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Winter Park, FL 55+ active adult communities & homes for sale
90 communities near Winter Park
2,487 homes near Winter Park
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4 rating (17 reviews)
![The Villages®]()
<$100k
- $1Ms
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
- $4Ms
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
$300Ks
- $1Ms
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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.
$100Ks
- $500Ks
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
- $300Ks
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
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
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5 rating (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
1,500 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 (8 reviews)
![Royal Highlands]()
$200Ks
- $500Ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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.
$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
1,300 homes
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
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$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
- $700Ks
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
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.
4.8 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
- $600Ks
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
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
Want to learn more about 55+ communities in Winter Park?
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Questions? Call us:
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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
1 rating (1 reviews)
![Sullivan Ranch]()
$300Ks
- $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
Spruce Creek South
![9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
3 beds
|2 baths
|1,450 sq ft
|House
9645 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
MLS G5095488 • TEAM WYN REALTY LLC, Gloria Wyning...
Traditions at Lake Ruby
![2919 WOODWARD LN, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884]()
3 beds
|2 baths
|1,649 sq ft
|House
2919 WOODWARD LN, WINTER HAVEN, FL, 3388...
Community: Traditions at Lake Ruby
MLS S5128004 • ZARZUELA REALTY, LLC, Usladys Zarz...
Twin Lakes
![2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,346 sq ft
|Villa
2482 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5116882 • WEICHERT REALTORS HALLMARK PRO, Sh...
Del Webb Sunbridge
![6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771]()
3 beds
|3 baths
|1,738 sq ft
|Townhouse
6501 CYRILS DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS S5126893 • THE LANDRUA GROUP REAL ESTATE INC,...
Solivita
![836 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6258190 • KELLER WILLIAMS LEGACY REALTY, Cam...
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Pelican Bay Daytona Beach
![149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
2 beds
|2 baths
|1,192 sq ft
|Condo
149 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS S5123673 • LPT REALTY, LLC, Yomari Ayala
The Villages®
![16950 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|2,687 sq ft
|House
16950 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
MLS O6318915 • CENTURY 21 CARIOTI, Kristi Matthew
Sullivan Ranch
![30113 JUTLAND CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|4 baths
|3,320 sq ft
|House
30113 JUTLAND CT, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5101223 • COLDWELL BANKER VANGUARD EDGE, Mic...
The Wellington
![689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,..., Winter Haven, FL 33880]()
2 beds
|2 baths
|1,050 sq ft
|Townhouse
689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,...
Community: The Wellington
MLS TB8360466 • RIVERA & ASSOCIATES REALTY, Maria...
Highland Lakes
![6419 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS O6301006 • SAND DOLLAR REALTY GROUP INC, Jeff...
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
![541 MILANO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5133852 • PELLEGO, LLC, Stan Wilson
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
Sullivan Ranch
![30532 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
4 beds
|2 baths
|2,426 sq ft
|House
30532 GIDRAN TER, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
MLS G5097695 • KELLIE & CO REAL ESTATE, Kellie Wh...
Grand Haven
![21 N VILLAGE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
3 beds
|2 baths
|2,289 sq ft
|House
21 N VILLAGE DR, PALM COAST, FL, 32137
Community: Grand Haven
MLS FC312631 • GRAND LIVING REALTY, David Boettge...
The Villages®
![892 NASH LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,090 sq ft
|House
892 NASH LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM683359 • GLOBALWIDE REALTY LLC, Natalie Hay...
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Questions? Call us:
(888) 625-4885
Royal Harbor
![5486 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5102161 • BHHS FLORIDA REALTY, Catherine Lan...
Kings Ridge
![2160 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS S5122295 • FUTURE HOME REALTY INC, Paul Shear...
Lake Ashton
![4124 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|2 baths
|1,682 sq ft
|House
4124 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS P4935581 • LAKE ASHTON REALTY INC., Candra Al...
Halifax Plantation
![3709 DONEGAL CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,186 sq ft
|House
3709 DONEGAL CIR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS V4938499 • WATSON REALTY CORP, Chris Calabucc...
VillageWalk at Lake Nona
![11807 PADUA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|4 baths
|3,000 sq ft
|House
11807 PADUA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS O6343624 • COMPLETE FLORIDA REALTY LLC, Greg ...
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®
![3233 LOWE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,056 sq ft
|House
3233 LOWE CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS TB8424737 • COASTAL PROPERTIES GROUP INTERNAT...
The Villages®
![925 BEECHWOOD AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,568 sq ft
|Manufactured Home
925 BEECHWOOD AVE, LADY LAKE, FL, 32159
Community: The Villages®
MLS O6315034 • FITRELY REALTY, Thomas Nguyen
Plantation at Leesburg
![3603 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|2,399 sq ft
|House
3603 WESTOVER CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6285590 • COMPASS FLORIDA LLC, Maria Nunez
The Villages®
![506 DEAUVILLE CT, THE VILLAGES, FL, 3216..., The Villages, FL 32163]()
3 beds
|2 baths
|1,914 sq ft
|House
506 DEAUVILLE CT, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5099658 • RE/MAX PREMIER REALTY, Mark Sevegn...
The Villages®
![12328 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484]()
3 beds
|2 baths
|1,495 sq ft
|House
12328 NE 48TH LOOP, OXFORD, FL, 34484
Community: The Villages®
MLS OM709504 • FLORIDA REALTY INVESTMENTS, Samuel...
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The Villages®
![110 TIMBER WAY, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,352 sq ft
|Manufactured Home
110 TIMBER WAY, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5092818 • DOWN HOME REALTY, LLLP, Colleen A....
Latitude Margaritaville
![595 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,464 sq ft
|House
595 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...
Community: Latitude Margaritaville
MLS 1216079 • Bob Hodges and Sons Realty, Kelley ...
Solivita
![517 MILANO RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5126980 • BORCHINI REALTY, Yamile Osorio Var...
Lake Ashton
![4056 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
2 beds
|2 baths
|1,530 sq ft
|House
4056 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
MLS S5129465 • EXP REALTY LLC, Miluska Parot
Twin Lakes
![5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
4 beds
|4 baths
|2,870 sq ft
|House
5075 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS S5115422 • WEICHERT REALTORS HALLMARK PRO, Sh...
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®
![594 LACY PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,397 sq ft
|House
594 LACY PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6342306 • COLDWELL BANKER REALTY, Cherry St ...
The Villages®
![1502 EL PASO WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1502 EL PASO WAY, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS O6293014 • ANGUS REALTY LLC, Andrea Fandino
Sullivan Ranch
![20945 OLDENBURG LOOP, MOUNT DORA, FL, 32..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,164 sq ft
|House
20945 OLDENBURG LOOP, MOUNT DORA, FL, 32...
Community: Sullivan Ranch
MLS G5098523 • ERA GRIZZARD REAL ESTATE, Dustin M...
Summer Trees
![125 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
2 beds
|2 baths
|1,855 sq ft
|House
125 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1217669 • Beninati Realty Group, Bart Beninat...
Harbor Hills Country Club
![5072 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,712 sq ft
|House
5072 GREENS DR, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5102017 • HARBOR HILLS SALES, INC, Sean Rich
Want to learn more about 55+ communities in Winter Park?
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Venetian Bay
![3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
4 beds
|2 baths
|1,662 sq ft
|House
3325 PINTELLO AVE, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS 1207370 • Collado Real Estate, Mary Johnston
Traditions at Lake Ruby
![3923 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
3 beds
|2 baths
|1,719 sq ft
|House
3923 BALDWIN LN, WINTER HAVEN, FL, 33884
Community: Traditions at Lake Ruby
MLS P4935847 • LPT REALTY, LLC, Brian Reeves
Twin Lakes
![2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772]()
2 beds
|2 baths
|1,464 sq ft
|Halfplex
2491 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
MLS O6343393 • PREFERRED REAL ESTATE BROKERS, Jus...
Lakes of Mount Dora
![8045 WATERBURY WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
3 beds
|2 baths
|2,152 sq ft
|House
8045 WATERBURY WAY, MOUNT DORA, FL, 3275...
Community: Lakes of Mount Dora
MLS G5098154 • ROBERT SLACK LLC, Randall Kain
Heritage Hills
![3538 BELLAND CIR B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3538 BELLAND CIR B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6343233 • EXP REALTY LLC, Stephanie Baldner
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Want to learn more about 55+ communities in Winter Park?
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REIN updates its listings on a daily basis. Data last updated: Nov 30, 2025.
This application does not include information on all of the properties available for sale at this time.
