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Winter Garden, FL 55+ active adult communities & homes for sale
108 communities near Winter Garden
3,667 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
Want to learn more about 55+ communities in Winter Garden?
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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
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 (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
- $500Ks
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]()
$400Ks
- $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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Questions? Call us:
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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]()
$400Ks
- $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:
(689) 407-5757
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
Plantation at Leesburg
![25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,737 sq ft
|House
25333 RIVER CREST DR, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5096317 • CENTURY 21 MYERS REALTY, Mary Jane...
Majestic Oaks Ocala
![5661 SW 88TH PL, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,830 sq ft
|House
5661 SW 88TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS OM708910 • RE/MAX ALLSTARS REALTY, Peggy Pitt...
On Top of the World
![9661 SW 95TH CT B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,412 sq ft
|Condo
9661 SW 95TH CT B, OCALA, FL, 34481
Community: On Top of the World
MLS OM701763 • KELLER WILLIAMS CORNERSTONE RE, Ca...
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...
Sun City Center
![2226 NOTTINGHAM GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,668 sq ft
|Villa
2226 NOTTINGHAM GREENS DR, SUN CITY CENT...
Community: Sun City Center
MLS TB8422439 • DALTON WADE INC, Kevin McPherson
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
The Villages®
![963 HART DR, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|2,024 sq ft
|House
963 HART DR, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6348154 • HOUWZER INC, Daniel Robinson
Summit Greens
![2495 SQUAW CRK, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6324845 • PREMIER SOTHEBYS INT'L REALTY, Deb...
Solivita
![151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,356 sq ft
|House
151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
MLS O6295181 • WATSON REALTY CORP, Maritza Jimene...
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
![9777 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM702417 • NEXT GENERATION REALTY OF MARION C...
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.
Thunderbird Hill
![3745 CAMRY CT, SEBRING, FL, 33872, Sebring, FL 33872]()
MLS 313726 • Home Town Realty Pros, Matthew Chris...
Sun City Center
![206 SOLA LN, SUN CITY CENTER, FL, 33573, Sun City Center, FL 33573]()
2 beds
|2 baths
|1,516 sq ft
|House
206 SOLA LN, SUN CITY CENTER, FL, 33573
Community: Sun City Center
MLS TB8434317 • CENTURY 21 BEGGINS ENTERPRISES, D...
Stone Creek
![9119 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM710478 • NEXT GENERATION REALTY OF MARION C...
Sun City Center
![672 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573]()
4 beds
|3 baths
|1,684 sq ft
|House
672 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
MLS TB8363811 • CENTURY 21 BEGGINS ENTERPRISES, L...
Solivita
![1309 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5129926 • PELLEGO, LLC, Claudia Gimenez-Carl...
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
Kings Ridge
![3713 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6348405 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
Sun City Center
![1908 CANTERBURY LN 20, SUN CITY CENTER, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|979 sq ft
|Condo
1908 CANTERBURY LN 20, SUN CITY CENTER, ...
Community: Sun City Center
MLS TB8434514 • CENTURY 21 BEGGINS ENTERPRISES, B...
On Top of the World
![9730 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,670 sq ft
|House
9730 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
MLS OM703495 • KELLER WILLIAMS CORNERSTONE RE, Ma...
Valencia Lakes
![16135 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|2,074 sq ft
|House
16135 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8348957 • HOMEXPRESS REALTY, INC., John Mis...
On Top of the World
![9805 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,596 sq ft
|House
9805 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM703256 • IT'S ALL ABOUT YOU...REAL ESTA, Me...
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®
![114 CYPRESS RD, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,144 sq ft
|Manufactured Home
114 CYPRESS RD, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5102823 • KELLER WILLIAMS ELITE PARTNERS III...
Latitude Margaritaville
![134 SALT SHAKER ST, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,563 sq ft
|House
134 SALT SHAKER ST, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1217363 • Bob Hodges and Sons Realty, Susan W...
Valencia Lakes
![15937 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,623 sq ft
|House
15937 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8397383 • DALTON WADE INC, Zoki Mbolekwa
Tohoqua Reserve
![1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,559 sq ft
|House
1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5128993 • LPT REALTY, LLC, Paola Jimenez
Valencia Lakes
![4938 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,486 sq ft
|House
4938 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8404677 • BHHS FLORIDA REALTY, Jamie Hoffma...
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Questions? Call us:
(689) 407-5757
Latitude Margaritaville
![216 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,321 sq ft
|House
216 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1214312 • Bob Hodges and Sons Realty, Kelley ...
On Top of the World
![10242 SW 98TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,476 sq ft
|House
10242 SW 98TH PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM710701 • ROBB HARRISON REALTY INC, Robb Har...
Southshore Bay
![17317 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,363 sq ft
|House
17317 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8418461 • ALIGN RIGHT REALTY SOUTH SHORE, E...
Pine Run Estates
![10035 SW 91ST TER, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,456 sq ft
|House
10035 SW 91ST TER, OCALA, FL, 34481
Community: Pine Run Estates
MLS OM707286 • MARTY & HUGGINS REALTY, Ella Torre...
Spruce Creek Country Club
![9603 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,126 sq ft
|House
9603 SE 137TH STREET RD, SUMMERFIELD, FL...
Community: Spruce Creek Country Club
MLS G5099254 • RE/MAX PREMIER REALTY LADY LK, Rob...
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
![9577 SW 82ND STREET RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,171 sq ft
|House
9577 SW 82ND STREET RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM701854 • DECCA REAL ESTATE, Ryan Reeves
Solivita
![243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5135378 • BELLA VERDE REALTY LLC, Miguel Elv...
Summer Trees
![71 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,415 sq ft
|Townhouse
71 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
MLS V4943055 • LPT REALTY LLC, Farrah Thacker
Latitude Margaritaville
![118 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
118 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS NS1085695 • EXP REALTY LLC, Geri Davis
Palms at Serenoa
![3903 WINGED ELM CT, CLERMONT, FL, 34714, Clermont, FL 34714]()
2 beds
|2 baths
|1,822 sq ft
|House
3903 WINGED ELM CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
MLS O6338254 • VISION HOME REAL ESTATE, LLC, Vict...
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
Solivita
![702 TORREY PINES WAY, POINCIANA, FL, 347..., Poinciana, FL 34759]()
3 beds
|3 baths
|2,190 sq ft
|House
702 TORREY PINES WAY, POINCIANA, FL, 347...
Community: Solivita
MLS 2077347 • MARYKATE & CO REALTY, MARY KATHLEEN...
On Top of the World
![9262 SW 102ND AVENUE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|3 baths
|2,703 sq ft
|House
9262 SW 102ND AVENUE RD, OCALA, FL, 3448...
Community: On Top of the World
MLS 848161 • Plantation Realty, Inc., Brittany Da...
Oak Run
![10909 SW 83RD CT, OCALA, FL, 34481, Ocala, FL 34481]()
MLS GC534025 • HOME ENV REALTY, Chad Shaffer
Solivita
![790 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5135724 • PELLEGO, LLC, Stan Wilson
Spruce Creek Country Club
![12024 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,488 sq ft
|House
12024 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5102453 • RE/MAX PREMIER REALTY LADY LK, Dia...
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?
3,667
homes
near Winter Garden
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REIN updates its listings on a daily basis. Data last updated: Nov 03, 2025.
This application does not include information on all of the properties available for sale at this time.
