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Winter Garden, FL 55+ active adult communities & homes for sale - Page 78
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
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 (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
Want to learn more about 55+ communities in Winter Garden?
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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
Pelican Bay Daytona Beach
![256 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,146 sq ft
|Halfplex
256 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS V4945783 • FLORIDA GLOBAL INT'L REALTY, Clara...
Sun City Center
![708 RUTGERS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,200 sq ft
|Condo
708 RUTGERS PL, SUN CITY CENTER, FL, 335...
Community: Sun City Center
MLS TB8435505 • DALTON WADE INC, Bryan Czajkowski
Highlands Ridge
![5056 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825]()
2 beds
|2 baths
|1,799 sq ft
|Villa
5056 BIRKDALE DR, AVON PARK, FL, 33825
Community: Highlands Ridge
MLS 316868 • RE/MAX REALTY PLUS, Lisa Kneram PA
Spruce Creek Country Club
![9019 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,419 sq ft
|House
9019 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek Country Club
MLS G5103411 • RE/MAX PREMIER REALTY LADY LK, Rob...
The Villages®
![2475 LAUREL BAY LN, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|House
2475 LAUREL BAY LN, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5104110 • RE/MAX PREMIER REALTY LADY LK, Guy...
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Sun City Center
![1417 INGRAM DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,857 sq ft
|Villa
1417 INGRAM DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
MLS TB8455965 • CHARLES RUTENBERG REALTY INC, Lor...
Sun City Center
![1927 ACADIA GREENS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,546 sq ft
|Villa
1927 ACADIA GREENS DR, SUN CITY CENTER, ...
Community: Sun City Center
MLS TB8442407 • LIPPLY REAL ESTATE, Megan Pargov
Venetian Bay
![209 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,288 sq ft
|House
209 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
MLS NS1086632 • EXIT REAL ESTATE PROPERTY SOL, Ca...
New
Del Webb Sunbridge
![2575 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771]()
3 beds
|3 baths
|2,483 sq ft
|House
2575 PINE PRESERVE CT, SAINT CLOUD, FL, ...
Community: Del Webb Sunbridge
MLS O6370525 • REAL BROKER, LLC, Peter Frano
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
![7965 SW 86TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|2 baths
|2,118 sq ft
|House
7965 SW 86TH TERRACE RD, OCALA, FL, 3448...
Community: On Top of the World
MLS OM714795 • ON TOP OF THE WORLD REAL EST, Tamm...
Solivita
![193 TORINO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6365110 • SENIOR TRANSITIONS REALTY, LLC, Ki...
On Top of the World
![9707 SW 79TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,659 sq ft
|House
9707 SW 79TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM711225 • NEXT GENERATION REALTY OF MARION C...
The Villages®
![1506 DELLANO WAY, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,782 sq ft
|House
1506 DELLANO WAY, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS TB8436860 • DIVINE ESTATES REALTY LLC, Nehad ...
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On Top of the World
![7732 SW 86TH CT, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,344 sq ft
|House
7732 SW 86TH CT, OCALA, FL, 34481
Community: On Top of the World
MLS 1214863 • RE/MAX Signature, Stephanie Cathey
Oak Run
![11621 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM714167 • DECCA REAL ESTATE, Ryan Reeves
Encore at Fishhawk Ranch
![6122 WATERCOLOR DR, LITHIA, FL, 33547, Lithia, FL 33547]()
2 beds
|3 baths
|2,670 sq ft
|House
6122 WATERCOLOR DR, LITHIA, FL, 33547
Community: Encore at Fishhawk Ranch
MLS TB8413172 • SIGNATURE REALTY ASSOCIATES, Anne...
Oak Run
![11481 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM709353 • DECCA REAL ESTATE, Ryan Reeves
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.
Oak Run
![11122 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476]()
MLS OM714846 • DECCA REAL ESTATE, Ryan Reeves
Southshore Bay
![17317 SCUBA CREST ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,363 sq ft
|House
17317 SCUBA CREST ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8418461 • 27NORTH REALTY, Elisa Stephens
New
The Villages®
![4624 WIGHTMAN CIR, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|3 baths
|1,905 sq ft
|House
4624 WIGHTMAN CIR, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5105934 • RE/MAX PREMIER REALTY LADY LK, Mat...
Spruce Creek Preserve
![11587 SW 139TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432]()
2 beds
|2 baths
|1,654 sq ft
|House
11587 SW 139TH PL, DUNNELLON, FL, 34432
Community: Spruce Creek Preserve
MLS OM710180 • RE/MAX PREMIER REALTY, Courtney Fo...
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The Villages®
![2693 PERSIMMON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
3 beds
|2 baths
|1,997 sq ft
|House
2693 PERSIMMON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5104036 • REALTY EXECUTIVES IN THE VILLAGES,...
Ocala Palms
![2083 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS GC535642 • LPT REALTY, LLC, David Amerio
New
Solivita
![461 INDIAN WELLS AVE, POINCIANA, FL, 347..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,548 sq ft
|House
461 INDIAN WELLS AVE, POINCIANA, FL, 347...
Community: Solivita
MLS S5140585 • ACKLEY LEGACY PROPERTIES, LLC, Kri...
Latitude Margaritaville
![233 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,768 sq ft
|House
233 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1220801 • Bob Hodges and Sons Realty, Didi Wo...
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
![5712 SUMMERBROOKE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,961 sq ft
|House
5712 SUMMERBROOKE CT, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS O6341032 • ALL REAL ESTATE & INVESTMENTS, Pat...
Latitude Margaritaville
![765 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124]()
3 beds
|3 baths
|2,493 sq ft
|House
765 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Community: Latitude Margaritaville
MLS 1220808 • Bob Hodges and Sons Realty, Didi Wo...
Ocala Preserve
![3862 NW 49TH CT, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM706836 • KELLER WILLIAMS CLASSIC, Riva Wall...
New
The Villages®
![3017 BATALLY CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,905 sq ft
|House
3017 BATALLY CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5106299 • DOWN HOME REALTY, LLLP, Rachel Sow...
On Top of the World
![9436 SW 97TH AVE, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,716 sq ft
|House
9436 SW 97TH AVE, OCALA, FL, 34481
Community: On Top of the World
MLS OM708823 • ON TOP OF THE WORLD REAL EST, Shel...
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Solivita
![2009 LAZIO LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5139454 • BORCHINI REALTY, Charles Borchini
Sun City Center
![906 HACIENDA DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573]()
2 beds
|1 baths
|1,344 sq ft
|House
906 HACIENDA DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
MLS TB8385448 • SIGNATURE REALTY ASSOCIATES, Anne...
The Villages®
![1057 CARVER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,270 sq ft
|Villa
1057 CARVER CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5099915 • FLORIDA FINE HOMES REALTY, LLC, Je...
New
Esplanade at Wiregrass Ranch
![4739 GAROFALO RD, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543]()
2 beds
|2 baths
|1,689 sq ft
|House
4739 GAROFALO RD, WESLEY CHAPEL, FL, 335...
Community: Esplanade at Wiregrass Ranch
MLS TB8459254 • YOU FIRST REALTY AND ASSOC LLC, M...
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.
Palm Cay
![8449 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM697609 • CB/ELLISON RLTY WEST, Cynthia Desm...
New
Palm Cay
![8305 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM715805 • CB/ELLISON RLTY WEST, Cynthia Desm...
Palm Cay
![8326 SW 107TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM708534 • CB/ELLISON RLTY WEST, Cynthia Desm...
New
Palm Cay
![8329 SW 106TH ST, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM715838 • CB/ELLISON RLTY WEST, Cynthia Desm...
Want to learn more about 55+ communities in Winter Garden?
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Palm Cay
![8274 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM706321 • CB/ELLISON RLTY WEST, Cynthia Desm...
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
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.
