192

Recently Sold Chester, NY Homes

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  • 326 Heritage Ln, Monroe, NY 10950

    $345,000 Sold Aug 05, 2025

    • 1,698 Sq Ft
    • $203/SF
    • 37 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1998

    326 Heritage Ln, Monroe, NY 10950

    Great starter or downsizer! 3 bedroom 2.5 bath End Unit Townhouse in sought after Windridge! Main living area offers spacious living room with wood burning fireplace & sliding doors to rear patio,1/2 bath, Large kitchen with plenty of counter, cabinet space & eat in area. Upper living are has a huge primary bedroom with balcony overlooking rear yard, primary bath & walk-in closet. 2 additional

    Ernie Acampora River Realty Services, Inc.

    326 Heritage Ln, Monroe, NY 10950
  • 559 Laroe Rd, Chester, NY 10918

    $465,000 Sold Aug 04, 2025

    • 1,900 Sq Ft
    • $245/SF
    • 239 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1970

    559 Laroe Rd, Chester, NY 10918

    Welcome to this stunning home located in the heart of Chester NY. Completely renovated, Spacious bedrooms, full baths, plenty of closets, Living/Dining room, Office room, bright kitchen, granite countertops, dishwasher oven and refrigerator, Situated on a relaxing property, while enjoying the peaceful views throughout, in addition to benefiting from a healthy living environment, Close to major

    Eliezer Safdie Sage Realty Center LLC

    559 Laroe Rd, Chester, NY 10918
  • 3816 Whispering Hills, Chester, NY 10918

    $380,000 Sold Jul 30, 2025

    • 1,331 Sq Ft
    • $285/SF
    • 28 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    3816 Whispering Hills, Chester, NY 10918

    WHISPERING HILLS!! END UNIT! MINT! MINT! Mint Condition! Move right in with Nothing to Do! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Updated Kitchen with Break Fast Nook, Stainless Steel Appliances, Custom Tile Back Splash with Sliders to Patio! Master Bedroom Suite With Walk in Closet! Updated Bathrooms! Living Room with New Fireplace! Dining Room! Newer Windows! New Garage

    Amanda Dnistrian ARC Realty 1 in Sales

    3816 Whispering Hills, Chester, NY 10918
  • 2816 Whispering Hills, Chester, NY 10918

    $350,000 Sold Jul 28, 2025

    • 1,331 Sq Ft
    • $263/SF
    • 23 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    2816 Whispering Hills, Chester, NY 10918

    Welcome to this spacious and beautifully maintained end-unit townhouse offering 3 bedrooms, 2.5 bathrooms, and an oversized two-car garage. The main level features a generous living room with a cozy fireplace, a dining area, and a well-appointed kitchen with a sliding glass door that opens to a private patio—ideal for outdoor entertaining. A convenient half bathroom completes the first

    Bernadette Giordano Howard Hanna Rand Realty

    2816 Whispering Hills, Chester, NY 10918
  • 7 Garden St, Chester, NY 10918

    $400,000 Sold Jul 28, 2025

    • 1,435 Sq Ft
    • $279/SF
    • 25 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    7 Garden St, Chester, NY 10918

    A/O CTS! Don't let the size of this home fool you. This perfectly proportioned farmhouse has so much to offer. The three nice sized bedrooms offer enough room for those looking for a starter home or even someone looking to downsize but still have extra space. Nice sized extra room on main level is perfect for a home office, den or even a guest bedroom. Two full sized bathrooms, one on each level

    Harmoni VanEtten eXp Realty

    7 Garden St, Chester, NY 10918
  • 12 Mari Rd, Chester, NY 10918

    $457,500 Sold Jul 25, 2025

    • 1,842 Sq Ft
    • $248/SF
    • 32 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1970

    12 Mari Rd, Chester, NY 10918

    Welcome to the market a charming 4-Bedroom raised ranch in a peaceful Sugar Loaf neighborhood. Situated in a serene and friendly neighborhood with Warwick schools. This home features four bedrooms and 1.5 baths. Wall-to-wall carpets have been removed to reveal untouched original hardwood floors. The lower level offers a versatile space, ideal for a family room or home office,

    Ryan Degnan Howard Hanna Rand Realty

    12 Mari Rd, Chester, NY 10918
  • 11 Vista Dr, Chester, NY 10918

    $525,000 Sold Jul 24, 2025

    • 2,122 Sq Ft
    • $247/SF
    • 43 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1998

    11 Vista Dr, Chester, NY 10918

    Welcome to 11 Vista Drive, a spacious 4-bedroom, 3-bathroom home nestled in one of Chester’s most desirable neighborhoods. With 2,122 square feet of living space, this property offers plenty of room for a growing family to make lasting memories.Situated on a lovely lot with municipal water and sewer, this home provides both convenience and potential. While some updates are needed—such as

    James Feldhaus eXp Realty

    11 Vista Dr, Chester, NY 10918
  • 26 W Meadow Way, Chester, NY 10918

    $869,000 Sold Jul 24, 2025

    • 3,100 Sq Ft
    • $280/SF
    • 85 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2024

    26 W Meadow Way, Chester, NY 10918

    TO BE BUILT-photo depicted is of another Skylark model built by Quality Craftsmen, Valentine Home Builders. THIS IS AN ABSOLUTELY STUNNING 5 ACRE LOT...SPECTACULAR VIEW. The Skylark Model CAN BE CUSTOM BUILT WITH DELIVERY BY SPRING. This brand new fabulous Colonial includes many comfortable features finished by quality guaranteed, Valentine Home Builders. This model offers an efficient home plan

    Nancy Sardo BHG Real Estate Green Team

    26 W Meadow Way, Chester, NY 10918
  • 189 Creamery Pond Rd, Chester, NY 10918

    $735,000 Sold Jul 21, 2025

    • 2,980 Sq Ft
    • $247/SF
    • 19 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    189 Creamery Pond Rd, Chester, NY 10918

    MOVE right into this Exquisite CUSTOM COLONIAL with many upgrades and extras in the perfect commuter friendly, prestigious development, " Creamery Pond Estates " which is located in the charming hamlet of Sugar Loaf with all the unique shops where handcrafted, one of a kind gifts can be purchased ,boutiques, incredible restaurants, breweries, wineries, skiing, hiking , apple orchards, farmers

    Patricia Brady Keller Williams Realty

    189 Creamery Pond Rd, Chester, NY 10918
  • 4706 Whispering Hills, Chester, NY 10918

    $310,000 Sold Jul 21, 2025

    • 1,086 Sq Ft
    • $285/SF
    • 18 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    4706 Whispering Hills, Chester, NY 10918

    ACCEPTED OFFER!- INSPECTION COMPLETED- CONTRACTS EXECUTED**Welcome to Whispering Hills – Where Comfort Meets Convenience!**Discover your dream home in this charming community, featuring 2 spacious bedrooms and 1.5 well-appointed bathrooms, complemented by a generous 2-car garage. The master suite is a true retreat, boasting a large walk-in closet and soaring cathedral ceilings that create

    Jessica Evans Keller Williams Hudson Valley

    4706 Whispering Hills, Chester, NY 10918
  • 174 Creamery Pond Rd, Chester, NY 10918

    $665,000 Sold Jul 15, 2025

    • 2,608 Sq Ft
    • $255/SF
    • 27 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    174 Creamery Pond Rd, Chester, NY 10918

    Welcome to this beautifully maintained 4 bedroom, 2.5 bath Colonial nestled in the historic craft village of Sugar Loaf and award winning Warwick Valley Schools. This classic home offers timeless curb appeal, a spacious layout perfect for entertaining. The great room features an elegant stone fireplace, perfect for cozy evenings. A flowing layout with separate living, dining and great rooms

    Michele Tobin Keller Williams Realty

    174 Creamery Pond Rd, Chester, NY 10918
  • 10 El Dorado Trail, Chester, NY 10918

    $265,000 Sold Jul 11, 2025

    • Land
    • 6 Acres
    • $42,063 per Acre
    • 152 Days On Market

    10 El Dorado Trail, Chester, NY 10918

    Amazing opportunity to own this 6.3 Acre Lot in Monroe School District, Drilled Well and Electric on site, drilled well in place, Level lot with panoramic views surrounded by exclusive homes. Come build your dream home only 60 Miles to NYC/Minutes to RT17/17M/I87

    Lisandra Rivera Keller Williams Realty

    10 El Dorado Trail, Chester, NY 10918
  • 2 Laura Dr, Chester, NY 10918

    $690,000 Sold Jul 09, 2025

    • 2,592 Sq Ft
    • $266/SF
    • 31 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1986

    2 Laura Dr, Chester, NY 10918

    Fall in love with this stunning updated 4-bedroom Colonial located in Sugar Loaf Heights within the Warwick School District. You will feel like you apparated into the latest issue of Better Homes & Gardens the moment you enter. Agents - better schedule extra long showings as your clients will never want to leave! Step into the inviting living room featuring warm hardwood floors, soft

    Virginia Corbett eXp Realty

    2 Laura Dr, Chester, NY 10918
  • 19 Taurus Ave, Monroe, NY 10950

    $389,000 Sold Jul 09, 2025

    • 1,288 Sq Ft
    • $302/SF
    • 30 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1954

    19 Taurus Ave, Monroe, NY 10950

    Welcome to 19 Taurus Drive, a beautifully updated 3-bedroom, 2 bath ranch in Monroe Woodbury School District. With 1,288 sq ft of living space, this home blends modern upgrades with timeless charm. Step inside to find brand-new flooring alongside refinished hardwood floors, creating a warm and inviting feel. The updated bathroom features stylish finishes, adding a fresh, modern touch. The

    Christian Baez Keller Williams Hudson Valley

    19 Taurus Ave, Monroe, NY 10950
  • 31 Leone Ln, Chester, NY 10918

    $75,000 Sold Jul 09, 2025

    • Land
    • 8 Acres
    • $10,000 per Acre
    • 73 Days On Market

    31 Leone Ln, Chester, NY 10918

    7.5 acres located in Leone Industrial Park in Chester. This is raw land and buyer will have to perform their due diligence regarding permits, etc. with town. There are some wetlands on this property, so there will be limitations on what can be built. Due diligence is a must.

    Carole McCann Hudson Heritage Realty

    31 Leone Ln, Chester, NY 10918
  • 100 Marian Ct, Warwick, NY 10990

    $411,000 Sold Jul 08, 2025

    • 1,528 Sq Ft
    • $269/SF
    • 26 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    100 Marian Ct, Warwick, NY 10990

    Step into a MINT beautiful 3-bedroom end-unit Townhouse gem, perfectly perched with panoramic views in Kings Estates! This spacious townhouse is move-in ready and offers the ideal blend of space, privacy, and everyday convenience. Enjoy municipal water, sewer, natural gas, central air, and NO HOA fees. Just one hour to NYC, it’s a commuter’s dream and ideally situated. Inside,

    Jennifer DiCostanzo RE/MAX Town & Country

    100 Marian Ct, Warwick, NY 10990
  • 138 Dug Rd, Chester, NY 10918

    $700,000 Sold Jul 08, 2025

    • 2,452 Sq Ft
    • $285/SF
    • 49 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1974

    138 Dug Rd, Chester, NY 10918

    Welcome home to this beautifully maintained Dutch Colonial situated on 2.6 serene acres within the desirable Monroe-Woodbury School District. This inviting home offers 4 spacious bedrooms, 2.5 bathrooms, and 2,452 square feet of well-appointed living space, thoughtfully designed for both comfort and functionality. Upon entering, you'll notice the natural light accentuating the gleaming hardwood

    Jake Garay Serhant LLC

    138 Dug Rd, Chester, NY 10918
  • 12 Oak St, Chester, NY 10918

    $415,000 Sold Jul 03, 2025

    • 1,038 Sq Ft
    • $400/SF
    • 24 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1959

    12 Oak St, Chester, NY 10918

    Located in a peaceful area on a picturesque corner lot in the Village of Chester, this ranch style home in the Cherry Heights neighborhood has been meticulously well maintained with perennial flowers, mature trees, and privacy hedges. Inside, the home boasts a spacious living room with a large picture window that offers views of the front covered porch and a vibrant Japanese maple tree. The

    Jennifer Loprieno Howard Hanna Rand Realty

    12 Oak St, Chester, NY 10918
  • 92 Pickerel Rd, Monroe, NY 10950

    $560,000 Sold Jul 01, 2025

    • 2,016 Sq Ft
    • $278/SF
    • 148 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1969

    92 Pickerel Rd, Monroe, NY 10950

    Year end gifts are always wonderful to receive. Welcome to 92 Pickerel road Monroe, New York. A meticulous home awaiting its new owners and features including 3 to 4 bedrooms, 2 full baths, hardwood flooring, recently installed windows, roof, and boiler. A large eat in custom kitchen with granite, stainless appliances and Sub-Zero refrigeration. Dining room is adjacent and well placed.

    Richard Wawrynek Howard Hanna Rand Realty

    92 Pickerel Rd, Monroe, NY 10950
  • 56 Sunset Ridge Rd, Monroe, NY 10950

    $725,000 Sold Jun 30, 2025

    • 3,626 Sq Ft
    • $200/SF
    • 34 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1993

    56 Sunset Ridge Rd, Monroe, NY 10950

    Welcome to 56 Sunset Ridge Road which sits by the private cozy cul-de-sac, a Magnificent backdrop on five luscious acres that envelope this tremendous center hall colonial. A beautiful driveway brings you home to your rocking chair front porch. Two story foyer gives way to the main level formal spaces. Living room, Dining Room, & a separate office leads you to an easy flowing, beautiful, recently

    Moses Schreiber MS Realty Group USA, Inc

    56 Sunset Ridge Rd, Monroe, NY 10950
  • 242 Meadow Ave, Chester, NY 10918

    $225,000 Sold Jun 30, 2025

    • 2,519 Sq Ft
    • $89/SF
    • 56 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1930

    242 Meadow Ave, Chester, NY 10918

    Newly listed Triplex. Showings must be okayed by the tenants. Additional Information: HeatingFuel:Oil Above Ground,

    Kathleen Strong Hudson Valley Griffith

    242 Meadow Ave, Chester, NY 10918
  • 904 Swan Hollow Rd, Monroe, NY 10950

    $340,000 Sold Jun 25, 2025

    • 1,320 Sq Ft
    • $258/SF
    • 125 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1979

    904 Swan Hollow Rd, Monroe, NY 10950

    WOW!! WOW!! This home in a private community has been totally renovated from kitchen, bathrooms, flooring, painting and more. One of the great features is you can sit outside on your patio and have a total lake view. This complex includes pools, clubhouse, playground and more. You are also close to all nature activities, shopping and easy access to major highways. HOA is 656.98 and includes

    Stephen Ramundo Keller Williams Valley Realty

    904 Swan Hollow Rd, Monroe, NY 10950
  • 20 Hubshop Rd, Chester, NY 10918

    $624,000 Sold Jun 23, 2025

    • 2,236 Sq Ft
    • $279/SF
    • 66 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    20 Hubshop Rd, Chester, NY 10918

    CAPTIVATING CAPE COD! 1.5 Private Acres! 4 Bedrooms! 2 1/2 Bathrooms! 1 Car Garage! Gorgeous Updated Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Breakfast Nook! Master Bedroom Suite with Walk In Closet Located on the First Floor! Living Room with Double Sided Fireplace! Gleaming Hard Wood Floors! New Carpeting! Recessed Lighting! Laundry Room! Full Basement! Rocking

    Amanda Dnistrian ARC Realty 1 in Sales

    20 Hubshop Rd, Chester, NY 10918
  • 3 Woodridge Dr, Chester, NY 10918

    $763,750 Sold Jun 20, 2025

    • 2,500 Sq Ft
    • $306/SF
    • 69 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1995

    3 Woodridge Dr, Chester, NY 10918

    Welcome to this stunning Center Hall Colonial, a true masterpiece of craftsmanship and modern luxury set on a beautifully landscaped 1.3-acre property in a prestigious executive neighborhood. From its grand facade adorned with masterful stonework to the thoughtfully designed interior, every detail of this home has been meticulously crafted for refined living. The outdoor space is a serene oasis,

    Gina Dudgeon Howard Hanna Rand Realty

    3 Woodridge Dr, Chester, NY 10918
  • 1610 Whispering Hills, Chester, NY 10918

    $334,900 Sold Jun 20, 2025

    • 1,331 Sq Ft
    • $252/SF
    • 185 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    1610 Whispering Hills, Chester, NY 10918

    Discover your perfect commuter condo in the Whispering Hills Neighborhood of Chester! This beautiful end unit features three spacious bedrooms and two and a half baths. As you step inside, you'll find a bright and airy open living space that showcases the well maintained hardwood floors and charming fireplace, which provides a cozy atmosphere for gatherings during the cooler months. Off the side

    Patricia Sassi RE/MAX Benchmark Realty Group

    1610 Whispering Hills, Chester, NY 10918
  • 55 Hudson St, Chester, NY 10918

    $460,000 Sold Jun 18, 2025

    • 1,576 Sq Ft
    • $292/SF
    • 20 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1956

    55 Hudson St, Chester, NY 10918

    Nestled on a dead end st in the heart of the Village of Chester, and lovingly cared for by the original family since 1956 is this meticulously maintained 3-bedroom ranch offering all the right elements you're looking for set in a village neighborhood location you simply can't beat. First floor consists of a galley kitchen, dining area, large livingroom with fireplace, full bath, office and two

    Lynelle Alessi Keller Williams Hudson Valley

    55 Hudson St, Chester, NY 10918
  • 29 Meadow Ave, Chester, NY 10918

    $899,999 Sold Jun 18, 2025

    • 3,167 Sq Ft
    • $284/SF
    • 163 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2023

    29 Meadow Ave, Chester, NY 10918

    The Fabulous Charlotte Model is up, sided and interior paint and trim/mill work work is completed. This 3167 sf ranch is located in a very favorable commuter locale, 5 minutes to all highways. A 500 sf finished bonus room above the garage. The 4 acres on which the home sits, is an exceptional piece of land to own, corner of Cul de sac for additional privacy. The exterior features front & side

    Nancy Sardo BHG Real Estate Green Team

    29 Meadow Ave, Chester, NY 10918
  • 152 Lake Region Blvd, Monroe, NY 10950

    $551,225 Sold Jun 17, 2025

    • 1,916 Sq Ft
    • $288/SF
    • 38 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1984

    152 Lake Region Blvd, Monroe, NY 10950

    Discover cozy lakeside living in this beautifully updated 4-bedroom, 2.5-bathroom home nestled in the desirable Lake Region Estates community. With 1,916 sq ft of comfortable living space, this move-in ready gem offers the perfect blend of modern updates and serene charm.Enjoy brand new flooring throughout the upstairs, a new roof, Anderson casement windows, and a spacious deck perfect for

    Raynilson Vasquez eXp Realty

    152 Lake Region Blvd, Monroe, NY 10950
  • 157 Creamery Pond Rd, Chester, NY 10918

    $875,000 Sold Jun 13, 2025

    • 4,021 Sq Ft
    • $218/SF
    • 17 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    157 Creamery Pond Rd, Chester, NY 10918

    Welcome to Creamery Estates of Sugarloaf, where your dream home awaits just an hour’s drive from New York City. Nestled within walking distance of the charming downtown hamlet of Sugarloaf, this lovely residence is minutes away from schools, boutique shops, restaurants, grocery stores, the Sugar Loaf Performing Arts Center, wineries, breweries, apple orchards, the Appalachian trails, local

    Carla Terranova Keller Williams Realty

    157 Creamery Pond Rd, Chester, NY 10918
  • 2754 Schroon River Rd, Chester, NY 12817
    2754 Schroon River Rd, Chester, NY 12817
    2754 Schroon River Rd, Chester, NY 12817
    /39

    $579,000 Sold Jun 12, 2025

    • 1,665 Sq Ft
    • $348/SF
    • 8 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    2754 Schroon River Rd, Chester, NY 12817

    Cedar sided contemporary with 955' of direct frontage on the stocked Schroon River! Sprawling 6.5 acres with small beach and dock. This property was made for entertaining with ample outdoor space including screened gazebo and tea room that easily doubles as an additional sleeping area. Home office, ample closet space throughout, attached 2C garage, Defiant Encore woodstove. Come play like the

    Angie Mead Gallo Realty ADK Inc

    2754 Schroon River Rd, Chester, NY 12817
  • 116 Carriage Knoll Rd, Chester, NY 12817
    116 Carriage Knoll Rd, Chester, NY 12817
    116 Carriage Knoll Rd, Chester, NY 12817
    /16

    $60,000 Sold Jun 12, 2025

    • Land
    • 5 Acres
    • $11,236 per Acre
    • 30 Days On Market

    116 Carriage Knoll Rd, Chester, NY 12817

    Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

    Walter Swartz Gallo Realty ADK Inc

    116 Carriage Knoll Rd, Chester, NY 12817
  • 7823 State Route 9, Chester, NY 12860
    7823 State Route 9, Chester, NY 12860
    7823 State Route 9, Chester, NY 12860
    /35

    $210,000 Sold Jun 09, 2025

    • 1,296 Sq Ft
    • $162/SF
    • 165 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1995

    7823 State Route 9, Chester, NY 12860

    Looking for the perfect getaway close to Gore Mountain and all the Adirondacks has to offer? If so, this could be the place for you. Enjoy the back deck and listen to the babbling creek that runs through the property. This vacation home is being sold fully furnished, you have nothing to do but start your time away! Currently being used as a successful Airbnb with excellent rental history. Well

    Vickie Reed Hunt ERA

    7823 State Route 9, Chester, NY 12860
  • 118 Murray Dr, Chester, NY 10918

    $800,000 Sold Jun 06, 2025

    • 3,418 Sq Ft
    • $234/SF
    • 110 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1978

    118 Murray Dr, Chester, NY 10918

    Nestled on 2.8 acres of lush, mature landscaping that borders the serene Goosepond Mountain State Park, this custom-designed contemporary ranch showcases a timeless blend of materials, with stone and brick construction lending both character and durability. Crafted by its original owners with meticulous attention to detail, the home offers a harmonious connection to its natural surroundings. A

    Brian Caplicki Keller Williams Hudson Valley

    118 Murray Dr, Chester, NY 10918
  • 4401 Whispering Hills Dr, Chester, NY 10918

    $290,000 Sold Jun 05, 2025

    • 1,118 Sq Ft
    • $259/SF
    • 30 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1989

    4401 Whispering Hills Dr, Chester, NY 10918

    Move-in ready, this attractive two-bedroom, one-bath townhouse with attached one car garage is located in the sought-after Whispering Hills Community of Chester. This second-floor end unit features hardwood floors in the main living areas, a vaulted ceiling, and inviting wood-burning fireplace. A sliding door off the living room opens to a private deck, perfect for relaxing. The kitchen,

    Annmarie Kovacs Howard Hanna Rand Realty

    4401 Whispering Hills Dr, Chester, NY 10918
  • 53 Gibson Hill Rd, Chester, NY 10918

    $960,000 Sold Jun 05, 2025

    • 5,312 Sq Ft
    • $181/SF
    • 45 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2010

    53 Gibson Hill Rd, Chester, NY 10918

    This house was built custom. You won't find another house like this one. Total privacy with this spectacular home sits in the middle of 3.1 mature acres which includes a beautiful natural waterfall. Surrounded by 400 plus acres of state owned land that can never be developed. Hike from your backyard to the Appalachian trial. Grand entryway with cathedral ceilings and heated marble floors.

    Roxanne Hartman Timothy W. Kramer

    53 Gibson Hill Rd, Chester, NY 10918
  • L47 Cobble Creek Rd, Chester, NY 12853
    L47 Cobble Creek Rd, Chester, NY 12853
    L47 Cobble Creek Rd, Chester, NY 12853
    /12

    $189,500 Sold Jun 02, 2025

    • Land
    • 97 Acres
    • $1,948 per Acre
    • 11 Days On Market

    L47 Cobble Creek Rd, Chester, NY 12853

    Must see property with endless opportunity. 97+ acres with mature timber including close to 40 acres of Maple. Enjoy all your recreational adventures. Dedicated logging road(built wide enough for two vehicles in some places, where needed). Great views of the pond and mountain. Located minutes from Gore Mountain Ski Area, Lake George and the Adirondacks. Build your dream home, enjoy privacy,

    Sara Gallipo-Sammis Century 21 - Adirondacks

    L47 Cobble Creek Rd, Chester, NY 12853
  • 18 Miller Dr, Chester, NY 10918

    $415,000 Sold May 30, 2025

    • 1,144 Sq Ft
    • $363/SF
    • 16 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1978

    18 Miller Dr, Chester, NY 10918

    **(10-12 Cancelled- Saturday 4/12 due to weather)** Nestled on a quiet cul-de-sac in the heart of Chester Village, this meticulously maintained 3-bedroom ranch offers all the right elements you're looking for—paired with a village neighborhood location you simply can't beat. With hardwood floors in excellent condition hidden beneath the carpeting, a spacious eat-in kitchen, and the warmth of a

    Jennifer DiCostanzo RE/MAX Town & Country

    18 Miller Dr, Chester, NY 10918
  • 2 Bell Way, Chester, NY 10918

    $609,000 Sold May 30, 2025

    • 2,032 Sq Ft
    • $300/SF
    • 50 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2019

    2 Bell Way, Chester, NY 10918

    This STUNNING Chester home with Chester Schools that sits on 0.36 acre of privacy is now available for you to call Home!!In the Center of Chester & Great location! Enter into a spacious Living room with with plenty of natural window light.A formal dining room with modern light fixtures & sliders that lead to a back deck. House is built in 2019 !!! fresh out of the box, trendy and modern, & plenty

    Shia Lieberman Blooming Realty

    2 Bell Way, Chester, NY 10918
  • 154 Hambletonian Rd, Chester, NY 10918

    $1,350,000 Sold May 30, 2025

    • 4,350 Sq Ft
    • $310/SF
    • 24 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2013

    154 Hambletonian Rd, Chester, NY 10918

    Welcome to this breathtaking equestrian estate nestled on close to 24 acres of Chester’s picturesque farmland in the Warwick Valley School district. This meticulously maintained colonial home offers 4 bedrooms, a den, and 3.5 baths, blending classic charm with modern luxury. A massive entryway greets you into the home. It boasts a chef’s kitchen featuring a Wolf stove, Sub-Zero refrigerator,

    Claudia Lepore Keller Williams Realty

    154 Hambletonian Rd, Chester, NY 10918
  • 8 Country Woods Dr, Chester, NY 10918

    $700,000 Sold May 23, 2025

    • 3,120 Sq Ft
    • $224/SF
    • 49 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2002

    8 Country Woods Dr, Chester, NY 10918

    Welcome to this freshly painted colonial home, perfectly situated on over 4 acres of private, picturesque land. With its timeless wrap-around porch and breathtaking views, this home combines classic elegance with modern upgrades.Inside, you'll find a grand 2-story entry, hardwood floors, and a thoughtfully designed first-floor layout. The living room, with its gas fireplace on a convenient

    Sheyla Falesto Howard Hanna Rand Realty

    8 Country Woods Dr, Chester, NY 10918

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New York Orange County Chester

Recently Sold Real Estate & Homes 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 $542,794.
What is the average time to sell a house in Chester, NY?
The houses for sale in Chester, NY spend an average of 61 days on the market.
What is the number of active homes for sale in Chester, NY?
There is 1 active home for sale in Chester, NY.
How many homes have sold over the last 12 months in Chester, NY?
37 homes have sold in Chester, NY over the last 12 months.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 61 days on the market compared to the national average of 70 days. The median sale price for homes in Chester, NY over the last 12 months is $565,000, down 26% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$565,000
Median Single Family Sale Price
$565,000
Median 2 Bedroom Sale Price
$345,000
Average Price Per Sq Ft
$268
Number of Homes for Sale
1
Last 12 months Home Sales
37
Months of Supply
0.30
Median List Price
$574,900
Median Change From 1st List Price
13%
Median Home Sale Price YoY Change
-26%
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