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Winter Garden, FL 55+ active adult communities & homes for sale - Page 34
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
Lake Jovita Golf and Country Club
![12518 LAKE JOVITA BLVD, DADE CITY, FL, 3..., Dade City, FL 33525]()
3 beds
|3 baths
|2,569 sq ft
|House
12518 LAKE JOVITA BLVD, DADE CITY, FL, 3...
Community: Lake Jovita Golf and Country Club
MLS TB8469947 • KING & ASSOCIATES REAL ESTATE LLC...
On Top of the World
![8707 SW 88TH COURT RD K, OCALA, FL, 3448..., Ocala, FL 34481]()
2 beds
|2 baths
|2,015 sq ft
|Villa
8707 SW 88TH COURT RD K, OCALA, FL, 3448...
Community: On Top of the World
MLS GC537730 • LPT REALTY, LLC, Alex Harding
Harbor Hills Country Club
![39644 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159]()
3 beds
|2 baths
|2,009 sq ft
|House
39644 HARBOR HILLS BLVD, LADY LAKE, FL, ...
Community: Harbor Hills Country Club
MLS OM719222 • FLORIDA ADVANTAGE REALTY GROUP, Aa...
The Villages®
![210 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|3 baths
|2,118 sq ft
|House
210 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5108098 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![812 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5108502 • FLORIDA PLUS REALTY, LLC, Christin...
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Questions? Call us:
(689) 407-5757
The Villages®
![840 FOLSUM PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,927 sq ft
|House
840 FOLSUM PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107822 • FLORIDA FINE HOMES REALTY, LLC, Ca...
The Villages®
![8645 SE 177TH GRASSMERE ST, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|3,085 sq ft
|House
8645 SE 177TH GRASSMERE ST, THE VILLAGES...
Community: The Villages®
MLS G5108514 • RE/MAX PREMIER REALTY LADY LK, Rob...
Gatherings of Lake Nona
![7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,445 sq ft
|Condo
7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6383756 • KELLER WILLIAMS ADVANTAGE REALTY, ...
Gatherings of Lake Nona
![7557 LAUREATE BLVD 6401, ORLANDO, FL, 32..., Orlando, FL 32827]()
2 beds
|2 baths
|1,368 sq ft
|Condo
7557 LAUREATE BLVD 6401, ORLANDO, FL, 32...
Community: Gatherings of Lake Nona
MLS O6383767 • KELLER WILLIAMS ADVANTAGE REALTY, ...
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.
Sandpiper Golf & Country Club
![6260 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,830 sq ft
|House
6260 CRANE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4959538 • COLDWELL BANKER REALTY, Ginger Qui...
Valencia Lakes
![4822 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,271 sq ft
|House
4822 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8478643 • DALTON WADE INC, Zoki Mbolekwa
The Villages®
![1305 LA ESTRELLITA WAY, THE VILLAGES, FL..., The Villages, FL 32162]()
3 beds
|2 baths
|1,817 sq ft
|House
1305 LA ESTRELLITA WAY, THE VILLAGES, FL...
Community: The Villages®
MLS G5107029 • BLU SEA DREAMS,LLC, Elizabeth Fox
On Top of the World
![8572 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,642 sq ft
|House
8572 SW 94TH CIR, OCALA, FL, 34481
Community: On Top of the World
MLS O6376379 • MARK SPAIN REAL ESTATE, Fina Perez
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The Country Club of Mount Dora
![1500 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,484 sq ft
|House
1500 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6383176 • UNITED REAL ESTATE PREFERRED, Kay ...
The Villages®
![1462 PELICAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,715 sq ft
|House
1462 PELICAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5108545 • WORTH CLARK REALTY, Chris Day
The Villages®
![242 JUAREZ WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,066 sq ft
|House
242 JUAREZ WAY, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5106248 • ERA GRIZZARD REAL ESTATE, Kaylyn H...
Windermere
![819 LANARK DR, INVERNESS, FL, 34453, Inverness, FL 34453]()
MLS 852366 • ERA American Suncoast Realty, Vicki ...
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
![5613 NW 27TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM718913 • HOMES TO RANCHES REALTY INC, Amy L...
The Villages®
![5546 COTTRELL CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,809 sq ft
|Villa
5546 COTTRELL CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5108519 • LPT REALTY, LLC, Lena Morgan
Stone Creek
![8413 SW 54TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM719266 • NEXT GENERATION REALTY OF MARION C...
On Top of the World
![8464 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|3,368 sq ft
|House
8464 SW 82ND CIR, OCALA, FL, 34481
Community: On Top of the World
MLS V4947311 • LANDSHARK REALTY, JoJo Locascio
Want to learn more about 55+ communities in Winter Garden?
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Stone Creek
![9439 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS O6384371 • KELLER WILLIAMS ADVANTAGE REALTY, ...
Ocala Preserve
![5579 NW 40TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS V4947444 • RE/MAX SIGNATURE, Stephanie Cathey
Sullivan Ranch
![20900 OLDENBURG LOOP, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
4 beds
|2 baths
|2,110 sq ft
|House
20900 OLDENBURG LOOP, MOUNT DORA, FL, 32...
Community: Sullivan Ranch
MLS G5108461 • KELLIE & CO REAL ESTATE, Kellie Wh...
Scottish Highlands
![2003 TWEED CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,360 sq ft
|House
2003 TWEED CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5108501 • ERA GRIZZARD REAL ESTATE, Cynthia ...
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.
Summer Trees
![73 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,228 sq ft
|Townhouse
73 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS O6383307 • WEMERT GROUP REALTY LLC, Jenny Wem...
Twin Lakes
![2461 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Halfplex
2461 DATURA LOOP, ST CLOUD, FL, 34772
Community: Twin Lakes
MLS S5144223 • KELLER WILLIAMS LEGACY REALTY, Ter...
Oakview
![1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,220 sq ft
|House
1581 OAKVIEW CIR, WINTER HAVEN, FL, 3388...
Community: Oakview
MLS G5108372 • LPT REALTY, LLC, Vanessa Aybar Bad...
Venetian Bay
![3102 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,916 sq ft
|House
3102 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS FC316181 • REALTY EXCHANGE COMMERCIAL RESIDEN...
Stone Creek
![9419 SW 53RD PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM719290 • RE/MAX PREMIER REALTY, Robert Forr...
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Pine Run Estates
![9050 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481]()
MLS GC537649 • KELLER WILLIAMS GAINESVILLE REALTY...
Spruce Creek South
![17587 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,652 sq ft
|House
17587 SE 96TH CT, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM719019 • KELLER WILLIAMS CORNERSTONE RE, Ri...
On Top of the World
![7777 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,737 sq ft
|House
7777 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
MLS OM718957 • COLDWELL BANKER ELLISON REALTY O, ...
The Villages®
![17283 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162]()
3 beds
|2 baths
|1,640 sq ft
|House
17283 SE 94TH COULTS CIR, THE VILLAGES, ...
Community: The Villages®
MLS G5108454 • CENTURY 21 ALTON CLARK, Regina Rod...
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
![7948 SW 89TH LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,737 sq ft
|House
7948 SW 89TH LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS G5108278 • JUDY L. TROUT REALTY, Kristina Tho...
The Villages®
![16715 SE 80TH CLOVERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,477 sq ft
|House
16715 SE 80TH CLOVERWOOD TER, THE VILLAG...
Community: The Villages®
MLS G5108215 • SALLY LOVE REAL ESTATE, Lee Harper
The Villages®
![2726 MONCAYO AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|1 baths
|1,034 sq ft
|Villa
2726 MONCAYO AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6384183 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![1134 SALIDO AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,542 sq ft
|House
1134 SALIDO AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108451 • REALTY EXECUTIVES IN THE VILLAGES,...
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Venetian Bay
![3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,338 sq ft
|House
3131 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
MLS 1223226 • RE/MAX Signature, Charles A Ottley
Lake Ashton
![5264 GREEN DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|2,011 sq ft
|House
5264 GREEN DR, WINTER HAVEN, FL, 33884
Community: Lake Ashton
MLS P4937885 • LAKE ASHTON REALTY INC., Lori Raat...
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.
