Dora
![1521 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
3 beds
|3 baths
|3,028 sq ft
|House
1521 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6339213 • UNITED REAL ESTATE PREFERRED, Kay ...
Stone Creek
![9119 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM710478 • NEXT GENERATION REALTY OF MARION C...
Solivita
![243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135378 • BELLA VERDE REALTY LLC, Miguel Elv...
Oak Run
![10909 SW 83RD CT, OCALA, FL, 34481, Ocala, FL 34481]()
MLS GC534025 • HOME ENV REALTY, Chad Shaffer
Want to learn more about 55+ communities in Winter Garden?
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Solivita
![1329 DEL MAR DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5131377 • PELLEGO, LLC, Stan Wilson
Spruce Creek Country Club
![9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,126 sq ft
|House
9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM698604 • SELLSTATE NGR- SUMMERFIELD, Virgil...
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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© 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: Jan 11, 2026.
This application does not include information on all of the properties available for sale at this time.
