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Winter Garden, FL 55+ active adult communities & homes for sale - Page 67
110 communities near Winter Garden
3,654 homes near Winter Garden
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4 rating (17 reviews)
![The Villages®]()
$100ks
- $1Ms
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]()
$100ks
- $800ks
Sun City Center, Sun City Center, FL
Resale Only
|
55+ age-restricted
|
Built 1961 - 2018
|
9,500 homes
4.2 rating (10 reviews)
![Stone Creek]()
$200ks
- $500ks
Stone Creek, Ocala, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
3,800 homes
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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4.5 rating (11 reviews)
![Spruce Creek Country Club]()
$100ks
- $400ks
Spruce Creek Country Club, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2007
|
3,250 homes
$300ks
- $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale
|
Age-targeted
|
Built 2004 - present
|
1,561 homes
5 rating (2 reviews)
![Plantation at Leesburg]()
$100ks
- $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2008
|
2,820 homes
4.1 rating (29 reviews)
![Oak Run]()
$100ks
- $300ks
Oak Run, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 2007
|
3,509 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.
3.6 rating (48 reviews)
![Latitude Margaritaville]()
$300ks
- $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2025
|
3,900 homes
5 rating (3 reviews)
![Stonecrest]()
$200ks
- $500ks
Stonecrest, Summerfield, FL
New and Resale
|
55+ age-restricted
|
Built 1990 - present
|
2,200 homes
4.6 rating (5 reviews)
![Ocala Preserve]()
$100ks
- $500ks
Ocala Preserve, Ocala, FL
New and Resale
|
55+ age-restricted
|
Built 2014 - present
|
1,800 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
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5 rating (1 reviews)
![Ocala Palms]()
$200ks
- $300ks
Ocala Palms, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1994 - 1997
|
1,076 homes
3.8 rating (4 reviews)
![Spruce Creek South]()
$100ks
- $200ks
Spruce Creek South, Summerfield, FL
Resale Only
|
55+ age-restricted
|
Built 1989 - 1995
|
1,650 homes
5 rating (5 reviews)
![SummerGlen]()
$200ks
- $400ks
SummerGlen, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 2004 - 2014
|
1,024 homes
$200ks
- $500ks
Southshore Bay, Wimauma, FL
New and Resale
|
55+ age-restricted
|
Built 2017 - present
|
655 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.
4.7 rating (11 reviews)
![Valencia Lakes]()
$200ks
- $700ks
Valencia Lakes, Wimauma, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2019
|
1,631 homes
5 rating (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
5 rating (1 reviews)
![Del Webb Sunbridge]()
$400ks
- $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
1,300 homes
5 rating (7 reviews)
![Kings Ridge]()
$200ks
- $400ks
Kings Ridge, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 1995 - 2000
|
2,088 homes
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4 rating (7 reviews)
![Tampa Bay Golf and Countr...]()
$200ks
- $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only
|
55+ age-restricted
|
Built 1994 - 2015
|
1,336 homes
3.8 rating (6 reviews)
![Trilogy® Orlando]()
$200ks
- $500ks
Trilogy® Orlando, Groveland, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2022
|
1,500 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
5 rating (1 reviews)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 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.
2.8 rating (6 reviews)
![Arlington Ridge]()
$200ks
- $500ks
Arlington Ridge, Leesburg, FL
New and Resale
|
55+ age-restricted
|
Built 2005 - present
|
629 homes
$100ks
- $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 homes
4 rating (4 reviews)
![Lakes of Mount Dora]()
$300ks
- $900ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
950 homes
2.3 rating (6 reviews)
![Cherrywood]()
$100ks
- $800ks
Cherrywood, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1996 - 2003
|
700 homes
4 rating (2 reviews)
![Harbor Hills Country Club]()
$300ks
- $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale
|
Age-targeted
|
Built 1989 - present
|
940 homes
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Questions? Call us:
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1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
3.6 rating (5 reviews)
![Heritage Hills]()
$200ks
- $400ks
Heritage Hills, Clermont, FL
New and Resale
|
55+ age-restricted
|
Built 2006 - present
|
1,154 homes
$100ks
- $200ks
Pine Run Estates, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1981 - 1989
|
880 homes
$300ks
- $500ks
Mirada, San Antonio, FL
New and Resale
|
55+ age-restricted
|
Built 2019 - present
|
858 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)
![Palm Cay]()
$100ks
- $200ks
Palm Cay, Ocala, FL
Resale Only
|
55+ age-restricted
|
Built 1985 - 1992
|
795 homes
$400ks
- $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale
|
Age-targeted
|
Built 1999 - present
|
875 homes
4.8 rating (6 reviews)
![Highland Lakes]()
$100ks
- $200ks
Highland Lakes, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1990 - 1999
|
938 homes
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 homes
Want to learn more about 55+ communities in Winter Garden?
55places can help!
Questions? Call us:
(689) 407-5757
5 rating (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
Sun City Center
![2016 E VIEW DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573]()
2 beds
|2 baths
|2,213 sq ft
|House
2016 E VIEW DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
MLS TB8448874 • DALTON WADE INC, Jack Stevens
On Top of the World
![9618 SW 86TH PL, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|3 baths
|2,255 sq ft
|House
9618 SW 86TH PL, OCALA, FL, 34481
Community: On Top of the World
MLS OM713025 • OCALA TOWN COUNTRY REAL ESTATE LLC...
Lakeside Landings
![4846 AUDREY MARIE CT, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|2,200 sq ft
|House
4846 AUDREY MARIE CT, OXFORD, FL, 34484
Community: Lakeside Landings
MLS G5104749 • SALLY LOVE REAL ESTATE, Carlos Fue...
Arlington Ridge
![27343 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,607 sq ft
|House
27343 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS R4910273 • ARROW STAR REALTY LLC, Eric Fiori
Southshore Bay
![17109 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
4 beds
|3 baths
|2,805 sq ft
|House
17109 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8449309 • EXP REALTY LLC, Sarah O'Reilly
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
(689) 407-5757
Pelican Bay Daytona Beach
![144 AVOCET CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119]()
3 beds
|3 baths
|2,072 sq ft
|Townhouse
144 AVOCET CT, DAYTONA BEACH, FL, 32119
Community: Pelican Bay Daytona Beach
MLS 1220172 • Realty Pros Assured, Caryn Baker
Del Webb Orlando
![536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837]()
3 beds
|2 baths
|1,508 sq ft
|House
536 ARENA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
MLS S5138798 • RIDGE REALTY GROUP LLC, Linda Spen...
Southshore Bay
![16830 ANCHOR ROOT ST, WIMAUMA, FL, 33598, Wimauma, FL 33598]()
3 beds
|3 baths
|2,128 sq ft
|House
16830 ANCHOR ROOT ST, WIMAUMA, FL, 33598
Community: Southshore Bay
MLS TB8449144 • 27NORTH REALTY, Darlene Colombo
On Top of the World
![10410 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,342 sq ft
|House
10410 SW 96TH LOOP, OCALA, FL, 34481
Community: On Top of the World
MLS OM713577 • ON TOP OF THE WORLD REAL EST, Tere...
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.
Highland Lakes
![6142 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS O6359435 • DIVERSIFIED REALTY HOLDINGS, James...
Lake Jovita Golf and Country Club
![13143 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525]()
3 beds
|3 baths
|2,750 sq ft
|Villa
13143 PALMILLA CIR, DADE CITY, FL, 33525
Community: Lake Jovita Golf and Country Club
MLS TB8449610 • THE SOMERDAY GROUP PL, Alexander ...
Sun City Center
![1811 BEDFORD LN 166, SUN CITY CENTER, FL..., Sun City Center, FL 33573]()
1 beds
|2 baths
|800 sq ft
|Condo
1811 BEDFORD LN 166, SUN CITY CENTER, FL...
Community: Sun City Center
MLS W7880568 • EXIT SUCCESS REALTY, Carol Ridlon
Sun City Center
![1811 BEDFORD LN, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573]()
1 beds
|2 baths
|800 sq ft
|Condo
1811 BEDFORD LN, SUN CITY CENTER, FL, 33...
Community: Sun City Center
MLS 2256744 • Exit Success Realty, Carol Ridlon
Want to learn more about 55+ communities in Winter Garden?
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Questions? Call us:
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Ocala Palms
![2323 NW 55TH AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482]()
3 beds
|2 baths
|1,640 sq ft
|House
2323 NW 55TH AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
MLS OM713694 • REMAX/PREMIER REALTY, Maria Bernal
Ocala Palms
![5096 NW 19TH PL, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM713815 • RE/MAX FOXFIRE - HWY200/103 S, Sh...
Stone Creek
![6176 SW 93RD AVE, OCALA, FL, 34481, Ocala, FL 34481]()
MLS OM713807 • ALL FLORIDA HOMES REALTY LLC, Luca...
Esplanade at Highland Ranch
![1023 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715]()
3 beds
|3 baths
|2,287 sq ft
|House
1023 TIMBERVALE TRL, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5104395 • WATSON REALTY CORP., REALTORS, Ron...
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.
Spruce Creek South
![10599 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,008 sq ft
|House
10599 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
MLS G5104689 • RE/MAX PREMIER REALTY LADY LK, Ger...
The Villages®
![870 TREVINO TER, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,087 sq ft
|Villa
870 TREVINO TER, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5104646 • MORRIS REALTY AND INVESTMENTS, Kim...
Huntington at Hunter's Ridge
![99 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,238 sq ft
|House
99 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
Community: Huntington at Hunter's Ridge
MLS O6359543 • SHAWFIELD REALTY GROUP, Carrie Sue...
The Villages®
![2544 ASHVILLE AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,485 sq ft
|House
2544 ASHVILLE AVE, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5104398 • REALTY EXECUTIVES IN THE VILLAGES,...
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Questions? Call us:
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Harbor Hills Country Club
![39023 GRIFFIN LNDG, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,833 sq ft
|House
39023 GRIFFIN LNDG, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5104651 • CHARLES RUTENBERG REALTY ORLANDO, ...
Breakaway Trails
![180 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,983 sq ft
|House
180 BLACK HICKORY WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
MLS 1220093 • Oceans Luxury Realty Full Service L...
Lake Ashton
![4048 PHOENICIAN WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
3 beds
|2 baths
|2,354 sq ft
|House
4048 PHOENICIAN WAY, WINTER HAVEN, FL, 3...
Community: Lake Ashton
MLS O6361389 • HEROES REAL ESTATE GROUP LLC, Arma...
On Top of the World
![8350 SW 93RD LN D, OCALA, FL, 34481, Ocala, FL 34481]()
2 beds
|2 baths
|1,409 sq ft
|Villa
8350 SW 93RD LN D, OCALA, FL, 34481
Community: On Top of the World
MLS OM713635 • RE/MAX FOXFIRE - HWY200/103 S, Bo...
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.
Trilogy® Orlando
![602 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736]()
2 beds
|3 baths
|1,900 sq ft
|House
602 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
MLS G5104630 • THE FLORIDA PROPERTY SHOP SALE, An...
Valencia Lakes
![16252 AMETHYST KEY DR DRIVE, WIMAUMA, FL..., Wimauma, FL 33598]()
3 beds
|2 baths
|1,524 sq ft
|Villa
16252 AMETHYST KEY DR DRIVE, WIMAUMA, FL...
Community: Valencia Lakes
MLS TB8448866 • KELLER WILLIAMS SOUTH SHORE, Cath...
On Top of the World
![8821 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481]()
3 beds
|2 baths
|2,420 sq ft
|House
8821 SW 82ND COURT RD, OCALA, FL, 34481
Community: On Top of the World
MLS OM713686 • OAK & SAGE REALTY LLC, Cynthia Woj...
Sun City Center
![1807 PINEAPPLE PALM CT, SUN CITY CENTER,..., Sun City Center, FL 33573]()
2 beds
|2 baths
|1,840 sq ft
|House
1807 PINEAPPLE PALM CT, SUN CITY CENTER,...
Community: Sun City Center
MLS TB8449050 • CENTURY 21 BEGGINS ENTERPRISES, C...
Venetian Bay
![3367 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,976 sq ft
|Halfplex
3367 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS NS1086621 • THE KEYES COMPANY, Lesley Lounsbu...
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(689) 407-5757
Pennbrooke Fairways
![32512 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,312 sq ft
|House
32512 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS O6360997 • COLDWELL BANKER REALTY, Mike Borah
Ocala Palms
![2370 NW 59TH AVE, OCALA, FL, 34482, Ocala, FL 34482]()
MLS OM713618 • LOKATION, Becky Alexander PA
Stone Creek
![7527 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481]()
3 beds
|4 baths
|2,604 sq ft
|House
7527 SW 97TH TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
MLS OM713631 • EXP REALTY LLC, Della Lazare
Cresswind DeLand
![1322 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724]()
MLS W7880423 • MALTBIE REALTY GROUP, Bill Maltbie
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
![8546 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476]()
2 beds
|2 baths
|1,497 sq ft
|House
8546 SW 79TH AVE, OCALA, FL, 34476
Community: On Top of the World
MLS OM713607 • RE/MAX FOXFIRE - HWY 40, Bobby Mat...
Venetian Bay
![3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|2,472 sq ft
|House
3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS O6360993 • WINSLOW HOMES, Megan Winslow
SummerGlen
![15680 SW 13TH CIR, OCALA, FL, 34473, Ocala, FL 34473]()
MLS OM713554 • RE/MAX PREMIER REALTY, James Barr
Stonecrest
![17824 SE 113TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,734 sq ft
|House
17824 SE 113TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS R4910231 • BLACK TIE REAL ESTATE PROFESSIONAL...
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The Villages®
![17627 SE 88TH COVINGTON CIR, THE VILLAGE..., The Villages, FL 32162]()
3 beds
|2 baths
|2,460 sq ft
|House
17627 SE 88TH COVINGTON CIR, THE VILLAGE...
Community: The Villages®
MLS G5104117 • REALTY EXECUTIVES IN THE VILLAGES,...
Solivita
![205 BELL TOWER XING, POINCIANA, FL, 3475..., Poinciana, FL 34759]()
2 beds
|2 baths
|1,405 sq ft
|House
205 BELL TOWER XING, POINCIANA, FL, 3475...
Community: Solivita
MLS S5138622 • BORCHINI REALTY, Dale Pautz
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?
3,654
homes
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REIN updates its listings on a daily basis. Data last updated: Apr 10, 2026.
This application does not include information on all of the properties available for sale at this time.
