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Winter Garden, FL 55+ active adult communities & homes for sale - Page 65
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
Del Webb Sunbridge
![6212 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771]()
4 beds
|3 baths
|2,842 sq ft
|House
6212 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
MLS O6349067 • PULTE REALTY OF NORTH FLORIDA LLC,...
Lakes of Mount Dora
![8228 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
2 beds
|2 baths
|2,161 sq ft
|House
8228 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS O6361695 • RE/MAX ASSURED, Brent DeHoop
Ocala Preserve
![4433 NW 37TH STREET RD, OCALA, FL, 34482, Ocala, FL 34482]()
4 beds
|3 baths
|2,147 sq ft
|House
4433 NW 37TH STREET RD, OCALA, FL, 34482
Community: Ocala Preserve
MLS OM707767 • ESTELA REALTY LLC, Kristin Prior
Cherrywood
![10452 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476]()
2 beds
|2 baths
|1,287 sq ft
|House
10452 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
MLS OM709678 • KELLER WILLIAMS CORNERSTONE RE, Jo...
Stone Creek
![9582 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM710551 • PREMIER SOTHEBY'S INTERNATIONAL RE...
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Questions? Call us:
(689) 407-5757
The Villages®
![16820 SE 74 SOULLIERE AVE, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,635 sq ft
|Villa
16820 SE 74 SOULLIERE AVE, THE VILLAGES,...
Community: The Villages®
MLS G5102538 • GERALD ANTHONY DIETRICH, Gerald Di...
Del Webb Sunbridge
![6403 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771]()
3 beds
|2 baths
|1,677 sq ft
|House
6403 SHIMMERING SHORES LN, SAINT CLOUD, ...
Community: Del Webb Sunbridge
MLS O6289147 • CHARLES RUTENBERG REALTY ORLANDO, ...
Solivita
![223 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6361778 • VYLLA HOME, Manny Duran
Plantation at Leesburg
![25720 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,478 sq ft
|House
25720 BELLE ALLIANCE, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS R4910376 • ELITE PROPERTIES GROUP OF LAKE , I...
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®
![2865 JUDAH ST, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,286 sq ft
|Villa
2865 JUDAH ST, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5104341 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Sun City Center
![301 CALOOSA PALMS CT, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,528 sq ft
|House
301 CALOOSA PALMS CT, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8367931 • KELLER WILLIAMS SOUTH SHORE, Sand...
On Top of the World
![9065 SW 82ND TER D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,369 sq ft
|House
9065 SW 82ND TER D, OCALA, FL, 34481
Community: On Top of the World
MLS RX-11109120 • Keller Williams Cornerstone RE,...
Sandpiper Golf & Country Club
![6065 MAGPIE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,501 sq ft
|House
6065 MAGPIE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS G5104761 • LPT REALTY, LLC, Alicia Salicrup
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Solivita
![915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5136337 • BORCHINI REALTY, Charles Borchini
Solivita
![176 CAPE FLORIDA DR, POINCIANA, FL, 3475..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,440 sq ft
|House
176 CAPE FLORIDA DR, POINCIANA, FL, 3475...
Community: Solivita
MLS RX-11110545 • Coral Cove Realty Inc, Helen Ma...
Pine Run Estates
![9360 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM712135 • REMAX/PREMIER REALTY, Cindy Foster
Stonecrest
![17355 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,179 sq ft
|House
17355 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS G5098071 • BLACK TIE REALTY, INC., Mark Dyer
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
![352 CALOOSA PALMS CT, SUN CITY CENTER, F..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,878 sq ft
|House
352 CALOOSA PALMS CT, SUN CITY CENTER, F...
Community: Sun City Center
MLS TB8442137 • CENTURY 21 BEGGINS ENTERPRISES, R...
The Villages®
![3032 BRIDGEFIELD CT, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|2,501 sq ft
|House
3032 BRIDGEFIELD CT, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5102446 • LPT REALTY, LLC, Willy Sybert
Oak Run
![8981 SW 116TH STREET RD, OCALA, FL, 3448..., Ocala, FL 34481]()
2 beds
|2 baths
|1,296 sq ft
|House
8981 SW 116TH STREET RD, OCALA, FL, 3448...
Community: Oak Run
MLS OM709338 • SHOWCASE PROPERTIES OF CENTRAL, La...
Ocala Palms
![4677 NW 51ST CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM706781 • GOLDEN OCALA REAL ESTATE INC, Kati...
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Tarawood
![10425 S DREW BRYANT CIR, FLORAL CITY, FL..., Floral City, FL 34436]()
3 beds
|2 baths
|1,744 sq ft
|House
10425 S DREW BRYANT CIR, FLORAL CITY, FL...
Community: Tarawood
MLS TB8455682 • MARK SPAIN REAL ESTATE, Tyana Alv...
Foxwood Lake Estates
![4874 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,248 sq ft
|Manufactured Home
4874 DEERWOOD DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS P4937266 • FLORIDA REALTY MARKETPLACE, Debra ...
Foxwood Lake Estates
![1819 SHERWOOD HILL DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,568 sq ft
|Manufactured Home
1819 SHERWOOD HILL DR, LAKELAND, FL, 338...
Community: Foxwood Lake Estates
MLS P4937268 • FLORIDA REALTY MARKETPLACE, Debra ...
Venetian Bay
![3343 CATERINA DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,251 sq ft
|House
3343 CATERINA DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1086781 • EXECUTIVE REALTY GROUP LLC, Lee T...
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.
Plantation at Leesburg
![3605 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,868 sq ft
|House
3605 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS G5105434 • RE/MAX PREMIER REALTY, Adriana Sko...
The Villages®
![7233 SE 171ST POND LN, THE VILLAGES, FL,..., The Villages, FL 32162]()
2 beds
|2 baths
|1,918 sq ft
|House
7233 SE 171ST POND LN, THE VILLAGES, FL,...
Community: The Villages®
MLS O6366062 • REAL PROPERTY INTERNATIONAL, Bob L...
Legacy of Leesburg
![5510 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,044 sq ft
|House
5510 CELEBRATION WAY, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
MLS G5105328 • CENTURY 21 CARIOTI, Bonnie Valenti...
Marion Landing
![6511 SW 85TH ST, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM714804 • REAL BROKER LLC - OCALA, Anthony A...
Sullivan Ranch
![20930 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
6 beds
|4 baths
|3,499 sq ft
|House
20930 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS O6362834 • HOME WISE REALTY GROUP, INC., Cher...
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(689) 407-5757
Latitude Margaritaville
![306 LOW TIDE LN, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124]()
3 beds
|2 baths
|1,848 sq ft
|House
306 LOW TIDE LN, DAYTONA BEACH, FL, 3212...
Community: Latitude Margaritaville
MLS 1220631 • Bob Hodges and Sons Realty, Didi Wo...
Twin Lakes
![5148 GARDENROW DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,322 sq ft
|Villa
5148 GARDENROW DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6365915 • PULTE REALTY OF NORTH FLORIDA LLC,...
Twin Lakes
![2759 BUCKEYE LN, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,322 sq ft
|Villa
2759 BUCKEYE LN, SAINT CLOUD, FL, 34772
Community: Twin Lakes
MLS O6365824 • PULTE REALTY OF NORTH FLORIDA LLC,...
Del Webb Sunbridge
![6456 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,405 sq ft
|House
6456 SHIMMERING SHORES LN, SAINT CLOUD, ...
Community: Del Webb Sunbridge
MLS O6350384 • PULTE REALTY OF NORTH FLORIDA LLC,...
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.
Kings Ridge
![3501 WESTERHAM DR, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,552 sq ft
|House
3501 WESTERHAM DR, CLERMONT, FL, 34711
Community: Kings Ridge
MLS S5139331 • MICKEY REALTY, Linda Brown
Sun City Center
![1026 MCDANIEL ST # 1026, SUN CITY CENTER..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,825 sq ft
|Condo
1026 MCDANIEL ST # 1026, SUN CITY CENTER...
Community: Sun City Center
MLS TB8420387 • BHHS FLORIDA REALTY, Linda Bessig...
Spruce Creek Country Club
![9541 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,936 sq ft
|House
9541 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS OM711030 • JUDY L. TROUT REALTY, Judy Trout
Solivita
![917 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5092308 • FLORIDA PLUS REALTY, LLC, Christin...
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Solivita
![101 PALAZZO LN, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS G5101546 • FLORIDA PLUS REALTY, LLC, Christin...
Four Seasons at Orlando
![1991 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1991 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS TB8421378 • MARK SPAIN REAL ESTATE, Tim Creso...
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.
