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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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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 (2 reviews)
![Heritage Isle]()
$200Ks
- $500Ks
Heritage Isle, Viera, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2017
|
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
$300Ks
- $800Ks
Del Webb at Viera, Melbourne, FL
New Construction
|
55+ age-restricted
|
Built 2021 - 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 (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 (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
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Questions? Call us:
(888) 625-4885
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
- $600Ks
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 Country Club
![13178 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,665 sq ft
|House
13178 SE 93RD TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS G5104154 • RE/MAX PREMIER REALTY LADY LK, Rob...
Spruce Creek Country Club
![13914 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,958 sq ft
|House
13914 SE 96TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM712777 • JUDY L. TROUT REALTY, Jennifer Tra...
Sandpiper Golf & Country Club
![6052 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
2 beds
|2 baths
|1,397 sq ft
|House
6052 CONDOR DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4957051 • COLDWELL BANKER REALTY, Sue Ward
Spruce Creek Country Club
![9446 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,779 sq ft
|House
9446 SE 125TH ST, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5103569 • RE/MAX PREMIER REALTY LADY LK, Rob...
Solivita
![759 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5135923 • PELLEGO, LLC, Stan Wilson
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Grand Haven
![10 OASIS CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313141 • GRAND LIVING REALTY, Cindy Tetreau...
The Villages®
![1175 JOHNSTON PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|2 baths
|2,205 sq ft
|House
1175 JOHNSTON PATH, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5102381 • ERA GRIZZARD REAL ESTATE, Stacy Br...
Del Webb at Viera
![8788 SPLASHING DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
2 beds
|2 baths
|1,579 sq ft
|Villa
8788 SPLASHING DR, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS O6341739 • PULTE REALTY OF NORTH FLORIDA LLC,...
Spruce Creek Country Club
![12900 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,149 sq ft
|House
12900 SE 97TH TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM708818 • SHEPPARD ASSOCIATES, LLC, Patrick ...
VillageWalk at Lake Nona
![11858 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827]()
3 beds
|2 baths
|1,941 sq ft
|House
11858 BARLETTA DR, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS S5132602 • LA ROSA REALTY INTERNACIONAL L, Ma...
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 Bay Golf & Country Club
![856 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,526 sq ft
|Townhouse
856 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC311467 • VENTURE DEVELOPMENT REALTY,INC, De...
The Country Club of Mount Dora
![9015 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,894 sq ft
|House
9015 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Community: The Country Club of Mount Dora
MLS G5099196 • WEICHERT REALTORS HALLMARK PRO, Ju...
Plantation Bay Golf & Country Club
![829 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
829 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC310286 • VENTURE DEVELOPMENT REALTY,INC, El...
Heritage Hills
![3210 SONESTA CT B, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,374 sq ft
|Villa
3210 SONESTA CT B, CLERMONT, FL, 34711
Community: Heritage Hills
MLS O6318494 • REAL BROKER, LLC, Patti Merrick
Cresswind at Victoria Gardens
![307 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,547 sq ft
|House
307 HERON POINT WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS V4945736 • KELLER WILLIAMS HERITAGE REALTY, D...
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Tohoqua Reserve
![1973 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
3 beds
|2 baths
|1,701 sq ft
|House
1973 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS P4936815 • KELLER WILLIAMS REALTY SMART 1, An...
Venetian Bay
![3654 PINI AVE, NEW SMYRNA BEACH, FL, 321..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|1,859 sq ft
|House
3654 PINI AVE, NEW SMYRNA BEACH, FL, 321...
Community: Venetian Bay
MLS O6352465 • WINSLOW HOMES, Megan Winslow
Grand Haven
![72 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC312959 • RE/MAX SELECT PROFESSIONALS, Cryst...
Solivita
![460 BEL AIR WAY, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5131066 • BORCHINI REALTY, Charles Borchini
Kings Ridge
![2010 BRAXTON ST, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6354447 • FANNIE HILLMAN & ASSOCIATES, Denis...
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.
Lakes at Laurel Highlands
![2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811]()
3 beds
|2 baths
|1,784 sq ft
|House
2162 BLUE HIGHLANDS DR, LAKELAND, FL, 33...
Community: Lakes at Laurel Highlands
MLS L4955966 • EXP REALTY LLC, Brian Stephens
Compass Pointe
![688 NAPLES CT, WEST MELBOURNE, FL, 32904, West Melbourne, FL 32904]()
4 beds
|3 baths
|1,763 sq ft
|House
688 NAPLES CT, WEST MELBOURNE, FL, 32904
Community: Compass Pointe
MLS 1051259 • Cloud 9 Real Estate Group, Darlene ...
Solivita
![2502 PALM TREE DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
2 beds
|2 baths
|1,539 sq ft
|Townhouse
2502 PALM TREE DR, POINCIANA, FL, 34759
Community: Solivita
MLS S5123237 • BELLA VERDE REALTY LLC, Suzanne Fo...
VillageWalk at Lake Nona
![11887 DELFINA LN, ORLANDO, FL, 32827, Orlando, FL 32827]()
2 beds
|2 baths
|1,708 sq ft
|House
11887 DELFINA LN, ORLANDO, FL, 32827
Community: VillageWalk at Lake Nona
MLS TB8422156 • SOUTH EARTH REALTY LLC, Ting Li
Solivita
![540 GENOA DR, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5115322 • BORCHINI REALTY, Cherie Pontes
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Royal Highlands
![5133 LINKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,701 sq ft
|House
5133 LINKS LN, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5104568 • CARLINO REAL ESTATE GROUP INC, Ale...
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
Cresswind at Victoria Gardens
![513 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724]()
2 beds
|2 baths
|1,446 sq ft
|House
513 HERON POINT WAY, DELAND, FL, 32724
Community: Cresswind at Victoria Gardens
MLS O6360153 • BETTER HOMES AND GARDENS REAL ESTA...
Plantation Bay Golf & Country Club
![584 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,991 sq ft
|House
584 ALDENHAM LN, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS A4671992 • FLORIDA REALTY INVESTMENTS, Denise...
The Villages®
![706 JASON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159]()
MLS OM713337 • KELLER WILLIAMS CORNERSTONE RE, Ci...
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.
Del Webb at Viera
![8969 SHORELINE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|4 baths
|2,838 sq ft
|House
8969 SHORELINE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
MLS 1049501 • Murray Realty of Brevard, Lisa A Mu...
Bridgewater at Viera
![8474 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|3 baths
|2,006 sq ft
|House
8474 ALISTER DR, MELBOURNE, FL, 32940
Community: Bridgewater at Viera
MLS 1048175 • RE/MAX Aerospace Realty, Annette Ca...
Bridgewater at Viera
![1572 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940]()
3 beds
|2 baths
|1,764 sq ft
|House
1572 GREAT BELT CIR, MELBOURNE, FL, 3294...
Community: Bridgewater at Viera
MLS 1059748 • Melbourne Realty, Inc., Laurie E Ro...
Halifax Plantation
![2853 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,113 sq ft
|House
2853 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
MLS 1218041 • Florida Bluewater Realty LLC, Natha...
Pelican Bay Daytona Beach
![128 GOLDEN EYE DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119]()
3 beds
|2 baths
|1,376 sq ft
|Condo
128 GOLDEN EYE DR B, DAYTONA BEACH, FL, ...
Community: Pelican Bay Daytona Beach
MLS 1215114 • EXP Realty LLC, Nhu-y Le
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Latitude Margaritaville
![575 BEACH BUM BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
2 beds
|3 baths
|2,339 sq ft
|House
575 BEACH BUM BLVD, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1219454 • Bob Hodges and Sons Realty, Kelley ...
Pelican Bay Daytona Beach
![102 BOB WHITE CT APT 9, DAYTONA BEACH, F..., Daytona Beach, FL 32119]()
1 beds
|1 baths
|894 sq ft
|Condo
102 BOB WHITE CT APT 9, DAYTONA BEACH, F...
Community: Pelican Bay Daytona Beach
MLS 1217844 • Ponce Inlet Realty, Inc, Lynette Sw...
Plantation Bay Golf & Country Club
![1109 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
2 beds
|3 baths
|1,604 sq ft
|Townhouse
1109 HANSBERRY CT, ORMOND BEACH, FL, 321...
Community: Plantation Bay Golf & Country Club
MLS 1219767 • The Barnett Group Inc., Sally LaCla...
Four Seasons at Orlando
![1991 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
1991 KEY BAY TRL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS TB8421378 • MARK SPAIN REAL ESTATE, Tim Creso...
Latitude Margaritaville
![173 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124]()
3 beds
|4 baths
|2,575 sq ft
|House
173 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Community: Latitude Margaritaville
MLS 1220042 • Bob Hodges and Sons Realty, Kelley ...
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2,487
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near 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.
