Call us at (888) 625-4885 to learn more about active adult communities near Winter Park
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:
(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
- $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
The Villages®
![9199 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162]()
3 beds
|2 baths
|1,850 sq ft
|House
9199 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
MLS G5090513 • KELLER WILLIAMS CORNERSTONE RE, Ka...
Colonnades
![4849 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,220 sq ft
|Modular
4849 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
MLS L4957426 • COLDWELL BANKER REALTY, Lisa Broch...
Solivita
![429 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5124646 • PELLEGO, LLC, Stan Wilson
Arlington Ridge
![3782 ARLINGTON RIDGE BLVD, LEESBURG, FL,..., Leesburg, FL 34748]()
3 beds
|2 baths
|1,711 sq ft
|House
3782 ARLINGTON RIDGE BLVD, LEESBURG, FL,...
Community: Arlington Ridge
MLS O6357871 • KELLER WILLIAMS REALTY AT THE PARK...
Del Webb Sunbridge
![6376 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771]()
2 beds
|2 baths
|1,781 sq ft
|House
6376 SHIMMERING SHORES LN, SAINT CLOUD, ...
Community: Del Webb Sunbridge
MLS O6334315 • GALLOWAY REAL ESTATE, Sidney Gallo...
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Solivita
![729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS O6221679 • LPT REALTY, LLC, Shaun Rourke
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®
![1403 ESPINOZA LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,121 sq ft
|Villa
1403 ESPINOZA LN, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5103682 • WORTH CLARK REALTY, Chuck Wilsey
The Villages®
![1850 LAKE RIDGE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162]()
3 beds
|3 baths
|2,964 sq ft
|House
1850 LAKE RIDGE DR, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5103482 • RE/MAX PREMIER REALTY LADY LK, Mat...
The Villages®
![2107 ESCOBAR AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159]()
2 beds
|2 baths
|1,143 sq ft
|House
2107 ESCOBAR AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
MLS G5103089 • RE/MAX FOXFIRE - LADY LAKE, Sharon...
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®
![301 PACOLET TER, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,392 sq ft
|House
301 PACOLET TER, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5101482 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![1224 BALLESTEROS DR, THE VILLAGES, FL, 3..., The Villages, FL 32162]()
2 beds
|2 baths
|1,148 sq ft
|House
1224 BALLESTEROS DR, THE VILLAGES, FL, 3...
Community: The Villages®
MLS G5098093 • LPT REALTY, LLC, Laura Carver
Foxwood Lake Estates
![1811 SHERWOOD HILL DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
2 beds
|2 baths
|1,316 sq ft
|Manufactured Home
1811 SHERWOOD HILL DR, LAKELAND, FL, 338...
Community: Foxwood Lake Estates
MLS L4956891 • LAKELAND HOMES AND REALTY, LLC, Mi...
Plantation at Leesburg
![5712 SUMMERBROOKE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,961 sq ft
|House
5712 SUMMERBROOKE CT, LEESBURG, FL, 3474...
Community: Plantation at Leesburg
MLS O6341032 • ALL REAL ESTATE & INVESTMENTS, Pat...
Royal Palm
![5402 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128]()
4 beds
|2 baths
|2,227 sq ft
|House
5402 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
MLS 1217817 • Executive Realty Group LLC, Lee Tou...
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Foxwood Lake Estates
![4928 FOXDALE DR, LAKELAND, FL, 33810, Lakeland, FL 33810]()
2 beds
|2 baths
|1,200 sq ft
|Manufactured Home
4928 FOXDALE DR, LAKELAND, FL, 33810
Community: Foxwood Lake Estates
MLS P4937094 • FLORIDA REALTY MARKETPLACE, Debra ...
Esplanade at Highland Ranch
![1038 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715]()
3 beds
|3 baths
|2,287 sq ft
|House
1038 TIMBERVALE TRL, CLERMONT, FL, 34715
Community: Esplanade at Highland Ranch
MLS G5104056 • OPTIMA ONE REALTY, INC., Heather W...
The Villages®
![2149 SANDALWOOD PL, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|2 baths
|1,357 sq ft
|Villa
2149 SANDALWOOD PL, THE VILLAGES, FL, 32...
Community: The Villages®
MLS TB8447148 • COMMUNITY REALTY ASSOCIATES, Doug...
Lake Ashton
![4433 VENTANA LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
3 beds
|2 baths
|2,512 sq ft
|House
4433 VENTANA LN, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4935864 • GLOBAL LIFESTYLE LLC, Brad Kirwan
Grand Haven
![25 MARLIN DR, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC314240 • GRAND LIVING REALTY, Lindsay Dolam...
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.
Cresswind DeLand
![1025 PORT BLUE WAY, DELAND, FL, 32724, Deland, FL 32724]()
3 beds
|2 baths
|1,724 sq ft
|House
1025 PORT BLUE WAY, DELAND, FL, 32724
Community: Cresswind DeLand
MLS W7880422 • MALTBIE REALTY GROUP, Bill Maltbie
Venetian Bay
![2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
3 beds
|3 baths
|1,754 sq ft
|House
2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS V4942853 • REALTY PROS ASSURED, Buzzy Porter
Four Seasons at Orlando
![1962 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747]()
4 beds
|3 baths
|2,452 sq ft
|House
1962 FLORA PASS PL, KISSIMMEE, FL, 34747
Community: Four Seasons at Orlando
MLS O6321873 • LUXE PROPERTIES LLC, Deanna Meredi...
Carlsberg Estates on Lake Suzanne
![400 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859]()
3 beds
|3 baths
|1,718 sq ft
|House
400 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Community: Carlsberg Estates on Lake Suzanne
MLS P4936389 • CENTURY 21 MYERS REALTY LAKE WALES...
The Villages®
![1722 MYRTLE BEACH DR, THE VILLAGES, FL, ..., The Villages, FL 32159]()
2 beds
|1 baths
|832 sq ft
|Manufactured Home
1722 MYRTLE BEACH DR, THE VILLAGES, FL, ...
Community: The Villages®
MLS O6359638 • ERA GRIZZARD REAL ESTATE, Jessica ...
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Pennbrooke Fairways
![409 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,232 sq ft
|House
409 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS G5098020 • MAXREV LLC, Jayne Marvin
The Villages®
![203 MODESTO RD, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
3 beds
|2 baths
|1,392 sq ft
|House
203 MODESTO RD, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5104495 • RE/MAX PREMIER REALTY LADY LK, Mat...
The Villages®
![1675 ABERNETHY PL, THE VILLAGES, FL, 321..., The Villages, FL 32162]()
3 beds
|2 baths
|2,122 sq ft
|House
1675 ABERNETHY PL, THE VILLAGES, FL, 321...
Community: The Villages®
MLS G5100695 • RE/MAX PREMIER REALTY LADY LK, Guy...
Venetian Bay
![3610 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168]()
3 beds
|2 baths
|2,079 sq ft
|House
3610 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
MLS V4944513 • RE/MAX SIGNATURE, Trena DeCandia
Tohoqua Reserve
![1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744]()
2 beds
|2 baths
|1,559 sq ft
|House
1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
MLS S5128993 • LPT REALTY, LLC, Paola Jimenez
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.
Kings Ridge
![3713 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS O6348405 • FLORIDA PRESTIGIOUS HOMES INC, Ian...
The Villages®
![3389 LUTY LN, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,547 sq ft
|House
3389 LUTY LN, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5099516 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![1819 ZIRCON PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
4 beds
|2 baths
|2,534 sq ft
|House
1819 ZIRCON PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5101195 • REALTY EXECUTIVES IN THE VILLAGES,...
Grand Isle
![1545 BOCA RIO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
MLS 1047099 • RE/MAX Aerospace Realty, Alexandra ...
Latitude Margaritaville
![317 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124]()
2 beds
|2 baths
|1,160 sq ft
|House
317 POP TOP LN, DAYTONA BEACH, FL, 32124
Community: Latitude Margaritaville
MLS 1219532 • LoKation, Aimee Aballo
Want to learn more about 55+ communities in Winter Park?
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The Villages®
![1524 LOZANO AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,143 sq ft
|House
1524 LOZANO AVE, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5104781 • SELLSTATE SUPERIOR REALTY, Karen M...
Arlington Ridge
![26939 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,631 sq ft
|Villa
26939 WHITE PLAINS WAY, LEESBURG, FL, 34...
Community: Arlington Ridge
MLS G5102246 • HOAD REALTY GROUP LLC, Lisa Hoad
Del Webb Sunbridge
![2722 RIVER CREEK LN, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771]()
3 beds
|4 baths
|3,778 sq ft
|House
2722 RIVER CREEK LN, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
MLS O6357275 • RE/MAX INNOVATION, Jory Williams
Plantation at Leesburg
![24515 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|3 baths
|2,204 sq ft
|House
24515 BOCAGE WAY, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5100791 • VISIONARY PROPERTIES INC, Judy Blu...
Del Webb Sunbridge
![6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771]()
3 beds
|3 baths
|2,077 sq ft
|House
6129 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
MLS O6311277 • RE/MAX INNOVATION, Jory Williams
Want more information about active adult communities around Winter Park?
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2,487
homes
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.
