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Winter Park, FL 55+ active adult communities & homes for sale - Page 35
90 communities near Winter Park
2,398 homes near Winter Park
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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
4.7 rating (18 reviews)
![Solivita]()
$100Ks
- $600Ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$200Ks
- $3Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 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
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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
Download the Ultimate 55+ Homebuying Guide
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$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 homes
$100Ks
- $400Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only
|
Age-targeted
|
Built 1980 - 2006
|
1,806 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
5 rating (1 reviews)
![Cypress Lakes]()
$100Ks
- $200Ks
Cypress Lakes, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1987 - 2016
|
1,604 homes
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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
5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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)
![Royal Highlands]()
$200Ks
- $400Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 homes
$400Ks
- $1Ms
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
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
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)
![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.
$200Ks
- $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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
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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
5 rating (2 reviews)
![Bridgewater at Viera]()
$300Ks
- $800Ks
Bridgewater at Viera, Melbourne, FL
Resale Only
|
55+ age-restricted
|
Built 2017 - 2023
|
870 homes
$200Ks
- $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only
|
Age-targeted
|
Built 1991 - 2005
|
827 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.
4.1 rating (9 reviews)
![Indian River Colony Club]()
$200Ks
- $400Ks
Indian River Colony Club, Melbourne, FL
New and Resale
|
55+ age-restricted
|
Built 1986 - present
|
777 homes
3.9 rating (7 reviews)
![Summit Greens]()
$300Ks
- $400Ks
Summit Greens, Clermont, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2019
|
769 homes
5 rating (1 reviews)
![Royal Harbor]()
$200Ks
- $400Ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$200Ks
- $500Ks
Lakeside Landings, Oxford, FL
New and Resale
|
Age-targeted
|
Built 2005 - present
|
700 homes
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1 rating (1 reviews)
![Sullivan Ranch]()
$200Ks
- $700Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Pennbrooke Fairways
![33409 PENNBROOKE PKWY, LEESBURG, FL, 347..., Leesburg, FL 34748]()
3 beds
|2 baths
|2,111 sq ft
|House
33409 PENNBROOKE PKWY, LEESBURG, FL, 347...
Community: Pennbrooke Fairways
MLS G5092982 • MAXREV LLC, Jayne Marvin
Trilogy® Orlando
![133 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,483 sq ft
|House
133 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5104020 • COMMUNITY ELITE REALTY, Nancy Aitk...
Trilogy® Orlando
![815 HIDDEN MOSS DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|3 baths
|2,339 sq ft
|House
815 HIDDEN MOSS DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5100077 • COLDWELL BANKER HUBBARD HANSEN, An...
The Villages®
![1302 LOPEZ LN, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,522 sq ft
|House
1302 LOPEZ LN, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099540 • LPT REALTY, LLC, Lizzy Bell
Traditions at Lake Ruby
![4016 CARTERET DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
4 beds
|3 baths
|1,927 sq ft
|House
4016 CARTERET DR, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS L4957096 • AMPLIFY REAL ESTATE SERVICES FL, D...
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The Villages®
![1238 THUNDERBIRD WAY, THE VILLAGES, FL, ..., The Villages, FL 32163]()
3 beds
|2 baths
|2,066 sq ft
|House
1238 THUNDERBIRD WAY, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5105003 • KELLER WILLIAMS ELITE PARTNERS III...
Park Place
![21 PARK PLACE CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
3 beds
|2 baths
|1,878 sq ft
|House
21 PARK PLACE CIR, PALM COAST, FL, 32164
Community: Park Place
MLS FC309817 • LPT REALTY, LLC, Marilynn Wolfe
Solivita
![154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759]()
3 beds
|4 baths
|2,616 sq ft
|House
154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347...
Community: Solivita
MLS S5133904 • PELLEGO, LLC, Stan Wilson
Breakaway Trails
![6 BLACK PINE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|4 baths
|3,289 sq ft
|House
6 BLACK PINE WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
MLS FC311606 • REALTY EXECUTIVES OCEANSIDE, Eric ...
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®
![1064 ALCOVE LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|2,000 sq ft
|House
1064 ALCOVE LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105530 • SALLY LOVE REAL ESTATE, Rachel Sch...
Kings Ridge
![2131 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5096629 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![2507 EVERWOOD CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,188 sq ft
|House
2507 EVERWOOD CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105208 • REALTY EXECUTIVES IN THE VILLAGES,...
Latitude Margaritaville
![430 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,160 sq ft
|House
430 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1221255 • Realty Hub, Cherri Tindall
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Del Webb Sunbridge
![6354 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,670 sq ft
|House
6354 SHIMMERING SHORES LN, SAINT CLOUD, ...
Community: Del Webb Sunbridge
MLS O6349610 • RE/MAX INNOVATION, Jory Williams
Kings Ridge
![4020 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5093209 • LAKE PROPERTY STARS, Robin Costopl...
Halifax Plantation
![1461 CARLOW CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,684 sq ft
|House
1461 CARLOW CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1220556 • Beach Towne Realtors, Jessica Arund...
The Villages®
![1422 SEGOVIA PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,044 sq ft
|House
1422 SEGOVIA PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5104028 • EXP REALTY LLC, Debbie Gentry
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®
![2573 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,472 sq ft
|House
2573 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102938 • EXP REALTY LLC, Debbie Gentry
Grand Haven
![67 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC310984 • TAKE ACTION PROPERTIES, LLC, Lucia...
Pennbrooke Fairways
![507 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|1 baths
|708 sq ft
|House
507 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5102820 • FLORIDA PLUS REALTY, LLC, Sharon L...
The Villages®
![19201 SANDALWOOD DR # 19201, WILDWOOD, F..., Wildwood, FL 34785]()
1 beds
|1 baths
|872 sq ft
|Condo
19201 SANDALWOOD DR # 19201, WILDWOOD, F...
Community: The Villages®
MLS G5101556 • BHHS FLORIDA REALTY, Joanne Levy
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Huntington at Hunter's Ridge
![34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,523 sq ft
|House
34 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Community: Huntington at Hunter's Ridge
MLS 1210270 • Realty Executives Oceanside, Traci ...
Solivita
![582 SAN JOAQUIN RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5127852 • PELLEGO, LLC, Diane Cisek
Cresswind at Victoria Gardens
![213 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,507 sq ft
|House
213 OLD MOSS CIR, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4946369 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![5631 FERNANDES CT, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
3 beds
|2 baths
|1,986 sq ft
|Villa
5631 FERNANDES CT, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5105251 • REALTY EXECUTIVES IN THE VILLAGES,...
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.
Solivita
![506 TAPATIO LN, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5135993 • PELLEGO, LLC, Stan Wilson
Lakes of Mount Dora
![8456 NORWICH WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|3 baths
|2,460 sq ft
|House
8456 NORWICH WAY, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
MLS O6278226 • KELLER WILLIAMS LEGACY, Thomas Hix...
Solivita
![806 EBB TIDE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5139382 • PELLEGO, LLC, Paul Maiatico
Solivita
![2448 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5117943 • PELLEGO, LLC, Paul Maiatico
Royal Palm
![1315 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128]()
4 beds
|2 baths
|1,989 sq ft
|House
1315 COCONUT PALM CIR, PORT ORANGE, FL, ...
Community: Royal Palm
MLS 1220297 • Florida Investment Realty, Arun Red...
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Arlington Ridge
![4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
4 beds
|2 baths
|1,857 sq ft
|House
4110 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS O6287135 • KELLER WILLIAMS HERITAGE REALTY, P...
Venetian Bay
![3124 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,916 sq ft
|House
3124 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS O6370398 • WINSLOW HOMES, Megan Winslow
Del Webb Minneola
![1517 EVENING SUMMIT CIR, MINNEOLA, FL, 3..., Minneola, FL 34715]()
4 beds
|4 baths
|2,808 sq ft
|House
1517 EVENING SUMMIT CIR, MINNEOLA, FL, 3...
Community: Del Webb Minneola
MLS O6369775 • REAL BROKER, LLC, James Goodyear
Lake Ashton
![4576 BACK NINE DR, WINTER HAVEN, FL, 338..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,514 sq ft
|House
4576 BACK NINE DR, WINTER HAVEN, FL, 338...
Community: Lake Ashton
MLS P4937279 • GLOBAL LIFESTYLE LLC, Brad Kirwan
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.
Vienna Square
![1614 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,164 sq ft
|Villa
1614 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS P4937382 • CENTURY 21 WATSON & MYERS REALTY, ...
The Villages®
![3165 HUDSON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|2,176 sq ft
|House
3165 HUDSON CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS TB8449973 • HOME SOLD REALTY LLC, Camilo Pere...
The Villages®
![2016 PEACEFUL PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
2 beds
|2 baths
|1,188 sq ft
|Villa
2016 PEACEFUL PL, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5105356 • EXP REALTY LLC, Dena Manning
Latitude Margaritaville
![205 CHEESEBURGER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,922 sq ft
|House
205 CHEESEBURGER DR, DAYTONA BEACH, FL, ...
Community: Latitude Margaritaville
MLS 1221229 • Bob Hodges and Sons Realty, Didi Wo...
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Halifax Plantation
![2745 PORTADOWN ST, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,514 sq ft
|House
2745 PORTADOWN ST, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS FC314143 • ATLANTIC OCEAN REALTY, Suzanne Mat...
Highland Lakes
![27107 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,474 sq ft
|House
27107 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
MLS G5102686 • FLORIDA PLUS REALTY, LLC, Garnet E...
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2,398
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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.
