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Winter Garden, FL 55+ active adult communities & homes for sale
106 communities near Winter Garden
3,573 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
- $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
- $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]()
$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 (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
- $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
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
- $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]()
$200Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 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
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]()
$300Ks
- $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
- $900Ks
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]()
$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
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
- $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
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:
(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
- $400Ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 homes
No reviews yet
![Pine Run Estates]()
<$100k
- $400Ks
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
Spring Lake Towers
![700 MIRROR TER 303, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881]()
2 beds
|2 baths
|1,029 sq ft
|Condo
700 MIRROR TER 303, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
MLS P4934745 • LPT REALTY, LLC, Kevin Tison
Twin Lakes
![2658 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,208 sq ft
|House
2658 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5122479 • WEICHERT REALTORS HALLMARK PRO, Sh...
On Top of the World
![8412 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,103 sq ft
|House
8412 SW 93RD CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM698535 • COMPASS FLORIDA LLC, Lucinda Strik...
On Top of the World
![9313 SW 102ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34481]()
2 beds
|2 baths
|1,469 sq ft
|House
9313 SW 102ND TERRACE RD, OCALA, FL, 344...
Community: On Top of the World
MLS OM697864 • ON TOP OF THE WORLD REAL EST, Tamm...
Solivita
![803 JASMINE CREEK RD, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
3 beds
|3 baths
|2,427 sq ft
|House
803 JASMINE CREEK RD, KISSIMMEE, FL, 347...
Community: Solivita
MLS W7876280 • LISTWITHFREEDOM.COM, Ralph Harvey
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
Lake Henry Estates
![422 HARBOURVIEW DR, HAINES CITY, FL, 338..., Haines City, FL 33844]()
3 beds
|2 baths
|1,793 sq ft
|House
422 HARBOURVIEW DR, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS O6324359 • LIONHEART BROKERS, Claudia Centesi...
Kings Ridge
![2112 SAINT IVES CT, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|2 baths
|2,028 sq ft
|House
2112 SAINT IVES CT, CLERMONT, FL, 34711
Community: Kings Ridge
MLS G5096490 • KELLER WILLIAMS ELITE PARTNERS III...
Cherrywood
![6113 SW 101ST PL, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM704293 • ROBERTS REAL ESTATE INC, Heather B...
Spruce Creek Country Club
![8601 SE 133RD ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,346 sq ft
|House
8601 SE 133RD ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5096953 • RE/MAX PREMIER REALTY LADY LK, Rob...
Del Webb Sunbridge
![2960 CHERRY BLOSSOM LOOP, SAINT CLOUD, F..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,584 sq ft
|Villa
2960 CHERRY BLOSSOM LOOP, SAINT CLOUD, F...
Community: Del Webb Sunbridge
MLS O6308174 • FLORIDA INT'NL REAL ESTATE LLC, Li...
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.
Quail Meadow
![4762 NW 30TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM687958 • FLORIDA REAL ESTATE LIFESTYLES, Se...
Highland Fairways
![3245 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,045 sq ft
|House
3245 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
MLS P4934841 • COLDWELL BANKER REALTY, Sherry Sap...
Valencia del Sol
![4905 AVILA LAKES DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,648 sq ft
|Villa
4905 AVILA LAKES DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
MLS TB8403962 • CENTURY 21 BEGGINS ENTERPRISES, A...
Venetian Bay
![505 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,758 sq ft
|House
505 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS O6322727 • EXP REALTY LLC, Veronica Figueroa
Twin Lakes
![5025 SUNFALLS AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
5025 SUNFALLS AVE, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS S5127546 • WEICHERT REALTORS HALLMARK PRO, Sh...
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(689) 407-5757
Sun City Center
![2021 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|2,039 sq ft
|House
2021 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8360851 • UNIVERSAL REALTY, Peggy Couch
Cherrywood
![15062 SW 63RD COURT RD, OCALA, FL, 34473, Ocala, FL 34473]()
4 beds
|3 baths
|1,560 sq ft
|House
15062 SW 63RD COURT RD, OCALA, FL, 34473
Community: Cherrywood
MLS O6240683 • THE FLORIDA LOUNGE REALTY LLC, Leo...
Solivita
![300 FALLING WATER DR, POINCIANA, FL, 347..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,171 sq ft
|Halfplex
300 FALLING WATER DR, POINCIANA, FL, 347...
Community: Solivita
MLS S5123200 • BELLA VERDE REALTY LLC, Miguel Elv...
Sun City Center
![322 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,686 sq ft
|Villa
322 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS TB8362289 • DALTON WADE INC, Nancy Stanton
Cresswind DeLand
![1235 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|4 baths
|2,496 sq ft
|House
1235 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
MLS O6323697 • KSH REALTY LLC, Alyssa Traficant
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
![2529 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,359 sq ft
|Condo
2529 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS TB8367575 • KELLER WILLIAMS SOUTH SHORE, Davi...
Marion Landing
![8485 SW 60TH CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM704708 • COLDWELL REALTY SOLD GUARANTEE, Sc...
SummerGlen
![1033 SW 159TH ST, OCALA, FL, 34473, Ocala, FL 34473]()
MLS OM692233 • SUMMERGLEN REALTY,LLC, Melissa Pow...
The Villages®
![739 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
739 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5096310 • VANTAGE POINT REALTY CO., Tracie R...
Tampa Bay Golf and Country Club
![29307 SCHINNECOCK HILLS LN, SAN ANTONIO,..., San Antonio, FL 33576]()
2 beds
|2 baths
|1,398 sq ft
|House
29307 SCHINNECOCK HILLS LN, SAN ANTONIO,...
Community: Tampa Bay Golf and Country Club
MLS TB8350406 • REST EASY REALTY POWERED BY SELLS...
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
Sun City Center
![2214 HIGHCLERE CIR # 6, SUN CITY CENTER,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,349 sq ft
|Condo
2214 HIGHCLERE CIR # 6, SUN CITY CENTER,...
Community: Sun City Center
MLS TB8392074 • RE/MAX REALTY UNLIMITED, Cedric R...
Ocala Preserve
![4379 NW 56TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM700524 • ROYAL OAK REALTY LLC, Mikhalea Epp...
On Top of the World
![10055 SW 90TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,662 sq ft
|House
10055 SW 90TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM695663 • RE/MAX FOXFIRE - HWY200/103 S, Bo...
Huntington at Hunter's Ridge
![24 SHEAR WATER TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,031 sq ft
|House
24 SHEAR WATER TRL, ORMOND BEACH, FL, 32...
Community: Huntington at Hunter's Ridge
MLS FC309988 • COMPASS FLORIDA, Debby Meyer
Pine Run Estates
![9960 SW 103RD LN, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM702628 • RE/MAX FOXFIRE - HWY200/103 S, Mi...
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.
JB Ranch
![6444 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
MLS G5096323 • RE/MAX FREEDOM, Jacob Pfaff
Venetian Bay
![3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
4 beds
|2 baths
|1,662 sq ft
|House
3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1083018 • COLLADO REAL ESTATE, Mary Johnsto...
On Top of the World
![8814 SW 93RD LN B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,411 sq ft
|Condo
8814 SW 93RD LN B, OCALA, FL, 34481
Community: On Top of the World
MLS G5096051 • WORTH CLARK REALTY, Chuck Wilsey
Cherrywood
![10121 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476]()
3 beds
|2 baths
|2,052 sq ft
|House
10121 SW 61ST TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
MLS 2092572 • LA ROSA REALTY NORTH FLORIDA, LLC.,...
Traditions at Lake Ruby
![3007 CANEEL ST, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,385 sq ft
|Villa
3007 CANEEL ST, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS O6310659 • KELLER WILLIAMS REALTY AT THE PARK...
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(689) 407-5757
Ocala Preserve
![3480 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM704703 • REMAX/PREMIER REALTY, Nay Lopez
The Villages®
![1722 BUGLE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,667 sq ft
|House
1722 BUGLE TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5098901 • COLDWELL BANKER VANGUARD LIFESTYLE...
Lake James
![7919 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,886 sq ft
|House
7919 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
MLS L4953045 • SKYELINE REALTY LLC, Sharon Billup...
Plantation at Leesburg
![25007 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
25007 BELLEVUE, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5098224 • CENTURY 21 MYERS REALTY, Lisa Wolf...
On Top of the World
![8218 SW 92ND CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,311 sq ft
|House
8218 SW 92ND CIR, OCALA, FL, 34481
Community: On Top of the World
MLS OM697908 • NEXT GENERATION REALTY OF MARION C...
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?
3,573
homes
near Winter Garden
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