Call us at (689) 407-5757 to learn more about active adult communities in Winter Garden
Winter Garden, FL 55+ active adult communities & homes for sale
106 communities near Winter Garden
3,952 homes near Winter Garden
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![Del Webb Oasis]()
$400Ks
- $1Ms
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
- $600Ks
Sun City Center, Sun City Center, FL
Resale Only
|
55+ age-restricted
|
Built 1961 - 2018
|
9,500 homes
4.7 rating (18 reviews)
![Solivita]()
$200Ks
- $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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(689) 407-5757
3.6 rating (46 reviews)
![Latitude Margaritaville]()
$300Ks
- $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
4.2 rating (10 reviews)
![Stone Creek]()
$200Ks
- $800Ks
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
- $400Ks
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]()
$200Ks
- $600Ks
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
- $1Ms
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
No reviews yet
![Pelican Bay Daytona Beach]()
<$100k
- $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]()
$200Ks
- $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]()
$200Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
5 rating (3 reviews)
![Lake Ashton]()
$200Ks
- $900Ks
Lake Ashton, Lake Wales, FL
Resale Only
|
55+ age-restricted
|
Built 2002 - present
|
1,600 homes
No reviews yet
![Venetian Bay]()
$200Ks
- $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.
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $400Ks
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)
![Del Webb Sunbridge]()
$300Ks
- $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 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
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(689) 407-5757
5 rating (8 reviews)
![Pennbrooke Fairways]()
$100Ks
- $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]()
$300Ks
- $500Ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
5 rating (1 reviews)
![Ocala Palms]()
$100Ks
- $400Ks
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
|
1,029 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
- $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$200Ks
- $800Ks
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
- $800Ks
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?
55places can help!
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
4.3 rating (15 reviews)
![Del Webb Orlando]()
$200Ks
- $500Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
No reviews yet
![Pine Run Estates]()
$100Ks
- $400Ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
No reviews yet
![Lake Jovita Golf and Coun...]()
$400Ks
- $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
- $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
868 homes
Stone Creek
![7454 SW 101ST AVE, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM694527 • ON TOP OF THE WORLD REAL EST, Kath...
Mirada
![10374 ECHO DOCK LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576]()
2 beds
|2 baths
|1,405 sq ft
|Villa
10374 ECHO DOCK LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
MLS TB8337359 • KELLER WILLIAMS TAMPA PROP., Glor...
Oak Run
![715 SW 77TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
MLS L4949385 • CAMBRIDGE REALTY OF CENTRAL FL, Ge...
On Top of the World
![10314 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,137 sq ft
|House
10314 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM696040 • ON TOP OF THE WORLD REAL EST, Jaso...
On Top of the World
![9725 SW 108TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481]()
2 beds
|2 baths
|2,145 sq ft
|House
9725 SW 108TH TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
MLS OM690725 • ON TOP OF THE WORLD REAL EST, Jaso...
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Oak Run
![10820 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM686329 • KELLER WILLIAMS CORNERSTONE RE, Ch...
The Villages®
![530 VALENCIA PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,383 sq ft
|House
530 VALENCIA PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5095425 • SELLSTATE SUPERIOR REALTY, Karen M...
Windermere
![821 INVERIE DR, INVERNESS, FL, 34453, Inverness, FL 34453]()
3 beds
|3 baths
|1,921 sq ft
|Townhouse
821 INVERIE DR, INVERNESS, FL, 34453
Community: Windermere
MLS OM685139 • REMAX/PREMIER REALTY, Courtney For...
Palm Cay
![9973 SW 107TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM699572 • ON TOP OF THE WORLD REAL EST, Jaso...
Ashley Oaks
![2036 ASHLEY OAKS CIR, SEBRING, FL, 33870, Sebring, FL 33870]()
3 beds
|2 baths
|1,493 sq ft
|House
2036 ASHLEY OAKS CIR, SEBRING, FL, 33870
Community: Ashley Oaks
MLS 315301 • Paradise Real Estate International L...
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
![10556 SW 96TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,142 sq ft
|House
10556 SW 96TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM700628 • ON TOP OF THE WORLD REAL EST, Jaso...
On Top of the World
![10557 SW 98TH LN, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,536 sq ft
|House
10557 SW 98TH LN, OCALA, FL, 34481
Community: On Top of the World
MLS OM696034 • ON TOP OF THE WORLD REAL EST, Jaso...
Cherrywood
![10734 SW 99TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM698057 • ON TOP OF THE WORLD REAL EST, Jaso...
Valencia del Sol
![4838 SEVILLA SHORES DR, WIMAUMA, FL, 335..., Wimauma, FL 33598]()
3 beds
|3 baths
|2,252 sq ft
|House
4838 SEVILLA SHORES DR, WIMAUMA, FL, 335...
Community: Valencia del Sol
MLS T3550183 • RE/MAX REALTY UNLIMITED, Carina Ba...
Del Webb Oasis
![13545 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787]()
2 beds
|2 baths
|1,579 sq ft
|Villa
13545 PEARL BEACH ST, WINTER GARDEN, FL,...
Community: Del Webb Oasis
MLS O6284989 • PULTE REALTY OF NORTH FLORIDA LLC,...
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(689) 407-5757
SummerGlen
![15702 SW 16TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473]()
3 beds
|2 baths
|2,320 sq ft
|House
15702 SW 16TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
MLS OM696744 • SUMMERGLEN REALTY,LLC, Melissa Pow...
Pennbrooke Fairways
![32512 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,312 sq ft
|House
32512 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS O6276970 • COLDWELL BANKER REALTY, Mike Borah
Highlands Ridge
![2886 S DOCKSIDE DR, AVON PARK, FL, 33825, Avon Park, FL 33825]()
2 beds
|2 baths
|1,120 sq ft
|Mobile Home
2886 S DOCKSIDE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
MLS 302126 • MB & A Realty, Leland Ernest Brooker
Lakes of Mount Dora
![2457 BAR HBR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,874 sq ft
|House
2457 BAR HBR, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
MLS G5096752 • WATSON REALTY CORP, Jonathan Faw
Sun City Center
![812 MCCALLISTER AVE, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,444 sq ft
|Condo
812 MCCALLISTER AVE, SUN CITY CENTER, FL...
Community: Sun City Center
MLS T3543332 • CENTURY 21 BEGGINS ENTERPRISES, Ja...
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
![17231 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|3 baths
|1,744 sq ft
|Villa
17231 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS T3546471 • SMITH & ASSOCIATES REAL ESTATE, Ja...
Oak Run
![10821 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM695457 • KELLER WILLIAMS CORNERSTONE RE, Al...
Scottish Highlands
![74 STONE HAVEN CT, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,104 sq ft
|House
74 STONE HAVEN CT, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5095260 • ERA GRIZZARD REAL ESTATE, Cynthia ...
Oak Run
![10913 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM691691 • DECCA REAL ESTATE, Thomas Reeves
Sun City Center
![609 FOX HILLS DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,852 sq ft
|House
609 FOX HILLS DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
MLS T3546513 • KELLER WILLIAMS SUBURBAN TAMPA, Ra...
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Highlands Ridge
![4028 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825]()
3 beds
|2 baths
|2,671 sq ft
|House
4028 CARTER CREEK DR, AVON PARK, FL, 338...
Community: Highlands Ridge
MLS 314982 • BHHS Florida Properties Group, Teri ...
Solivita
![972 LADERA RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
3 beds
|3 baths
|2,318 sq ft
|House
972 LADERA RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
MLS S5116540 • ARISTA REALTY GROUP, LLC, Douglas ...
Sun City Center
![102 CAMBRIDGE TRL APT 225, SUN CITY CENT..., Sun City Center, FL 33573]()
2 beds
|2 baths
|960 sq ft
|Condo
102 CAMBRIDGE TRL APT 225, SUN CITY CENT...
Community: Sun City Center
MLS TB8339796 • CENTURY 21 BEGGINS ENTERPRISES, J...
Pennbrooke Fairways
![32915 CROOKED OAKS LN, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,564 sq ft
|House
32915 CROOKED OAKS LN, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
MLS G5086182 • CENTURY 21 ALTON CLARK, Regina Rod...
Summer Trees
![147 MAGNOLIA LOOP, PORT ORANGE, FL, 3212..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,048 sq ft
|House
147 MAGNOLIA LOOP, PORT ORANGE, FL, 3212...
Community: Summer Trees
MLS 1209175 • Beach Towne Realtors, Mark Valerien
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.
Sullivan Ranch
![20811 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,590 sq ft
|House
20811 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS O6269632 • CHARLES RUTENBERG REALTY ORLANDO, ...
Solivita
![634 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6309515 • SMOOTH LANDINGS REAL ESTATE, Misty...
On Top of the World
![9649 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,933 sq ft
|House
9649 SW 90TH ST, OCALA, FL, 34481
Community: On Top of the World
MLS OM701176 • NEXT GENERATION REALTY OF MARION C...
Stone Creek
![6651 SW 93RD CT, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM701323 • NEXT GENERATION REALTY OF MARION C...
Valencia Lakes
![16101 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|2 baths
|1,912 sq ft
|House
16101 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8383803 • ELEVATE REAL ESTATE BROKERS OF FL...
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(689) 407-5757
On Top of the World
![6569 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|3 baths
|1,458 sq ft
|Townhouse
6569 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM701649 • DR HORTON REALTY OF WEST CENTRAL F...
On Top of the World
![6567 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|3 baths
|1,458 sq ft
|Townhouse
6567 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM701647 • DR HORTON REALTY OF WEST CENTRAL F...
On Top of the World
![6561 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|3 baths
|1,458 sq ft
|Townhouse
6561 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM701644 • DR HORTON REALTY OF WEST CENTRAL F...
On Top of the World
![10427 SW 98TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,467 sq ft
|House
10427 SW 98TH PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM701648 • CB/ELLISON RLTY WEST, Brian McCart...
On Top of the World
![6563 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|3 baths
|1,458 sq ft
|Townhouse
6563 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM701645 • DR HORTON REALTY OF WEST CENTRAL F...
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 143 days. The average price of homes for sale in these communities is approximately $502,460, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $502,460.
Want more information about active adult communities around Winter Garden?
3,952
homes
near Winter Garden
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