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Winter Garden, FL 55+ active adult communities & homes for sale - Page 21
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
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 (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
Liberty Village
![7651 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
4 beds
|3 baths
|2,039 sq ft
|House
7651 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
MLS O6287501 • HOMESMART, Allyson Peterson
Spruce Creek Preserve
![13834 SW 114TH AVE, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
3 beds
|2 baths
|1,760 sq ft
|House
13834 SW 114TH AVE, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM715658 • RE/MAX FOXFIRE - HWY200/103 S, Ka...
Sun City Center
![1529 ALLEGHENY DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,226 sq ft
|House
1529 ALLEGHENY DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS TB8316888 • CENTURY 21 BEGGINS ENTERPRISES, B...
Ocala Palms
![2100 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM704380 • PEGASUS REALTY & ASSOC INC, Lena B...
Ocala Preserve
![3642 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM690338 • PEGASUS REALTY & ASSOC INC, Lena B...
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Questions? Call us:
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The Villages®
![1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,388 sq ft
|House
1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS R4910370 • BLACK TIE REAL ESTATE PROFESSIONAL...
Stonecrest
![17645 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,686 sq ft
|House
17645 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM698674 • ROBB HARRISON REALTY INC, Robb Har...
Enclave at VillageWalk
![11741 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|4 baths
|3,197 sq ft
|House
11741 SAVONA WAY, ORLANDO, FL, 32827
Community: Enclave at VillageWalk
MLS O6311711 • KELLER WILLIAMS CLASSIC, Cassie La...
Spruce Creek South
![15913 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
4 beds
|2 baths
|1,498 sq ft
|House
15913 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM712496 • DR HORTON REALTY OF WEST CENTRAL F...
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
![6138 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM715579 • ROBERT SLACK LLC, Jaimee Hibbs
Spruce Creek South
![15919 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,328 sq ft
|House
15919 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM713910 • DR HORTON REALTY OF WEST CENTRAL F...
Latitude Margaritaville
![422 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
422 LIME AVE, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS V4945467 • ADAMS, CAMERON & CO., REALTORS, Bi...
Majestic Oaks Ocala
![4777 SW 89TH ST, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,672 sq ft
|House
4777 SW 89TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS OM713637 • DR HORTON REALTY OF WEST CENTRAL F...
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Solivita
![417 LAKE BUTLER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8346674 • CHARLES RUTENBERG REALTY INC, Al ...
Heritage Hills
![3201 SONESTA CT A, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3201 SONESTA CT A, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5105573 • KELLER WILLIAMS ELITE PARTNERS III...
Four Seasons at Orlando
![7661 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
7661 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Community: Four Seasons at Orlando
MLS O6368190 • VIVA ORLANDO REALTY INC., Susan Ri...
Four Seasons at Orlando
![1825 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
1825 FLORA PASS PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6355192 • VIVA ORLANDO REALTY INC., Susan Ri...
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
![1306 SPRY CT # 1306, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,219 sq ft
|Condo
1306 SPRY CT # 1306, SUN CITY CENTER, FL...
Community: Sun City Center
MLS TB8430954 • KELLER WILLIAMS SUBURBAN TAMPA, C...
The Villages®
![1639 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1639 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6333604 • REDFIN CORPORATION, Jo Holton
The Villages®
![458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|1,830 sq ft
|House
458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5103594 • HOAD REALTY GROUP LLC, Lisa Hoad
Stone Creek
![8468 SW 52ND LANE RD, OCALA, FL, 34481, Ocala, FL 34481]()
4 beds
|2 baths
|1,853 sq ft
|House
8468 SW 52ND LANE RD, OCALA, FL, 34481
Community: Stone Creek
MLS OM713517 • CHARLES JOYCE REAL ESTATE, Joy Sum...
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Valencia Lakes
![4948 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,185 sq ft
|House
4948 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8423241 • SALTZBERG & ASSOCIATES REAL ESTAT...
Ocala Preserve
![4119 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS NS1085885 • ENGEL & VOLKERS NEW SMYRNA, Nate ...
The Villages®
![14202 SANDALWOOD DR # 202, WILDWOOD, FL,..., Wildwood, FL 34785]()
2 beds
|2 baths
|1,085 sq ft
|Condo
14202 SANDALWOOD DR # 202, WILDWOOD, FL,...
Community: The Villages®
MLS G5101963 • MORRIS REALTY AND INVESTMENTS, The...
Sun City Center
![1417 LANGLEY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,529 sq ft
|Condo
1417 LANGLEY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
MLS TB8392293 • CENTURY 21 BEGGINS ENTERPRISES, D...
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.
Heritage Landings
![2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
6 beds
|3 baths
|2,696 sq ft
|House
2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS L4958127 • KELLER WILLIAMS REALTY SMART 1, He...
Lakes at Laurel Highlands
![2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
6 beds
|3 baths
|2,696 sq ft
|House
2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Lakes at Laurel Highlands
MLS L4958127 • KELLER WILLIAMS REALTY SMART 1, He...
Ocala Preserve
![4264 NW 57TH AVE, OCALA, FL, 34482, Ocala, FL 34482]()
MLS TB8458011 • REALTY OF RIVERVIEW LLC, Stephen ...
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...
Sun City Center
![2335 E DEL WEBB BLVD, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
3 beds
|2 baths
|1,322 sq ft
|House
2335 E DEL WEBB BLVD, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8361675 • LPT REALTY, LLC, Keegan Siegfried
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The Villages®
![528 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,624 sq ft
|House
528 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5105291 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
The Villages®
![802 MIRANDA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,471 sq ft
|House
802 MIRANDA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5105223 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
Palm Cay
![8304 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM715574 • PREMIER SOTHEBY'S INTERNATIONAL RE...
Ocala Preserve
![4235 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM706335 • DEBUIRE INTERNATIONAL REALTY, Sand...
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 Country Club of Mount Dora
![5061 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,922 sq ft
|House
5061 GREENBRIAR TRL, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5104656 • MOUNT DORA GOLF AND LAKE RLTY, Joh...
Royal Harbor
![5151 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
4 beds
|2 baths
|2,091 sq ft
|House
5151 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS O6349567 • DAPORE REALTY INC, Diane Dapore Ro...
The Villages®
![2845 CHARITY LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,206 sq ft
|House
2845 CHARITY LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
MLS TB8444383 • WWW.HOMEZU.COM, Jason Saphire
Sun City Center
![322 GLOUCESTER BLVD # 322, SUN CITY CENT..., Sun City Center, FL 33573]()
1 beds
|2 baths
|800 sq ft
|Condo
322 GLOUCESTER BLVD # 322, SUN CITY CENT...
Community: Sun City Center
MLS TB8409500 • COLDWELL BANKER REALTY, Yaremi Ga...
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Colonnades
![4823 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,196 sq ft
|House
4823 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4956860 • COLDWELL BANKER REALTY, Lisa Broch...
Plantation at Leesburg
![25504 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,674 sq ft
|Manufactured Home
25504 BELLE ALLIANCE, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5104384 • CENTURY 21 MYERS REALTY, Cary Fier
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.
