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Winter Park, FL 55+ active adult communities & homes for sale - Page 38
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
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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
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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
Huntington at Hunter's Ridge
![6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|1,637 sq ft
|House
6 FOX LAIR CT, ORMOND BEACH, FL, 32174
Community: Huntington at Hunter's Ridge
MLS FC311356 • REALTY PROS ASSURED, Tyler Renick
Solivita
![670 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5133347 • BORCHINI REALTY, Charles Borchini
The Villages®
![1605 CHAVEZ CT, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,638 sq ft
|House
1605 CHAVEZ CT, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5099171 • BROKER ASSOCIATES REALTY, Kim Asch...
Solivita
![3390 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5130722 • BORCHINI REALTY, Yamile Osorio Var...
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...
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Solivita
![502 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5123661 • PELLEGO, LLC, Paul Maiatico
Royal Highlands
![21636 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,642 sq ft
|House
21636 KING HENRY AVE, LEESBURG, FL, 3474...
Community: Royal Highlands
MLS O6279378 • KELLER WILLIAMS WINTER PARK, Lana ...
Solivita
![537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS G5096869 • BACK PORCH REALTY, LLC, Jackie Rog...
Spruce Creek Country Club
![13709 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,537 sq ft
|House
13709 SE 86TH TER, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM715384 • BROKER ASSOCIATES REALTY, Rich Den...
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.
Halifax Plantation
![3231 GALTY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,943 sq ft
|House
3231 GALTY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1218539 • EXP Realty LLC, Jeff Dillard
Halifax Plantation
![3227 GALTY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|2 baths
|2,059 sq ft
|House
3227 GALTY CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
MLS 1216283 • EXP Realty LLC, Jeff Dillard
The Villages®
![1133 DEL TORO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,332 sq ft
|House
1133 DEL TORO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5103791 • HOAD REALTY GROUP LLC, John Hoad
The Villages®
![12347 NE 52ND LOOP, OXFORD, FL, 34484, Oxford, FL 34484]()
4 beds
|4 baths
|2,092 sq ft
|House
12347 NE 52ND LOOP, OXFORD, FL, 34484
Community: The Villages®
MLS O6321690 • REAL BROKER, LLC, Eddie Gonzalez
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The Villages®
![1638 DURAN DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,179 sq ft
|House
1638 DURAN DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102310 • SALLY LOVE REAL ESTATE, Donna Pull...
The Villages®
![1411 JUAREZ PL, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,388 sq ft
|House
1411 JUAREZ PL, THE VILLAGES, FL, 32159
Community: The Villages®
MLS R4910370 • BLACK TIE REAL ESTATE PROFESSIONAL...
Stonecrest
![17645 SE 117TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|3 baths
|1,686 sq ft
|House
17645 SE 117TH CIR, SUMMERFIELD, FL, 344...
Community: Stonecrest
MLS OM698674 • ROBB HARRISON REALTY INC, Robb Har...
Enclave at VillageWalk
![11741 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827]()
4 beds
|4 baths
|3,197 sq ft
|House
11741 SAVONA WAY, ORLANDO, FL, 32827
Community: Enclave at VillageWalk
MLS O6311711 • KELLER WILLIAMS CLASSIC, Cassie La...
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
![15913 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
4 beds
|2 baths
|1,498 sq ft
|House
15913 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM712496 • DR HORTON REALTY OF WEST CENTRAL F...
Spruce Creek South
![15919 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,328 sq ft
|House
15919 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
MLS OM713910 • DR HORTON REALTY OF WEST CENTRAL F...
Latitude Margaritaville
![422 LIME AVE, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,466 sq ft
|House
422 LIME AVE, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS V4945467 • ADAMS, CAMERON & CO., REALTORS, Bi...
Solivita
![417 LAKE BUTLER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS TB8346674 • CHARLES RUTENBERG REALTY INC, Al ...
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Heritage Hills
![3201 SONESTA CT A, CLERMONT, FL, 34711, Clermont, FL 34711]()
2 beds
|2 baths
|1,503 sq ft
|Villa
3201 SONESTA CT A, CLERMONT, FL, 34711
Community: Heritage Hills
MLS G5105573 • KELLER WILLIAMS ELITE PARTNERS III...
Four Seasons at Orlando
![7661 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747]()
2 beds
|2 baths
|1,437 sq ft
|Villa
7661 SAND PIERRE CT, KISSIMMEE, FL, 3474...
Community: Four Seasons at Orlando
MLS O6368190 • VIVA ORLANDO REALTY INC., Susan Ri...
Four Seasons at Orlando
![1825 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
2 beds
|2 baths
|1,557 sq ft
|Villa
1825 FLORA PASS PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6355192 • VIVA ORLANDO REALTY INC., Susan Ri...
Carmel Condominium
![1420 HUNTINGTON LN 2502, ROCKLEDGE, FL, ..., Rockledge, FL 32955]()
2 beds
|2 baths
|1,008 sq ft
|Condo
1420 HUNTINGTON LN 2502, ROCKLEDGE, FL, ...
Community: Carmel Condominium
MLS O6349457 • MARK SPAIN REAL ESTATE, Mark Vesci...
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®
![1639 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1639 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS O6333604 • REDFIN CORPORATION, Jo Holton
The Villages®
![458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3..., The Villages, FL 32163]()
3 beds
|2 baths
|1,830 sq ft
|House
458 JUNGLE PLUM WAY, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5103594 • HOAD REALTY GROUP LLC, Lisa Hoad
Plantation Bay Golf & Country Club
![48 TREETOP CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|3 baths
|2,079 sq ft
|House
48 TREETOP CIR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS 1218073 • Weichert Realtors Hallmark Properti...
The Villages®
![14202 SANDALWOOD DR # 202, WILDWOOD, FL,..., Wildwood, FL 34785]()
2 beds
|2 baths
|1,085 sq ft
|Condo
14202 SANDALWOOD DR # 202, WILDWOOD, FL,...
Community: The Villages®
MLS G5101963 • MORRIS REALTY AND INVESTMENTS, The...
Plantation Bay Golf & Country Club
![715 COBBLESTONE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
2 beds
|3 baths
|1,875 sq ft
|Townhouse
715 COBBLESTONE DR, ORMOND BEACH, FL, 32...
Community: Plantation Bay Golf & Country Club
MLS 1221142 • Adams, Cameron & Co., Realtors, Nan...
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The Villages®
![2369 TRAVIS PL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
2 beds
|2 baths
|1,156 sq ft
|Villa
2369 TRAVIS PL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5099301 • IM REALTY, Ira Miller
Lakes at Laurel Highlands
![2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
6 beds
|3 baths
|2,696 sq ft
|House
2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Lakes at Laurel Highlands
MLS L4958127 • KELLER WILLIAMS REALTY SMART 1, He...
Heritage Landings
![2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811]()
6 beds
|3 baths
|2,696 sq ft
|House
2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
MLS L4958127 • KELLER WILLIAMS REALTY SMART 1, He...
Solivita
![151 BELL TOWER XING W, KISSIMMEE, FL, 34..., Kissimmee, FL 34759]()
2 beds
|2 baths
|1,356 sq ft
|House
151 BELL TOWER XING W, KISSIMMEE, FL, 34...
Community: Solivita
MLS O6295181 • WATSON REALTY CORP, Maritza Jimene...
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®
![528 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,624 sq ft
|House
528 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5105291 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
The Villages®
![802 MIRANDA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,471 sq ft
|House
802 MIRANDA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5105223 • OLYMPUS EXECUTIVE REALTY INC, Jen ...
The Country Club of Mount Dora
![5061 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
4 beds
|3 baths
|2,922 sq ft
|House
5061 GREENBRIAR TRL, MOUNT DORA, FL, 327...
Community: The Country Club of Mount Dora
MLS G5104656 • MOUNT DORA GOLF AND LAKE RLTY, Joh...
Royal Harbor
![5151 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
4 beds
|2 baths
|2,091 sq ft
|House
5151 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS O6349567 • DAPORE REALTY INC, Diane Dapore Ro...
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The Villages®
![2845 CHARITY LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163]()
2 beds
|2 baths
|1,206 sq ft
|House
2845 CHARITY LOOP, THE VILLAGES, FL, 321...
Community: The Villages®
MLS TB8444383 • WWW.HOMEZU.COM, Jason Saphire
Colonnades
![4823 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,196 sq ft
|House
4823 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4956860 • COLDWELL BANKER REALTY, Lisa Broch...
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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.
