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Winter Park, FL 55+ active adult communities & homes for sale - Page 27
90 communities near Winter Park
2,513 homes near Winter Park
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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
4.7 rating (18 reviews)
![Solivita]()
$300ks
- $700ks
Solivita, Kissimmee, FL
New and Resale
|
55+ age-restricted
|
Built 2000 - present
|
5,900 homes
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
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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
5 rating (1 reviews)
![Plantation Bay Golf &...]()
$400ks
- $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1988 - present
|
3,500 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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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 (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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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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$200ks
- $800ks
Grand Haven, Palm Coast, FL
New and Resale
|
Age-targeted
|
Built 1997 - present
|
1,901 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
$300ks
- $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1980 - present
|
1,000 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)
![Sandpiper Golf & Coun...]()
$100ks
- $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale
|
55+ age-restricted
|
Built 1985 - present
|
1,193 homes
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
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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
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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 homes
5 rating (2 reviews)
![Heritage Isle]()
$300ks
- $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)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 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 (1 reviews)
![Royal Harbor]()
$200ks
- $800ks
Royal Harbor, Tavares, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2008
|
755 homes
$300ks
- $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2017 - present
|
557 homes
5 rating (1 reviews)
![Cresswind at Victoria Gar...]()
$200ks
- $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only
|
55+ age-restricted
|
Built 2001 - 2022
|
1,070 homes
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$100ks
- $200ks
Scottish Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1983 - 1992
|
653 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
$300ks
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 homes
4.4 rating (16 reviews)
![Del Webb Orlando]()
$200ks
- $500ks
Del Webb Orlando, Davenport, FL
Resale Only
|
55+ age-restricted
|
Built 2007 - 2021
|
937 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 (5 reviews)
![Traditions at Lake Ruby]()
$200ks
- $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
552 homes
$200ks
- $400ks
The Lakes at Harmony, Harmony, FL
New and Resale
|
55+ age-restricted
|
Built 2016 - present
|
400 homes
$200ks
- $400ks
Summer Trees, Port Orange, FL
Resale Only
|
55+ age-restricted
|
Built 1976 - 2005
|
500 homes
$400ks
- $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale
|
Age-targeted
|
Built 1985 - present
|
976 homes
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Questions? Call us:
(888) 625-4885
$100ks
- $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only
|
55+ age-restricted
|
Built 1982 - 1987
|
545 homes
Pennbrooke Fairways
![32747 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,192 sq ft
|House
32747 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5108173 • MAXREV LLC, Jayne Marvin
Solivita
![246 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6381333 • WEMERT GROUP REALTY LLC, Jenny Wem...
Halifax Plantation
![1309 WICKLOW LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,267 sq ft
|House
1309 WICKLOW LN, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS O6382189 • REDFIN CORPORATION, Tammy Shaver
The Villages®
![752 BAISLEY TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,978 sq ft
|House
752 BAISLEY TRL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5107748 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Halifax Plantation
![1346 MIDDLE LAKE DR, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,672 sq ft
|House
1346 MIDDLE LAKE DR, ORMOND BEACH, FL, 3...
Community: Halifax Plantation
MLS 1222981 • Realty Pros Assured, Aimee Haase
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Spruce Creek Country Club
![9333 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|2,148 sq ft
|House
9333 SE 124TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS O6381935 • GAILEY ENTERPRISES REAL ESTATE, Ri...
The Villages®
![933 OLEANDER ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
2 beds
|2 baths
|1,388 sq ft
|Modular
933 OLEANDER ST, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5108064 • RE/MAX FOXFIRE - SUMMERFIELD, Shar...
Royal Harbor
![6002 ARMADA ST, TAVARES, FL, 32778, Tavares, FL 32778]()
MLS G5107804 • LPT REALTY, LLC, Kathy Tucker
Lakes of Mount Dora
![8064 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,625 sq ft
|House
8064 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
MLS O6382333 • RE/MAX ASSURED, Vilmari Caraballo
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®
![721 TANGERINE DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
721 TANGERINE DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5108159 • SELLSTATE SUPERIOR REALTY, Willi M...
Trilogy® Orlando
![152 BALMY COAST RD, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|2,295 sq ft
|House
152 BALMY COAST RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5107887 • OLYMPUS EXECUTIVE REALTY INC, Lee ...
Twin Lakes
![5043 VANTAGE CT, ST. CLOUD, FL, 34772, St. Cloud, FL 34772]()
MLS 1069272 • Blue Marlin Real Estate, Kimberly C...
The Villages®
![103 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,560 sq ft
|Manufactured Home
103 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5108063 • DOWN HOME REALTY, LLLP, Britney He...
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Twin Lakes
![5043 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772]()
MLS O6382007 • BLUE MARLIN REAL ESTATE, Kimberly ...
Plantation Bay Golf & Country Club
![60 KINGSLEY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,144 sq ft
|House
60 KINGSLEY CIR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC316097 • CLAIRE HUNTER REALTY, Brian Hunter
Indian River Colony Club
![1311 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940]()
4 beds
|3 baths
|1,859 sq ft
|House
1311 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Community: Indian River Colony Club
MLS 1069235 • Four Star Real Estate LLC, Shellie ...
Alamanda Key
![570 MARTELLO WAY, MELBOURNE, FL, 32901, Melbourne, FL 32901]()
3 beds
|2 baths
|1,874 sq ft
|House
570 MARTELLO WAY, MELBOURNE, FL, 32901
Community: Alamanda Key
MLS 1069199 • Compass Florida, LLC, Lindsey N. Wh...
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.
Royal Highlands
![21821 KING JOHN ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,694 sq ft
|House
21821 KING JOHN ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS O6382093 • CENTURY 21 CARIOTI, Kristi Matthew
Plantation at Leesburg
![5036 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,791 sq ft
|House
5036 EL DESTINO DR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS TB8475797 • JACK KELLER INC, John Keller
Latitude Margaritaville
![189 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
189 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS O6380824 • LPT REALTY, LLC, Karen Ripperger
Kings Ridge
![3817 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6376372 • COLDWELL BANKER REALTY, Alex Vasta...
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Questions? Call us:
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Preserve at Lakeside Landings
![5828 MARSH LANDING DR, WINTER HAVEN, FL,..., Winter Haven, FL 33881]()
4 beds
|2 baths
|2,078 sq ft
|House
5828 MARSH LANDING DR, WINTER HAVEN, FL,...
Community: Preserve at Lakeside Landings
MLS L4958953 • FLORIDA REAL ESTATE COMPANY, Cyles...
The Villages®
![2730 MORVEN PARK WAY, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|2 baths
|2,018 sq ft
|House
2730 MORVEN PARK WAY, THE VILLAGES, FL, ...
Community: The Villages®
MLS O6380989 • FLORIDA REALTY INVESTMENTS, Tina V...
The Country Club of Mount Dora
![5039 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,509 sq ft
|House
5039 GREENBRIAR TRL, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS O6381993 • LPT REALTY, LLC, Barry McSwain
Palms at Serenoa
![17421 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714]()
2 beds
|2 baths
|1,621 sq ft
|House
17421 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
MLS G5107670 • COLDWELL BANKER HUBBARD HANSEN, Ly...
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®
![3322 BOARDROOM TRL, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|2,097 sq ft
|House
3322 BOARDROOM TRL, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5107977 • REALTY EXECUTIVES IN THE VILLAGES,...
Del Webb Sunbridge
![6403 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771]()
3 beds
|2 baths
|1,682 sq ft
|House
6403 SHIMMERING SHORES LN, ST CLOUD, FL,...
Community: Del Webb Sunbridge
MLS O6376557 • REAL BROKER, LLC, Chad Vaughan
Traditions at Lake Ruby
![3343 LIVINGSTON WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884]()
2 beds
|2 baths
|1,118 sq ft
|House
3343 LIVINGSTON WAY, WINTER HAVEN, FL, 3...
Community: Traditions at Lake Ruby
MLS P4937723 • CENTURY 21 MYERS REALTY LAKE WALES...
Trilogy® Orlando
![306 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
3 beds
|2 baths
|1,925 sq ft
|House
306 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5108109 • COMMUNITY ELITE REALTY, Nancy Aitk...
Harbor Hills Country Club
![39513 HILLRISE LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|3 baths
|2,512 sq ft
|House
39513 HILLRISE LN, LADY LAKE, FL, 32159
Community: Harbor Hills Country Club
MLS G5107395 • MORRIS REALTY AND INVESTMENTS, The...
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The Villages®
![329 BISHOPVILLE LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162]()
3 beds
|3 baths
|2,075 sq ft
|House
329 BISHOPVILLE LOOP, THE VILLAGES, FL, ...
Community: The Villages®
MLS G5107292 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![2756 CUTTERS COR, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
4 beds
|4 baths
|3,976 sq ft
|House
2756 CUTTERS COR, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5107913 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![7132 SE 172ND HAZELWOOD LOOP, THE VILLAG..., The Villages, FL 32162]()
3 beds
|2 baths
|1,854 sq ft
|House
7132 SE 172ND HAZELWOOD LOOP, THE VILLAG...
Community: The Villages®
MLS G5108066 • WORTH CLARK REALTY, Denise Marie T...
Lakes of Mount Dora
![1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757]()
3 beds
|3 baths
|2,330 sq ft
|House
1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
MLS G5108039 • EXP REALTY LLC, Angie Cable
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®
![1374 PATRICK PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|3 baths
|2,543 sq ft
|House
1374 PATRICK PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5106476 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![2318 NEHAUL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,397 sq ft
|Villa
2318 NEHAUL TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5108017 • FLORIDA FINE HOMES REALTY, LLC, De...
The Villages®
![1950 ALISTAR CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
1950 ALISTAR CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5108029 • KELLER WILLIAMS CORNERSTONE RE, De...
Cresswind DeLand
![1226 TRIDENT LOOP, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,724 sq ft
|House
1226 TRIDENT LOOP, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7882942 • MALTBIE REALTY GROUP, Bill Maltbie
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The Villages®
![8185 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
3 beds
|2 baths
|1,568 sq ft
|Manufactured Home
8185 COUNTY RD 109, LADY LAKE, FL, 32159
Community: The Villages®
MLS G5107934 • EXP REALTY LLC, Lili Whittington
The Villages®
![2670 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
2670 PRIVADA DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5106970 • REALTY EXECUTIVES IN THE VILLAGES,...
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2,513
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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.
