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Winter Garden, FL 55+ active adult communities & homes for sale
109 communities near Winter Garden
3,537 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
- $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
- $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
- $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
- $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 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 (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
$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
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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
- $700Ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 homes
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
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]()
$200Ks
- $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 homes
5 rating (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
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]()
$300Ks
- $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only
|
Age-targeted
|
Built 2006 - 2016
|
1,300 homes
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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
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
$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
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, FL?
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Questions? Call us:
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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
$100Ks
- $300Ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
$300Ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
The Villages®
![17722 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,000 sq ft
|House
17722 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
MLS G5104573 • REALTY EXECUTIVES IN THE VILLAGES,...
Stone Creek
![9539 SW 71ST LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM710159 • REAL BROKER, LLC, Nina Sandoval
On Top of the World
![9452 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,947 sq ft
|House
9452 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM700352 • RE/MAX FOXFIRE - HWY200/103 S, Bo...
Heritage Hills
![3791 SANIBEL ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
3 beds
|3 baths
|2,615 sq ft
|House
3791 SANIBEL ST, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5103629 • KELLER WILLIAMS ELITE PARTNERS III...
Stone Creek
![8467 SW 55TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,948 sq ft
|House
8467 SW 55TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
MLS TB8433780 • PULTE REALTY OF WEST FLORIDA LLC,...
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Stone Creek
![5981 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|3 baths
|2,483 sq ft
|House
5981 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
MLS TB8433740 • PULTE REALTY OF WEST FLORIDA LLC,...
Stone Creek
![5967 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
2 beds
|3 baths
|2,269 sq ft
|House
5967 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
MLS TB8433589 • PULTE REALTY OF WEST FLORIDA LLC,...
Stone Creek
![8343 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS TB8421993 • PULTE REALTY OF WEST FLORIDA LLC,...
Stone Creek
![8360 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS TB8416880 • PULTE REALTY OF WEST FLORIDA LLC,...
Stone Creek
![8323 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
MLS TB8393414 • PULTE REALTY OF WEST 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.
Stone Creek
![5953 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|3 baths
|2,483 sq ft
|House
5953 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
MLS TB8404852 • PULTE REALTY OF WEST FLORIDA LLC,...
Stone Creek
![9009 SW 52ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|3 baths
|2,080 sq ft
|House
9009 SW 52ND PLACE RD, OCALA, FL, 34481
Community: Stone Creek
MLS TB8348850 • PULTE REALTY OF WEST FLORIDA LLC,...
Southshore Bay
![17253 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|1,956 sq ft
|House
17253 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8409852 • CHARLES RUTENBERG REALTY INC, Jul...
The Villages®
![528 VALENCIA PL, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,175 sq ft
|House
528 VALENCIA PL, LADY LAKE, FL, 32159
Community: The Villages®
MLS OM712880 • KELLER WILLIAMS CORNERSTONE RE, Ma...
The Villages®
![1403 ESPINOZA LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1403 ESPINOZA LN, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5103682 • WORTH CLARK REALTY, Chuck Wilsey
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(689) 407-5757
The Villages®
![901 CHULA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
901 CHULA CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5092725 • FLORIDA FINE HOMES REALTY, LLC, Ca...
On Top of the World
![9055 SW 106TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|2,365 sq ft
|House
9055 SW 106TH AVE, OCALA, FL, 34481
Community: On Top of the World
MLS OM707165 • ENGEL & VOLKERS OCALA, Alair Boshe...
The Villages®
![1613 CHERRY HILL RD, THE VILLAGES, FL, 3..., The Villages, FL 32159]()
2 beds
|2 baths
|1,357 sq ft
|House
1613 CHERRY HILL RD, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5092223 • FLORIDA FINE HOMES REALTY, LLC, Ca...
On Top of the World
![9781 SW 79TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|3 baths
|2,616 sq ft
|House
9781 SW 79TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM691228 • ON TOP OF THE WORLD REAL EST, Jaso...
Sullivan Ranch
![21224 NORIC CV, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
5 beds
|3 baths
|2,638 sq ft
|House
21224 NORIC CV, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS P4936337 • DALTON WADE INC, Christian Clay
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®
![1203 LAUREL OAK LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,444 sq ft
|House
1203 LAUREL OAK LN, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5105498 • CENTURY 21 ALTON CLARK, Regina Rod...
On Top of the World
![7269 SW 89TH TER, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,467 sq ft
|House
7269 SW 89TH TER, OCALA, FL, 34481
Community: On Top of the World
MLS OM713026 • ON TOP OF THE WORLD REAL EST, Jaso...
Pennbrooke Fairways
![131 WILLOW BROOK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,720 sq ft
|House
131 WILLOW BROOK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5104392 • KELLER WILLIAMS ELITE PARTNERS III...
Foxwood Lake Estates
![1811 SHERWOOD HILL DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,316 sq ft
|Manufactured Home
1811 SHERWOOD HILL DR, LAKELAND, FL, 338...
Community: Foxwood Lake Estates
MLS L4956891 • LAKELAND HOMES AND REALTY, LLC, Mi...
Kings Ridge
![4012 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6323263 • COLDWELL BANKER RESIDENTIAL RE, Ke...
Want to learn more about 55+ communities in Winter Garden, FL?
55places can help!
Questions? Call us:
(689) 407-5757
The Villages®
![2109 SUAREZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,248 sq ft
|House
2109 SUAREZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102011 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![718 VILLITA LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
1 beds
|1 baths
|920 sq ft
|House
718 VILLITA LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102695 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![505 MILLIFIORA LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8368928 • NHR BROKERAGE LLC, Madalina Tat
Solivita
![507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,302 sq ft
|House
507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
MLS TB8429298 • NHR BROKERAGE LLC, Madalina Tat
The Villages®
![852 SAPPHIRE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,407 sq ft
|Villa
852 SAPPHIRE PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102943 • WORTH CLARK REALTY, Greg Szablewsk...
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
![8707 SW 95TH LN A, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,676 sq ft
|House
8707 SW 95TH LN A, OCALA, FL, 34481
Community: On Top of the World
MLS OM711434 • SOUTHERN CHARM REALTY OF CF, Jeann...
Mirada
![31763 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576]()
3 beds
|3 baths
|2,141 sq ft
|House
31763 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
MLS TB8448703 • COLDWELL BANKER REALTY, Tania Bor...
The Villages®
![3068 SPANISH MOSS WAY, THE VILLAGES, FL,..., The Villages, FL 32163]()
3 beds
|2 baths
|2,309 sq ft
|House
3068 SPANISH MOSS WAY, THE VILLAGES, FL,...
Community: The Villages®
MLS G5104883 • REALTY EXECUTIVES IN THE VILLAGES,...
Valencia Lakes
![4918 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,461 sq ft
|House
4918 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8411418 • COLDWELL BANKER REALTY, Tania Bor...
Valencia Lakes
![4947 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
2 beds
|2 baths
|2,061 sq ft
|House
4947 SANDY BROOK CIR, WIMAUMA, FL, 33598
Community: Valencia Lakes
MLS TB8411354 • COLDWELL BANKER REALTY, Tania Bor...
Want to learn more about 55+ communities in Winter Garden, FL?
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(689) 407-5757
Liberty Village
![7755 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,548 sq ft
|House
7755 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
MLS OM712624 • SELLSTATE NEXT GENERATION REAL, Cr...
On Top of the World
![8685 SW 94TH LN H, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,414 sq ft
|Villa
8685 SW 94TH LN H, OCALA, FL, 34481
Community: On Top of the World
MLS OM711570 • REAL BROKER, LLC, Nicole Garcia
The Villages®
![278 MATISSE AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,966 sq ft
|House
278 MATISSE AVE, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5095422 • HOMESMART, Maria Czarnecki
Ocala Preserve
![5297 NW 34TH ST, OCALA, FL, 34482, Ocala, FL 34482]()
MLS O6338540 • KELLER WILLIAMS CLASSIC, Cassie La...
The Villages®
![2369 TRAVIS PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2369 TRAVIS PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5099301 • IM REALTY, Ira Miller
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?
3,537
homes
near Winter Garden
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© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Dec 18, 2025.
This application does not include information on all of the properties available for sale at this time.
