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Winter Garden, FL 55+ active adult communities & homes for sale - Page 49
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
The Villages®
![103 ROBIN LN, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,152 sq ft
|Manufactured Home
103 ROBIN LN, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5105959 • DOWN HOME REALTY, LLLP, Kristen Pi...
Plantation at Leesburg
![3639 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,709 sq ft
|House
3639 WESTOVER CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS W7881684 • SANDPEAK REALTY, Rubi Teicher
Ocala Preserve
![5575 NW 43RD LANE RD, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,856 sq ft
|House
5575 NW 43RD LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
MLS V4946389 • RE/MAX SIGNATURE, Stephanie Cathey
Ridgehaven
![187 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,454 sq ft
|House
187 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
MLS O6345911 • MERITAGE HOMES OF FL REALTY, Tatia...
Huntington at Hunter's Ridge
![6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,637 sq ft
|House
6 FOX LAIR CT, ORMOND BEACH, FL, 32174
Community: Huntington at Hunter's Ridge
MLS FC311356 • REALTY PROS ASSURED, Tyler Renick
Want to learn more about 55+ communities in Winter Garden?
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Solivita
![670 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5133347 • BORCHINI REALTY, Charles Borchini
Pine Run Estates
![9035 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,144 sq ft
|House
9035 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates
MLS G5099406 • HARRISON REAL PROPERTY GROUP, Aman...
The Villages®
![1605 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,638 sq ft
|House
1605 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099171 • BROKER ASSOCIATES REALTY, Kim Asch...
Majestic Oaks Ocala
![5351 SW 80TH PL, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,520 sq ft
|House
5351 SW 80TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS OM701005 • FRENCH REAL ESTATE CO., Jericho Fr...
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
![8532 SW 93RD PL B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,385 sq ft
|Villa
8532 SW 93RD PL B, OCALA, FL, 34481
Community: On Top of the World
MLS OM708024 • FONTANA REALTY, Javier Rojas
On Top of the World
![9694 SW 79TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,893 sq ft
|House
9694 SW 79TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM698147 • FONTANA REALTY, Javier Rojas
Stonecrest
![17187 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,026 sq ft
|House
17187 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
MLS GC536130 • MILLER REAL ESTATE, Anthony Brock
Solivita
![3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5130722 • BORCHINI REALTY, Yamile Osorio Var...
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Questions? Call us:
(689) 407-5757
Southshore Bay
![17523 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,406 sq ft
|Townhouse
17523 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8329292 • DALTON WADE INC, Kelly DeCarlucci
The Villages®
![3233 LOWE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,056 sq ft
|House
3233 LOWE CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS TB8424737 • COASTAL PROPERTIES GROUP INTERNAT...
Solivita
![502 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5123661 • PELLEGO, LLC, Paul Maiatico
Royal Highlands
![21636 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,642 sq ft
|House
21636 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS O6279378 • KELLER WILLIAMS WINTER PARK, Lana ...
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
![301 THORN HILL PL, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
3 beds
|2 baths
|2,402 sq ft
|House
301 THORN HILL PL, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS C7515255 • RE/MAX PALM REALTY, Jill Kerekes U...
On Top of the World
![8890 SW 104TH CIR, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|1,651 sq ft
|House
8890 SW 104TH CIR, OCALA, FL, 34481
Community: On Top of the World
MLS TB8374654 • PRIME REAL ESTATE SALES, LLC, Doy...
Solivita
![537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS G5096869 • BACK PORCH REALTY, LLC, Jackie Rog...
Windermere
![747 INVERIE DR, INVERNESS, FL, 34453, Inverness, FL 34453]()
2 beds
|3 baths
|1,599 sq ft
|Townhouse
747 INVERIE DR, INVERNESS, FL, 34453
Community: Windermere
MLS G5104279 • WORTH CLARK REALTY, Lisbeth Cline
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Spruce Creek Country Club
![13709 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,537 sq ft
|House
13709 SE 86TH TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM715384 • BROKER ASSOCIATES REALTY, Rich Den...
The Villages®
![1133 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,332 sq ft
|House
1133 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5103791 • HOAD REALTY GROUP LLC, John Hoad
Sun City Center
![2403 NANTUCKET GREEN CT, SUN CITY CENTER..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,125 sq ft
|Condo
2403 NANTUCKET GREEN CT, SUN CITY CENTER...
Community: Sun City Center
MLS TB8317169 • COLDWELL BANKER REALTY, Sandra Ca...
Ocala Palms
![5137 NW 20TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM713529 • COLDWELL REALTY SOLD GUARANTEE, Sc...
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®
![12347 NE 52ND LOOP, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|2,092 sq ft
|House
12347 NE 52ND LOOP, OXFORD, FL, 34484
Community: The Villages®
MLS O6321690 • REAL BROKER, LLC, Eddie Gonzalez
The Villages®
![1638 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,179 sq ft
|House
1638 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102310 • SALLY LOVE REAL ESTATE, Donna Pull...
Sun City Center
![445 NOBLE FAIRE DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
3 beds
|3 baths
|2,637 sq ft
|House
445 NOBLE FAIRE DR, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS TB8382934 • KELLER WILLIAMS SOUTH SHORE, Sand...
On Top of the World
![8896 SW 90TH ST B, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,521 sq ft
|Villa
8896 SW 90TH ST B, OCALA, FL, 34481
Community: On Top of the World
MLS OM706717 • RE/MAX FOXFIRE - HWY200/103 S, Da...
Ocala Palms
![5065 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM690973 • REDI REAL ESTATE, LLC, Joseph Regn...
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(689) 407-5757
Sun City Center
![316 KELSEY WAY # 316, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,078 sq ft
|Condo
316 KELSEY WAY # 316, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8403563 • RE/MAX REALTY UNLIMITED, Jennifer...
Sun City Center
![2237 MAYFIELD PALMS LN # 2237, SUN CITY ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,629 sq ft
|Condo
2237 MAYFIELD PALMS LN # 2237, SUN CITY ...
Community: Sun City Center
MLS TB8417754 • RE/MAX REALTY UNLIMITED, Jennifer...
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...
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
![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...
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...
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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...
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.
