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Chester Homes for Sale

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  • 7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    /48

    $730,000

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft

    7 Park Place, Chester, NY 10918

    Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

    Agent Photo

    Luanne McGann

    Century 21 Full Service Realty

    (845) 447-0221

    7 Park Place, Chester, NY 10918
  • 5 Roggia Rd, Chester, NY 10918
    5 Roggia Rd, Chester, NY 10918
    5 Roggia Rd, Chester, NY 10918
    /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

    Agent Photo

    Nazma Sooknanan

    Nazma Real Estate LLC

    (845) 606-3972

    5 Roggia Rd, Chester, NY 10918
  • 53 Gibson Hill Rd, Chester, NY 10918
    53 Gibson Hill Rd, Chester, NY 10918
    53 Gibson Hill Rd, Chester, NY 10918
    /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

    Agent Photo

    Ammar Iqbal

    eXp Realty

    (845) 328-2396

    53 Gibson Hill Rd, Chester, NY 10918
  • 22 Cambridge Cir, Monroe, NY 10950
    22 Cambridge Cir, Monroe, NY 10950
    22 Cambridge Cir, Monroe, NY 10950
    /45

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    22 Cambridge Cir, Monroe, NY 10950

    Exceptional value in Monroe Woodbury! Well maintained contemporary raised ranch in Lake Region Estates on prime corner lot, featuring an open floor plan ideal for everyday living and entertaining. Updated kitchen with center island, stainless steel appliances, and a bright garden window perfect for herbs and plants. Spacious living room offers a cathedral ceiling and oversized windows for

    Agent Photo

    Jade Oliverio

    Howard Hanna Rand Realty

    (329) 666-0425

    22 Cambridge Cir, Monroe, NY 10950
  • 34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    /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
  • 9 Mount Ridge Ct, Monroe, NY 10950
    9 Mount Ridge Ct, Monroe, NY 10950
    9 Mount Ridge Ct, Monroe, NY 10950
    /49

    $635,000

    • 5 Beds
    • 3 Baths
    • 2,983 Sq Ft

    9 Mount Ridge Ct, Monroe, NY 10950

    Spacious Center Hall Colonial with open concept kitchen, fireplace, deck, and large primary suite with walk-in closets. A dramatic two-story entry leads to an open concept kitchen with abundant counter space, large dinette area, and sliding doors to a spacious deck --perfect for entertaining. The kitchen flows into the open family room and living room with fireplace, creating an ideal setup for

    Richard Froehlich RE/MAX Benchmark Realty Group

    9 Mount Ridge Ct, Monroe, NY 10950
  • 90 Pewter Cir, Chester, NY 10918
    90 Pewter Cir, Chester, NY 10918
    90 Pewter Cir, 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
  • 10 Hidden Dr, Monroe, NY 10950
    10 Hidden Dr, Monroe, NY 10950
    10 Hidden Dr, Monroe, NY 10950
    /47

    $690,000

    • 4 Beds
    • 3 Baths
    • 3,636 Sq Ft

    10 Hidden Dr, Monroe, NY 10950

    This expansive home offers 4 large bedrooms and 3 full bathrooms, providing the perfect blend of space and comfort. The updated kitchen and baths add a modern touch, while hardwood floors and high hats throughout enhance the home’s warm and inviting feel. An abundance of large windows fills the home with natural light. The full basement offers space galore, A beautiful brick fireplace serves as

    rosemary mcginn Century 21 Full Service Realty

    10 Hidden Dr, Monroe, NY 10950
  • 1414 Kings Hwy, Chester, NY 10918
    1414 Kings Hwy, Chester, NY 10918
    1414 Kings Hwy, Chester, NY 10918
    /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
  • 149 Creamery Pond Rd, Chester, NY 10918
    149 Creamery Pond Rd, Chester, NY 10918
    149 Creamery Pond Rd, Chester, NY 10918
    /50

    $887,500 Open Sun 1PM - 4PM

    • 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
  • 10 Well Sweep Ln, Chester, NY 10918
    10 Well Sweep Ln, Chester, NY 10918
    10 Well Sweep Ln, Chester, NY 10918
    /8

    $869,900

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    10 Well Sweep Ln, 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

    10 Well Sweep Ln, Chester, NY 10918
  • 4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    /50

    $840,000

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

    4 Debbie Ct, Chester, NY 10918

    DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year

    Joseph Rosenfeld Flag Realty Group

    4 Debbie Ct, Chester, NY 10918
  • 487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    /50

    $725,000

    • 6 Beds
    • 3.5 Baths
    • 4,204 Sq Ft

    487 Black Meadow Rd, Chester, NY 10918

    A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

    Dominic Santagato Joseph Baratta Company Realty

    487 Black Meadow Rd, Chester, NY 10918
  • 78 Pickerel Rd, Monroe, NY 10950
    78 Pickerel Rd, Monroe, NY 10950
    78 Pickerel Rd, Monroe, NY 10950
    /41

    $569,000

    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    78 Pickerel Rd, Monroe, NY 10950

    Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized

    Mary Ann Mitchell eXp Realty

    78 Pickerel Rd, Monroe, NY 10950
  • 52 Wilson Rd, Monroe, NY 10950
    52 Wilson Rd, Monroe, NY 10950
    52 Wilson Rd, Monroe, NY 10950
    /38

    $565,000

    • 4 Beds
    • 3 Baths
    • 1,846 Sq Ft

    52 Wilson Rd, Monroe, NY 10950

    Welcome to this beautifully maintained 4-bedroom, 3-bath raised ranch in the highly sought-after Lake Hill Farms community, located within the Monroe-Woodbury School District.Upon entry, you’re greeted by an oversized foyer featuring wide stairs updated with stunning hardwood that runs throughout. The main level offers a bright eat-in kitchen with sliding glass doors that open to a deck

    Claudia Lepore Keller Williams Realty

    52 Wilson Rd, Monroe, NY 10950
  • 16 Sunset Ridge, Monroe, NY 10950
    16 Sunset Ridge, Monroe, NY 10950
    /2

    $1,299,000 Coming Soon

    • 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
  • 16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    /49

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    16 Oakland Ave, Chester, NY 10918

    Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potential and great commuter location with close proximity tohighway! Welcome to this spacious 4-bedroom, 2.5-bath home nestled in the picturesque town of Chester, NY, in the heart of the beautifulHudson Valley. Offering 2,090 sq ft of living space, plus a finished rec room with an additional 1,026 sq ft,

    Vikki Garby BHG Real Estate Green Team

    16 Oakland Ave, Chester, NY 10918
  • 32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, 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
  • 2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    /24

    $275,000

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    2113 Whispering Hills Unit 178, Chester, NY 10918

    Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

    Valerie Quinn Keller Williams Realty

    2113 Whispering Hills Unit 178, Chester, NY 10918
  • 145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    /50

    $1,450,000 Open Sat 11AM - 1PM

    • 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
  • 5 N Hudson St Unit N, Chester, NY 10918
    5 N Hudson St Unit N, Chester, NY 10918
    5 N Hudson St Unit N, 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
  • 503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    /13

    $239,900

    • 2 Beds
    • 1.5 Baths
    • 1,240 Sq Ft

    503 Mountain Laurel Dr, Monroe, NY 10950

    Peaceful country living in this two-story center lakefront unit with full basement located in Windridge community. Enjoy incredible mountain views from this large private Townhome. Primary bedroom on upper level with walk in closet and large sitting area which can be used as home office. Slider to rear patio with beautiful lake views!! Large living and dining area. Beautiful quiet complex close

    Margaret Galatro ARC Realty 1 in Sales

    503 Mountain Laurel Dr, Monroe, NY 10950
  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, 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
  • 38 Jefferson Dr, Monroe, NY 10950
    38 Jefferson Dr, Monroe, NY 10950
    38 Jefferson Dr, Monroe, NY 10950
    /21

    $549,000

    • 3 Beds
    • 1.5 Baths
    • 1,644 Sq Ft

    38 Jefferson Dr, Monroe, NY 10950

    Welcome home! This wonderful quiet neighborhood, Lake Hill Farms, off of Lakes Rd. On the outskirts of Monroe, makes this a great commuter and convenient location, from hiking trails, parks, Woodbury Commons, shopping, train station, and dinning. This home has a nice sized backyard. The deck furniture and gazebo are included, underneath your deck is an enclosed screened in patio which will give

    Lance Gibbs Arrowhead Realty

    38 Jefferson Dr, Monroe, NY 10950
  • 607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    /39

    $319,900

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    607 Mountain Laurel Dr, Monroe, NY 10950

    Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

    Rosalie Cook Weichert Realtors

    607 Mountain Laurel Dr, Monroe, NY 10950
  • 53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    /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
  • 2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    /9

    $149,900

    • Land
    • 0.2 Acre
    • $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
  • 30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    /7

    $500,000

    • Land
    • 9.78 Acres
    • $51,125 per Acre

    30 Harding Way, Chester, NY 10950

    An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • 1005 Whispering Hills, Chester, NY 10918
    1005 Whispering Hills, Chester, NY 10918
    /2

    $249,900

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft

    1005 Whispering Hills, Chester, NY 10918

    ONLY CASH OFFERS!! LOW TAXES! Two Level Living! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage! Updated Kitchen! Updated Bathrooms! Living Room with Fireplace! Sliders To Patio! Perfect Commuter Location! Walk to NYC Bus & Shopping! Close to Major Highways! Country Club Living! Clubhouses! Pools! Tennis! Tot Lot! Basketball! Dog Walk!

    Amanda Dnistrian ARC Realty 1 in Sales

    1005 Whispering Hills, Chester, NY 10918
  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, 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
  • 50 Elkay Dr, Chester, NY 10918
    50 Elkay Dr, Chester, NY 10918
    50 Elkay Dr, Chester, 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
  • 85 Surrey Rd, Chester, NY 10918
    85 Surrey Rd, Chester, NY 10918
    85 Surrey Rd, Chester, NY 10918
    /35

    $524,900

    • 4 Beds
    • 2 Baths
    • 2,076 Sq Ft

    85 Surrey Rd, Chester, NY 10918

    Welcome to 85 Surrey Road in Chester, NY, a beautifully updated home that blends modern upgrades with timeless comfort in the heart of the Hudson Valley. This move-in-ready property offers everything today’s buyers are searching for—energy efficiency, stylish finishes, and exceptional indoor-outdoor living.Step inside to discover a fabulously updated kitchen, designed for both everyday living

    Rebecca Matta-Candela Keller Williams Realty

    85 Surrey Rd, Chester, NY 10918
  • 150 Lake Region Blvd, Monroe, NY 10950
    150 Lake Region Blvd, Monroe, NY 10950
    150 Lake Region Blvd, Monroe, NY 10950
    /50

    $580,000

    • 4 Beds
    • 2.5 Baths
    • 2,112 Sq Ft

    150 Lake Region Blvd, Monroe, NY 10950

    Welcome to 150 Lake Region Blvd — a well-maintained home located in Monroe’s desirable Lake Region / Walton Park area. The moment you step inside, you’re greeted by warm hardwood floors and an open, comfortable layout that feels welcoming without being overwhelming. The home offers a natural flow from room to room, making everyday living and entertaining easy and functional. With 4 oversized

    Pete Wolven Hudson Valley Home Connection

    150 Lake Region Blvd, Monroe, NY 10950
  • 7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    /23

    $410,000

    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    7 Hambletonian Ave, Chester, NY 10918

    This 2 bedroom charmer with additional room offers potential 3 bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • 195 Eagleton Dr, Monroe, NY 10950
    195 Eagleton Dr, Monroe, NY 10950
    195 Eagleton Dr, Monroe, NY 10950
    /26

    $394,900

    • 3 Beds
    • 2.5 Baths
    • 1,762 Sq Ft

    195 Eagleton Dr, Monroe, NY 10950

    Beautifully maintained 3-bedroom, 2.5 bath home offering scenic lake views and a comfortable, well-designed layout. This home features stainless steel appliances, fireplace, hardwood floors and numerous recent updates throughout. Enjoy tranquil water views from the charming Juliette balcony perfect for morning coffee or relaxing evenings watching the sunset. Experience the ease of condo living

    Patricia Spagna Century 21 Realty Center

    195 Eagleton Dr, Monroe, NY 10950
  • 1367 Kings Hwy, Chester, NY 10918
    1367 Kings Hwy, Chester, NY 10918
    1367 Kings Hwy, Chester, NY 10918
    /13

    $460,000

    • 3 Beds
    • 1.5 Baths
    • 1,728 Sq Ft

    1367 Kings Hwy, Chester, NY 10918

    Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

    Mark Karten Karten Real Estate Svcs LLC

    1367 Kings Hwy, Chester, NY 10918
  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /36

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    2 Pine Hill Rd, Chester, NY 10918

    The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

    Richard Ellis Ellis Sotheby's Intl Realty

    2 Pine Hill Rd, Chester, NY 10918
  • 2203 Whispering Hills, Chester, NY 10918
    2203 Whispering Hills, Chester, NY 10918
    2203 Whispering Hills, Chester, NY 10918
    /24

    $362,900

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

    2203 Whispering Hills, Chester, NY 10918

    Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

    Marie Altieri Howard Hanna Rand Realty

    2203 Whispering Hills, Chester, NY 10918
  • 558 Pine Hill Rd, Chester, NY 10918
    558 Pine Hill Rd, Chester, NY 10918
    558 Pine Hill Rd, Chester, NY 10918
    /50

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 3,120 Sq Ft

    558 Pine Hill Rd, Chester, NY 10918

    Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

    Charnie Guttmann eRealty Advisors, Inc

    558 Pine Hill Rd, Chester, NY 10918
  • 40 Poplar Dr, Monroe, NY 10950
    40 Poplar Dr, Monroe, NY 10950
    40 Poplar Dr, Monroe, NY 10950
    /48

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,108 Sq Ft

    40 Poplar Dr, Monroe, NY 10950

    HIGHEST AND BEST BY 4/20 at 6PM------Best Value in Monroe — Updated Ranch on Quiet Street with Room to Grow! There may be no better house for the money in Monroe. This adorable, well-maintained ranch clearly shows the pride of ownership from 16 years of loving care. A brand-new front entrance door welcomes you into a bright foyer and spacious living room featuring a large picture window that

    Richard Froehlich RE/MAX Benchmark Realty Group

    40 Poplar Dr, Monroe, NY 10950

Showing Results 1 - 40, Page 1 of 2

New York Orange County Chester Chester

Real Estate & Homes for Sale in Chester, Chester

Frequently Asked Questions Why Live in Chester

Is Chester a good place to live?
Chester is a good place to live. Chester is considered very car-dependent and somewhat bikeable. Chester is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Chester has 4 parks for recreational activities. It has a median age of 41. The average household income is $137,158 which is above the national average. College graduates make up 39% of residents. A majority of residents in Chester are home owners, with 21.5% of residents renting and 78.5% of residents owning their home. A local real estate agent serving Chester can help you decide if this neighborhood is the right one for you. Learn more on our Chester neighborhood guide.
Is Chester, NY a safe neighborhood?
Chester, NY is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $500,000. If you put a 20% down payment of $100,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $2,480 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $106K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chester is $137K.
What are the best public schools in Chester?
The best public schools that serve Chester are:
What are the best private schools in Chester?
The best private schools that serve Chester are:
What are the most popular zip codes in Chester, Chester, NY?
The most popular zip codes in Chester, Chester, NY include 10918, 10990, 10950, 10924 and 10921.
Learn more about living in Chester

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 55 days on the market compared to the national average of 56 days. The median sale price for homes in Chester, NY over the last 12 months is $475,000, down 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$475,000
Median Single Family Sale Price
$575,000
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$299,500
Average Price Per Sq Ft
$269
Number of Homes for Sale
41
Last 12 months Home Sales
117
Months of Supply
4.20
Median List Price
$500,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
How to Buy a Home How to Finance a Home How to Sell a Home

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