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Winter Park, FL 55+ active adult communities & homes for sale - Page 53
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 (8 reviews)
![Royal Highlands]()
$200ks
- $400ks
Royal Highlands, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1999 - 2006
|
1,500 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 (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
1 rating (1 reviews)
![Sullivan Ranch]()
$200ks
- $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only
|
55+ age-restricted
|
Built 2005 - 2020
|
692 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
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.
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
5 rating (8 reviews)
![Pennbrooke Fairways]()
<$100k
- $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only
|
55+ age-restricted
|
Built 1980 - 2004
|
1,200 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
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
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
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
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
- $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction
|
55+ age-restricted
|
Built 2021 - present
|
258 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
Want to learn more about 55+ communities in Winter Park?
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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
Arlington Ridge
![26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748]()
4 beds
|3 baths
|2,318 sq ft
|House
26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...
Community: Arlington Ridge
MLS G5103238 • WATSON REALTY CORP, Nancy McCloske...
Trilogy® Orlando
![251 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|2 baths
|1,900 sq ft
|House
251 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS O6351663 • COMMUNITY ELITE REALTY, Nancy Aitk...
Solivita
![915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5136337 • BORCHINI REALTY, Charles Borchini
Scottish Highlands
![803 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,436 sq ft
|House
803 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS G5103224 • HARRISON REAL PROPERTY GROUP, Aman...
The Villages®
![16946 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|2,002 sq ft
|House
16946 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
MLS OM711180 • DANIEL J MCNULTY PLLC LLC, Dan McN...
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Royal Highlands
![20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748]()
2 beds
|2 baths
|1,722 sq ft
|House
20504 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
MLS G5103173 • FLORIDA PLUS REALTY, LLC, Tonya Ti...
Plantation at Leesburg
![24841 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|1,040 sq ft
|Manufactured Home
24841 PINE HL, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS O6351403 • INFINITE REAL ESTATE, LLC, Yenel V...
The Villages®
![17602 SE 82ND WOODLAWN AVE, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,924 sq ft
|House
17602 SE 82ND WOODLAWN AVE, THE VILLAGES...
Community: The Villages®
MLS G5103146 • CENTURY 21 ALTON CLARK, Kathi Hill
Sullivan Ranch
![30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757]()
4 beds
|3 baths
|3,452 sq ft
|House
30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
MLS O6351059 • LA ROSA REALTY PREMIER LLC, Tavis ...
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.
Grand Haven
![16 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137]()
MLS FC313306 • COASTAL GATEWAY REAL ESTATE GROUP,...
Del Webb Sunbridge
![3122 VANGUARD CT, ST CLOUD, FL, 34771, St Cloud, FL 34771]()
5 beds
|4 baths
|3,460 sq ft
|House
3122 VANGUARD CT, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
MLS O6351489 • ORLANDO PROPERTY ADVISORS, Justin ...
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...
Royal Highlands
![4528 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|2 baths
|2,200 sq ft
|House
4528 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5103095 • VANGIE BERRY SIGNATURE REALTY, Ang...
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Plantation Bay Golf & Country Club
![1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174]()
4 beds
|5 baths
|5,352 sq ft
|House
1117 OXBRIDGE LN, ORMOND BEACH, FL, 3217...
Community: Plantation Bay Golf & Country Club
MLS V4943822 • WATSON REALTY CORP, Theresa Geyer
Grand Haven
![455 RIVERFRONT DR A104, PALM COAST, FL, ..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,167 sq ft
|Condo
455 RIVERFRONT DR A104, PALM COAST, FL, ...
Community: Grand Haven
MLS FC313284 • COASTAL GATEWAY REAL ESTATE GR, Ma...
American Village
![31 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164]()
4 beds
|2 baths
|1,986 sq ft
|House
31 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
MLS FC313292 • DR HORTON REALTY INC., Charlie Rog...
The Villages®
![1130 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159]()
2 beds
|3 baths
|1,780 sq ft
|Condo
1130 AVENIDA DE LAS CASAS, LADY LAKE, FL...
Community: The Villages®
MLS G5102991 • LPT REALTY, LLC, Kevin Lanier
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.
Highland Fairways
![2137 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810]()
3 beds
|2 baths
|1,808 sq ft
|House
2137 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
MLS B4902076 • CRAIG BURKE REAL ESTATE GROUP, LLC...
Spruce Creek Country Club
![12176 SE 91ST AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|2,120 sq ft
|House
12176 SE 91ST AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS G5103054 • KELLER WILLIAMS ELITE PARTNERS III...
The Villages®
![1092 INCORVAIA WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163]()
3 beds
|3 baths
|2,409 sq ft
|House
1092 INCORVAIA WAY, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5103012 • REALTY EXECUTIVES IN THE VILLAGES,...
Plantation at Leesburg
![3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748]()
3 beds
|3 baths
|2,664 sq ft
|House
3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
Community: Plantation at Leesburg
MLS G5102758 • CENTURY 21 MYERS ROSE REALTY, Mary...
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The Lakes at Harmony
![3436 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773]()
2 beds
|2 baths
|1,637 sq ft
|House
3436 SAGEBRUSH ST, HARMONY, FL, 34773
Community: The Lakes at Harmony
MLS S5136072 • CHARLES RUTENBERG REALTY ORLANDO, ...
The Villages®
![939 KOLLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,880 sq ft
|House
939 KOLLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS O6350238 • REAL PROPERTY INTERNATIONAL, Bob L...
The Villages®
![6052 CHASE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
2 beds
|2 baths
|1,227 sq ft
|Villa
6052 CHASE CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5102957 • REALTY EXECUTIVES IN THE VILLAGES,...
Highland Lakes
![5606 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748]()
MLS G5102950 • FLORIDA PLUS REALTY, LLC, Claire B...
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.
Pennbrooke Fairways
![615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748]()
1 beds
|1 baths
|490 sq ft
|Manufactured Home
615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
MLS OM710883 • SUNBURST PROPERTIES, Scott Hutchin...
The Villages®
![2573 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,472 sq ft
|House
2573 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102938 • EXP REALTY LLC, Debbie Gentry
The Villages®
![712 JASON DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,292 sq ft
|Manufactured Home
712 JASON DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5102567 • IM REALTY, Ira Miller
The Country Club of Mount Dora
![3016 ANDOVER CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757]()
2 beds
|2 baths
|1,522 sq ft
|House
3016 ANDOVER CT, MOUNT DORA, FL, 32757
Community: The Country Club of Mount Dora
MLS G5102671 • ERA GRIZZARD REAL ESTATE, Ruth Bac...
Royal Harbor
![5138 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778]()
3 beds
|2 baths
|1,889 sq ft
|House
5138 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
MLS G5102936 • DOWN HOME REALTY, LLLP, Amber Byrn...
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The Villages®
![1258 WEATON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,477 sq ft
|House
1258 WEATON CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5102656 • REALTY EXECUTIVES IN THE VILLAGES,...
The Villages®
![870 HENDERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162]()
3 beds
|2 baths
|1,375 sq ft
|House
870 HENDERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
MLS G5101221 • CENTURY 21 MYERS ROSE REALTY, Mari...
Plantation Bay Golf & Country Club
![875 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
3 beds
|3 baths
|2,101 sq ft
|Townhouse
875 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS FC313186 • OLIVE GROVE REAL ESTATE, Sean Tabo...
Sandpiper Golf & Country Club
![6096 KITTIWAKE DR, LAKELAND, FL, 33809, Lakeland, FL 33809]()
3 beds
|2 baths
|1,489 sq ft
|House
6096 KITTIWAKE DR, LAKELAND, FL, 33809
Community: Sandpiper Golf & Country Club
MLS L4956091 • GOLDSMITH PROPERTY SOLUTIONS, Corr...
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
![5401 ESSEX CT, LEESBURG, FL, 34748, Leesburg, FL 34748]()
2 beds
|3 baths
|2,009 sq ft
|House
5401 ESSEX CT, LEESBURG, FL, 34748
Community: Royal Highlands
MLS G5102657 • BONJORN REAL ESTATE, Pamela Bonjor...
Twin Lakes
![2606 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772]()
3 beds
|3 baths
|2,365 sq ft
|House
2606 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...
Community: Twin Lakes
MLS O6349312 • GILLISPIE TEAM REAL ESTATE BUY AND...
Summer Trees
![130 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128]()
3 beds
|2 baths
|1,363 sq ft
|House
130 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
MLS 1218501 • RE/MAX Signature, Amy Wilson
Plantation at Leesburg
![25273 LOST OAK CIR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,702 sq ft
|House
25273 LOST OAK CIR, LEESBURG, FL, 34748
Community: Plantation at Leesburg
MLS G5102745 • WORTH CLARK REALTY, Jim McDonald
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Breakaway Trails
![94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|3,261 sq ft
|House
94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
MLS 1218486 • Realty Pros Assured, Bill Navarra
Kings Ridge
![3572 CAPLAND AVE, CLERMONT, FL, 34711, Clermont, FL 34711]()
MLS G5101649 • REAL BROKER, LLC, Diane Rogers
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2,513
homes
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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.
