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Winter Garden, FL 55+ active adult communities & homes for sale - Page 13
109 communities near Winter Garden
3,495 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
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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)
![VillageWalk at Lake Nona]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 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
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:
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$300Ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
Venetian Bay
![3417 GALLIA ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|2,402 sq ft
|Townhouse
3417 GALLIA ST, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
MLS NS1086817 • LOCAL LIVING REALTY GROUP, Kerria...
Cresswind at Victoria Gardens
![1547 LAMBROOK DR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,651 sq ft
|House
1547 LAMBROOK DR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4945444 • LPT REALTY LLC, Sheree Frazier
New
Palm Cay
![10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM716272 • CB/ELLISON RLTY WEST, Cynthia Desm...
On Top of the World
![6239 SW 93RD LOOP, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|1,853 sq ft
|House
6239 SW 93RD LOOP, OCALA, FL, 34476
Community: On Top of the World
MLS OM712192 • SOUTHERN ASSOCIATES REALTY LLC, Cy...
New
Latitude Margaritaville
![488 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,308 sq ft
|House
488 HIGH TIDE LN, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS FC315102 • REALTY PROS ASSURED, Daniel Robins...
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Foxwood Lake Estates
![5013 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,056 sq ft
|Manufactured Home
5013 FOXWOOD BLVD, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS S5108231 • BETTER HOMES & GARDENS RE LIFESTYL...
New
Carillon Lakes
![4145 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811]()
3 beds
|2 baths
|2,408 sq ft
|House
4145 WHISTLEWOOD CIR, LAKELAND, FL, 3381...
Community: Carillon Lakes
MLS L4958202 • REMAX EXPERTS, Maria Santillo
New
Solivita
![209 LOS GATOS PL, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5140999 • BORCHINI REALTY, Charles Borchini
New
Kings Ridge
![3674 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6371538 • NETWORTH REALTY OF ORLANDO, LLC, W...
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.
New
Valencia del Sol
![15433 SANTA POLA DR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,599 sq ft
|House
15433 SANTA POLA DR, WIMAUMA, FL, 33598
Community: Valencia del Sol
MLS TB8460680 • SALTZBERG & ASSOCIATES REAL ESTAT...
New
Venetian Bay
![3451 LUNA BELLA LN, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,420 sq ft
|House
3451 LUNA BELLA LN, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
MLS O6372046 • KELLER WILLIAMS REALTY AT THE PARK...
New
Valencia Lakes
![16144 COQUINA BAY LN, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|2,058 sq ft
|House
16144 COQUINA BAY LN, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8462208 • GOOD 2 GO PROPERTY, LLC, Helene R...
New
The Villages®
![116 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,066 sq ft
|Manufactured Home
116 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5106351 • FLORIDA REALTY INVESTMENTS, Dalton...
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New
Enclave at VillageWalk
![10819 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827]()
5 beds
|6 baths
|5,437 sq ft
|House
10819 SAVONA WAY, ORLANDO, FL, 32827
Community: Enclave at VillageWalk
MLS O6370862 • COLDWELL BANKER RESIDENTIAL RE, Da...
New
Royal Highlands
![4636 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,864 sq ft
|House
4636 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS O6371423 • REDFIN CORPORATION, Jo Holton
New
Southshore Bay
![16912 ANCHOR ROOT ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,128 sq ft
|House
16912 ANCHOR ROOT ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8462359 • 27NORTH REALTY, Elisa Stephens
New
Kings Ridge
![3721 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5106345 • OLYMPUS EXECUTIVE REALTY INC, Mars...
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.
New
Ocala Preserve
![4848 NW 39TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM716265 • DR HORTON REALTY OF WEST CENTRAL F...
New
Venetian Bay
![3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,214 sq ft
|House
3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1086951 • MG REAL ESTATE GROUP, Matt Guarro
New
Ocala Preserve
![4812 NW 39TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM716252 • DR HORTON REALTY OF WEST CENTRAL F...
New
Arlington Ridge
![27143 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,699 sq ft
|House
27143 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5106223 • COOPER HOMEFRONT REALTY, Joe Coope...
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New
Venetian Bay
![424 LUNA BELLA LN APT 415, NEW SMYRNA BE..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,478 sq ft
|Condo
424 LUNA BELLA LN APT 415, NEW SMYRNA BE...
Community: Venetian Bay
MLS O6371725 • EXP REALTY LLC, David Knight
New
Ocala Preserve
![4043 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM716245 • DR HORTON REALTY OF WEST CENTRAL F...
New
The Villages®
![2571 FOXBRIDGE TER, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|1,861 sq ft
|House
2571 FOXBRIDGE TER, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5106164 • REALTY EXECUTIVES IN THE VILLAGES,...
New
Spruce Creek Country Club
![13166 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,913 sq ft
|House
13166 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM716192 • JUDY L. TROUT REALTY, Judy Trout
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.
New
The Villages®
![17065 SE 79TH MCLAWREN TER, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,684 sq ft
|House
17065 SE 79TH MCLAWREN TER, THE VILLAGES...
Community: The Villages®
MLS O6371976 • REALTY HUB, Ariel Senderowsky
Arlington Ridge
![26939 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,631 sq ft
|Villa
26939 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5102246 • HOAD REALTY GROUP LLC, Lisa Hoad
On Top of the World
![9901 SW 82ND STREET RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|3,081 sq ft
|House
9901 SW 82ND STREET RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM710729 • RE/MAX FOXFIRE - HWY200/103 S, Bo...
Lake Jovita Golf and Country Club
![34120 AMERICANA AVE, DADE CITY, FL, 3352..., Dade City, FL 33525]()
3 beds
|3 baths
|2,586 sq ft
|House
34120 AMERICANA AVE, DADE CITY, FL, 3352...
Community: Lake Jovita Golf and Country Club
MLS TB8429966 • KING & ASSOCIATES REAL ESTATE LLC...
New
The Villages®
![3153 GOODING PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,911 sq ft
|House
3153 GOODING PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5105953 • REALTY EXECUTIVES IN THE VILLAGES,...
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New
Majestic Oaks Ocala
![5583 SW 83RD LN, OCALA, FL, 34476, Ocala, FL 34476]()
3 beds
|2 baths
|2,127 sq ft
|House
5583 SW 83RD LN, OCALA, FL, 34476
Community: Majestic Oaks Ocala
MLS TB8457926 • KELLER WILLIAMS TAMPA PROP., Rich...
Venetian Bay
![664 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
4 beds
|4 baths
|3,221 sq ft
|House
664 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6365891 • TAYLOR MORRISON REALTY OF FLORIDA ...
Ridgehaven
![1126 CLIFFHAVEN CT, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,344 sq ft
|House
1126 CLIFFHAVEN CT, ORMOND BEACH, FL, 32...
Community: Ridgehaven
MLS O6365890 • LPT REALTY, LLC, James Bessinger
The Villages®
![1501 ALFONSO LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,014 sq ft
|House
1501 ALFONSO LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5103576 • HOMERUN REALTY, LLC, Michael Engla...
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®
![7796 SE 168TH LONE OAK LOOP, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|1,540 sq ft
|House
7796 SE 168TH LONE OAK LOOP, THE VILLAGE...
Community: The Villages®
MLS OM709769 • LPT REALTY, LLC, Gary Martin
Arlington Ridge
![3621 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,052 sq ft
|House
3621 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS O6254624 • KELLER WILLIAMS HERITAGE REALTY, P...
The Villages®
![712 DEVON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,404 sq ft
|Manufactured Home
712 DEVON DR, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM712459 • CENTRAL CITY REALTY, Juan Galvez
The Villages®
![1013 ANN AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
1013 ANN AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM709854 • CENTRAL CITY REALTY, Juan Galvez
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Sun City Center
![505 FOXGLOVE CIR B, SUN CITY CENTER, FL,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,245 sq ft
|Halfplex
505 FOXGLOVE CIR B, SUN CITY CENTER, FL,...
Community: Sun City Center
MLS TB8408604 • FLIP SIDE REALTY BY DESIGN, Rosem...
Sun City Center
![1620 BENTWOOD DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,860 sq ft
|House
1620 BENTWOOD DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
MLS TB8446251 • FUTURE HOME REALTY INC, Kristen M...
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?
3,495
homes
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REIN updates its listings on a daily basis. Data last updated: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.
