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Newest Homes for Sale in Chester, NY

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  • 2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    /10

    $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
  • 7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    /20

    $425,000

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

    7 Hambletonian Ave, Chester, NY 10918

    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 atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • 34 Booth Rd, Chester, NY 10918
    34 Booth Rd, Chester, NY 10918
    34 Booth Rd, Chester, NY 10918
    /42

    $720,000

    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    34 Booth Rd, Chester, NY 10918

    Updated 4BR Colonial in Chester – Monroe-Woodbury Schools! Welcome home to this beautifully maintained 4-bedroom, 3-bath Colonial offering timeless style, functional space, and significant updates in the highly sought-after Monroe-Woodbury Central School District! A grand two-story entry foyer with a dramatic cathedral ceiling makes an impressive first impression, filling the home with natural

    Kristie Jacques Century 21 Full Service Realty

    34 Booth Rd, Chester, NY 10918
  • 2913 Whispering Hills Unit 595, Chester, NY 10918
    2913 Whispering Hills Unit 595, Chester, NY 10918
    2913 Whispering Hills Unit 595, Chester, NY 10918
    /29

    $279,900

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

    2913 Whispering Hills Unit 595, Chester, NY 10918

    Welcome to 2913 Whispering Hills Drive – A Move-In Ready End Unit in the Heart of Chester! This bright and spacious 2-bedroom, 1-bath townhouse offers an open-concept layout with soaring vaulted ceilings and an abundance of natural light. As an end unit, you’ll enjoy added privacy along with extra windows that make the space feel even more expansive. The inviting living room features a cozy

    Devon King HomeSmart Homes & Estates

    2913 Whispering Hills Unit 595, Chester, NY 10918
  • 4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    /46

    $849,999

    • 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

    Yenty Weiss Flag Realty Group

    4 Debbie Ct, Chester, NY 10918
  • 20 Goshen Rd, Chester, NY 10918
    20 Goshen Rd, Chester, NY 10918
    20 Goshen Rd, Chester, NY 10918
    /50

    $1,725,000

    • 4 Beds
    • 2.5 Baths
    • 3,348 Sq Ft

    20 Goshen Rd, Chester, NY 10918

    THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

    Ramanjit Dhanoa eXp Realty

    20 Goshen Rd, Chester, NY 10918
  • 607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    /39

    $339,900

    • 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
  • 487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    /30

    $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
  • 5 Bens Way, Chester, NY 10918
    5 Bens Way, Chester, NY 10918
    5 Bens Way, Chester, NY 10918
    /28

    $744,999 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,544 Sq Ft

    5 Bens Way, Chester, NY 10918

    Welcome to 5 Bens Way, a beautifully positioned residence tucked away on a quiet cul-de-sac in the highly sought-after Town of Chester, New York. This property offers an exceptional blend of privacy, space, and convenience, making it an outstanding opportunity for buyers seeking a well-rounded Hudson Valley lifestyle with easy access to modern amenities, commuter routes, and recreational

    Anthony Rivas Keller Williams Hudson Valley

    5 Bens Way, Chester, NY 10918
  • 38 Granite Ridge Rd, Chester, NY 12817
    38 Granite Ridge Rd, Chester, NY 12817
    38 Granite Ridge Rd, Chester, NY 12817
    /19

    $83,500

    • Land
    • 2.84 Acres
    • $29,401 per Acre

    38 Granite Ridge Rd, Chester, NY 12817

    Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

    Nicholas Khachadourian KW Platform

    38 Granite Ridge Rd, Chester, NY 12817
  • 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
  • 111 Lake Region Blvd, Monroe, NY 10950
    111 Lake Region Blvd, Monroe, NY 10950
    111 Lake Region Blvd, Monroe, NY 10950
    /22

    $309,900

    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    111 Lake Region Blvd, Monroe, NY 10950

    Charming 2BR/1BA ranch on a level lot featuring an oversized detached 2-car garage and rear deck. Bright eat-in kitchen with ample cabinetry and vinyl plank flooring. Rear deck overlooks a spacious, usable yard—ideal for outdoor enjoyment. Convenient location close to shopping, schools, and major commuter routes. Great opportunity for owner-occupants or investors alike.

    Donna Ramundo Keller Williams Valley Realty

    111 Lake Region Blvd, Monroe, NY 10950
  • 83 Lake Region Blvd, Monroe, NY 10950
    83 Lake Region Blvd, Monroe, NY 10950
    83 Lake Region Blvd, Monroe, NY 10950
    /42

    $725,890

    • 3 Beds
    • 2.5 Baths
    • 1,793 Sq Ft

    83 Lake Region Blvd, Monroe, NY 10950

    A gardeners and vacationers paradise. Look no further than a vacation in your backyard with a fully 6ft fenced in yard throughout most and a 4ft fenced in section behind thee greenhouse with 4 gates of access. Two driveways with plenty of parking! A small pond with frogs, a wooden bridge, water lilies, rocks and beautiful landscape that will soothe your soul. Over 20 fruit trees and bushes

    Wendy Todoric Keller Williams Realty

    83 Lake Region Blvd, 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
  • 4 Camelback Rd, Chester, NY 10918
    4 Camelback Rd, Chester, NY 10918
    4 Camelback Rd, Chester, NY 10918
    /48

    $999,000

    • 5 Beds
    • 4 Baths
    • 5,080 Sq Ft

    4 Camelback Rd, Chester, NY 10918

    Welcome home to 4 Camelback Road. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This

    Alexander Fayn Prominent Properties Sotheby's

    4 Camelback Rd, Chester, NY 10918
  • 34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    34 Carriage Knolls Rd, Chester, NY 12817
  • 62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    /23

    $62,000

    • Land
    • 11.11 Acres
    • $5,581 per Acre

    62 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    62 Carriage Knolls Rd, Chester, NY 12817
  • 20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    /7

    $49,500

    • Land
    • 3.36 Acres
    • $14,732 per Acre

    20 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    20 Carriage Knolls Rd, Chester, NY 12817
  • 3 Tulip Ln, Monroe, NY 10950
    3 Tulip Ln, Monroe, NY 10950
    3 Tulip Ln, Monroe, NY 10950
    /22

    $465,000

    • 4 Beds
    • 2 Baths
    • 1,932 Sq Ft

    3 Tulip Ln, Monroe, NY 10950

    Spacious raised ranch style home offering three bedrooms and two full bathrooms with 1,932 square feet of comfortable living space. Features a 1-car garage and a functional layout perfect for everyday living. The home has been freshly painted, giving it a bright, clean, move-in ready feel. A great opportunity for buyers seeking space, style, and value.

    Geni Silva Ethos Realty LLC

    3 Tulip Ln, Monroe, NY 10950
  • 60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    /10

    $37,500

    • Land
    • 1.62 Acres
    • $23,148 per Acre

    60 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for

    Walter Swartz Gallo Realty ADK Inc

    60 Carriage Knolls Rd, Chester, NY 12817
  • 22 Carriage Knolls Rd, Chester, NY 12817
    22 Carriage Knolls Rd, Chester, NY 12817
    22 Carriage Knolls Rd, Chester, NY 12817
    /7

    $39,500

    • Land
    • 2.38 Acres
    • $16,597 per Acre

    22 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    22 Carriage Knolls Rd, Chester, NY 12817
  • 13 Carriage Knolls Rd, Chester, NY 12817
    13 Carriage Knolls Rd, Chester, NY 12817
    13 Carriage Knolls Rd, Chester, NY 12817
    /16

    $37,500

    • Land
    • 2 Acres
    • $18,750 per Acre

    13 Carriage Knolls Rd, Chester, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    13 Carriage Knolls Rd, Chester, NY 12817
  • 50 Elkay Dr, Chester, NY 10918
    50 Elkay Dr, Chester, NY 10918
    50 Elkay Dr, Chester, NY 10918
    /3

    $675,000

    • Land
    • 2 Acres
    • $337,500 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
  • 145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    /15

    $1,399,999

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

    145 Kings Highway Bypass, Chester, NY 10918

    A Refined Custom Estate in One of Warwick’s Most Coveted Enclaves. Set on 3.8 private acres and surrounded by similarly distinguished luxury residences, this exceptional custom home offers the rare balance of architectural elegance, lifestyle amenities, and commuter convenience—located within the highly regarded Warwick School District. Offering over 4,500 square feet of beautifully finished

    Courtney Tablante Keller Williams Realty

    145 Kings Highway Bypass, Chester, NY 10918
  • 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
  • 5 Gabriels Dr, Chester, NY 10918
    5 Gabriels Dr, Chester, NY 10918
    5 Gabriels Dr, Chester, NY 10918
    /49

    $899,000

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

    5 Gabriels Dr, Chester, NY 10918

    Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand

    Claudia Lepore Keller Williams Realty

    5 Gabriels Dr, Chester, NY 10918
  • 12 Damian Ct, Chester, NY 10918
    12 Damian Ct, Chester, NY 10918
    12 Damian Ct, Chester, NY 10918
    /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
  • 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
  • 108 Pine Hill Rd, Chester, NY 10918
    108 Pine Hill Rd, Chester, NY 10918
    108 Pine Hill Rd, Chester, NY 10918
    /37

    $449,000

    • 4 Beds
    • 1.5 Baths
    • 1,780 Sq Ft

    108 Pine Hill Rd, Chester, NY 10918

    Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs,

    Avi Samet Avion

    108 Pine Hill Rd, Chester, NY 10918
  • 2 Garnett Hill Rd, Chester, NY 10918
    2 Garnett Hill Rd, Chester, NY 10918
    2 Garnett Hill Rd, Chester, NY 10918
    /35

    $999,999

    • 5 Beds
    • 3.5 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
  • 360 Prospect Rd, Chester, NY 10918
    360 Prospect Rd, Chester, NY 10918
    360 Prospect Rd, Chester, NY 10918
    /50

    $699,000

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

    360 Prospect Rd, Chester, NY 10918

    B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

    Joseph Mendlowitz eRealty Advisors, Inc

    360 Prospect Rd, Chester, NY 10918
  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $75,000

    • Land
    • 12 Acres
    • $6,250 per Acre

    L62.2 Moffitt Rd, Chester, NY 12817

    12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

    Carol Monroe Najer Realty

    L62.2 Moffitt Rd, Chester, NY 12817
  • 3917 Whispering Hills, Chester, NY 10918
    3917 Whispering Hills, Chester, NY 10918
    3917 Whispering Hills, Chester, NY 10918
    /28

    $314,000

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

    3917 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

    Jie Liu Keller Williams Hudson Valley

    3917 Whispering Hills, Chester, NY 10918
  • 101 Oxford Rd, Chester, NY 10918
    101 Oxford Rd, Chester, NY 10918
    /2

    $669,000

    • 3 Beds
    • 1.5 Baths
    • 1,816 Sq Ft

    101 Oxford Rd, Chester, NY 10918

    This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need

    Nathan Landau Loop Realty Inc

    101 Oxford Rd, Chester, NY 10918
  • 71 Greycourt Rd, Chester, NY 10918
    71 Greycourt Rd, Chester, NY 10918
    71 Greycourt Rd, Chester, NY 10918
    /38

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    71 Greycourt Rd, Chester, NY 10918

    Discover comfort, privacy, and convenience in this beautifully maintained home set on a 2 acre property. Located in a peaceful area, this residence offers a warm and inviting layout with a nicely sized kitchen, three comfortable bedrooms, and two well kept bathrooms.The outdoors is offering a stunning fenced backyard, lots of playground space for entertainment. Minutes to all major highways

    Lazar Schvimmer Blooming Realty

    71 Greycourt Rd, Chester, NY 10918
  • 503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    /11

    $261,250

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

    503 Mountain Laurel Dr, Monroe, NY 10950

    Two story center unit with full basement located in Windridge community. Primary bedroom has large sitting area which can be used as home office. Sliders to rear patio with lake views!! Large living and dining area. Beautiful complex with mountain views.

    Margaret Galatro ARC Realty 1 in Sales

    503 Mountain Laurel Dr, Monroe, NY 10950
  • 2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    /45

    $1,395,000

    • 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
  • 16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    /48

    $750,000

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft

    16 Oxford Springs Rd, Chester, NY 10918

    Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all

    Jennifer Gold RE/MAX Benchmark Realty Group

    16 Oxford Springs Rd, Chester, NY 10918
  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    /33

    $289,500

    • 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 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /31

    $875,000

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

    2 Pine Hill Rd, Chester, NY 10918

    Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center.

    Debbie Walsh SHAHAR Management LLC

    2 Pine Hill Rd, Chester, NY 10918

Showing Results 1 - 40, Page 1 of 2

New York Orange County Chester

Newest Listings for Sale in Chester, NY

Frequently Asked Questions

What is the average home price in Chester, NY?
Homes for sale in Chester, NY have an average home price of $604,090.
How many homes have sold over the last 12 months in Chester, NY?
101 homes have sold in Chester, NY over the last 12 months.
What are the most popular zip codes in Chester, NY?
The most popular zip codes in Chester, NY include 10918, 10990, 10950, 10924 and 10921.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $541,950. If you put a 20% down payment of $108,400 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $2,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, NY?
Chester, NY has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Greenwood Lake Elementary School, Warwick Valley High School and Warwick Valley Middle School. Browse all the schools in Chester, NY to learn more.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 58 days on the market compared to the national average of 54 days. The median sale price for homes in Chester, NY over the last 12 months is $520,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$520,000
Median Single Family Sale Price
$649,500
Median Townhouse Sale Price
$330,000
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$270
Number of Homes for Sale
28
Last 12 months Home Sales
101
Months of Supply
3.30
Median List Price
$541,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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