Homes for Sale in 10918

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  /41

  $1,159,900

  • 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

  (845) 493-2930

  16 Lori Ln, Chester, NY 10918
• 

  

  

  /9

  $369,900

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

  3910 Whispering Hills, Chester, NY 10918

  Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

  

  Randolph Rogers

  eXp Realty

  (845) 957-9249

  3910 Whispering Hills, Chester, NY 10918
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  /32

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  5 Roggia Rd, Chester, NY 10918

  Welcome to this spacious and versatile home nestled at a dead end st. in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking privacy, comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and

  

  Nazma Sooknanan

  Nazma Real Estate LLC

  (845) 606-3972

  5 Roggia Rd, Chester, NY 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

  (845) 328-2396

  53 Gibson Hill Rd, Chester, NY 10918
• 

  

  /2

  $425,000 Open Sun 12PM - 2PM

  • 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 completely updated end unit featuring two car garage, brand new floors, freshly painted, update kitchen with new stainless steel appliances and so much more. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Low taxes! Town and County, $1,110.66, Village

  

  Erin Connolly-Frontino

  Artisan Realty

  (845) 932-1237

  2722 Whispering Hills Unit 542, Chester, NY 10918
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  /4

  $350,000

  • 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

  (845) 713-9754

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
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  /16

  $900,000

  • 5 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  32 Fox Hollow Dr, Blooming Grove, NY 10918

  SINGLE LEVEL LIFESTYLE! Discover this Modern Farmhouse Style RANCH on almost 6 acres. Boasting over 3,500 finished sq. ft., this thoughtfully designed home offers 5 spacious bedrooms, one of them set up as a completely private guest quarters located above the oversized 2-car garage, perfect for hosting overnight guests. From the moment you arrive, the eye-catching details and inviting 32 ft long

  

  Julissa Amaro

  Keller Williams Hudson Valley

  (845) 581-2763

  32 Fox Hollow Dr, Blooming Grove, NY 10918
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  /27

  $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
• 

  

  /5

  $759,900

  • 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
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  /47

  $799,999 Open Sat 11AM - 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
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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
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  /48

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,467 Sq Ft

  53 Odyssey Dr, Chester, NY 10918

  Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

  Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
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  /50

  $849,900

  • 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
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  /45

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Welcome to Blooming Grove NY (Chester) Monroe/Woodbury Schools! Wow! This home has a vibe! Custom built 4 bedroom colonial with a front porch, sitting on 3.2 acres fully fenced green property to protect all the flowers, foliage and specimen plantings. This home features spacious rooms throughout, hardwood floors on the main level, Eat in kitchen with open feel to the family room with a warm

  Naomi Streicher Q Home Sales

  5 Gabriels Dr, Chester, NY 10918
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  /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
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  /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
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  /34

  $999,000

  • 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
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  /8

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  /49

  $735,000

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  55 Beverly Rd, Chester, NY 10918

  Welcome to 55 Beverly Road, Chester—A Stunning, Move-In Ready Home This beautifully updated 3,156 square-foot home blends timeless charm with modern upgrades, offering space, comfort, and style throughout. The expansive floor plan features bright, inviting living areas with soaring vaulted ceilings, gleaming hardwood floors throughout, and a cozy masonry fireplace that serves as a perfect focal

  Jay Himelson Howard Hanna Rand Realty

  55 Beverly Rd, Chester, NY 10918
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  /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
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  /8

  $699,990

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  /2

  $199,000

  • Land
  • 2.6 Acres
  • $76,538 per Acre

  0 Oxford Rd Unit KEY945194, Blooming Grove, NY 10918

  2.6 Acre Vacant land, Nice piece of land

  Chaim Spitzer Blooming Realty

  0 Oxford Rd Unit KEY945194, Blooming Grove, NY 10918
• 

  

  /5

  $259,000

  • Land
  • 20.18 Acres
  • $12,834 per Acre

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  /23

  $690,000

  • 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
• 

  

  /50

  $1,450,000 Open Sun 10AM - 12PM

  • 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

  $1,195,000

  • 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
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  /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
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  /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
• 

  

  /23

  $400,000

  • 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
• 

  

  /31

  $389,000

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

  1221 Whispering Hills, Chester, NY 10918

  Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural

  Malia Leonard BUY NY REALTY LLC

  1221 Whispering Hills, Chester, NY 10918
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  /48

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 3,112 Sq Ft

  15 Old Dominion Rd, Blooming Grove, NY 10914

  With over 3,000 sq ft of living space and set on 7.5 open, level acres, this sun-filled Colonial delivers unbeatable value, inside and out. From the moment you arrive, you're greeted by wide-open skies, sweeping lawn, and views that stretch as far as the eye can see. This home has been lovingly maintained by caring owners and offers a thoughtful layout ideal for both everyday living and

  Lazar Schvimmer Blooming Realty

  15 Old Dominion Rd, Blooming Grove, NY 10914
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  /11

  $349,999

  • Land
  • 4.9 Acres
  • $71,428 per Acre

  8 Camelback Rd, Chester, NY 10918

  Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

  James Feldhaus eXp Realty

  8 Camelback Rd, Chester, NY 10918
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  /9

  $149,900

  • Land
  • 8,873 Sq Ft
  • $735,886 per Acre

  2 Imperial Park, Chester, NY 10918

  Large 2 story storage barn approx 80' x 30' with silo for sale in the Town of Chester. 5 garage doors - 4 are 6 feet high, 1 door is 7 foot high with loading dock. Plenty of storage on first and second level. Small office. Has electric, but is turned off. Has well water, but no septic - lot is too small - only .20 acre. Not a buildable lot. Barn was subdivided off from neighboring farm. Has loft

  William Scolza HomeSmart Homes & Estates

  2 Imperial Park, 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 Exit Realty Venture

  220 Oxford Rd, 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
• 

  

  /13

  $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
• 

  

  /45

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,866 Sq Ft

  2948 State Route 94, Chester, NY 10918

  Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

  Elizabeth Broderick Tuxedo Hudson Realty Corp

  2948 State Route 94, Chester, NY 10918
• 

  

  /33

  $260,000

  • 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
• 

  

  /3

  $650,000

  • Land
  • 2 Acres
  • $325,000 per Acre

  50 Elkay Dr, Chester, NY 10918

  Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

  Leib Glanz Point Realty USA

  50 Elkay Dr, Chester, NY 10918

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