82 Houses For Sale in Chester, NY

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Shannon Stewart

$264,900Est. Payment
2 Beds | 2 Baths | 1,260 Sqft
3038 State Route 94, Chester, NY 10918
House For Sale

Set back on a large 3/4 acre lot is this adorable Cape Cod in the Washingtonville School District. This home features an oversized living room with crown molding, a fireplace and hardwood floors, a large formal dining room with hardwood flooring, closet space and bay window - can also be used as a 3rd bedroom or office - and a nice size kitchen updated in 2014 with granite counters, a pantry with pull-out drawers, eat-in area with a large bay window offering plenty of natural lighting and a walk-out to the backyard. So much potential for gatherings with a covered cement patio area, a privacy fence and ample space for BBQ's on those long summer nights! A full updated bathroom completes the lower level. Upstairs offers 2 large bedrooms with plenty of closet space, hardwood flooring and a 1/2 bathroom. 1 Car garage under the home, carport and potting shed. Updates include: Kitchen (2014), All newer windows except for 1, Nest Thermostat, Septic Pumped 5/2021, Refrigerator (2020), Dishwasher (2018). Within 10 minutes to Route 17, Under 15 minutes to the Woodbury Commons Premium Outlets, and a little over an hour to NYC.

$479,000Est. Payment
4 Beds | 4 Baths | 3,097 Sqft
240 Renies Road, Monroe, NY 10918
House For Sale

Pack your bags and move in! This 9-year young Colonial home in the Monroe-Woodbury School District awaits its new owners! Greeted by a spacious foyer entrance, hardwood floors throughout the entire home, high ceilings, and generous room sizes. Living, Formal Dining and Family Rooms boast stunning coffered ceilings, fireplace, eat-in-kitchen with granite counters, powder room, 2-car attached garage and access to a covered back porch complete the first floor. Second floor includes the primary bedroom suite with triple tray ceiling, recessed lighting, walk-in closet and private en suite, 3 additional bedrooms, bathroom and laundry room. Looking for some flex space, home gym or office? Finished basement with a full bathroom offers possibilities to cater to your needs. Located on a private road close to Walton Lake, Village shopping and restaurants, Woodbury Common Premium Outlets, Greenwood Lake, Harriman Train Station, Park and Ride Bus, NYS Thruway, I-84, and Palisades Pkwy. 1 hour to NYC.

$799,900Est. Payment
6 Beds | 5 Baths | 4,241 Sqft
17 Country Woods Drive, Blooming Grove, NY 10918
House For Sale

* Breathtaking Mother Daughter Residence set on a Cul de Sac in "Country Woods" an Executive Subdivision of Fine Homes, Located in Blooming Grove, on One of the Most Beautiful Streets in Monroe-Woodbury School District * With 4241 Sq Ft this Legal Single family home with an Accessory Apartment In-Law Suite has room for Mom and Dad * Separate entrances with easy access to both * First level has HW Floors and tons of recessed lighting * The Cook's Gourmet Kitchen w expansive cement island, chefs sink, subway tile backsplash, industrial hood, St Stl appliances and breakfast area opens to the family room with fireplace complimented by the mantel * Spacious living room and Elegant dining room * Master bedroom has tray ceilings w bathroom suite, separate shower and WIC plus 3 additional bdrms * Mothers Apartment offers 2 levels of designer living * 2nd Stunning Kitchen, 2nd Master Bedrm suite, additional bedroom, Hardwood floors and moldings * The Outdoor living has a new level of perfection * Breathtaking 3 tiered deck w pergola and Your own soccer field * Pavers front and back * Owners have Loved their home and it shows * Additional 900 sq ft of storage in basement *

David Field

$430,000Est. Payment
3 Beds | 3 Baths | 2,170 Sqft
39 Hudson Street, Chester, NY 10918
House For Sale

Well maintained 3 bed 3 bath in Chester, NY....This home is meticulous and move in ready....High ceilings in the Living room and Kitchen, Stainless appliances, Granite countertops, Family room with Den/Office on the lower level, huge 2 car garage with plenty of storage, brand new water heater, 2 Sheds in great shape with electricity, Big fenced in back yard, Big deck off the back ( Gazebo included), Garden already planted ( so you will have veggies by July ) and much more....You gotta check this place out, it won't last long...

$390,000Est. Payment
4 Beds | 2 Baths | 1,600 Sqft
86 Goosepond Mountain Road, Chester, NY 10918
House For Sale

This charming farmhouse, luxuriously situated on 3.6 picturesque acres has been completely renovated in 2001! The meticulously maintained endless lush green grass is adorned by attractive trees and bushes! You will be welcomed by an inviting wraparound front deck with a gazebo and as you enter through the hardwood floored foyer, coziness and convenience await! The nice-sized dining room with a lovely fireplace and an impressive white wooden L-shaped wall unit bookcase is open to a sun-filled, homey living room. The kitchen includes stainless steel side-by-side fridge, double sink, gas/oven, and dishwasher. The spacious tiled dinette with fireplace is overlooking the beautiful backyard allowing nature year-round. As you head upstairs there is a master bedroom, one full, one-half bath, and three additional bedrooms. This property includes a barn with a 2-horse stall, a workshop, and great storage as well as for feed hay. This is farmland and the state park permits horse riding, so you will have access to hundreds of acres to ride on. Additional amenities include a security system, above ground pool, basketball court, and a small pretty pond at the far end of this one-of-a-kind property!

$339,900Est. Payment
5 Beds | 3 Baths | 2,348 Sqft
5 Gumwood Drive, Chester, NY 10924
House For Sale

Welcome to this spacious bilevel in the Town of Goshen. This oversized bilevel boasts 5 bedrooms and 3 baths. This home provides endless indoor and outdoor space for everyone. The kitchen features a large eat in area with sliding glass doors that take you to an enclosed porch. The living area offers great space for entertaining. There are 3 bedrooms on the top floor including the oversized master bedroom with a large walk in closet and wheelchair accessible master bathroom. There is even a cozy deck off of the master bedroom where you can enjoy some peace and tranquility after a long day. You will find lots more living space on the lower level including the 5th bedroom that can also double as a home office. The backyard is leveled and expansive, there is plenty of room for a pool and fire pit to enjoy those lazy summer nights. Situated at the end of the street with municipal water, sewer and gas. Conveniently located near Rt. 17 and the commuter park and ride. Enjoy walks along the nearby Heritage Trail. Close proximity to schools, shopping, dining and hospitals.

$239,999Est. Payment
2 Beds | 1 Bath | 940 Sqft
237 Meadow Avenue, Chester, NY 10918
House For Sale

Accepted Offer. No more showings at this time. Cozy 2 bedroom home with plenty of front and backyard space. Features privacy and expansive views. Convenient access to all village amenities. Great commuter location.

$539,900Est. Payment
4 Beds | 3 Baths | 2,166 Sqft
14 Lori Lane, Chester, NY 10918
House For Sale

Welcome to 14 Lori Lane, One of the most Beautiful Streets in Chester N.Y. 4 Bedrooms & 2.5 baths, A Gorgeous New Chefs Kitchen will Wow you when you see the Expansive Carrera Marble Island, Pendant Lighting, Stainless Steel Appliances, Tile Floors, Farmhouse Sink & Gorgeous Stone Backsplash, Large Dining Room is Open to the Kitchen, for Great Family Get Togethers, Family Room has Vaulted Ceilings w/Skylights & Stone Fireplace w/Wood Burning Insert to Heat your Home, Beautiful Hardwood Floors Throughout Both Levels - NO Carpet, Updated Bathrooms, Central Air installed in 2006. Sitting Perfectly on 1.4 Level Acres with a Huge Young Paver Patio for Fabulous Back Yard Entertaining, Barbeques, Kids Play area w/ Swing Set, Hot Tub & Plenty of room for the Pets to play too. Professionally Landscaped Young Driveway. Easy Commuter Location , yet Tucked away w/Privacy & Property, This Home has been Loved and it shows Lower Town of Chester Taxes w/MW Schools.

$539,900Est. Payment
4 Beds | 3 Baths | 2,784 Sqft
14 Bianca Boulevard, Chester, NY 10918
House For Sale

* Spectacular Brick Faced Contemporary Colonial in an Executive Neighborhood in Chester * Walls of Glass Flood this Beauty with Natural Light All Day * Gorgeous Entry Invites you into the 2 Story Entry, Contemporary Stairway and Open Floor Plan * Each Room Flows into the other for Great Entertaining * The Spacious Kitchen offers a Large Island, Eat In Area, 3 Skylights and 2 French Doors Leading to Your Fabulous Backyard Oasis: Double Decks and 800 sq. ft. Gunite In Ground Pool - Vacation at Home on the 1.4 Parklike Acres that back up to Goosepond Mountain State Park (over 1500 Acres of Trails and Wooded Area for Hikers and Horseback Riding) * As you look at the 1.4 acres take note that this Property Extends Past the Rock Wall and Opens to the Field that belongs to this Property-Perfect for Ball Games and Picnics * The Family Room has a Beautiful Stone Fireplace to Enjoy on Cool Nights, Adjacent is the Bright Living Room * The Whole Family can fit at Holiday Time in the Large Dining Room * Masters Suite Offers a Master Bath with Jacuzzi Tub * 3 Additional Guest Bedrooms are all Very Nicely Sized * Stunning Home was Designed to Let Nature Inside w Beautiful Views from All The Amazing Oversized Windows * Easy Commuter Location, Close to all Highways and Shopping yet Tucked Away for Privacy * Chester Schools *

$319,000Est. Payment
3 Beds | 2 Baths | 1,452 Sqft
1390 Kings Highway, Chester, NY 10918
House For Sale

This residential property in the Hamlet of Sugar Loaf is considered multisite because of the additional living space offered by the home trailer on the property. The main home has 3 beds/2 baths and the trailer home has an additional 2 beds/1 bath along with a kitchen and living rm. In the main house a sun-filled enclosed front porch greets you when you arrive. Through the entrance enjoy a large living rm and eat-in kitchen. A full bath and laundry are conveniently located on the main level. Upstairs are 3 privately situated bedrms along with an additional room which can be used as an office. A second full bathrm is just down the hall. The property is zoned Local Business Sugar Loaf which gives you the opportunity if you desire to have your own business where you live. Circa 1900 this home has been well cared for by its owner with new furnace -1/2021, newer roof & driveway. This is an "as is" estate sale. A pre-building inspection has been done to ensure that everything is in order.

$179,000Est. Payment
2 Beds | 1 Bath | 700 Sqft
1397 Kings Highway, Chester, NY 10918
House For Sale

Welcome home to your Charming Cottage located in the heart of Sugarloaf. You will enter this humble abode via a walkway over a stream to your peaceful deck overlooking the downtown, where you can enjoy a cup of coffee in the morning or a glass of wine at the end of the day. You will enter into the living/dining area. To the left is a kitchen with a newly installed sink. To the right, there are 2 bedrooms with old wide plank flooring. Sugar Loaf features many artisans and boutique shops. Experience the small town vibe. Grab lunch from the deli across the street. Enjoy live music at the Tin Barn Brewery and dining at the Sugar Loaf Tap House or the Cancun Inn. Located only 10 minutes away, the historic Town of Warwick also boasts many beautiful shops, restaurants, and wineries. Whether a full-time residence or just a weekend getaway, a home in this quaint hamlet of Sugarloaf is sure to make many memories.

$599,999Est. Payment
6 Beds | 3 Baths | 3,501 Sqft
65 Greycourt Road, Chester, NY 10918
House For Sale

Located on a serene and beautiful street, this amazing home is one of a kind. With 6 bedrooms and 3 full baths, 2 BONUS rooms, and a 3 season enclosed porch, this home can accommodate even the largest of families. Updated and renovated in 2020/2021 with all new paint, windows, and electrical. This home has tons of storage and a legal accessory apartment perfect for multigenerational living! Some additional windows have been ordered and will be installed prior to closing.

$349,000Est. Payment
3 Beds | 2 Baths | 1,900 Sqft
576 Bull Mill Road, Chester, NY 10918
House For Sale

Don't wait! Come see this very very comfortable and charming house located in a wonderful neighborhood surround in nature! Features Living room, kitchen, formal dining room, 2 bath and 3 bedrooms, Home was freshly painted in 2021, new ceiling fan. driveway was redone in 2020. Home features huge flat front property and beautiful backyard - with above ground pool - to relax and enjoy with family & friends. close to all major amenities such as Woodbury Common outlets, Greenwood Lake, local shopping and restaurants. This house has a lot to offer, schedule your showing today!

$829,000Est. Payment
4 Beds | 3 Baths | 3,268 Sqft
12 Lori Lane, Chester, NY 10918
House For Sale

Absolute gem in award winning Monroe Woodbury School District! Why wait for new construction when you could own this custom built 4 possible 5 bedroom English Tudor Colonial w/ well over 3000 sq feet which has it all! Home features an open floor plan with fireplace perfect for entertaining, formal dinning room w/ oak floors, 20x44 in ground pool (liner 6 years old) w/ direct access to surface well to refill every year, 28x40 multilevel barn equipped with electricity and chain hoist, 2 car garage, and new 140 sq ft deck to overlook your property. Schedule your tour today!

$660,000Est. Payment
4 Beds | 3 Baths | 3,100 Sqft
1739 Kings Hwy, Chester, NY 10918
House For Sale

Active construction site. This exceptional, quality built home reflects the builders vision of beauty & efficiency that you won't find elsewhere. Surrounded by nature from every point of view, you'll find the peace and calm of how home should feel. The sun drenched spacious open design will be inviting to family & friends for formal or informal gatherings. The living room has a gas fireplace for warm cozy evenings. Spacious kitchen has super white quartz countertops, Fabuwood cabinetry, stainless steel appliances and LED lighting. USB charging ports are thru out and Bluetooth connections in the bathrooms. Spacious master bathroom has a soaking tub and walk-in over sized glass shower.. Lower level has double-car garage with 581 sq.ft. of space for possible media or hobby room. Foam insulation and Simonten windows insure lower heating costs. Hardwood floors thru out including bedrooms. Minutes from Rt. 17 and bus station for commuters. Verify tax info when CO is issued.

$379,000Est. Payment
4 Beds | 2 Baths | 1,882 Sqft
93 Greycourt Road, Chester, NY 10918
House For Sale

Live a life with Peace and Happiness! This is 93 Greycourt Rd all about! Gorgeously maintained Single Family House, 4 Bedrooms 2 full Bath, Spacious living room with hardwood floors, Nice size and quality kitchen, Eat in-Formal dining room, Huge bright Yard perfect for gatherings and entertaining, Backyard offers a beautiful above ground pool, Excellent commuter location, just minutes to major highways, public transportation and Much More. Charm is apparent throughout this Home, it's a MUST SEE! Schedule your showing today.

$480,000Est. Payment
4 Beds | 3 Baths | 2,400 Sqft
81 Ridge Road, Sugar Loaf, NY 10918
House For Sale

Welcome to beautiful 81 Ridge Road,a 2400 sf 4 bedroom Ranch conveniently located 3 miles to major commuter routes to NYC & Orange County, NY. If you ever dreamed of owning your own manicured 1 acre yard with a garden full of love, well here it grows amidst mountains and sensational sky top views.This sweet home boasts vaulted ceilings throughout, a Master en suite, fabulous new master bath and additional adjoining room for office/nursery. The spacious kitchen with double doors leads to your 1 acre yard to pick vegetables or flowers for the day. The pellet stove at center of the home will keep your living space toasty warm throughout any season. A mud/laundry room is perfectly situated at second entrance. A living room a wood burning fireplace is another great space to entertain. The 3 remaining bedrooms with vaulted ceilings allows the sunny views to shine through! The fabulous gardens speak for themselves, raised beds, weed protected with full rubber matting. The pellet stove and solar panels will keep your utility costs low year round!!

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