Newest Homes for Sale in Chester, NY

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  /37

  $419,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft

  332 Heritage Ln, Monroe, NY 10950

  Spacious and well-maintained 3BR/2.5BA townhouse in desirable Windridge community. Features include updated laminate hardwood flooring, fireplace, eat-in kitchen, stainless steel appliances, private balcony off primary bedroom, sliding glass doors to private patio, attached 1-car garage with storage loft, and pull-down attic access. Community amenities include pool, clubhouse, and park.

  Martin Remo RE/MAX Prime Properties

  332 Heritage Ln, Monroe, NY 10950
• Explore Chester

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  /47

  $985,000

  Coming Soon

  • 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

  (845) 606-3942

  86 Long Vista Ln, Chester, NY 10918
• 

  

  

  /25

  $779,000

  Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 2,948 Sq Ft

  270 Bull Mill Rd, Chester, NY 10918

  Welcome to 270 Bull Mill Road — a timeless country retreat nestled in the heart of Chester. Set on beautifully landscaped property with mature trees, stone walls, and exceptional privacy, this stunning 1822 farmhouse seamlessly blends historic charm with modern comfort.From the moment you arrive, you’ll be captivated by the home’s character and warmth. Inside, an inviting open floor plan

  Rebecca Matta-Candela Keller Williams Realty

  270 Bull Mill Rd, Chester, NY 10918
• 

  

  

  /21

  $590,000

  Open Sat 1PM - 2PM

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

  94 Booth Rd, Chester, NY 10918

  Solid, sturdy and well maintained home in a quiet neighborhood adjacent to state parkland. Woods, pond and manicured lawn, close to transportation.

  Craig Watters Compass Greater NY, LLC

  94 Booth Rd, Chester, NY 10918
• 

  

  /2

  $65,000

  • Land
  • 1 Acre
  • $65,000 per Acre

  888 Landon Hill Rd, Chester, NY 12817

  One acre building lot. Property is cleared for building, 200 amp electric service installed and a point well on the property. There is currently a 14x40 ''tiny home'' on the property that can be purchased separately or the seller will remove. Minutes from Pottersville, close to Chestertown and Schroon Lake. Appx 20 mins to Gore Mnt Ski Center, 15 mins to Schroon Lake and only 10 mins from Loon

  Kelli May Better Way Realty

  888 Landon Hill Rd, Chester, NY 12817
• 

  /2

  $275,000

  • Land
  • 7.53 Acres
  • $36,521 per Acre

  00 McPhillips Pine Ln, Chester, NY 12817

  If you are looking for an ultra private lot with access (dock and beach rights) to one the pristine exclusive lakes in the Adirondacks, you found it. Friends Lake is the home to cool people and is private, jet-ski free, with a water ski course and simply no nonsense. Only 2O minutes to Lake George and Gore Mountain Ski Area. About 4 hours from NYC and 2.5 hours to Montreal. Saratoga Springs is an

  Michael Lynch Coldwell Banker Prime Properties

  00 McPhillips Pine Ln, Chester, NY 12817
• 

  

  /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
• 

  

  /49

  $799,000

  • 5 Beds
  • 5.5 Baths
  • 5,403 Sq Ft

  4 Debbie Ct, Chester, NY 10918

  Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
• 

  

  /39

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  35 Maple Ln, Monroe, NY 10950

  Looking for the perfect blend of comfort, convenience, and outdoor living in Monroe? This beautifully maintained ranch delivers easy single level living with bonus space inside and out. Featuring 3 bedrooms and 2 full bathrooms, this home also offers a finished lower level complete with an additional room, giving you the flexibility for a home office, guest space, gym, playroom, or recreation

  Kewin Garabito eXp Realty

  35 Maple Ln, Monroe, NY 10950
• 

  

  /50

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,389 Sq Ft

  18 Fernglade Ct, Chester, NY 10918

  Welcome to this beautifully appointed Colonial that perfectly blends timeless design with modern living. Offering 3 generously sized bedrooms—including a spacious primary suite with a large walk-in closet and a spa-like ensuite bath featuring a soaking tub and separate 4-foot shower—this home delivers both comfort and style. A versatile bonus room provides the flexibility for a home office,

  Richard Froehlich RE/MAX Benchmark Realty Group

  18 Fernglade Ct, Chester, NY 10918
• 

  

  /47

  $825,000

  Open Sun 11AM - 1PM

  • 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
• 

  

  /25

  $125,000

  • Land
  • 13.33 Acres
  • $9,377 per Acre

  L9 Byrd Pond, Chester, NY 12853

  Open walking trail around the property and very easy to navigate. Private 13+ acre building parcel just minutes from Gore Mountain and the conveniences of North Creek. The land is gently sloping with a roughed-in driveway/road already leading in from Bird Pond Road, offering a great head start for future access and site planning. Several attractive building locations can be found throughout the

  Walter Swartz Gallo Realty ADK Inc

  L9 Byrd Pond, Chester, NY 12853
• 

  

  /17

  $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

  (845) 582-7035

  492 Black Meadow Rd, Chester, NY 10918
• 

  

  /26

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  11 Oxford Depot, Chester, NY 10918

  Discover the charm and potential of 11 Oxford Depot Rd, Chester, NY — a spacious and inviting 3-bedroom, 2-bath home packed with character, versatility, and value. From the moment you enter, you’ll appreciate the warm hardwood floors, oversized living spaces, and flexible layout designed for today’s lifestyle. Whether you need a home office, playroom, guest room, or creative space, this home

  Aneudy Rosa Keller Williams Realty

  11 Oxford Depot, Chester, NY 10918
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  /38

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,778 Sq Ft

  1 N Hudson St Unit N, Chester, NY 10918

  Welcome home to 1 North Hudson Street — a meticulously maintained Cape Cod that is truly beautiful inside and out. From the moment you arrive, the curb appeal speaks for itself. Lush, manicured grounds frame this charming brick and white-sided Cape Cod, where mature trees, vibrant landscaping, and a stunning bluestone patio set the stage for a lifestyle of comfort and ease. Whether you're hosting

  

  Alison Orlando

  Keller Williams Hudson Valley

  (845) 448-9391

  1 N Hudson St Unit N, 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
• 

  

  /18

  $189,000

  • Land
  • 3.14 Acres
  • $60,191 per Acre

  2 Dixon Rd, Chester, NY 12817

  Fish, Paddle, Build! Own an incredible 509' of private frontage on the Schroon River, complete with your very own mini island and over 3 buildable acres to create your Adirondack escape. Driveway is already in place with power available at the road, making your future plans even easier. Located just south of the dam (no direct access to Schroon Lake), this peaceful setting is ideal for fishing,

  Angie Mead Gallo Realty ADK Inc

  2 Dixon Rd, Chester, NY 12817
• 

  

  /23

  $315,000

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  301 Mountain Ave, Monroe, NY 10950

  Move right into this beautifully renovated 2 bedroom 1 bathroom home which has been fully updated for modern living. Upon entry you will find an open dining and kitchen area with new stainless steel appliances, quartz countertops and ample cooking space. The living room leads into the updated bathroom and two spacious bedrooms. Find new oak floors, new paint and tons of natural light throughout

  Samantha McCrory Exit Realty Connections

  301 Mountain Ave, Monroe, NY 10950
• 

  

  /36

  $495,000

  • 4 Beds
  • 3 Baths
  • 1,792 Sq Ft

  18 Southside Dr, Monroe, NY 10950

  Welcome to 18 Southside Drive, this charming ranch-style home nestled in the highly sought-after Walton Park neighborhood of Monroe. Offering the ultimate ease of effortless one level living, this spacious residence boasts 4 bedrooms, 3 full bathrooms, and a versatile layout situated within the premier Monroe-Woodbury School District. Major mechanical updates over the past decade provide ultimate

  Nikki Grzegorzewski Keller Williams Realty

  18 Southside Dr, Monroe, NY 10950
• 

  

  /37

  $425,000

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

  2722 Whispering Hills Unit 542, Chester, NY 10918

  New beginnings offered in this light and bright fully refreshed end unit in the highly sought after Whispering Hills community. Featuring new designer paint throughout, brand new luxury vinyl plank (LVP) flooring, new stainless steel appliances, two car garage with recently installed garage doors and so much more. Located close to major highway, NYC bus and shopping. Club house with gym,

  

  Erin Connolly-Frontino

  Artisan Realty

  (845) 932-1237

  2722 Whispering Hills Unit 542, Chester, NY 10918
• 

  

  /50

  $370,000

  • 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
• 

  

  /3

  $999,000

  • 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
• 

  

  /35

  $999,999

  • 5 Beds
  • 2.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, Chester, NY 10918
• 

  

  /45

  $529,000

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  63 Hubshop Rd, Chester, NY 10918

  Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

  Charles Moore Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
• 

  

  /46

  $799,999

  Open Sun 12PM - 2PM

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

  58 Nancy Ln, Chester, NY 10918

  Brand new to the market! This spectacular spacious colonial has room for everyone! Perched at the top of the Fieldcrest subdivision with sweeping views that can’t be missed you will find this property that offers something for everyone.Set on 1.3 picturesque acres in a desirable neighborhood, this beautifully maintained home offers the perfect blend of comfort, space, and functionality. Enjoy

  Gina Dudgeon Howard Hanna Rand Realty

  58 Nancy Ln, Chester, NY 10918
• 

  

  /30

  $550,000

  • 5 Beds
  • 2.5 Baths
  • 1,815 Sq Ft

  208 Glenmere Rd, Chester, NY 10918

  Welcome to 208 Glenmere Rd, Chester, NY! This charming country home, nestled on picturesque grounds, is now available for sale. The main level features an eat-in kitchen, a formal dining room, and two spacious bedrooms, while the upper level offers three additional bedrooms. The newly renovated cottage boasts new flooring, windows, kitchen, and heating system. The interior has been freshly

  David Kraus MK Realty Inc

  208 Glenmere Rd, Chester, NY 10918
• 

  

  /43

  $450,000

  • 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
• 

  

  /50

  $1,195,000

  • 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
• 

  

  /12

  $640,000

  • 3 Beds
  • 1.5 Baths
  • 2,136 Sq Ft

  4 Greycourt Rd, Chester, NY 10918

  Welcome to 4 Greycourt Road, your dream home awaits! This delightful residence boasts a spacious 6-room layout, featuring 3 generous bedrooms and 1.5 baths, all nestled on over 2.5 acres of stunning greenery. Imagine whipping up culinary masterpieces in the well-appointed kitchen, complete with ample cabinetry and modern appliances—perfect for any cooking enthusiast! Each bedroom is a serene

  Nathen Singer MK Realty Inc

  4 Greycourt Rd, Chester, NY 10918
• 

  

  /8

  $1,299,000

  • 4 Beds
  • 3.5 Baths
  • 5,712 Sq Ft

  16 Sunset Ridge, Monroe, NY 10950

  Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates Community, this expansive Colonial-style estate delivers classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertaining, this home offers generous spaces, lush

  Carmela Lopez Borrazas Serhant LLC

  16 Sunset Ridge, Monroe, NY 10950
• 

  

  /32

  $319,900

  $4K PRICE INCREASE

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  2820 Whispering Hills, Chester, NY 10918

  Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

  Anne Marie Scouarnec R2M Realty Inc.

  2820 Whispering Hills, Chester, NY 10918
• 

  

  /45

  $899,900

  • 5 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
• 

  

  /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
• 

  

  /29

  $529,900

  $20K 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
• 

  

  /50

  $849,900

  $38K 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! 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 layout designed for everyday living. The updated kitchen,

  Carla Terranova Keller Williams Realty

  149 Creamery Pond Rd, Chester, NY 10918
• 

  

  /50

  $679,900

  $69K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  17 Woodridge Dr, Chester, NY 10918

  Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4 years young. The pools heating system runs on propane tank. Entire home was freshly

  Sharon Kushner eXp Realty

  17 Woodridge Dr, Chester, NY 10918
• 

  

  /24

  $165,000

  • Land
  • 31,798 Sq Ft
  • $226,027 per Acre

  L3 Emily Ln Unit Lot 3, Chester, NY 12817

  Rare opportunity to own a .73-acre vacant building lot with deeded dock and lake rights on beautiful Loon Lake. Located within the small and intimate Lakemont Association--featuring just 8 members--this property offers a unique chance to secure one of the few lake rights parcels with guaranteed docking. The lot is level and has already undergone selective clearing, making it an ideal canvas for

  Saraha Millington Gallo Realty ADK Inc

  L3 Emily Ln Unit Lot 3, Chester, NY 12817
• 

  

  /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

  (845) 328-2396

  53 Gibson Hill Rd, Chester, NY 10918
• 

  

  /49

  $1,399,777

  New Construction $50K 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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