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Chester NY Real Estate & Homes for Sale

32 Properties Found

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$400,000

16 Oakland Ave Chester, NY 10918

MLS: 888870 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,090
Status:
NEW LISTING
MLS#:
888870
Type:
Single Family
Lot size:
0.43 Acres
Year built:
1986
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: BHG Real Estate Green Team 845-208-9928
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ADDITIONAL INFORMATION

Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potential and great commuter location with close proximity to highway! Welcome to this spacious 4-bedroom, 2.5-bath home nestled in the picturesque town of Chester, NY, in the heart of the beautiful Hudson Valley. Offering 2,090 sq ft of living space, plus a finished rec room with an additional 1,026 sq ft, this home is brimming with potential and ready for your personal touch! Step inside to find generously sized rooms, a traditional layout with excellent flow, and a finished basement that opens up endless possibilities—recreation room, home gym, playroom, or even a private studio space. Turn the spacious primary suite into a true retreat, featuring a private screened-in balcony, perfect for enjoying your morning coffee or winding down with a peaceful view at the end of the day. While the home does need a bit of TLC, it's priced to sell and presents a fantastic opportunity for anyone looking to customize a home to their liking. Whether you're a first-time buyer, someone ready to create your dream space, or even an experienced real estate investor, this could be the opportunity you've been waiting for. Set on a lovely lot in a quiet neighborhood, you’ll enjoy peace and privacy while still being close to local shops, restaurants, parks, and commuter routes. Chester offers small-town charm with easy access to all the natural beauty and attractions the Hudson Valley has to offer. Don't miss out on this incredible value—bring your vision and make this house your home!

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$610,000

391 Bull Mill Rd Chester, NY 10918

MLS: 880804 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,800
Status:
NEW LISTING
MLS#:
880804
Type:
Single Family
Lot size:
1.7 Acres
Year built:
1900
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Century 21 Realty Center 845-781-8100
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ADDITIONAL INFORMATION

Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular driveway, this home offers privacy, character, and modern updates. Step onto not one, but two front porches, perfect for morning coffee or unwinding at the end of the day. Enjoy summer gatherings on the large patio with propane-connected grill and a metal canopy for shade ideal for entertaining. Make a wish at your very own fully functioning wishing well, a whimsical touch that makes this property feel like home. Nature lovers will appreciate the grapevine, blueberry bush, and pear tree, as well as the proximity Goose Pond Mountain State Park making this a fantastic retreat for hikers and outdoor enthusiasts. Inside, you'll find the warmth of hardwood floors throughout and a cozy, rustic feel highlighted by original wooden peg support beams and stunning stone fireplace with a wood-burning stove insert, recently cleaned and inspected. The eat-in kitchen with bar seating is perfect for casual meals and conversations. Upstairs the prime bedroom features an ensuite, with two additional generously sized bedrooms offer ample space. The main bathroom includes a charming clawfoot tub and direct access to the backyard, adding convenience and vintage character. Additional highlights include: Detached garage with attached workshop, recently updated shed and barn, woodshed included, septic system pumped and cleaned June 2025 and furnace serviced and maintained annually. This farm house truly combines timeless charm with everyday functionality. Whether you're enjoying sled rides in the yard or summer evenings on the porch, this home offers the best of country living - just minutes from trails, nature, and small-town comfort. The area is rich in local attractions, including West Point Military Academy, Woodbury Commons premium outlets, Harriman state park, Bear Mountain State Park, Lego Land, Vinyards and Farms and so much more... Great location for commuters with plenty of Public transportation and minutes away from major highways.

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$529,000

57 Hubshop Rd Chester, NY 10918

MLS: 884109 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
1,788
Status:
NEW LISTING
MLS#:
884109
Type:
Single Family
Lot size:
0.22 Acres
Year built:
1954
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Avion 845-388-1216
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ADDITIONAL INFORMATION

Welcome to 57 Hubshop Rd, where comfort and convenience will make you feel right at home when walking through the door. The kitchen is a chef's dream featuring plenty of counter space, a center island and comfortable seating for all your guest. The living room is cozy and welcoming with many couches ready to embrace you after a long day. The family room is basked in sunshine, with a door leading out to a deck, where you can enjoy the backyard views. The bonus room on the first floor can be used as a bedroom, study, home office. The second floor features 3 spacious bedrooms ready to house your family and guests. The basement, attic and shed offer plenty of space for storage. The landscaped backyard is calling for you to enjoy it in every weather. Many upgrades throughout the home. Grab this opportunity before it's gone.

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$624,000

81 Hambletonian Rd Chester, NY 10918

MLS: 885869 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,938
Status:
Active
MLS#:
885869
Type:
Single Family
Lot size:
6.2 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

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, as well as a plaque embedded onto a rock in front of the property, honoring the significance (see photos) . . . . . . Gorgeous lot includes two ponds, a beautiful front yard setting to watch magnificent sunsets from the front porch, and a back wooded area. Some key features of the home include central air, hardwood floors, detached garage, primary en suite, and a full unfinished walkout basement with high ceilings (ripe for finishing, if so desired). Enter front classic country porch into tiled foyer, then into beautiful oversized living room with vaulted ceilings, a woodburning fireplace, and lots of natural light with many windows. Primary en suite sits on one side of the house, and includes a walk-in closet, as well as a primary bathroom with dual sinks, while the other two bedrooms sit on the other side of the house, where there's also a full bathroom (also with double sinks). Large eat-in kitchen includes plenty of cabinet and counter space, along with a built-in desk, and back door access to the deck, and sits adjacent to formal dining room. Easy single floor living on a fabulous property! Could easily be a horse property (or other animals -- alpacas, goats, chickens, cows, you name it), or utilize the historic barns for any other variety of uses. Original owners (and also the third generation dairy farmers of this property). Just outside the artisan hamlet of Sugar Loaf, while downtown Warwick and all it also has to offer is just a few minutes away. Also a terrific commuter location just minutes to Route 17, not to mention bus park & ride spots into NYC. And also literally minutes to restaurants, shopping, entertainment, wineries, breweries, farmer's markets, hiking, skiing, boating, hospital, and everything else the amazing Warwick Valley has to offer!

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$525,000

25 High St Chester, NY 10918

MLS: 883804 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,898
Status:
Active
MLS#:
883804
Type:
Single Family
Lot size:
0.63 Acres
Year built:
1850
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Christie's Int. Real Estate 914-266-9200
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ADDITIONAL INFORMATION

25 High St in Chester, NY, is a Victorian gem rich with character and ready for your personal touch. Step inside to discover original wide-plank wood floors throughout and preserved under carpeting, offering timeless warmth and authenticity. The bright modern kitchen is ready for gatherings, while the spacious formal dining room sets the stage for memorable meals. Two large living rooms provide ample space for relaxation and entertainment, ensuring there’s room for everyone. Upstairs, four comfortable bedrooms await, serviced by two full bathrooms—one conveniently located on the main floor—and two staircases for easy access. The walk-up attic features two unfinished rooms brimming with potential, and the unfinished basement offers extra space for work, play, or storage. Outside, enjoy the convenience of a large garage and additional carport, perfect for vehicles and hobbies. Located just minutes from Route 84, this home is only about an hour and forty minutes from New York City, making it ideal for weekend getaways or everyday living. Chester, NY, is a vibrant town surrounded by natural beauty, offering parks, recreational activities, and local attractions such as Glenmere Lake, Goose Pond Mountain State Park, and The Castle Fun Center.

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$370,000

2503 Whispering Hls Chester, NY 10918

MLS: 884338 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
1,316
Status:
Active
MLS#:
884338
Type:
Condo
Year built:
1986
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams Hudson Valley 845-610-6065
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ADDITIONAL INFORMATION

Discover this beautiful 3-bedroom, 2.5-bath duplex offering 1,316 sq ft of comfortable living in the highly desirable Whispering Hills condo community in Chester, NY. Enjoy great outdoor space, perfect for relaxing or entertaining. Ideal for commuters with easy access to major highways, and located within the sought-after Chester School District. Don’t miss the opportunity to call this charming home yours!

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$899,000

10 Spectrum Dr Chester, NY 10918

MLS: 882886 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
4,496
Status:
Active
MLS#:
882886
Type:
Single Family
Lot size:
5.4 Acres
Year built:
1991
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: eRealty Advisors, Inc 914-712-6330
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ADDITIONAL INFORMATION

Serene Country Retreat in an Upscale Chester Neighborhood! Set on over 5 peaceful acres with sweeping mountain views, this stunning contemporary home offers the perfect mix of style, comfort, and privacy. With 4 bedrooms and 4 bathrooms, the layout is ideal for both everyday living and effortless entertaining. The sun-drenched living room is a true showpiece—featuring dramatic cathedral ceilings, oversized windows, custom built-ins with a rolling library ladder, and a beautiful marble wood-burning fireplace as the centerpiece. Skylights bathe the space in natural light, creating a warm and inviting atmosphere. Upstairs, the spacious master suite offers a quiet escape with its own private balcony, an oversized marble bath, and a jacuzzi tub—perfect for unwinding in comfort. The updated eat-in kitchen includes granite countertops and a professional-grade 6-burner stove, ready for any culinary enthusiast. Additional highlights include a first-floor bedroom, multi-level decking, an above-ground pool, and a walk-out guest quarters with its own entrance, bathroom, and kitchenette—ideal for extended stays or creative use. A 26x34 horse barn with two stalls, Horse Arena, a tack room, and hay storage completes this versatile property. Located just minutes from the charming Villages of Sugar Loaf and Warwick, with easy access to Route 17 and NYC, this home offers peaceful country living without sacrificing convenience.

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$1,100,000

53 Odyssey Dr Chester, NY 10918

MLS: 881474 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
4,467
Status:
Active
MLS#:
881474
Type:
Single Family
Subdivision:
Black Meadow Farms
Lot size:
5.5 Acres
Year built:
1993
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Howard Hanna Rand Realty 845-294-3100
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ADDITIONAL INFORMATION

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 harmonious main floor, where an open-flow layout seamlessly blends with versatile spaces tailored for a home office, music room, or study. Freshly painted in a neutral palette, the living room, complete with a TV and Bose surround sound system (included), sets the stage for memorable gatherings. The adjacent kitchen flows effortlessly into a convenient laundry and pantry room, strategically positioned off the garage for easy grocery unloading and discreet meal prep, keeping your entertaining space pristine.Ascend to the upper level, where the master suite serves as a tranquil retreat, boasting brand-new flooring, fresh paint, a modern ceiling fan, and a luxurious 2024-renovated bathroom featuring new fixtures, elegant tiles, and a rejuvenating steam shower. Three additional bedrooms share a fully renovated, contemporary bathroom with sleek fixtures and a walk-in shower, ensuring comfort for family or guests. The walk-out basement, currently a stylish home office, offers boundless potential as a guest suite or multi-generational living space, complete with a private bathroom and dining area for extended stays.The festivities continue outdoors on a private deck and patio, where you can luxuriate in the hot tub, take a refreshing dip in the pool, or gather around the firepit for s’mores under the stars. Host unforgettable gatherings with the poolside TV, outdoor kitchen, and gazebo bar area, perfect for grilling favorites or crafting cocktails. Nestled just minutes from Harriman, Legoland, Woodbury Commons, and major shopping, with easy access to train and bus lines, this home offers both seclusion and convenience. A scenic drive to the charming Village of Warwick and approximately 50 miles to the George Washington Bridge make this an ideal retreat for those seeking a blend of rural serenity and urban accessibility. This is more than a home—it’s a lifestyle.

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$789,000

48 Brennan Ct Chester, NY 10918

MLS: 881084 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,063
Status:
Active
MLS#:
881084
Type:
Single Family
Lot size:
5 Acres
Year built:
2006
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Hudson Valley Griffith 845-294-9333
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ADDITIONAL INFORMATION

Open and sun filled 4 BR, 2 1/2 bath Colonial is set on beautifully landscaped 5 acre grounds on a private cul de sac! 2 story foyer! Soaring ceilings in family room with large custom window and gas fireplace! Formal LR and DR, vaulted Great room! Kitchen has granite counters, stainless steel appliances, and lots of cabinets and opens to eating area with sliders to large deck with pergola! Walkout basement leads to private yard with large above ground pool and another pergola with a canopy! HW floors! Recessed lights! Chester Schools! Convenient to Route 17, shopping and the quaint village of Chester!

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$699,000

4 Debbie Ct Chester, NY 10918

MLS: 876408 Photos
Beds:
5
Baths:
6.00
Sq.Ft.:
5,403
Status:
Active
MLS#:
876408
Type:
Single Family
Lot size:
5.4 Acres
Year built:
1982
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Flag Realty Group 845-205-0089
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ADDITIONAL INFORMATION

Experience unparalleled luxury and spaciousness in this stunning 5400 sq. ft. 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 family moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year round!! Featuring a main house of 3800 sq. ft. with 4 bedrooms and 3.5 baths, complemented by a beautifully finished basement that adds three additional rooms and another bath. The open kitchen boasts elegant granite countertops, while two sunrooms and spacious living areas provide ample space for relaxation and entertainment. The attached 1600 sq. ft. post & beam (log house) in-law suite ensures complete privacy for guests or extended family, featuring its own entrance, kitchen, and living spaces. With Central AC, and modernized bathrooms, this home is move-in ready. Step outside to a stunning park-like backyard, perfect for outdoor enthusiasts, complete with three private decks, lush gardens, stone patios, a greenhouse,, fire pit, and a dedicated BBQ area. This property is a must-see and an incredible value!!

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$975,000

2 Primrose Ln Chester, NY 10918

MLS: 880111 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,370
Status:
Active
MLS#:
880111
Type:
Single Family
Lot size:
18.5 Acres
Year built:
2012
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: MS Realty Group USA, Inc 845-367-7470
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ADDITIONAL INFORMATION

Introducing an exceptional opportunity to own your dream property with over 18 acres wooded land! This stunning colonial is a perfect blend of luxury and functionality. Spanning 2370 square footage plus finished basement with 4 spacious bedrooms and 3 elegantly designed bathrooms, this home boasts an inviting atmosphere that caters to both relaxation and entertaining. As you step inside, you'll be greeted by a huge foyer with a lot of sunlight and high ceiling, creating a warm and welcoming ambiance. The gourmet kitchen is a chef's paradise it ideal for crafting culinary masterpieces or hosting memorable gatherings. Venture outside to discover your own private oasis. The above ground pool, kiddie park, and best of all huge wooded property provides the perfect setting for outdoor entertaining or simply enjoying a tranquil afternoon in the sun. This is a once-in-a-lifetime chance to secure a fabulous home that enhances your lifestyle. Don’t miss out! Schedule a private showing and experience all that this remarkable property has to offer. Act quickly—opportunities like this don’t last long!

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$649,000

9 June Rd Chester, NY 10918

MLS: 880239 Photos

Open House:

Saturday, 7/19 11:00-1:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
2,402
Status:
Active
MLS#:
880239
Type:
Single Family
Lot size:
0.31 Acres
Year built:
1999
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Exp Realty 888-276-0630
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ADDITIONAL INFORMATION

Welcome to 9 June Road, a rare gem offering 3,122 square feet of well-designed living space in the heart of the Village of Chester. From the moment you arrive, the curb appeal draws you in with a classic rocking chair front porch and custom pavers lining the driveway and walkways. Step into a grand open foyer with a formal living room to the right and an elegant dining room to the left, perfect for hosting special gatherings. Toward the rear of the home, the spacious kitchen with center island flows seamlessly into the cozy family room with a fireplace — ideal for everyday living and entertaining. Just beyond the sliding glass doors, a composite Trex deck invites you to experience the showstopper backyard, complete with a pergola for shaded relaxation, built-in firepit, children’s swing set, and a half basketball court — all surrounded by thoughtfully landscaped grounds that create a private retreat for the entire family. Upstairs, the primary suite offers a peaceful escape with a huge walk-in closet and a newly renovated bathroom featuring an oversized soaker tub. Three additional bedrooms and a full bathroom complete the second floor, providing plenty of space for everyone. The first-floor laundry room and half bath add convenience, while the large garage provides direct entry into the home. The finished 720-square-foot basement is a flexible space perfect for a media room, playroom, or home gym, and the pull-down attic offers even more storage. With fully owned and paid-off solar panels, energy efficiency is already built in. As a bonus, an additional lot comes with the home, expanding your outdoor space to nearly half an acre for extra privacy and play. This is more than just a home — it's a lifestyle property in one of Chester’s most desirable neighborhoods. Don’t miss your chance to make it yours.

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$485,000

212 Sugarloaf Mountain Rd Chester, NY 10918

MLS: 866658 Photos
Beds:
2
Baths:
3.00
Sq.Ft.:
1,696
Status:
Active
MLS#:
866658
Type:
Single Family
Lot size:
1.2 Acres
Year built:
1900
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: BHG Real Estate Green Team 845-208-9928
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ADDITIONAL INFORMATION

Picture your mountain retreat in this farmhouse built in 1900, blending historic charm with modern potential, set in the scenic Warwick Valley. Just two miles from Sugar Loaf’s artisan shops and dining, this 2-bedroom home offers tranquility and an express bus to NYC. Enter the living room, where exposed beams, hardwood floors, and a fireplace create a cozy feel. Sliding doors lead to a back deck with a heated inground pool and outdoor shower. Host gatherings in the spacious dining room with pine floors. The kitchen features stainless steel appliances, skylights, and a finished side porch for relaxed moments. Upstairs, the master bedroom with hardwood floors is joined by a second bedroom and bathroom. The private backyard includes a pond, gardens, and a multi-level deck for quiet evenings. Close to shopping, hiking, Greenwood Lake and the Village of Warwick.

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$325,000

3107 Whispering Hls Chester, NY 10918

MLS: 879298 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
1,086
Status:
Active
MLS#:
879298
Type:
Condo
Subdivision:
Whispering Hills
Year built:
1987
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Master Realty Group Inc. 845-208-2115
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ADDITIONAL INFORMATION

Whispering Hills – Updated 2 Bedroom, 2 Bath Apartment-Style Unit! Spacious and stylish multi-level condo featuring an updated kitchen with stainless steel appliances, fireplace, and central A/C. Unique layout with bedrooms and baths on separate levels for added privacy. The primary bedroom includes a walk-through closet with direct access to the bathroom. Enjoy the convenience of a 2-car garage, plus ample storage. Located in a prime commuter location, just a short walk to NYC bus and shopping, and close to major highways, Lowe’s, and local shops. Enjoy country club-style living with access to clubhouses, tennis courts, basketball, pools, and more. Low-maintenance lifestyle in a vibrant community—a must-see!

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$365,000

3911 Whispering Hls Chester, NY 10918

MLS: 879295 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,316
Status:
Active
MLS#:
879295
Type:
Condo
Year built:
1987
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Master Realty Group Inc. 845-208-2115
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ADDITIONAL INFORMATION

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 a walk-in closet, charming window seat, and updated en-suite bath. Newer windows and carpet throughout, beautifully updated bathrooms, private deck, and great storage. Enjoy resort-style amenities including clubhouses, pools, tennis and basketball courts. Prime commuter location—close to NYC bus and shopping, and just minutes to major highways and retail. Low-maintenance living in a vibrant, amenity-filled community—this one won’t last!

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$699,000

114 Old Mansion Rd Chester, NY 10918

MLS: 833920 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
3,330
Status:
Active
MLS#:
833920
Type:
Single Family
Lot size:
0.92 Acres
Year built:
1930
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Master Realty Group Inc. 845-208-2115
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ADDITIONAL INFORMATION

Charming Colonial with 4 Bedrooms on Nearly an Acre – Prime Location! Welcome to this beautifully maintained Colonial-style home nestled on a generous 0.92-acre lot, offering space, comfort, and convenience. This freshly painted home features 4 spacious bedrooms, 2 full bathrooms, and a versatile layout perfect for modern living. The first floor boasts gleaming hardwood floors, a warm wood kitchen with tiled countertops, a formal dining room, and a massive living room with windows all around, flooding the space with natural light. You'll also find a cozy family room, a private office, and a full bathroom, along with a walkout door leading to a nice patio and the backyard – perfect for indoor-outdoor living and entertaining. Upstairs, you’ll find brand-new carpeting throughout, including in the expansive master bedroom with a huge walk-in closet. Three additional generously sized bedrooms and a full bathroom complete the second level. There’s also an unfinished attic with pull-down stairs, offering potential for future expansion or ample storage. Additional features include an unfinished basement, window A/C units, a 2-car garage, and a long driveway with plenty of parking space. Step outside to enjoy the in-ground pool, which is fully fenced for safety, a playground area, and a spacious backyard ready for gatherings or quiet relaxation. Ideally located right off the highway, this home offers an easy commute while still providing the peace and privacy of a suburban setting. Don't miss the opportunity to own this spacious and versatile home – perfect for families, work-from-home lifestyles, or anyone looking for comfort and convenience in one package!

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$1,775,000

20 Goshen Rd Chester, NY 10918

MLS: 875731 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
3,348
Status:
Active
MLS#:
875731
Type:
Single Family
Lot size:
53 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating. Nature lovers and hobby farmers will appreciate the large chicken coop housing up to 200 chickens, an 8x12 shed formerly used for hunting dogs, and over 40 mature fruit trees, including pear, cherry, apple, and peach. Enjoy miles of well-maintained horse trails and approximately $30,000 in marketable timber. Whether you’re envisioning a private retreat, equestrian estate, or long-term investment, this exceptional property delivers endless possibilities.

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$650,000

65 Oxford Springs Rd Chester, NY 10918

MLS: 873817 Photos
Beds:
5
Baths:
4.00
Sq.Ft.:
3,617
Status:
Active
MLS#:
873817
Type:
Single Family
Lot size:
2.3 Acres
Year built:
1995
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: eXp Realty 888-276-0630
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ADDITIONAL INFORMATION

Welcome to 65 Oxford Springs Road, Chester, NY, a one-of-a-kind custom-built Country Contemporary home perfectly set on a private 2.3-acre hilltop. This unique property offers a rare blend of privacy, space, and convenience, just minutes from the NYS Thruway, nearby state parks, and only 45 minutes to New York City. The bright, open floor plan is designed to welcome natural light into every room. Rich hardwood floors, custom trim work, and soaring 26-foot ceilings create a warm and inviting atmosphere. The living room, highlighted by a striking stone-accented wood Fire Place, flows seamlessly into a spacious modern kitchen featuring granite countertops, an oversized island, and stainless steel appliances, ideal for gatherings and everyday living. Offering five bedrooms and four bathrooms, the home’s thoughtful layout includes a primary suite with its own cozy fireplace and a private balcony overlooking the peaceful landscape. French doors open from the formal dining area to the private backyard deck, perfect for enjoying quiet mornings or entertaining guests. Adding to its value, the property includes a two-story detached cottage of approximately 1,000 square feet, ready to be transformed into an art studio, home office, workshop, or guest retreat. The property also features a brand-new oil heating system with an above-ground tank and all surrounded by tranquil scenery. Experience the perfect balance of country charm and modern living in this extraordinary hilltop retreat. A rare opportunity to own a special home in the heart of Orange County, New York.

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$499,000

15 Mari Rd Chester, NY 10918

MLS: 868443 Photos
Beds:
4
Baths:
2.00
Sq.Ft.:
1,888
Status:
Active
MLS#:
868443
Type:
Single Family
Lot size:
0.45 Acres
Year built:
1971
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: HomeSmart Homes & Estates 845-547-0005
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ADDITIONAL INFORMATION

Move right into beautiful 15 Mari Road. Situated in a choice neighborhood and inclusive of Warwick Valley Schools, you will appreciate your newly updated home featuring mature landscaping, ample parking and close proximity to the arts and crafts hamlet of Sugarloaf. Stepping inside you will notice the brand-new gleaming hardwood floors throughout the main level. This level provides an open floor plan between the dining area and kitchen as well as the living room with gorgeous views from the bay window. Your newly updated kitchen is outfitted with stainless appliances, ample counter space and quiet close cabinetry. The main level also features sliding doors to an expansive and private rear deck, 3 generous sized bedrooms along with an updated full bathroom with marble tile. On the lower level you will find a large family room with a cozy wood burning stove as well as a walk-out to the side yard that provides easy access to the rear deck as well. A fourth bedroom is also on the lower level along with an updated bathroom inclusive of a stall shower and laundry area. This lower level also provides garage access and an additional bonus room that can be utilized for storage or a possible home office. Just a short distance to hiking trails, restaurants, shops, breweries, wineries and easy access to major highways.

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$724,000

278 Gibson Hill Rd Chester, NY 10918

MLS: 872269 Photos

Open House:

Thursday, 7/17 5:00-7:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
3,977
Status:
Active
MLS#:
872269
Type:
Single Family
Lot size:
5.1 Acres
Year built:
1988
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot colonial farmhouse on 5.1 private acres, and with a pool, 5 bay carport, a 38x40 garage (with it's own entrance from road -- can rent out for income), and so much more! . . . Located in the Warwick Valley School District (and just a half mile to the Warwick town line). Just minutes to all downtown Warwick has to offer, while the eclectic hamlet of Sugar Loaf is literally just around the corner . . . Enter house from classic country porch (which features tin roof), and note the attention to detail, the beautiful hardwood floors, and the rustic feel. Main floor includes living room with wood burning fireplace, formal dining room, recently updated powder room, walk-through kitchen with induction/convection range, warming, salad & freezer drawers and a separate pantry, and into a fantastic family room encased in windows. Upstairs includes all four bedrooms -- the primary bedroom features oversized windows and faux beams, along with a primary bathroom with jetted tub. Other upstairs bathroom with walk-in shower recently updated. Finished walkout basement (928 SF) includes pellet stove. Patio off family room includes hot tub (which wraps around to front of house), walk down to majestic pool area (18x33 half above/half below with custom decking) -- all perfect for entertaining & staycations! Pool area includes screened-in porch. Two outbuildings -- a shed off the pool area (which includes extra power for mig welders and other handyman tools), and a huge 38x40 garage one level down with its own driveway entrance off the road, which is complete with its own boiler (oil heat) & electric meter, 12 feet overhead door, water, loft space, and huge gravel driveway area for big trucks. Perfect for a home-based business, or rent it out! Incredibly efficient home, Peerless boiler, FULL house generator, Tesla solar, two new oil tanks (insulated). Property features 2 streams and a natural pond, plus a conservation easement behind it (so no building ever). Gorgeous & lush landscaping throughout the property. The current owners have taken meticulous care of this great property -- and it shows from the moment you pull in the driveway! Sale includes HOME WARRANTY for one year. Fabulous commuter location, and also close to terrific hiking, skiing, watersports, entertainment, breweries, wineries, orchards, farmers markets, Warwick's annual AppleFest event, and so much more! Must see to fully appreciate all the upgrades & details!

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$459,900

8 Hom St Chester, NY 10918

MLS: 871906 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,410
Status:
Active
MLS#:
871906
Type:
Single Family
Lot size:
0.38 Acres
Year built:
1962
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Preferred Properties Real Esta 845-783-4147
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ADDITIONAL INFORMATION

This well kept ranch located on a quiet cul-de-sac offers over 1400 sqft and boasts an open and welcoming floor plan with plenty of natural light, making it a warm and inviting space for both you and your guests. With three bedrooms, living room, family room and 1 and 1 1/2 baths, there's plenty of space for a growing family. Hardwood floors throughout creates a cohesive look and feel, while the well maintained backyard provides a private outdoor setting with plenty of room to allow for a swimming pool. The walkout basement offers plenty of potential for future entertainment and storage needs. Close proximity to NYC, public transportation, highways, schools, shopping, dining LegoLand and Garnet Health. This home is ideal for those seeking small town charm! Don't miss this one!

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$899,000

7 Gabriels Dr Chester, NY 10918

MLS: 867007 Photos
Beds:
4
Baths:
4.00
Sq.Ft.:
3,929
Status:
Active
MLS#:
867007
Type:
Single Family
Lot size:
3.9 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Exit Realty Venture 845-999-3948
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ADDITIONAL INFORMATION

Don’t miss this opportunity to own a beautifully designed Colonial on 3.9 acres in a child-safe cul-de-sac, built with craftsmanship, comfort, and connection to nature in mind. Offering 3,929 sq ft of living space across 10 well-appointed rooms, this 4-bedroom, 3.5-bath home is very well maintained and features a spacious kitchen with granite countertops and stainless steel appliances—perfect for both everyday living and entertaining. The finished walk-out basement provides extra versatility, while a soothing jacuzzi and private golf putting green add luxury and relaxation to your lifestyle. Surrounded by lush greenery with mature trees and manicured grass, you can unwind in nature and enjoy birdsong from morning to evening. Additional highlights include a 2014 solar panel system with a $111/month lease, a new well pump, new water pressure tank, white modern bathroom fixtures, and a 24-ft round above-ground pool. Conveniently located near shopping, grocery stores, schools, and major roadways. This home is a treasure now—and an even greater one for the future, full of potential and promise.

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$1,099,000

5 Gabriels Dr Chester, NY 10918

MLS: 863852 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,722
Status:
Active
MLS#:
863852
Type:
Single Family
Lot size:
3.2 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams Realty 845-928-8000
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ADDITIONAL INFORMATION

Exquisite Colonial Estate: Timeless Grandeur Meets Modern Luxury Nestled gracefully on a private cul-de-sac amidst meticulously manicured grounds, this sprawling Colonial estate offers an unparalleled blend of classic elegance and contemporary comfort. From the moment you approach the stately wrought-iron fenced property and enter through the grand foyer, you are greeted by a magnificent staircase and an undeniable sense of prestige. The main level unfolds with gleaming hardwood floors and exquisite architectural details, including extensive crown molding and recessed lighting throughout. The amazing formal living room boasts with custom built-ins that softly illuminate cherished collections, perfectly complemented by French doors leading to the family room with additional access to the wrap-around front porch – an idyllic spot for morning coffee or evening reflections. The gourmet kitchen is a chef's delight, boasting top-of-the-line stainless steel appliances, a generous pantry, and a convenient built-in desk. Adjacent to the kitchen, a spacious laundry room offers ample storage and utility. The cozy family room features a charming wood-burning fireplace, creating a warm and inviting atmosphere, while a beautifully appointed half-bath serves guests on the first floor. Ornate lighting and dazzling chandeliers add a touch of sophisticated brilliance to every space. Ascend the grand staircase to the second floor, where plush carpeting ensures comfort and tranquility. The sanctuary of the primary bedroom suite awaits, featuring dramatic cathedral ceilings and two expansive "his and her" closets. The custom primary bathroom is a spa-like retreat, designed for ultimate relaxation with radiant heated floors and an oversized shower, offering a luxurious start or end to your day. Three additional generously sized bedrooms provide ample private space for family or guests. Beyond the interior, the property continues to shine. Step into the outstanding three-season room, where retractable windows invite the outdoors in, creating a seamless connection with nature and providing a serene escape. The expansive back deck is an entertainer's dream, complete with self-watering planters for effortless gardening. The fully fenced backyard, enveloped by mature landscaping, ensures privacy and keeps wildlife at bay, offering a secure haven for recreation and relaxation. Further enhancing this magnificent estate are a two-car garage and a full, unfinished walk-out basement presenting endless possibilities for customization – imagine a home theater, gym, or additional living space. This is more than just a home; it's a lifestyle. Experience the epitome of refined living in this spectacular Colonial estate, where every detail has been thoughtfully curated for the discerning homeowner.

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$1,300,000

90 Main St Chester, NY 10918

MLS: 866395 Photos

Open House:

Saturday, 7/19 12:00-2:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
3,955
Status:
Active
MLS#:
866395
Type:
Single Family
Lot size:
9.68 Acres
Year built:
1851
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Serhant LLC 646-480-7665
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ADDITIONAL INFORMATION

"The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy barn, and multiple additional outbuildings—perfect for storage, hobbies, or future repurposing. The main residence is a classic 4-bedroom, 2.5-bath old-style home, full of original details and thoughtful design. From the moment you step onto the covered front porch, you’re greeted with panoramic views and a sense of timeless charm. Inside, the first floor offers high ceilings, hardwood floors, a wood-burning fireplace, multiple living rooms, and an eat-in kitchen with space to gather. Two separate staircases lead upstairs to four bedrooms and two full bathrooms, along with a bonus space. A walk-up third floor includes two additional rooms that can serve as offices, playrooms, or guest quarters. The walk-out basement features a second fireplace, a built-in bar, and direct access to a sunken courtyard—a unique and private setting for entertaining or relaxing outdoors. The guest cottage is ideal for extended family, visitors, or rental income, offering 2 bedrooms, 1 full bath, and its own private space away from the main home. Outside, the sprawling front lawn, mature trees, and open acreage provide both seclusion and a sense of grandeur. Whether you're dreaming of a small farm, multigenerational living, or simply a private escape with room to grow, this property is a rare find with deep roots and lasting appeal. Conveniently located just minutes from shops, schools, parks, and major commuter routes, this is an incredible opportunity to own a storied piece of Chester history—with the space and structure to shape your future.

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$925,000

2 Pine Hill Rd Chester, NY 10918

MLS: H6251643 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,302
Status:
Active
MLS#:
H6251643
Type:
Single Family
Lot size:
0.97 Acres
Year built:
1910
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: SHAHAR Management LLC 845-476-7101
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ADDITIONAL INFORMATION

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. Enjoy morning coffee on the porch and head to work in your office with custom built library and pocket doors on the first level. With a whole house generator on stand-by you never have to worry about a storm leaving you without power. Purchased by an artist this home has been extensively and lovingly restored in every possible way to enhance your living experience. There are custom moldings, central air, central vac system, pocket doors, Navian high efficiency tankless boiler, 50-year shingle roof in 2006, a custom copper Yankee gutter system, and more. Love to cook-the kitchen has beautiful natural lighting and plenty of space for family and friends. When you walk through the door you will know this house is different from the rest and stands above. Just an hour to NYC!

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.


Chester Real Estate

Chester is located in New York. Chester, New York has a population of 12,477. Chester is more family-centric than the surrounding county with 37.24% of the households containing married families with children. The county average for households married with children is 36.93%.

The median household income in Chester, New York is $120,288. The median household income for the surrounding county is $85,640 compared to the national median of $69,021. The median age of people living in Chester is 39.1 years.

Chester Weather

The average high temperature in July is 83.4 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 47.1 inches per year, with 39.1 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $617,000
    17.6%
    change since last quarter

  • # Active listings

    51
    30-day change

Chester Schools and Demographics

Education near Chester, NY

City County
High School Graduates 95.19 89.92
College Degree - 2 year 9.51 10.52
College Degree - 4 year 37.38 31.44
Graduate Degree 12.24 10.46
Expenditures per Student 27,939 27,939
Students per Teacher 12.3 12.3

Elementary Schools near Chester, NY

Grades Students P/T Ratio ZIP
Chester Elementary School KG - 05 469 14.7 10918
Golden Hill Elementary School PK - 05 388 12.4 10921
Goshen Intermediate School 03 - 05 655 15.2 10924
Kiryas Joel Village School PK - KG 149 6 10950
North Main Street School 02 - 05 558 13.9 10950
Pine Tree Elementary School 02 - 05 833 13.5 10950
Round Hill Elementary School PK - 05 540 17.4 10992
Scotchtown Avenue School KG - 02 591 16 10924
Taft Elementary School KG - 05 785 18.3 10992

Middle Schools near Chester, NY

Grades Students P/T Ratio ZIP
C J Hooker Middle School 06 - 08 720 14.3 10924
Greenwood Lake Middle School 04 - 08 303 12.4 10950
Washingtonville Middle School 06 - 08 1,027 13.7 10992

High Schools near Chester, NY

Grades Students P/T Ratio ZIP
Chester Academy-Middle/High School 06 - 12 556 13.2 10918
Goshen Central High School 09 - 12 925 13.6 10924
Washingtonville Senior High School 09 - 12 1,411 13.5 10992

Ungraded Schools near Chester, NY

Grades Students P/T Ratio ZIP
* Goshen Secure Center 08 - 12 56 10924
Orange-Ulster Boces KG - 12 1,007 26.4 10924
S S Seward Institute 06 - 12 465 11.4 10921

Demographics near Chester, NY

City County
Neighborhood Type Suburban
Population 12,477 398,277
Population Density 379 490
Median Age 39.1 37
People per Household 2.8 2.9
Median Household Income 120,288 85,640
Average Income per Capita 49,991 37,651

Real estate near Chester

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