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Winter Garden, FL 55+ active adult communities & homes for sale - Page 30
109 communities near Winter Garden
3,517 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
- $2Ms
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
- $700Ks
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
- $600Ks
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
- $900Ks
Stone Creek, Ocala, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
3,800 homes
4.1 rating (29 reviews)
![Oak Run]()
$100Ks
- $500Ks
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
Download the Ultimate 55+ Homebuying Guide
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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
5 rating (3 reviews)
![Stonecrest]()
$200Ks
- $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
- $600Ks
Twin Lakes, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
2,000 homes
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$100Ks
- $400Ks
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
4.7 rating (3 reviews)
![Spruce Creek South]()
$100Ks
- $400Ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
4.7 rating (11 reviews)
![Valencia Lakes]()
$200Ks
- $600Ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 homes
Download the Ultimate 55+ Homebuying Guide
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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
$200Ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
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5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
4 rating (7 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]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
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.
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
- $400Ks
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
- $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
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5 rating (5 reviews)
![SummerGlen]()
$100Ks
- $400Ks
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
$400Ks
- $800Ks
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
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 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
4.8 rating (6 reviews)
![Highland Lakes]()
$100Ks
- $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
<$100k
- $300Ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
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Questions? Call us:
(689) 407-5757
$300Ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
New
Vienna Square
![1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,329 sq ft
|Villa
1620 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS TB8460219 • FLAT FEE MLS REALTY, Stephen Hach...
Plantation at Leesburg
![4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,780 sq ft
|House
4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Community: Plantation at Leesburg
MLS G5091359 • CARLINO REAL ESTATE GROUP INC, Jon...
New
Valencia Lakes
![4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33..., Wimauma, FL 33598]()
3 beds
|2 baths
|1,756 sq ft
|Villa
4949 MARBLE SPRINGS CIR, WIMAUMA, FL, 33...
Community: Valencia Lakes
MLS TB8461004 • CHARLES RUTENBERG REALTY INC, Urs...
The Villages®
![17086 SE 75TH WICKSON CT, THE VILLAGES, ..., The Villages, FL 32162]()
2 beds
|2 baths
|1,150 sq ft
|Villa
17086 SE 75TH WICKSON CT, THE VILLAGES, ...
Community: The Villages®
MLS G5103159 • MORRIS REALTY AND INVESTMENTS, Lin...
On Top of the World
![9260 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,246 sq ft
|House
9260 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM708651 • KELLER WILLIAMS CORNERSTONE RE, Ch...
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New
Spruce Creek South
![9806 SE 175TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,688 sq ft
|House
9806 SE 175TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS OM716011 • DALTON WADE INC, Tammy Luce
On Top of the World
![8785 SW 91ST ST B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,204 sq ft
|Villa
8785 SW 91ST ST B, OCALA, FL, 34481
Community: On Top of the World
MLS OM711779 • RE/MAX FOXFIRE - HWY200/103 S, Pa...
Pelican Bay Daytona Beach
![148 BOB WHITE CT 1480, DAYTONA BEACH, FL..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,189 sq ft
|Condo
148 BOB WHITE CT 1480, DAYTONA BEACH, FL...
Community: Pelican Bay Daytona Beach
MLS NS1086326 • RE/MAX SIGNATURE, Chris Leon
New
On Top of the World
![9015 SW 94TH ST D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,861 sq ft
|Villa
9015 SW 94TH ST D, OCALA, FL, 34481
Community: On Top of the World
MLS OM716069 • ON TOP OF THE WORLD REAL EST, Kath...
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.
Pelican Bay Daytona Beach
![240 BOB WHITE CT # 240, DAYTONA BEACH, F..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,093 sq ft
|Condo
240 BOB WHITE CT # 240, DAYTONA BEACH, F...
Community: Pelican Bay Daytona Beach
MLS NS1085647 • RE/MAX SIGNATURE, Kimberly Sbordo...
The Villages®
![2583 RAINTREE DR, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
2583 RAINTREE DR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5106004 • REAL BROKER, LLC, Katy Kelly
New
Arlington Ridge
![4834 INDEPENDENCE TRL, LEESBURG, FL, 347..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,772 sq ft
|House
4834 INDEPENDENCE TRL, LEESBURG, FL, 347...
Community: Arlington Ridge
MLS G5105914 • REALTY EXECUTIVES IN THE VILLAGES,...
Spruce Creek Country Club
![13835 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,822 sq ft
|House
13835 SE 85TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM714747 • JUDY L. TROUT REALTY, Jennifer Tra...
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Venetian Bay
![349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,520 sq ft
|House
349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1085211 • CENTURY 21 SUNDANCE REALTY, Bryan...
Plantation at Leesburg
![5140 DESOTO WAY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,224 sq ft
|Manufactured Home
5140 DESOTO WAY, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5104066 • CENTURY 21 MYERS REALTY, Cary Fier
The Country Club of Mount Dora
![9071 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,494 sq ft
|House
9071 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Community: The Country Club of Mount Dora
MLS O6367575 • KELLER WILLIAMS REALTY AT THE PARK...
Cresswind at Victoria Gardens
![104 OVERTON GARDENS LN, DELAND, FL, 3272..., Deland, FL 32724]()
3 beds
|2 baths
|1,820 sq ft
|House
104 OVERTON GARDENS LN, DELAND, FL, 3272...
Community: Cresswind at Victoria Gardens
MLS V4946464 • LANE REALTY SERVICES, LLC, Pam Dea...
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.
Valencia Lakes
![4938 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|3 baths
|2,362 sq ft
|House
4938 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8429976 • DALTON WADE INC, Zoki Mbolekwa
Valencia Lakes
![4820 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|2,107 sq ft
|House
4820 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8413688 • DALTON WADE INC, Zoki Mbolekwa
On Top of the World
![9273 SW 91ST COURT RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,311 sq ft
|House
9273 SW 91ST COURT RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM711588 • RE/MAX FOXFIRE - HWY200/103 S, Bo...
New
Solivita
![2285 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5140993 • BORCHINI REALTY, Dale Pautz
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New
On Top of the World
![4947 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|3 baths
|1,782 sq ft
|Townhouse
4947 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS TB8462151 • REALTY HUB, Vania Palmer PA
New
Spruce Creek Country Club
![9479 SE 130TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,346 sq ft
|House
9479 SE 130TH STREET RD, SUMMERFIELD, FL...
Community: Spruce Creek Country Club
MLS G5106280 • RE/MAX PREMIER REALTY LADY LK, Rob...
New
Stone Creek
![5992 SW 90TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|5 baths
|2,892 sq ft
|House
5992 SW 90TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
MLS OM716211 • RE/MAX ALLSTARS REALTY, Marcia Kas...
New
Foxwood Lake Estates
![1570 HEATHER HILL DR, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,630 sq ft
|Manufactured Home
1570 HEATHER HILL DR, LAKELAND, FL, 3381...
Community: Foxwood Lake Estates
MLS P4937447 • FLORIDA REALTY MARKETPLACE, Debra ...
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.
New
On Top of the World
![8878 SW 96TH ST B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,341 sq ft
|Villa
8878 SW 96TH ST B, OCALA, FL, 34481
Community: On Top of the World
MLS OM716197 • ON TOP OF THE WORLD REAL EST, Carl...
New
Foxwood Lake Estates
![4815 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,312 sq ft
|Manufactured Home
4815 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS P4937443 • FLORIDA REALTY MARKETPLACE, Debra ...
New
Marion Landing
![8735 SW 67TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS O6371700 • LENNAR REALTY, Ben Goldstein
New
Lake Henry Estates
![516 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844]()
2 beds
|2 baths
|1,393 sq ft
|House
516 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS B4902146 • KLINE REAL ESTATE SERVICES, Scott ...
New
Quail Meadow
![3150 NW 50TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM715951 • REAL PROPERTY MGMT DIVERSIFIED, Le...
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New
Colonnades
![1678 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,224 sq ft
|House
1678 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4958204 • REMAX EXPERTS, Maria Santillo
New
Baytree
![239 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5106007 • COLDWELL BANKER VANGUARD EDGE, Aly...
New
Plantation at Leesburg
![4802 SUMMERBRIDGE CIR, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,162 sq ft
|House
4802 SUMMERBRIDGE CIR, LEESBURG, FL, 347...
Community: Plantation at Leesburg
MLS G5105827 • CENTURY 21 MYERS REALTY, Mary Jane...
New
Ridgehaven
![442 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,487 sq ft
|House
442 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6369364 • MERITAGE HOMES OF FL REALTY, Tatia...
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.
New
The Country Club of Mount Dora
![9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,587 sq ft
|House
9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Community: The Country Club of Mount Dora
MLS O6366325 • REAL BROKER, LLC, Brian Batiz Sala...
New
Mirada
![10998 GABLE DIG LOOP, SAN ANTONIO, FL, 3..., San Antonio, FL 33576]()
2 beds
|2 baths
|1,405 sq ft
|Villa
10998 GABLE DIG LOOP, SAN ANTONIO, FL, 3...
Community: Mirada
MLS TB8456614 • COMPASS FLORIDA LLC, Kevin Daniel
Quail Meadow
![3276 NW 44TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM715399 • RE/MAX FOXFIRE - HWY 40, Jose Mate...
Quail Meadow
![3340 NW 44TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM715401 • RE/MAX FOXFIRE - HWY 40, Jose Mate...
Want to learn more about 55+ communities in Winter Garden?
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(689) 407-5757
Ocala Palms
![1921 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM710680 • KELLER WILLIAMS CORNERSTONE RE, Ju...
The Villages®
![17285 SE 85TH WILLOWICK CIR, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|2,003 sq ft
|House
17285 SE 85TH WILLOWICK CIR, THE VILLAGE...
Community: The Villages®
MLS G5103061 • WORTH CLARK REALTY, Christine Mazz...
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?
3,517
homes
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REIN updates its listings on a daily basis. Data last updated: Jan 11, 2026.
This application does not include information on all of the properties available for sale at this time.
