152

Recently Sold Chester Homes

Section Image
  • 4 Wood Rd, Chester, NY 10918

    $475,000 Sold Sep 08, 2025

    • 1,554 Sq Ft
    • $306/SF
    • 73 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1960

    4 Wood Rd, Chester, NY 10918

    Welcome to this stunning 4 bedroom ranch situated in sought after Sugar Loaf! As you enter you'll notice the spacious family room with vaulted ceilings, fire place, and hardwood flooring. This home is full of many updates such as a central air system, updated main bathroom, Trex front porch, SS appliances, and new flooring / paint on the lower level. Garage currently set up as a bonus room with

    Matthew Skowronski HomeSmart Homes & Estates

    4 Wood Rd, Chester, NY 10918
  • 81 Hambletonian Rd, Chester, NY 10918

    $612,500 Sold Sep 05, 2025

    • 1,938 Sq Ft
    • $316/SF
    • 23 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    81 Hambletonian Rd, Chester, NY 10918

    OWN A PIECE OF HISTORY! AND SO MUCH MORE! This 3 bedroom, 2 full bathroom ranch built in 2002 sits on 6.2 bucolic acres in the Warwick Valley School District -- formerly part of a dairy farm, it also includes multiple barns with a variety of potential uses . . . The GREAT THOROUGHBRED RACEHORSE HAMBLETONIAN WAS FOALED (BORN) ON THIS PROPERTY -- there's even a state historical marker on the road,

    Dean Diltz Keller Williams Realty

    81 Hambletonian Rd, Chester, NY 10918
  • 1711 Kings Hwy, Chester, NY 10918

    $765,000 Sold Sep 05, 2025

    • 2,020 Sq Ft
    • $379/SF
    • 36 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    1711 Kings Hwy, Chester, NY 10918

    Nestled amidst the tranquil woods of Chester, NY, this stunning contemporary home offers a perfect sanctuary for those seeking a harmonious blend of modern design and natural beauty. The moment you step inside, floor-to-ceiling windows reveal breathtaking wooded vistas, flooding the interior with natural light and creating a seamless connection between indoor comfort and outdoor serenity. This

    Carmela Lopez Borrazas Keller Williams Realty

    1711 Kings Hwy, Chester, NY 10918
  • 10 Tulip Ln, Monroe, NY 10950

    $525,000 Sold Sep 02, 2025

    • 1,758 Sq Ft
    • $299/SF
    • 38 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1961

    10 Tulip Ln, Monroe, NY 10950

    Welcome to this meticulously maintained 4-bedroom, 2-bath raised ranch in a quiet and friendly neighborhood, ideally situated in the highly rated Monroe-Woodbury School District. With thoughtful updates, quality finishes, and a flexible floor plan, this home is ready for its next chapter.The main level features gleaming hardwood floors throughout the living room, dining room, and three

    Philip Szumlaski Keller Williams Realty

    10 Tulip Ln, Monroe, NY 10950
  • 3911 Whispering Hills, Chester, NY 10918

    $367,500 Sold Aug 29, 2025

    • 1,316 Sq Ft
    • $279/SF
    • 25 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    3911 Whispering Hills, Chester, NY 10918

    Whispering Hills – End Unit Condo! Beautifully updated 3 Bedroom, 2 Full Bath unit with 1-Car Attached Garage. Features an updated kitchen with quartz countertops, stainless steel appliances, and hardwood floors in the kitchen, dining area, and primary bedroom. Spacious living room with cathedral ceilings, electric fireplace with blower, and a decorative tiled accent wall. Primary suite includes

    Hershel Lowy Master Realty Group Inc.

    3911 Whispering Hills, Chester, NY 10918
  • 2402 Whispering Hills Dr, Chester, NY 10918

    $350,000 Sold Aug 28, 2025

    • 1,316 Sq Ft
    • $266/SF
    • 23 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    2402 Whispering Hills Dr, Chester, NY 10918

    Welcome to Whispering Hills—Chester’s highly desirable condo community offering comfort, convenience, and lifestyle! This spacious 3-bedroom, 2-bathroom unit features soaring ceilings, generous room sizes, and excellent storage throughout. The stylish kitchen boasts brand-new appliances and modern two-tone cabinets, creating a sleek and inviting space that opens to a private deck—ideal for

    Kewin Garabito eXp Realty

    2402 Whispering Hills Dr, Chester, NY 10918
  • 1 Winding Trail, Chester, NY 10918

    $540,000 Sold Aug 28, 2025

    • 2,040 Sq Ft
    • $265/SF
    • 35 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1991

    1 Winding Trail, Chester, NY 10918

    Welcome to 1 Winding Trail in the Town of Chester. This well-maintained home sits on a picturesque 1.2 acre lot located in the desirable Bull Mill Road area with Monroe-Woodbury Schools. With an easy flow, the home’s first floor boasts a spacious family room with fireplace, an office/den and a half bath. Walk-up a few steps into the large living room and a formal dining room both of which

    Donald Serotta Howard Hanna Rand Realty

    1 Winding Trail, Chester, NY 10918
  • 15 Birch Dr, Monroe, NY 10950

    $600,000 Sold Aug 28, 2025

    • 1,868 Sq Ft
    • $321/SF
    • 23 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1971

    15 Birch Dr, Monroe, NY 10950

    Now Active! This beautifully updated Raised Ranch sits on over 1.6 acres in one of Monroe’s most charming neighborhoods—ready for you to explore today. With four bedrooms and two full baths, this move-in-ready home offers the ideal blend of style, comfort, and convenience. Unwind in your private backyard oasis, take a dip in the in-ground pool or enjoy a peaceful stroll to the lake—complete with

    Rebecca Bank Keller Williams Realty

    15 Birch Dr, Monroe, NY 10950
  • 22 Able Noble Dr, Chester, NY 10918

    $460,000 Sold Aug 28, 2025

    • 1,770 Sq Ft
    • $260/SF
    • 40 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1968

    22 Able Noble Dr, Chester, NY 10918

    Welcome to 22 Able Noble Drive, a charming and spacious Raised Ranch nestled in a neighborhood within the highly sought-after Monroe Woodbury School District. Offering 1,770 square feet of living space, this 4-bedroom, 2-bathroom home is the perfect blend of comfort, functionality, and location.Step inside to find a bright and inviting layout, ideal for both everyday living and entertaining

    Robin Kelly Picture It Sold, LLC

    22 Able Noble Dr, Chester, NY 10918
  • 7 Cambridge Cir, Monroe, NY 10950

    $585,000 Sold Aug 27, 2025

    • 2,516 Sq Ft
    • $233/SF
    • 57 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1992

    7 Cambridge Cir, Monroe, NY 10950

    Move in ready Colonial with ADA Accessable features! Welcome to 7 Cambridge Circle, a perfect blend of colonial home living with access for ALL! This home welcomes you into a large entry foyer with HW floors, flowing into your formal living room to your right and your formal dining to your left. Past the large staircase, is your updated kitchen with new SS appliances and corian countertops. Off

    Alissa Taylor-Vetell Keller Williams Realty

    7 Cambridge Cir, Monroe, NY 10950
  • 4501 Whispering Hills Dr, Chester, NY 10918

    $305,000 Sold Aug 22, 2025

    • 1,084 Sq Ft
    • $281/SF
    • 27 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1987

    4501 Whispering Hills Dr, Chester, NY 10918

    Effortless Living with Exceptional AmenitiesWelcome to this beautifully refreshed 2-bedroom, 1-bathroom condo where comfort meets convenience in a vibrant, amenity-rich community. Thoughtfully updated and truly move-in ready, this home is the perfect choice for those who want style, function, and low-maintenance living.Step inside to find freshly painted interiors and brand new carpeting

    Bernadette Giordano Howard Hanna Rand Realty

    4501 Whispering Hills Dr, Chester, NY 10918
  • 15 Vivian Ln, Chester, NY 10918

    $459,000 Sold Aug 19, 2025

    • 1,872 Sq Ft
    • $245/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1968

    15 Vivian Ln, Chester, NY 10918

    Desirable Family Neighborhood! This 4BR, 2BA Colonial Home is in sought-after Surrey Meadows. It's a great place to start or for a family looking for more space and bedrooms. The main floor has an open floor plan living/dining room. Updated kitchen with newer stainless steel appliances. First-floor laundry room. Both bathrooms are updated as well. The second floor has a master bedroom plus three

    Joseph Giglio Keller Williams Realty

    15 Vivian Ln, Chester, NY 10918
  • 21 Jeffrey Dr, Chester, NY 10918

    $560,000 Sold Aug 19, 2025

    • 2,240 Sq Ft
    • $250/SF
    • 37 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1993

    21 Jeffrey Dr, Chester, NY 10918

    Cozy Four-Bedroom Home with Mountain ViewsThis lovely Colonial-style home sits at the end of a quiet street in Sugar Loaf Heights. Enjoy peaceful surroundings and beautiful mountain views every day.Inside, the home has a large and open layout that makes daily living easy and comfortable. The bright kitchen has sliding glass doors that lead to the back deck—perfect for sipping coffee and

    Kevin Tuhy Keller Williams Realty

    21 Jeffrey Dr, Chester, NY 10918
  • 27 Grand View Terrace, Chester, NY 10918

    $780,000 Sold Aug 15, 2025

    • 4,490 Sq Ft
    • $174/SF
    • 43 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2004

    27 Grand View Terrace, Chester, NY 10918

    Spectacular colonial located on the highly desired executive subdivision, Valley View Phase II. The grand double door entryway is just a hint of what awaits inside this almost 5,000 square foot Colonel home. This home sits up high with fantastic mountain views and sunsets, it has 5 bedrooms, 3 full baths all with double high ceilings and hardwood floors. Super large master with two walk in

    Randolph Rogers eXp Realty

    27 Grand View Terrace, Chester, NY 10918
  • 4503 Whispering Hills, Chester, NY 10918

    $330,000 Sold Aug 15, 2025

    • 1,331 Sq Ft
    • $248/SF
    • 142 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    4503 Whispering Hills, Chester, NY 10918

    WELCOME TO WHISPERING HILLS CONDOMINIMUM COMMUNITY!!! Check out this 3 Bedroom, 2.5 Bathroom Condominium nestled in the Village of Chester and in the Chester School District. This Condo is located a mile from the Village of Chester featuring a variety of Village amenities including local restaurants, shopping centers, medical offices, banking services, home improvement stores, close to

    Richard Baxter Keller Williams Realty

    4503 Whispering Hills, Chester, NY 10918
  • 98 High St, Chester, NY 10918

    $323,500 Sold Aug 11, 2025

    • 1,360 Sq Ft
    • $238/SF
    • 35 Days On Market
    • 4 Beds
    • 1.5 Baths
    • Built 1950

    98 High St, Chester, NY 10918

    First time on the market! Welcome to 98 High Street, Chester – a well-loved, original-owner home full of potential. This 4-bedroom, 1.5-bath property offers a spacious layout and solid bones, ready for your personal touch. Step in through the mudroom into an open-concept kitchen and living area, perfect for gathering and entertaining. Down the hall, you’ll find the primary bedroom, a full bath,

    Zachary Foley eXp Realty

    98 High St, Chester, NY 10918
  • 16 Ayr Rd, Chester, NY 10918

    $536,000 Sold Aug 06, 2025

    • 1,716 Sq Ft
    • $312/SF
    • 62 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1972

    16 Ayr Rd, Chester, NY 10918

    3/31/25 Multiple offers received. Please submit your highest and best by Wednesday, April 2, at 5:00. Include in your offer how any potential appraisal gap will be handled. Thank you for your interest in this home.This beautifully situated ranch style home offers amazing views, privacy, and convenience. The kitchen window displays a huge backyard with beautiful greenery in the spring and

    Luanne McGann Century 21 Full Service Realty

    16 Ayr Rd, Chester, NY 10918
  • 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
  • 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
    • 7.5 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
  • 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

Showing Results 1 - 40, Page 1 of 4

Frequently Asked Questions Why Live in Chester

What is the average time to sell a house in Chester, NY?
The houses for sale in Chester, NY spend an average of 64 days on the market.
What is the number of active homes for sale in Chester, NY?
There are 27 active homes for sale in Chester, NY.

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$475,000
Median Single Family Sale Price
$572,499
Median Townhouse Sale Price
$335,000
Median 2 Bedroom Sale Price
$290,000
Median 1 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$269
Number of Homes for Sale
27
Last 12 months Home Sales
147
Months of Supply
2.20
Median List Price
$520,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home