Call us at (689) 407-5757 to learn more about active adult communities near Winter Garden
Winter Garden, FL 55+ active adult communities & homes for sale
108 communities near Winter Garden
3,648 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
- $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]()
<$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
- $700Ks
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
- $700Ks
Stone Creek, Ocala, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
3,800 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
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
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
Download the Ultimate 55+ Homebuying Guide
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5 rating (3 reviews)
![Stonecrest]()
<$100k
- $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
- $900Ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
No reviews yet
![Pelican Bay Daytona Beach]()
$100Ks
- $600Ks
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
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4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $300Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
4.7 rating (11 reviews)
![Valencia Lakes]()
$200Ks
- $900Ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 homes
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
No reviews yet
![Venetian Bay]()
$300Ks
- $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 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.
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$300Ks
- $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
3.8 rating (6 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
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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
- $300Ks
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
- $500Ks
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
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 (5 reviews)
![SummerGlen]()
$200Ks
- $500Ks
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
No reviews yet
![Breakaway Trails]()
$300Ks
- $1Ms
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
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
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
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4.8 rating (6 reviews)
![Highland Lakes]()
$200Ks
- $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
No reviews yet
![Pine Run Estates]()
<$100k
- $300Ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
No reviews yet
![Lake Jovita Golf and Coun...]()
$300Ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
No reviews yet
![Esplanade at Wiregrass Ra...]()
$400Ks
- $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
868 homes
Sun City Center
![2433 NEW HAVEN CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,125 sq ft
|Condo
2433 NEW HAVEN CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS TB8442045 • KELLER WILLIAMS SOUTH SHORE, Davi...
Spruce Creek North
![6340 SW 111TH ST, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,248 sq ft
|House
6340 SW 111TH ST, OCALA, FL, 34476
Community: Spruce Creek North
MLS OM712389 • ROBB HARRISON REALTY INC, Jennifer...
Summer Trees
![6037 WHISPERING TREES LN, PORT ORANGE, F..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,820 sq ft
|House
6037 WHISPERING TREES LN, PORT ORANGE, F...
Community: Summer Trees
MLS 1212722 • Heritage Realty Associates, Pam Aci...
Harbor Hills Country Club
![5528 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
4 beds
|3 baths
|3,639 sq ft
|House
5528 CITATION CT, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5103752 • EXIT REALTY TRI-COUNTY, Jaret Whit...
Pennbrooke Fairways
![461 GLEN ARBOR LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,559 sq ft
|Villa
461 GLEN ARBOR LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS O6355412 • KELLER WILLIAMS ELITE PARTNERS III...
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Palm Cay
![10856 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM712224 • CHARLES RUTENBERG REALTY ORLANDO, ...
Huntington at Hunter's Ridge
![23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|1,852 sq ft
|House
23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS FC313604 • REALTY PROS ASSURED, Terri Wilkins...
The Villages®
![4434 SHOCKOE CIR, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,950 sq ft
|House
4434 SHOCKOE CIR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5103310 • FLORIDA REALTY INVESTMENTS, Katie ...
Solivita
![428 BEL AIR WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5134079 • BELLA VERDE REALTY LLC, Miguel Elv...
The Villages®
![1222 ZAPATA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|1 baths
|936 sq ft
|Manufactured Home
1222 ZAPATA PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM712295 • LEGACY REALTY & ASSOCIATES, Mailyn...
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.
Spruce Creek South
![10476 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,473 sq ft
|House
10476 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5091955 • OCALA REALTY WORLD LLC, Kimberly M...
Lakes at Laurel Highlands
![1829 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811]()
4 beds
|2 baths
|1,867 sq ft
|House
1829 PRISTINE LOOP, LAKELAND, FL, 33811
Community: Lakes at Laurel Highlands
MLS L4955000 • XCELLENCE REALTY, INC, Annette Col...
Stonecrest
![11280 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,251 sq ft
|House
11280 SE 170TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS G5103231 • ARROWSMITH REALTY, INC, Tyler Adam...
The Villages®
![1505 LAVACA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,897 sq ft
|House
1505 LAVACA LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102401 • RE/MAX FOXFIRE - LADY LAKE, Kelly ...
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The Villages®
![219 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,831 sq ft
|House
219 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5097906 • REALTY EXECUTIVES IN THE VILLAGES,...
The Country Club of Mount Dora
![1741 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
5 beds
|5 baths
|5,573 sq ft
|House
1741 EDGEWATER DR, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS O6322129 • CHARLES RUTENBERG REALTY ORLANDO, ...
Kings Ridge
![2225 ELVERSON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|1,892 sq ft
|House
2225 ELVERSON AVE, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5100270 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![809 ALVARADO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,268 sq ft
|Villa
809 ALVARADO PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5103292 • COLDWELL BANKER VANGUARD LIFESTYLE...
Plantation at Leesburg
![4525 EAGLEWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,214 sq ft
|House
4525 EAGLEWOOD DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6330470 • MARK SPAIN REAL ESTATE, Jamey Bris...
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.
Spruce Creek Preserve
![11628 SW 140TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432]()
2 beds
|2 baths
|1,536 sq ft
|House
11628 SW 140TH LOOP, DUNNELLON, FL, 3443...
Community: Spruce Creek Preserve
MLS OM700996 • RE/MAX FOXFIRE - HWY200/103 S, We...
Spruce Creek Preserve
![11298 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
2 beds
|2 baths
|1,408 sq ft
|House
11298 SW 138TH LN, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM705287 • RE/MAX FOXFIRE - HWY200/103 S, We...
Spruce Creek Preserve
![11552 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
3 beds
|2 baths
|1,760 sq ft
|House
11552 SW 138TH LN, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM711279 • RE/MAX FOXFIRE - HWY200/103 S, We...
Spruce Creek Preserve
![11369 SW 139TH ST, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
2 beds
|2 baths
|1,654 sq ft
|House
11369 SW 139TH ST, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM711421 • RE/MAX FOXFIRE - HWY200/103 S, We...
Ocala Preserve
![3862 NW 49TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM706836 • KELLER WILLIAMS CLASSIC, Riva Wall...
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
The Villages®
![1178 BETHUNE WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|2,085 sq ft
|House
1178 BETHUNE WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5100369 • RE/MAX PREMIER REALTY LADY LK, Guy...
Ormond Renaissance
![799 STERTHAUS DR 207, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,523 sq ft
|Condo
799 STERTHAUS DR 207, ORMOND BEACH, FL, ...
Community: Ormond Renaissance
MLS A4670127 • INVESTY REALTY, LLC., Amy Stanley
Del Webb Oasis
![13846 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787]()
2 beds
|3 baths
|2,108 sq ft
|House
13846 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
MLS O6346706 • REAL BROKER, LLC, Ken Pozek
Sun City Center
![2301 GRENOBLE PL # 1, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,008 sq ft
|Condo
2301 GRENOBLE PL # 1, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8352699 • WALKER AND ASSOCIATES REALTY, Che...
Pelican Bay Daytona Beach
![224 BOB WHITE CT # 224, DAYTONA BEACH, F..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,668 sq ft
|Condo
224 BOB WHITE CT # 224, DAYTONA BEACH, F...
Community: Pelican Bay Daytona Beach
MLS NS1086334 • REALTY PROS ASSURED, Bryan Morfor...
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
![305 SIENA VISTA PL, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
2 beds
|3 baths
|1,984 sq ft
|House
305 SIENA VISTA PL, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS A4655474 • WAGNER REALTY, Shannon Dodge
Lake Ashton
![4315 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|2,229 sq ft
|House
4315 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4935963 • KELLER WILLIAMS REALTY SMART 1, La...
Cherrywood
![6027 SW 98TH STREET RD, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,484 sq ft
|House
6027 SW 98TH STREET RD, OCALA, FL, 34476
Community: Cherrywood
MLS O6328485 • BB GROUP REALTY CORP, Lucy Martins
Summit Greens
![793 SUMMIT GREENS BLVD, CLERMONT, FL, 34..., Clermont, FL 34711]()
2 beds
|2 baths
|1,731 sq ft
|House
793 SUMMIT GREENS BLVD, CLERMONT, FL, 34...
Community: Summit Greens
MLS G5101007 • TRINITY REAL ESTATE SALES LLC, Rob...
Palm Cay
![7556 SW 112TH LN, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM710051 • BERKSHIRE HATHAWAY HS FLORIDA, Mar...
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Encore at Fishhawk Ranch
![13937 SWALLOW HILL DR, LITHIA, FL, 33547, Lithia, FL 33547]()
2 beds
|3 baths
|2,213 sq ft
|House
13937 SWALLOW HILL DR, LITHIA, FL, 33547
Community: Encore at Fishhawk Ranch
MLS TB8421865 • SIGNATURE REALTY ASSOCIATES, Bren...
The Lakes at Harmony
![3428 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,474 sq ft
|House
3428 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5126461 • CORCORAN CONNECT LLC, Jeanine Corc...
Ocala Preserve
![3480 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM704703 • REMAX/PREMIER REALTY, Nay Lopez
Solivita
![316 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5136994 • ARISTA REALTY GROUP, LLC, Douglas ...
The Villages®
![3326 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,204 sq ft
|House
3326 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8417715 • LPT REALTY, LLC, Giselle Rachels
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?
3,648
homes
near Winter Garden
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REIN updates its listings on a daily basis. Data last updated: Nov 05, 2025.
This application does not include information on all of the properties available for sale at this time.
