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Winter Garden, FL 55+ active adult communities & homes for sale - Page 44
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
Want to learn more about 55+ communities in Winter Garden?
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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
Tohoqua Reserve
![1911 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,579 sq ft
|Villa
1911 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS O6378988 • LPT REALTY, LLC, Patricia Tanner
Palm Cay
![10960 SW 75TH AVE, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM717992 • RE/MAX FOXFIRE - HWY200/103 S, Ka...
Heritage Hills
![2823 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|3 baths
|2,573 sq ft
|House
2823 MAYPORT ST, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6379098 • FLORIDA REALTY INVESTMENTS, Fred P...
Oak Run
![8695 SW 116TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|2 baths
|2,073 sq ft
|House
8695 SW 116TH STREET RD, OCALA, FL, 3448...
Community: Oak Run
MLS OM718003 • RE/MAX PREMIER REALTY, Kevin Combs
The Villages®
![2223 WESTCHESTER WAY, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|2,004 sq ft
|House
2223 WESTCHESTER WAY, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5106938 • RE/MAX PREMIER REALTY, Tammy Freil...
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Questions? Call us:
(689) 407-5757
Quail Meadow
![4634 NW 35TH ST, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM718004 • RE/MAX FOXFIRE - HWY 40, Jose Mate...
Venetian Bay
![3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,092 sq ft
|Townhouse
3074 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1087227 • MAGNOLIA PROPERTIES, Margie Lints
Tampa Bay Golf and Country Club
![10118 CLEGHORN DR, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576]()
3 beds
|2 baths
|1,799 sq ft
|House
10118 CLEGHORN DR, SAN ANTONIO, FL, 3357...
Community: Tampa Bay Golf and Country Club
MLS TB8471776 • TOOLBOX SISTERS REALTY LLC, Allis...
On Top of the World
![8711 SW 92ND PL D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,687 sq ft
|House
8711 SW 92ND PL D, OCALA, FL, 34481
Community: On Top of the World
MLS OM717914 • RE/MAX PREMIER REALTY HWY 200, Nan...
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®
![3258 SYLEWOOD AVE, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,956 sq ft
|House
3258 SYLEWOOD AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS TB8471834 • MCBRIDE KELLY & ASSOCIATES, Matth...
Solivita
![786 CIELO TRL, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5142864 • ARISTA REALTY GROUP, LLC, Douglas ...
The Villages®
![444 MAYWOOD WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
444 MAYWOOD WAY, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107437 • WORTH CLARK REALTY, Diane McCoach
The Villages®
![13811 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|2 baths
|2,280 sq ft
|Manufactured Home
13811 COUNTY RD, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6379162 • THE PROPERTY PROS REAL ESTATE, INC...
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Questions? Call us:
(689) 407-5757
Highland Lakes
![6514 WILANDER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,546 sq ft
|House
6514 WILANDER ST, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5107603 • FLORIDA PLUS REALTY, LLC, Renee Wi...
Summit Greens
![2833 FALCON RDG, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|3 baths
|2,804 sq ft
|House
2833 FALCON RDG, CLERMONT, FL, 34711
Community: Summit Greens
MLS O6379095 • ENGEL & VOLKERS ORLANDO DR PHILLIP...
The Country Club of Mount Dora
![8013 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,256 sq ft
|House
8013 PINE HOLLOW DR, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5106558 • COLDWELL BANKER VANGUARD EDGE, Lyn...
Marion Landing
![8594 SW 61ST CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM717441 • FLORIDA REAL ESTATE LIFESTYLES, Se...
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.
Ocala Palms
![5801 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM717930 • COLDWELL REALTY SOLD GUARANTEE, Sc...
Lake Ashton
![6216 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,045 sq ft
|House
6216 PINEHURST LOOP, WINTER HAVEN, FL, 3...
Community: Lake Ashton
MLS P4937694 • LAKE ASHTON REALTY INC., Lori Raat...
Spruce Creek Country Club
![13700 SE 90TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|2,054 sq ft
|House
13700 SE 90TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5107526 • LPT REALTY, LLC, Sara Chase
Lake Ashton
![4424 WATERFORD DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4424 WATERFORD DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4937693 • LAKE ASHTON REALTY INC., Lori Raat...
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Traditions at Lake Ruby
![3008 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Villa
3008 CANEEL ST, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4937668 • CENTURY 21 MYERS REALTY LAKE WALES...
Southshore Bay
![5328 STOIC VALE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,636 sq ft
|Villa
5328 STOIC VALE DR, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8471607 • 27NORTH REALTY, Elisa Stephens
Oak Run
![10821 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM717887 • KELLER WILLIAMS CORNERSTONE RE, Al...
Heritage Hills
![4027 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,866 sq ft
|House
4027 SERENA LN, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6378762 • BHHS FLORIDA REALTY, Patti Kincaid
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
![16909 APRIL PLUSH DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|3 baths
|1,713 sq ft
|Villa
16909 APRIL PLUSH DR, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8471493 • 27NORTH REALTY, Elisa Stephens
Del Webb Minneola
![2750 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715]()
2 beds
|2 baths
|1,409 sq ft
|House
2750 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
MLS G5107474 • CENTURY 21 MYERS ROSE REALTY, Dawn...
Tampa Bay Golf and Country Club
![10133 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576]()
3 beds
|2 baths
|2,500 sq ft
|House
10133 COLLAR DR, SAN ANTONIO, FL, 33576
Community: Tampa Bay Golf and Country Club
MLS TB8470767 • REST EASY REALTY POWERED BY SELLS...
Plantation at Leesburg
![24239 BELLE MEDE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,289 sq ft
|House
24239 BELLE MEDE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5107374 • ERA GRIZZARD REAL ESTATE, Lisa Car...
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
The Villages®
![8371 SE 168TH TRINITY PL, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,496 sq ft
|House
8371 SE 168TH TRINITY PL, THE VILLAGES, ...
Community: The Villages®
MLS O6378880 • BEYCOME OF FLORIDA LLC, Steven Kol...
Stone Creek
![9325 SW 54TH ST, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM717361 • NEXT GENERATION REALTY OF MARION C...
Valencia Lakes
![15814 AURORA LAKE CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598]()
2 beds
|2 baths
|1,321 sq ft
|Villa
15814 AURORA LAKE CIR, WIMAUMA, FL, 3359...
Community: Valencia Lakes
MLS TB8468657 • SALTZBERG & ASSOCIATES REAL ESTAT...
Valencia Lakes
![4963 SAPPHIRE SOUND DR, WIMAUMA, FL, 335..., Wimauma, FL 33598]()
3 beds
|3 baths
|2,437 sq ft
|House
4963 SAPPHIRE SOUND DR, WIMAUMA, FL, 335...
Community: Valencia Lakes
MLS TB8467039 • SALTZBERG & ASSOCIATES REAL ESTAT...
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®
![885 IRON OAK WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
4 beds
|3 baths
|3,340 sq ft
|House
885 IRON OAK WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS OM717593 • LPT REALTY, LLC, Martin Gregory
Stone Creek
![9345 SW 52ND LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM717570 • PREFERRED RE BROKERS III, Stacey R...
The Villages®
![1601 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,332 sq ft
|House
1601 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5107468 • BROKER ASSOCIATES REALTY, Kim Asch...
Plantation at Leesburg
![25607 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,345 sq ft
|House
25607 BELLE HELENE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5106688 • DOWN HOME REALTY, LLLP, Colleen A....
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(689) 407-5757
The Villages®
![1106 BERKSHIRE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,100 sq ft
|House
1106 BERKSHIRE PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5107097 • ERA GRIZZARD REAL ESTATE, Holly We...
Pelican Bay Daytona Beach
![126 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,237 sq ft
|Condo
126 BLUE HERON DR B, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1222461 • EXIT Beach Realty, Beth Anderson
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.
