Chester Homes for Sale

Welcome to Chester, a charming town nestled in the heart of Orange County, New York. Known for its picturesque landscapes and a close-knit community, Chester offers the perfect blend of rural tranquility and modern convenience. With its stunning views of the nearby mountains and lush greenery, this town is a haven for nature lovers and outdoor enthusiasts alike.

Chester boasts an array of recreational opportunities, from hiking and biking trails to serene lakes ideal for fishing and kayaking. The town is also home to several parks, making it a great place for families to enjoy picnics and outdoor activities. With a rich history and a vibrant arts scene, Chester hosts various local events and festivals throughout the year, fostering a strong sense of community among its residents.

For those considering a move to this idyllic location, Chester features an enticing selection of homes for sale. Whether you’re searching for a cozy cottage, a spacious family home, or a luxurious estate, Chester has something to suit every lifestyle and budget. Many properties boast stunning views, ample outdoor space, and modern amenities, ensuring that you can find your dream home in this enchanting town.

With its friendly atmosphere, beautiful surroundings, and a variety of homes for sale, Chester is not just a place to live; it's a place to thrive. Explore the possibilities of making Chester your new home and discover the charm that awaits you in this delightful corner of New York!

Newest Chester Homes for Sale

$370,000

3 Beds ⋅ 1 Baths ⋅ 1033159 MLS

One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk to the village!

33 Meadow Avenue, Chester

$868,000

4 Beds ⋅ 3 Baths ⋅ MDQA2018142 MLS

A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

$160,000

3 Beds ⋅ 1 Baths ⋅ PADE2120866 MLS

Completely Renovated | Bonus Room | Huge Backyard | Minutes to I-95, Philadelphia & Delaware Welcome home to this beautifully renovated 3-bedroom, 1-bath home in the heart of Chester, where modern updates meet everyday convenience. From the moment you step inside, you’ll appreciate the bright, open feel, stylish finishes, recessed lighting, updated flooring, and the pride of craftsmanship throughout. The spacious layout offers comfortable living with an additional bonus room that’s perfect for a home office, playroom, gym, guest room, or flex space to fit your lifestyle. The oversized bathroom provides plenty of room to relax, while the generous bedrooms offer comfort and versatility. Step outside to enjoy the huge backyard, providing endless possibilities for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. Conveniently located just minutes from I-95, this home offers easy access to Philadelphia, Delaware, and surrounding areas—making commuting a breeze while still enjoying the charm of a quiet residential block. Whether you’re a first-time homebuyer, looking to upgrade, or searching for a move-in-ready property, this home checks all the boxes. Property Highlights: * ✔ Completely renovated * ✔ 3 spacious bedrooms * ✔ 1 oversized bathroom * ✔ Bonus room for office, gym, or flex space * ✔ Huge backyard * ✔ Modern finishes throughout * ✔ Quiet block * ✔ Minutes to I-95, Philadelphia, and Delaware * ✔ Move-in ready Don’t miss your opportunity to own this beautifully updated home that offers space, style, and an unbeatable location. Schedule your private showing today!

925 Walnut St, Chester

$856,000

3 Beds ⋅ 3 Baths ⋅ MDQA2018122 MLS

Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors. A chef's dream, the Gourmet Kitchen is the heart of the home, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining, and a separate beverage center! Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers a spacious loft, a flexible area perfect for a second family room, hobby space, and an additional bedroom and bathroom for overnight guests. Also, the large above attic storage room is fully finished. More storage is available in the oversized fully finished two car garage with extra room for a golf cart. Off the dining area is a screened-in porch and patio, and the community run irrigation system to keep your lawn lush and green! You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis (17 miles), DC (45 miles), Baltimore (45 miles), and BWI (30 miles). Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by endless views of the Chester River.

193 Spinnaker Way, Chester

$555,000

4 Beds ⋅ 3 Baths ⋅ MDQA2017890 MLS

Eastern Shore living begins here! Welcome to 532 Cross Creek Court in the desirable Claybourne Woods community of Chester. This beautifully maintained 4-bedroom, 2.5-bath home offers plenty of space to gather, relax, and create lasting memories. Whether you're hosting gatherings, enjoying quiet evenings at home, or entertaining friends, this home provides the perfect setting. Located on Kent Island, you'll enjoy the best of both worlds peaceful neighborhood living with convenient access to waterfront dining, marinas, shopping, recreation, and major commuter routes. Just minutes from the Bay Bridge, this home is ideal for those seeking the charm of the Eastern Shore without sacrificing convenience.

532 Cross Creek Ct, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1031147 MLS

Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.

3 Hilltop Lane, Chester

$180,000

5 Beds ⋅ 1 Baths ⋅ PADE2120550 MLS

Welcome to 1110 Morton Ave, Chester, PA 19013 — a spacious single-family home offering five bedrooms and one bathroom. The main level features a living room and a kitchen, with additional space in the basement for storage or flexible use. This property provides ample room for a variety of layouts and uses across its multiple bedrooms. Conveniently located in Chester, the home presents an opportunity to personalize and update to suit your needs.

1110 Morton Ave, Chester

$465,000

4 Beds ⋅ 3 Baths ⋅ VACF2001588 MLS

Welcome to this beautiful home in the desirable Brooks Chapel neighborhood! Offering 4 bedrooms, 2.5 bathrooms, and approximately 2,462 square feet of living space, this home combines a spacious floor plan with inviting indoor and outdoor features. The property offers excellent curb appeal with a full front porch featuring recessed lighting, a paved driveway, and a two-car attached garage. Inside, the open-concept main level features hardwood flooring, plantation blinds, and a private office or study—perfect for working from home. The spacious family room includes a ceiling fan and flows seamlessly into the gourmet kitchen, featuring granite countertops, stainless steel appliances, a tile backsplash, pantry, recessed lighting, and a center island with breakfast-bar seating. The bright and expansive morning room showcases a vaulted ceiling and provides direct access to the large composite deck with vinyl railings. Upstairs, the primary suite features a ceiling fan, walk-in closet, and private bathroom with tile flooring, a double vanity with granite countertop, jetted soaking tub, and separate tile shower. Three additional generously sized bedrooms offer carpeting, ceiling fans, and ample closet space. The fenced backyard provides plenty of room for entertaining, pets, and outdoor enjoyment. Beautifully maintained and move-in ready, this wonderful home is waiting for its next owner! Some images in this listing have been virtually staged. SCHEDULE SHOWINGS THROUGH SHOWINGTIME!

10007 Ethens Castle Dr, Chester

$689,000

3 Beds ⋅ 2 Baths ⋅ MDQA2017816 MLS

Get ready to be wowed!!! This home has undergone an extensive renovation over the last 5 years. The owners have poured so much love into this home, and it shows. On the interior one of the big standouts is the gourmet kitchen that will surely be the heart of the house. From the granite counters to the 10x4 quartz center island with seating and a built in beverage fridge, to the cozy built in window seating. The living area offers a great pellet stove for those chilly winter nights. Two bedrooms off the living area share a beautifully updated hall bath. The second sitting area is the family room that has a custom pine ceiling and direct access to your Trex deck to enjoy your morning coffee. But wait till you see the primary bedroom with a built in electric fireplace to cozy up too! Cold feet in the mornings no more with the heated primary bath floor, gorgeous shower with rainfall shower head and dual vanities. The exterior of this home is just as amazing as the interior. Get ready all you motorheads for this 30x46 outbuilding with 12 ft ceiling, 200-amp electric service, 2 automatic garage doors, a 18x10 bump out and a craft room for an added bonus! But wait there's more! The above ground pool was just purchased in 2022, with extensive decking for lounging about, or maybe an afternoon cocktail at your own tiki bar. Tired of having to purchase new plants every season well now you can safely store them over the winter in your own 10x12 greenhouse. The backyard even offers a great firepit area for those chilly evenings. Don't take my word for it come and experience all this property has to offer for yourself, you won't be disappointed!

2702 Harrington Rd, Chester

$1,400,000

2 Beds ⋅ 3 Baths ⋅ MDQA2018096 MLS

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

216 Kingfisher Ln, Chester

$350,000

4 Beds ⋅ 1 Baths ⋅ 1031155 MLS

A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious Dining Room and large Kitchen with sliders to a rear deck and yard. It also features 4 nice sized bedrooms. With a "little love and vision" this home could be a lovely family home! Could be a wonderful opportunity for investors! Close to shops and restaurants! Great commuter location! Come preview today!

151 Main Street, Chester

$750,000

5 Beds ⋅ 3 Baths ⋅ 1031045 MLS

1 Hilltop Lane, Chester

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