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Winter Garden, FL 55+ active adult communities & homes for sale - Page 35
113 communities near Winter Garden
3,497 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
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 rating (56 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
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
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3,250 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
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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
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300ks
- $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
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3,900 homes
$300ks
- $1Ms
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.
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 (1 reviews)
![Ocala Palms]()
$200ks
- $300ks
Ocala Palms, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1994 - 1997
|
1,076 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
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 2024
|
2,224 homes
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 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
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5 rating (5 reviews)
![SummerGlen]()
$200ks
- $400ks
SummerGlen, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
1,024 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
$200ks
- $500ks
Southshore Bay, Wimauma, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
655 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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 (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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 (4 reviews)
![Spruce Creek South]()
$100ks
- $200ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
4.7 rating (11 reviews)
![Valencia Lakes]()
$200ks
- $700ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 homes
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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
$400ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 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
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 (5 reviews)
![Heritage Hills]()
$200ks
- $400ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
$300ks
- $500ks
Mirada, San Antonio, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
858 homes
3.8 rating (5 reviews)
![Marion Landing]()
$100ks
- $300ks
Marion Landing, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
600 homes
2.3 rating (6 reviews)
![Cherrywood]()
$100ks
- $800ks
Cherrywood, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2003
|
700 homes
$200ks
- $400ks
Quail Meadow, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1988 - 2006
|
460 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
$100ks
- $200ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 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.
Scottish Highlands
![2218 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,500 sq ft
|House
2218 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5110470 • ERA GRIZZARD REAL ESTATE, Cynthia ...
Lake Henry Estates
![558 PINNACLE DR, HAINES CITY, FL, 33844, Haines City, FL 33844]()
2 beds
|2 baths
|1,273 sq ft
|House
558 PINNACLE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
MLS L4960781 • LIVE FLORIDA REALTY, Ramone Harris
The Lakes at Harmony
![3464 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,404 sq ft
|House
3464 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6394042 • RESORT REALTY GROUP LTD INC, David...
Arlington Ridge
![27118 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,713 sq ft
|House
27118 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5110376 • HARRISON REAL PROPERTY GROUP, Wend...
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Spruce Creek Country Club
![14160 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,238 sq ft
|Villa
14160 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM721734 • SELLSTATE NGR- SUMMERFIELD, Linda ...
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 G5110081 • WORTH CLARK REALTY, Tamara Nelson-...
Venetian Bay
![3209 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,273 sq ft
|House
3209 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1087782 • KINCAID REALTY, Samantha McHugh
Stone Creek
![8364 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS TB8489949 • PULTE REALTY OF WEST FLORIDA LLC,...
Stone Creek
![5868 SW 86TH AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,655 sq ft
|House
5868 SW 86TH AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
MLS TB8489938 • PULTE REALTY OF WEST FLORIDA LLC,...
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®
![17431 SE 93RD RETFORD TER, THE VILLAGES,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,160 sq ft
|Villa
17431 SE 93RD RETFORD TER, THE VILLAGES,...
Community: The Villages®
MLS R4910963 • BLACK TIE REAL ESTATE PROFESSIONAL...
On Top of the World
![8404 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,701 sq ft
|House
8404 SW 82ND CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM721956 • ON TOP OF THE WORLD REAL EST, Naja...
Solivita
![1309 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6395320 • REAL BROKER, LLC, Ken Pozek
The Villages®
![1253 GREENVILLE WAY, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,967 sq ft
|House
1253 GREENVILLE WAY, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5109327 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![1953 YEARLING WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|2,140 sq ft
|House
1953 YEARLING WAY, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5110255 • FLORIDA FINE HOMES REALTY, LLC, Ca...
Pelican Bay Daytona Beach
![576 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119]()
4 beds
|4 baths
|3,542 sq ft
|House
576 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
Community: Pelican Bay Daytona Beach
MLS V4948269 • VOLUSIA COUNTY GUIDE, Lindsey Hunt...
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
High Vista at Ridgewood Lakes
![612 VISTA OAKS WAY, DAVENPORT, FL, 33837, Davenport, FL 33837]()
2 beds
|2 baths
|1,797 sq ft
|House
612 VISTA OAKS WAY, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS S5146853 • KELLER WILLIAMS REALTY AT THE LAKE...
Plantation at Leesburg
![4844 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,289 sq ft
|House
4844 HERON RUN CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5110301 • CENTURY 21 MYERS ROSE REALTY, Mild...
The Lakes at Harmony
![3224 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773]()
4 beds
|4 baths
|2,732 sq ft
|House
3224 OXBOW CT, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5146906 • FIERCE REALTY, Rachel Coolidge
Lake Ashton
![5352 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
2 beds
|2 baths
|2,354 sq ft
|House
5352 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
MLS L4960750 • BHHS FLORIDA PROPERTIES GROUP, Wes...
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
![984 PEMBROKE POINT WAY, SUN CITY CENTER,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,854 sq ft
|Villa
984 PEMBROKE POINT WAY, SUN CITY CENTER,...
Community: Sun City Center
MLS TB8492677 • KELLER WILLIAMS SOUTH TAMPA, Bren...
Encore at Fishhawk Ranch
![13892 KINGFISHER GLEN DR, LITHIA, FL, 33..., Lithia, FL 33547]()
2 beds
|2 baths
|1,612 sq ft
|Villa
13892 KINGFISHER GLEN DR, LITHIA, FL, 33...
Community: Encore at Fishhawk Ranch
MLS TB8482479 • EATON REALTY, Rebecca Kelly
The Villages®
![1763 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159]()
2 beds
|2 baths
|1,306 sq ft
|Manufactured Home
1763 W SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
MLS A4688380 • JOSEPH WALTER REALTY LLC, Scott Fa...
Liberty Village
![7369 SW 77TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
4 beds
|2 baths
|2,292 sq ft
|House
7369 SW 77TH AVE, OCALA, FL, 34481
Community: Liberty Village
MLS O6395381 • HOMESMART, Allyson Peterson
Stone Creek
![9491 SW 52ND LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS G5110012 • LPT REALTY, LLC, Vanessa Aybar Bad...
Sun City Center
![202 BEDFORD ST 68, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|960 sq ft
|Condo
202 BEDFORD ST 68, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS TB8491703 • REAL BROKER, LLC, Anita Frank
The Lakes at Harmony
![3470 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
3 beds
|2 baths
|1,426 sq ft
|House
3470 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS O6394523 • COLDWELL BANKER REALTY, Elizabeth ...
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
Majestic Oaks Ocala
![5393 SW 86TH PL, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|2,116 sq ft
|House
5393 SW 86TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS OM721883 • GAILEY ENTERPRISES REAL ESTATE, Br...
The Villages®
![3737 COSMOS WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,392 sq ft
|House
3737 COSMOS WAY, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6395357 • REAL PROPERTY INTERNATIONAL, Bob L...
Pelican Bay Daytona Beach
![105 SAND FIDDLER CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|3 baths
|1,919 sq ft
|House
105 SAND FIDDLER CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1224724 • Watson Realty Corp., Patricia Shook
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.
VillageWalk at Lake Nona
![7972 ESTA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|5 baths
|3,460 sq ft
|House
7972 ESTA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6394136 • KELLER WILLIAMS ADVANTAGE III, She...
The Villages®
![1307 PANAMA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,499 sq ft
|House
1307 PANAMA PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5110367 • EXP REALTY LLC, Norma Pollitt-Slot...
Tohoqua Reserve
![2733 SERENITY MEADOW DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,670 sq ft
|House
2733 SERENITY MEADOW DR, KISSIMMEE, FL, ...
Community: Tohoqua Reserve
MLS O6395315 • PULTE REALTY OF NORTH FLORIDA LLC,...
Solivita
![825 GLENDORA RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5146751 • BORCHINI REALTY, Charles Borchini
Stone Creek
![6816 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM721359 • PREMIER SOTHEBY'S INTERNATIONAL RE...
Stone Creek
![6824 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM721375 • PREMIER SOTHEBY'S INTERNATIONAL RE...
Sun City Center
![1901 CANTERBURY LN 4, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,120 sq ft
|Condo
1901 CANTERBURY LN 4, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8492397 • FLORIDA'S 1ST CHOICE RLTY LLC, ch...
Plantation at Leesburg
![4644 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,456 sq ft
|House
4644 RIVER RIDGE DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6395172 • KELLER WILLIAMS ADVANTAGE REALTY, ...
Want to learn more about 55+ communities in Winter Garden?
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Venetian Bay
![3355 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,267 sq ft
|House
3355 BELLINO BLVD, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS V4948214 • REAL BROKER, LLC, Nicole Chapman
Sun City Center
![2003 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
3 beds
|2 baths
|2,350 sq ft
|House
2003 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
MLS TB8491524 • RE/MAX COLLECTIVE, Katherine Crid...
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.
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.
On average, listings in 55+ communities in Winter Garden stay on the market for around 399 days. The average price of homes for sale in these communities is approximately $476,615, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $476,615.
Want more information about active adult communities around Winter Garden?
Want to learn more about 55+ communities in Winter Garden?
3,497
homes
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REIN updates its listings on a daily basis. Data last updated: May 25, 2026.
This application does not include information on all of the properties available for sale at this time.
