Homes for Sale in 10918

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  /48

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 5,312 Sq Ft

  53 Gibson Hill Rd, Chester, NY 10918

  Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

  

  Ammar Iqbal

  eXp Realty

  53 Gibson Hill Rd, Chester, NY 10918
• 

  

  

  /41

  $1,139,900

  $20K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,624 Sq Ft

  16 Lori Ln, Chester, NY 10918

  Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the

  

  Randolph Rogers

  eXp Realty

  16 Lori Ln, Chester, NY 10918
• 

  

  

  /50

  $1,000,000

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  1 Oakland Ave, Chester, NY 10918

  Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

  

  Christina Rowan

  Howard Hanna Rand Realty

  1 Oakland Ave, Chester, NY 10918
• 

  

  

  /18

  $399,000

  • Land
  • 46 Acres
  • $8,674 per Acre

  492 Black Meadow Rd, Chester, NY 10918

  Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching,

  

  Ewa Kusmierek

  eXp Realty

  492 Black Meadow Rd, Chester, NY 10918
• 

  

  

  /47

  $985,000

  • 5 Beds
  • 3.5 Baths
  • 3,764 Sq Ft

  86 Long Vista Ln, Chester, NY 10918

  Some properties are simply worth talking about... this one has all the bells & whistles you're seeking! Privately set on 5.2 scenic acres within the Warwick School District and just one hour from NYC, this distinguished Colonial pairs timeless elegance with resort-style outdoor living, mountain views, and exceptional multi-generational flexibility. A gracious front porch sets the tone, welcoming

  

  Jennifer DiCostanzo

  RE/MAX Town & Country

  86 Long Vista Ln, Chester, NY 10918
• 

  

  /4

  $350,000

  $50K PRICE INCREASE

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  

  Theresa Powers

  Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
• 

  

  /37

  $789,900

  Open Sat 12PM - 2PM

  • 5 Beds
  • 4 Baths
  • 4,697 Sq Ft

  19 Grand View Terrace, Chester, NY 10918

  Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living

  

  Randolph Rogers

  eXp Realty

  19 Grand View Terrace, Chester, NY 10918
• 

  

  /50

  $675,000

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  9 Derose Ln, Chester, NY 10918

  Welcome to this elegant colonial in the highly regarded Warwick School District, where timeless charm meets modern comfort. Relax on the inviting front porch while enjoying your morning coffee and breathtaking mountain views. Inside, spacious sun-filled rooms and hardwood flooring throughout the formal living and dining areas create a warm, welcoming atmosphere. A dramatic two-story foyer sets

  Donna Gennaro Howard Hanna Rand Realty

  9 Derose Ln, Chester, NY 10918
• 

  

  /50

  $370,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  3815 Whispering Hills Dr, Chester, NY 10918

  Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

  David Kraus MK Realty Inc

  3815 Whispering Hills Dr, Chester, NY 10918
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  /38

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,711 Sq Ft

  63 Whitetail Run, Chester, NY 10918

  This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

  Artan Kukaj SPIRAL NY Real Estate LLC

  63 Whitetail Run, Chester, NY 10918
• 

  

  /23

  $390,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow Ave, Chester, NY 10918
• 

  

  /50

  $440,800

  • 3 Beds
  • 1 Bath
  • 2,016 Sq Ft

  815 Craigville Rd, Chester, NY 10918

  We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property.Originally built

  MaryBeth O'Hara Ellis Sotheby's Intl Realty

  815 Craigville Rd, Chester, NY 10918
• 

  

  /44

  $649,999

  Open House 7/11 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 2,316 Sq Ft

  424 Laroe Rd, Chester, NY 10918

  Welcome to 424 Laroe Road in Chester, a move-in–ready home that blends classic Hudson Valley charm with thoughtful updates. A bright main level offers a comfortable living area, dedicated dining space, and a well-appointed kitchen with ample storage and workspace. Upstairs, well-proportioned rooms provide flexible layouts for sleeping, a home office, or hobbies. Refreshed baths feature clean,

  Jeffrey Morrissey Epique Realty

  424 Laroe Rd, Chester, NY 10918
• 

  

  /35

  $879,999

  Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  24 Boville Ct, Chester, NY 10918

  Welcome to 24 Boville Court, a beautifully situated home tucked away on a quiet cul-de-sac in the desirable Town of Chester. Offering a wonderful blend of comfort, privacy, and convenience, this property is the perfect place to call home. Step inside to discover bright and inviting living spaces, generously sized rooms, and a functional floor plan designed for both everyday living and

  Jennifer Acevedo KW Hudson Valley United

  24 Boville Ct, Chester, NY 10918
• 

  

  /5

  $759,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  90 Pewter Cir, Chester, NY 10918

  This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a

  Carla Terranova Keller Williams Realty

  90 Pewter Cir, Chester, NY 10918
• 

  

  /23

  $650,000

  $49K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft

  35 Peddler Hill Rd, Monroe, NY 10950

  "High-Value Property – Exceptional Location, Endless Potential" Discover an exceptional investment opportunity in a highly sought-after area! This charming home sits on over half an acre of prime real estate, making it perfect for investors, builders, or anyone looking to secure a valuable asset. With its spacious lot and desirable location, this property promises not only immediate returns but

  Joseph Rosenfeld Flag Realty Group

  35 Peddler Hill Rd, Monroe, NY 10950
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  /48

  $1,299,900

  New Construction $150K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,508 Sq Ft

  145 Kings Highway Bypass, Chester, NY 10918

  Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.

  Courtney Tablante Keller Williams Realty

  145 Kings Highway Bypass, Chester, NY 10918
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  /50

  $1,145,000

  $50K PRICE DROP

  • 9 Beds
  • 6.5 Baths
  • 4,965 Sq Ft

  19 High St, Chester, NY 10918

  Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

  Beth Palma Keller Williams Realty

  19 High St, Chester, NY 10918
• 

  

  /28

  $500,000

  • 3 Beds
  • 2 Baths
  • 2,688 Sq Ft

  5 N Hudson St Unit N, Chester, NY 10918

  3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

  Bernadette Corrigan Keller Williams Realty

  5 N Hudson St Unit N, Chester, NY 10918
• 

  

  /43

  $430,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,177 Sq Ft

  151 Laroe Rd, Chester, NY 10918

  What a remarkable property in the town of Chester, NY-a highly sought after town in the southern Hudson Valley, only 45 minutes from the GW Bridge! This 3 bedroom, 2 bathroom house boasts tons of modern and energy efficient features. A massive renovation done only 5 years ago leaves you with nothing to maintain except to pick your paint colors and finishes. 1st floor main bedroom and additional

  Todd Sullivan Keller Williams Realty

  151 Laroe Rd, Chester, NY 10918
• 

  

  /47

  $825,000

  • 4 Beds
  • 2.5 Baths
  • 2,732 Sq Ft

  45 Whitetail Run, Chester, NY 10918

  Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely

  Melissa Forsyth Hudson Valley Home Connection

  45 Whitetail Run, Chester, NY 10918
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  /49

  $769,000

  $31K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,718 Sq Ft

  58 Nancy Ln, Chester, NY 10918

  Price improvement! Wait until you see all this home has to offer! Perched atop the desirable Fieldcrest subdivision with sweeping panoramic views and unforgettable sunsets, this spectacular Colonial offers exceptional space, comfort, and versatility both inside and out. Set on 1.3 picturesque acres, this beautifully maintained home is designed for everyday living and effortless entertaining.A

  Gina Dudgeon Howard Hanna Rand Realty

  58 Nancy Ln, Chester, NY 10918
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  /9

  $879,900

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  1414 Kings Hwy, Chester, NY 10918

  Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

  Carla Terranova Keller Williams Realty

  1414 Kings Hwy, Chester, NY 10918
• 

  

  /29

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  3318 State Route 94, Chester, NY 10918

  This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the

  Asha Keegan Howard Hanna Rand Realty

  3318 State Route 94, Chester, NY 10918
• 

  

  /3

  $899,000

  $100K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,535 Sq Ft

  220 Oxford Rd, Chester, NY 10918

  220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

  Moche Halpern Blooming Realty

  220 Oxford Rd, Chester, NY 10918
• 

  

  /23

  $550,000

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,083 Sq Ft

  94 Booth Rd, Chester, NY 10918

  Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths,

  Craig Watters Compass Greater NY, LLC

  94 Booth Rd, Chester, NY 10918
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  /46

  $825,000

  Open Sat 1PM - 4PM $63K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  149 Creamery Pond Rd, Chester, NY 10918

  Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick school district!. This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow

  Carla Terranova Keller Williams Realty

  149 Creamery Pond Rd, Chester, NY 10918
• 

  /2

  $350,000

  • Land
  • 2 Acres
  • $175,000 per Acre

  220 Oxford Rd, Chester, NY 10918

  A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

  Chaim Weiss MS Realty Group USA, Inc

  220 Oxford Rd, Chester, NY 10918
• 

  

  /44

  $869,000

  $31K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,846 Sq Ft

  2 Heidi Ln, Chester, NY 10918

  Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every

  Frank Muccari Cronin & Company Real Estate

  2 Heidi Ln, Chester, NY 10918
• 

  

  /50

  $3,400,000

  • 4 Beds
  • 4 Baths
  • 7,750 Sq Ft

  19 Greentree Ln, Chester, NY 10918

  Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

  Jake Garay Serhant LLC

  19 Greentree Ln, Chester, NY 10918
• 

  

  /28

  $579,999

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft

  24 Walnut St, Chester, NY 10918

  Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange

  Tara Roufanis Keller Williams Village Sq Rlt

  24 Walnut St, Chester, NY 10918
• 

  

  /39

  $365,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  2703 Whispering Hills, Chester, NY 10918

  Welcome to 2703 Whispering Hills in Chester, NY — a beautifully updated home that stands out from the rest. This well-maintained unit features numerous recent improvements, including new windows, a new garage door, and a new hot water heater, providing peace of mind for years to come. The central air conditioning system is approximately five years old and keeps the home comfortable throughout the

  Rebecca Matta-Candela Keller Williams Realty

  2703 Whispering Hills, Chester, NY 10918
• 

  

  /7

  $900,000

  • 4 Beds
  • 2.5 Baths
  • 2,588 Sq Ft

  60 Whitetail Run, Chester, NY 10918

  Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and

  Isaac Rottenberg Realty Blue Corp

  60 Whitetail Run, Chester, NY 10918
• 

  

  /33

  $260,000

  $35K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  1401 Whispering Hills, Chester, NY 10918

  Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

  Debbie Goldstein Howard Hanna Rand Realty

  1401 Whispering Hills, Chester, NY 10918
• 

  /2

  $199,000

  • Land
  • 7.2 Acres
  • $27,639 per Acre

  0 Oxford Rd Unit KEY946546, Blooming Grove, NY 10918

  7.20 Acre Vacant land, Nice partly cleared and private land

  Chaim Spitzer Blooming Realty

  0 Oxford Rd Unit KEY946546, Blooming Grove, NY 10918
• 

  

  /40

  $500,000

  • 4 Beds
  • 2 Baths
  • 1,730 Sq Ft

  37 Surrey Rd, Chester, NY 10918

  Looking for a 4-bed home in Chester, NY with a pool, major system updates, generous outdoor living space, and convenient access to schools, parks, shopping, and commuter routes? Welcome to 37 Surrey Road, a beautifully maintained raised ranch offering 4 bedrooms, 2 full bathrooms, approximately 1,730 square feet of living space, and a backyard designed for entertaining and relaxation. Set on a

  Lady Castro eXp Realty

  37 Surrey Rd, Chester, NY 10918
• 

  

  /29

  $499,900

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,032 Sq Ft

  35 Maple Ave, Chester, NY 10918

  Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances,

  Joanne Timperio RE/MAX Benchmark Realty Group

  35 Maple Ave, Chester, NY 10918
• 

  

  /42

  $849,900

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft

  2 Primrose Ln, Chester, NY 10918

  Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

  Janet Rendle Weichert Realtors

  2 Primrose Ln, Chester, NY 10918
• 

  

  /34

  $949,000

  $50K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
• 

  

  /43

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  19 Bull Mine Rd, Chester, NY 10918

  Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

  James Cosenza BHG Real Estate Green Team

  19 Bull Mine Rd, Chester, NY 10918

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