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Winter Park, FL 55+ active adult communities & homes for sale - Page 40
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
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
Solivita
![729 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141045 • BORCHINI REALTY, Heather Hayes
The Villages®
![444 HILDALGO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159]()
2 beds
|2 baths
|1,121 sq ft
|Villa
444 HILDALGO DR, THE VILLAGES, FL, 32159
Community: The Villages®
MLS G5106376 • EXP REALTY LLC, David Gonzalez
Scottish Highlands
![1507 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788]()
2 beds
|2 baths
|1,478 sq ft
|House
1507 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
MLS OM716235 • COLDWELL BANKER VANGUARD EDGE, Val...
The Villages®
![3472 JAGUAR CT, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,392 sq ft
|House
3472 JAGUAR CT, THE VILLAGES, FL, 32163
Community: The Villages®
MLS OM716260 • WORTH CLARK REALTY, Diana Killen
Venetian Bay
![3643 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168]()
2 beds
|3 baths
|1,824 sq ft
|Townhouse
3643 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
MLS NS1086954 • OCEANBREEZE PROPERTIES, Teresa Vo...
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Lakes of Mount Dora
![3944 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
2 beds
|2 baths
|1,639 sq ft
|House
3944 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS O6372623 • DR HORTON REALTY OF CENTRAL FLORID...
Halifax Plantation
![3324 WESTMEATH DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,724 sq ft
|House
3324 WESTMEATH DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
MLS FC315116 • GRAND LIVING REALTY, Perry Gambrel...
Solivita
![405 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141125 • LPT REALTY, LLC, Leticia Morales
Lakes of Mount Dora
![3963 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,732 sq ft
|House
3963 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
MLS O6372583 • DR HORTON REALTY OF CENTRAL FLORID...
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®
![1433 ARBOR TRL, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,490 sq ft
|House
1433 ARBOR TRL, THE VILLAGES, FL, 32162
Community: The Villages®
MLS OM715023 • SHOWCASE PROPERTIES OF CENTRAL, Ti...
Traditions at Lake Ruby
![2733 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884]()
3 beds
|3 baths
|2,032 sq ft
|House
2733 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Community: Traditions at Lake Ruby
MLS P4937444 • CENTURY 21 MYERS REALTY LAKE WALES...
Stonecrest
![11193 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
3 beds
|2 baths
|1,974 sq ft
|House
11193 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
MLS OM716182 • KELLER WILLIAMS CORNERSTONE RE, Ri...
Trilogy® Orlando
![224 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736]()
2 beds
|3 baths
|2,107 sq ft
|House
224 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
MLS G5106261 • MORRIS REALTY AND INVESTMENTS, Len...
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The Villages®
![1803 PALO ALTO AVE, THE VILLAGES, FL, 32..., The Villages, FL 32159]()
3 beds
|2 baths
|2,104 sq ft
|House
1803 PALO ALTO AVE, THE VILLAGES, FL, 32...
Community: The Villages®
MLS G5105595 • COLDWELL BANKER VANGUARD EDGE, Mar...
Sullivan Ranch
![20946 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757]()
6 beds
|4 baths
|3,499 sq ft
|House
20946 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
MLS G5106228 • LPT REALTY, LLC, Nick Poulsen
The Villages®
![3017 BATALLY CT, THE VILLAGES, FL, 32162, The Villages, FL 32162]()
3 beds
|2 baths
|1,905 sq ft
|House
3017 BATALLY CT, THE VILLAGES, FL, 32162
Community: The Villages®
MLS G5106299 • DOWN HOME REALTY, LLLP, Rachel Sow...
Heritage Isle
![6977 FLORISTANA DR, MELBOURNE, FL, 32940, Melbourne, FL 32940]()
3 beds
|2 baths
|2,127 sq ft
|House
6977 FLORISTANA DR, MELBOURNE, FL, 32940
Community: Heritage Isle
MLS O6372367 • YHSGR-PIONEER, XENIA Geelhoed
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.
Venetian Bay
![2820 S ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168]()
4 beds
|3 baths
|2,314 sq ft
|House
2820 S ASCIANO CT, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay
MLS NS1086939 • RE/MAX SIGNATURE, Susan Stewart
Trilogy® Orlando
![383 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736]()
2 beds
|2 baths
|1,568 sq ft
|Villa
383 ALCOVE DR, GROVELAND, FL, 34736
Community: Trilogy® Orlando
MLS G5106373 • CENTURY 21 MYERS ROSE REALTY, Gret...
The Villages®
![116 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785]()
2 beds
|2 baths
|1,066 sq ft
|Manufactured Home
116 LYONIA LN, WILDWOOD, FL, 34785
Community: The Villages®
MLS G5106351 • FLORIDA REALTY INVESTMENTS, Dalton...
Enclave at VillageWalk
![10819 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827]()
5 beds
|6 baths
|5,437 sq ft
|House
10819 SAVONA WAY, ORLANDO, FL, 32827
Community: Enclave at VillageWalk
MLS O6370862 • COLDWELL BANKER REALTY, David Plas...
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Grand Haven
![455 RIVERFRONT DR UNIT A201, PALM COAST,..., Palm Coast, FL 32137]()
3 beds
|3 baths
|2,167 sq ft
|Condo
455 RIVERFRONT DR UNIT A201, PALM COAST,...
Community: Grand Haven
MLS FC315019 • COASTAL GATEWAY REAL ESTATE GR, Er...
Venetian Bay
![424 LUNA BELLA LN 415, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168]()
2 beds
|2 baths
|1,478 sq ft
|Condo
424 LUNA BELLA LN 415, NEW SMYRNA BEACH,...
Community: Venetian Bay
MLS O6371725 • EXP REALTY LLC, David Knight
Arlington Ridge
![27143 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748]()
3 beds
|2 baths
|1,699 sq ft
|House
27143 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
MLS G5106223 • COOPER HOMEFRONT REALTY, Joe Coope...
Spruce Creek Country Club
![13166 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,913 sq ft
|House
13166 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek Country Club
MLS OM716192 • JUDY L. TROUT REALTY, Judy Trout
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®
![17065 SE 79TH MCLAWREN TER, THE VILLAGES..., The Villages, FL 32162]()
3 beds
|2 baths
|1,684 sq ft
|House
17065 SE 79TH MCLAWREN TER, THE VILLAGES...
Community: The Villages®
MLS O6371976 • REALTY HUB, Ariel Senderowsky
Halifax Plantation
![1324 TULLAMORE BLVD, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174]()
4 beds
|3 baths
|2,598 sq ft
|House
1324 TULLAMORE BLVD, ORMOND BEACH, FL, 3...
Community: Halifax Plantation
MLS O6367567 • REDFIN CORPORATION, Tammy Shaver
The Villages®
![5754 SHEALY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|2 baths
|1,569 sq ft
|House
5754 SHEALY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5106068 • WORTH CLARK REALTY, Jim McDonald
The Villages®
![4515 BIGGS PL, THE VILLAGES, FL, 32163, The Villages, FL 32163]()
3 beds
|3 baths
|2,837 sq ft
|House
4515 BIGGS PL, THE VILLAGES, FL, 32163
Community: The Villages®
MLS G5106121 • LPT REALTY, LLC, Kerry Hanson
Solivita
![141 MARABELLA LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759]()
MLS S5141012 • BORCHINI REALTY, Valerie Williams
Want to learn more about 55+ communities in Winter Park?
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Vienna Square
![1620 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884]()
2 beds
|2 baths
|1,329 sq ft
|Villa
1620 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
MLS TB8460219 • FLAT FEE MLS REALTY, Stephen Hach...
Plantation Bay Golf & Country Club
![844 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174]()
2 beds
|2 baths
|1,526 sq ft
|House
844 PINEWOOD DR, ORMOND BEACH, FL, 32174
Community: Plantation Bay Golf & Country Club
MLS O6369906 • REDFIN CORPORATION, Tammy Shaver
Lake Henry Estates
![656 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844]()
2 beds
|2 baths
|1,681 sq ft
|House
656 SWEETWATER WAY, HAINES CITY, FL, 338...
Community: Lake Henry Estates
MLS P4937438 • FLORIDA HOME CHOICE REALTY, Janell...
Spruce Creek Country Club
![9479 SE 130TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491]()
3 beds
|3 baths
|2,346 sq ft
|House
9479 SE 130TH STREET RD, SUMMERFIELD, FL...
Community: Spruce Creek Country Club
MLS G5106280 • RE/MAX PREMIER REALTY LADY LK, Rob...
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 Country Club
![9345 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491]()
2 beds
|2 baths
|1,989 sq ft
|House
9345 SE 136TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek Country Club
MLS G5106276 • RE/MAX PREMIER REALTY LADY LK, Rob...
Solivita
![2316 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759]()
MLS S5141190 • ARISTA REALTY GROUP, LLC, Douglas ...
Colonnades
![1678 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811]()
2 beds
|2 baths
|1,224 sq ft
|House
1678 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
MLS L4958204 • REMAX EXPERTS, Maria Santillo
The Country Club of Mount Dora
![9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757]()
3 beds
|2 baths
|1,587 sq ft
|House
9089 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
Community: The Country Club of Mount Dora
MLS O6366325 • REAL BROKER, LLC, Brian Batiz Sala...
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Spruce Creek Country Club
![13185 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491]()
2 beds
|2 baths
|1,244 sq ft
|House
13185 SE 93RD TERRACE RD, SUMMERFIELD, F...
Community: Spruce Creek Country Club
MLS OM715956 • RE/MAX PREMIER REALTY LADY LK, Jay...
Lake Ashton
![4189 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859]()
2 beds
|2 baths
|2,227 sq ft
|House
4189 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
MLS P4937366 • A+ REALTY LLC, Emily Muscarella
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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.
