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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
Want to learn more about 55+ communities in Winter Garden?
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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?
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
- $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
Spruce Creek North
![10800 SW 62ND AVE, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,526 sq ft
|House
10800 SW 62ND AVE, OCALA, FL, 34476
Community: Spruce Creek North
MLS OM693230 • RE/MAX FOXFIRE - HWY200/103 S, Ka...
Ocala Preserve
![5610 NW 37TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482]()
2 beds
|2 baths
|1,454 sq ft
|House
5610 NW 37TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
MLS V4942269 • RE/MAX SIGNATURE, Stephanie Cathey
Carlsberg Estates on Lake Suzanne
![464 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|1,429 sq ft
|House
464 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS P4935255 • CENTURY 21 MYERS REALTY LAKE WALES...
Solivita
![247 BELL TOWER XING, POINCIANA, FL, 3475..., Poinciana, FL 34759]()
2 beds
|1 baths
|1,085 sq ft
|House
247 BELL TOWER XING, POINCIANA, FL, 3475...
Community: Solivita
MLS S5125755 • BORCHINI REALTY, Cherie Pontes
Ocala Preserve
![3642 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM690338 • PEGASUS REALTY & ASSOC INC, Lena S...
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55places can help!
Questions? Call us:
(689) 407-5757
High Vista at Ridgewood Lakes
![725 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,594 sq ft
|House
725 HIGH VISTA DR, DAVENPORT, FL, 33837
Community: High Vista at Ridgewood Lakes
MLS O6299170 • CALL IT CLOSED INTL REALTY, Melani...
Sun City Center
![1715 S PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,618 sq ft
|House
1715 S PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
MLS TB8321141 • FIRESIDE REAL ESTATE, Nancy Monsi...
Thunderbird Hill
![3716 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872]()
2 beds
|2 baths
|1,080 sq ft
|Villa
3716 SUNBIRD CIR, SEBRING, FL, 33872
Community: Thunderbird Hill
MLS 313343 • Paradise Real Estate International L...
Ocala Palms
![2100 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM704380 • PEGASUS REALTY & ASSOC INC, Lena S...
Solivita
![152 GLENDALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6320991 • STAR BAY REALTY CORP., Abraham Bid...
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.
Solivita
![1703 ENCINITAS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5127657 • PELLEGO, LLC, Stan Wilson
The Villages®
![3441 POSSEHL PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,148 sq ft
|Villa
3441 POSSEHL PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5094216 • FLORIDA REALTY INVESTMENTS, Robyn ...
Marco Polo Village
![11147 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|2,030 sq ft
|House
11147 SW 53RD CIR, OCALA, FL, 34476
Community: Marco Polo Village
MLS OM702051 • PROFESSIONAL REALTY OF OCALA, Step...
Oak Run
![8225 SW 108TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481]()
2 beds
|2 baths
|1,790 sq ft
|House
8225 SW 108TH STREET RD, OCALA, FL, 3448...
Community: Oak Run
MLS TB8392106 • BY OWNER.COM, Greg Sullivan
Sun City Center
![411 BLOOM CT # 2A, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|952 sq ft
|Condo
411 BLOOM CT # 2A, SUN CITY CENTER, FL, ...
Community: Sun City Center
MLS TB8357589 • FLORIDA'S 1ST CHOICE RLTY LLC, ch...
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Highland Lakes
![26800 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|2,133 sq ft
|House
26800 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5094022 • COLDWELL BANKER REALTY, Sara Suthe...
Colonnades
![4901 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811]()
2 beds
|2 baths
|1,305 sq ft
|House
4901 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
MLS O6232076 • HOMETOWN REALTY GROUP INC, Meredit...
Ocala Preserve
![3947 NW 46TH TER, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM690618 • ASSET CAPITAL REALTY, LLC, Jenna P...
Royal Harbor
![3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778]()
3 beds
|3 baths
|2,012 sq ft
|House
3257 BALTIC SEA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
MLS G5097415 • COLDWELL BANKER VANGUARD EDGE, Chr...
Solivita
![2502 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
2 beds
|2 baths
|1,539 sq ft
|Townhouse
2502 PALM TREE DR, POINCIANA, FL, 34759
Community: Solivita
MLS S5123237 • BELLA VERDE REALTY LLC, Suzanne Fo...
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.
Pennbrooke Fairways
![615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
1 beds
|1 baths
|490 sq ft
|Manufactured Home
615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS OM695172 • SUNBURST PROPERTIES, Scott Hutchin...
Cherrywood
![10459 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM703853 • CENTURY 21 AFFILIATES, Michelle Hu...
The Villages®
![1451 ROSEDALE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|1,612 sq ft
|House
1451 ROSEDALE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5096559 • DOWN HOME REALTY, LLLP, Star Hallm...
The Villages®
![507 TORRES PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,383 sq ft
|House
507 TORRES PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5095424 • NEXTHOME SALLY LOVE REAL ESTATE, C...
Traditions at Lake Ruby
![3565 RALEIGH DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|1,866 sq ft
|House
3565 RALEIGH DR, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4934495 • CENTURY 21 WATSON & MYERS REALTY, ...
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Palm Cay
![8152 SW 106TH ST, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM690699 • EPIQUE REALTY, INC., Noris Roche
On Top of the World
![9367 SW 83RD AVE C, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,249 sq ft
|Villa
9367 SW 83RD AVE C, OCALA, FL, 34481
Community: On Top of the World
MLS OM704068 • RE/MAX FOXFIRE - HWY200/103 S, Pa...
Highlands Ridge
![3243 E ANGLERS STRM, AVON PARK, FL, 3382..., Avon Park, FL 33825]()
3 beds
|3 baths
|2,476 sq ft
|House
3243 E ANGLERS STRM, AVON PARK, FL, 3382...
Community: Highlands Ridge
MLS 315908 • BHHS Florida Properties Group, Helen...
Latitude Margaritaville
![208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,482 sq ft
|House
208 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Community: Latitude Margaritaville
MLS 1211549 • LoKation, Aimee Aballo
The Villages®
![1041 REIDVILLE RD, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
2 beds
|2 baths
|1,196 sq ft
|Villa
1041 REIDVILLE RD, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5098664 • DOWN HOME REALTY, LLLP, Kristen Pi...
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
![8677 SW 95TH LN A, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,530 sq ft
|Villa
8677 SW 95TH LN A, OCALA, FL, 34481
Community: On Top of the World
MLS OM704126 • FLORIDA ADVANTAGE REALTY GROUP, Co...
Solivita
![516 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5128269 • TRANSCEND REALTY, Steven Friedland
Sun City Center
![2253 OAKLEY GREEN DR # 26, SUN CITY CENT..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,854 sq ft
|Condo
2253 OAKLEY GREEN DR # 26, SUN CITY CENT...
Community: Sun City Center
MLS TB8358554 • DALTON WADE INC, Natalie Pellerin
The Villages®
![8425 SE 177TH BARTRAM LOOP, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
8425 SE 177TH BARTRAM LOOP, THE VILLAGES...
Community: The Villages®
MLS G5093777 • KELLER WILLIAMS CORNERSTONE RE, Ka...
On Top of the World
![9871 SW 99TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,469 sq ft
|House
9871 SW 99TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM691773 • KELLER WILLIAMS CORNERSTONE RE, Jo...
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(689) 407-5757
Pine Run Estates
![10080 SW 97TH CT, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,144 sq ft
|House
10080 SW 97TH CT, OCALA, FL, 34481
Community: Pine Run Estates
MLS OM702770 • LOT & BLOCK REALTY, Betti Silverma...
On Top of the World
![9979 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,845 sq ft
|House
9979 SW 88TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM698373 • ROBB HARRISON REALTY INC, Jackie P...
On Top of the World
![8798 SW 79TH CT, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,469 sq ft
|House
8798 SW 79TH CT, OCALA, FL, 34476
Community: On Top of the World
MLS OM699874 • KELLER WILLIAMS CORNERSTONE RE, Ma...
Spruce Creek South
![17925 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,248 sq ft
|House
17925 SE 100TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS G5090750 • RE/MAX PREMIER REALTY LADY LK, Ger...
The Villages®
![3533 ROANOKE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|1 baths
|1,069 sq ft
|House
3533 ROANOKE ST, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8367861 • FLAT FEE MLS REALTY, Stephen Hach...
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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