Chester Real Estate

Welcome to Chester, New York—a hidden gem nestled in the heart of Orange County. Known for its stunning natural beauty and charming small-town atmosphere, Chester offers a perfect blend of rural tranquility and vibrant community life. This picturesque town is surrounded by lush landscapes, including the breathtaking views of the nearby Hudson Valley and the majestic Catskill Mountains, making it an ideal location for outdoor enthusiasts and nature lovers alike.

Chester is steeped in history, with its roots dating back to the 18th century. The town's rich heritage is reflected in its well-preserved architecture and quaint downtown area, where you can find delightful shops, cozy cafes, and local eateries. Every corner of Chester tells a story, inviting residents and visitors to explore its unique character.

Families will appreciate Chester's excellent school system and strong sense of community, fostering a safe and welcoming environment for children to grow and thrive. With numerous parks, recreational facilities, and community events throughout the year, there’s always something happening in Chester, whether it’s a summer festival or a winter holiday celebration.

For those who seek a peaceful lifestyle while still enjoying easy access to urban amenities, Chester is ideally situated just a short drive from larger cities like Newburgh and Middletown. This makes it convenient for commuters while still providing the charm of a small town.

Discover the enchanting allure of Chester, NY, where every day feels like a getaway. Whether you’re looking to settle down or simply explore, Chester is ready to welcome you home.

Newest Listings in Chester

$75,000

3 Beds ⋅ 1 Baths ⋅ PADE2123822 MLS

ONLINE AUCTION - Bankruptcy Ordered Auction. Package Sale! This property is being sold with 2 other seperate property in Chester, PA- 940 Highland Ave & 1105 Madison St Chester, PA all being sold together! This property includes 3 bedroom, 1 bath 2 story rowhome in Edgemont Park neighborhood. Property sells via online auction, and list price reflects opening bid amount. Final sale price will be determined through competitive bidding, and this sale is subject to court approval. Sale is being conducted pursuant to Chapter 11 bankruptcy proceedings pending in the U.S. Bankruptcy Court, Middle District of Florida, Case No. 8:26-bk-01636-CPM, In re: RAD Diversified REIT, Inc., et al. Please contact listing agent for more information regarding the auction terms and conditions.

1026 Kerlin St, Chester

$779,900

4 Beds ⋅ 3 Baths ⋅ 1050193 MLS

PRIVATE WOODED COLONIAL!! 4 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Pantry! Master Bedroom Suite with Walk In Closet! Living Room with Wood Burning Fireplace & Built-Ins! Large Formal Dining Room with French Doors! Crown Molding! Gleaming Hard Wood Floors! Recessive Lighting! Walk Up Attic & Full Basement for Endless Possibilities! Two Story Entry/Foyer! Deck with Beautiful Awning! Over Sized Driveway for Plenty of Parking! Perfect Commuter Location! Close to Major Highways, Buses & Shopping!

1168 Craigville Road, Chester

$525,000

2 Beds ⋅ 2 Baths ⋅ 1050131 MLS

Welcome to Chester, NY!! Come see this spacious home with features 3 bedrooms and 2 full baths. This home has plenty of possibilities, includes a finished basement and finished attic for all your storage needs. Large 2 car garage for all the gadgets. This home has a large open concept for entertaining family and friends. Additional energy saving feature of solar panels and oversized deck with above ground pool for outdoor enjoyment for all. Home boost with charm and beautiful hardwood flooring throughout many areas of the home. This home is conveniently located near shopping, fine dining and many leisure activities for all age groups. Easy commute to the city and major transportation hubs for commuters. Local highway and interstate access within minutes.. This s a property you want to see, comes see what Meadow Av has to offer. Welcome Home!!!

19 Meadow Avenue, Chester

$379,900

1 Beds ⋅ 2 Baths ⋅ MDQA2018696 MLS

Enjoy waterfront living in the sought-after Queens Landing community! This Mediterranean style 1-bedroom, 1.5-bath end unit condo offers a unique layout with beautiful water views and multiple outdoor spaces designed to make the most of the setting. The first-level primary bedroom and full bath allow for convenient main-level living. The upper-level loft adds valuable flex space with a wood-burning fireplace, skylights, and an abundance of natural light making it the perfect space for a home office, sitting area, guest space, or cozy retreat. Step outside and choose your view, from the garden-style front patio to the waterside patio out back or the upper-level balcony overlooking the water. With inviting indoor spaces, plenty of natural light, and multiple places to relax outdoors, this condo offers an easy, low maintenance, Eastern Shore lifestyle in a beautiful waterfront community.

12 Queen Anne Way Unit #J, Chester

$499,000

3 Beds ⋅ 3 Baths ⋅ 1049026 MLS

This beautifully updated Chester home in the Monroe-Woodbury School District sits on 1.5 acres with a level open yard, a creek, and a wooded backdrop. From the moment you arrive, the paver walkway, landscaping, and inviting curb appeal set the tone. Inside, the main level boasts hardwood floors and an open layout with a brand-new kitchen featuring white cabinets, granite counters, and stainless steel appliances, plus a living and dining area with sliding glass doors to the deck and backyard. The first floor also has a full hallway bath and three bedrooms, including a bright primary suite with custom windows, crown molding, and an updated ensuite bath with custom tile and glass shower doors. The lower level offers a large den with a stone fireplace and wood-burning stove insert, a half bath, laundry room, and access to the attached two-car garage. Outdoor spaces include a deck off the kitchen and a covered deck from the den, perfect for relaxing or entertaining. The expansive yard is ideal for recreation, gardening, or gatherings, with the creek and woods adding privacy. Just 57 miles to NYC, this home offers both tranquility and easy access to amenities, including nearby parks with 1,500 acres of trails, playgrounds, and more. Additional perks include central air, newer siding, roof, oversized energy-efficient windows, shed, oil burner, hot water heater, and several updated appliances. Conveniently located near shopping, major highways and public transportation.

264 Bull Mill Road, Chester

$35,000

3 Beds ⋅ 1 Baths ⋅ PADE2123646 MLS

INVESTOR / REHAB OPPORTUNITY PROPERTY IN SHELL CONDITION. Property is in need of complete renovation and is being sold strictly AS-IS, WHERE-IS. Seller and listing broker/agent make no representations or warranties regarding the condition of the property, including but not limited to structural integrity, roof, mechanical systems, plumbing, electrical, utilities, environmental conditions, code compliance, or suitability for occupancy or any particular use. Listing broker/agent has limited knowledge of the property and has not independently verified its condition, systems, measurements, or other property information. Interior access may present hazardous conditions. ENTER AT YOUR OWN RISK AND EXERCISE EXTREME CAUTION. Showings/access by confirmed appointment only. Buyers and their agents are responsible for conducting their own inspections, investigations, municipal inquiries, and all other due diligence necessary to satisfy themselves as to the condition and intended use of the property. Buyer is responsible for verifying all listing information. Seller will make no repairs or provide credits.

708 Hinkson St, Chester

$789,000

3 Beds ⋅ 3 Baths ⋅ MDQA2018418 MLS

Professional Photos Coming Soon! Welcome to 402 Macum Creek Drive, ideally situated along Macum Creek in the beautiful waterfront community of Gibson’s Grant. This thoughtfully designed Hartley model by Koch Homes offers three bedrooms, two-and-a-half baths, and an open floor plan perfect for everyday living and entertaining. A beautiful stone propane fireplace creates a warm and inviting focal point in the main living area. Double porches provide the perfect place to relax and take in breathtaking sunset views over the creek. Positioned on a desirable corner lot, the home also features a fenced backyard, spacious deck, and hardscape patio—ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A rear-entry two-car garage with a large parking pad provides ample space for residents and guests. Gibson’s Grant is conveniently located near waterfront dining, shopping, and the Cross Island Trail, with easy access to the Bay Bridge for commuting or exploring all that the Eastern Shore has to offer. Experience the perfect blend of waterfront community living, everyday convenience, and the relaxed Shore lifestyle.

402 Macum Creek Dr, Chester

$185,000

3 Beds ⋅ 1 Baths ⋅ PADE2123428 MLS

Welcome to 219 Houston St, a well-located Chester rowhome offering an excellent opportunity for an owner-occupant or investor. This 3-bedroom, 1-bath home features approximately 1,152 square feet of living space, a full basement, and classic brick construction. The property offers a practical layout with plenty of potential to make the space your own. Conveniently located near major roadways, shopping, dining, public transportation, and the many amenities Chester has to offer. Whether you're looking to build equity through homeownership or add to your investment portfolio, this property is worth a closer look. Schedule your showing today!

219 Houston St, Chester

$879,000

4 Beds ⋅ 4 Baths ⋅ 1048079 MLS

Welcome to 101 Beverly Road, a beautifully renovated 4-bedroom, 2 full and 2 half bath home offering approximately 3,764 square feet of total finished living space on 1.9 private acres in the Warwick Valley School District. Backing to woods for added privacy and a peaceful setting, this move-in-ready home combines generous living space, thoughtful updates and wonderful indoor-outdoor living. The heart of the home is the renovated kitchen, featuring quartz countertops, under-cabinet lighting and a built-in mini wine refrigerator. Wood flooring creates a warm, cohesive feel throughout the living spaces, while built-in speakers in the kitchen and living room are perfect for everyday enjoyment and entertaining. French doors further enhance the home’s inviting atmosphere and connection to the outdoors. The spacious primary suite includes a walk-in closet and beautifully renovated bath with a soaking tub and separate walk-in shower, creating a comfortable private retreat. Three additional bedrooms provide plenty of flexibility for guests or home-office space. A dedicated laundry room adds everyday convenience. Approximately 900 square feet of finished lower-level space expands the home’s possibilities even further. Complete with an added half bath and walk-out access to a stamped-concrete patio, this level is ideal for a recreation room, media space, home gym, playroom, office or additional entertaining area. Outside, enjoy 1.9 acres backing to woods, providing privacy and a beautiful natural backdrop. An aboveground pool and deck create the perfect setting for summer days and gatherings, while stamped-concrete walkways and patio areas extend the outdoor living space. An asphalt driveway leads to the attached two car garage. The home has also been extensively improved with many of the major updates already completed, including a new roof, vinyl siding, vinyl windows, garage doors and a new 200-amp electrical panel. A new ducted high-efficiency heat-pump system provides heating and central air conditioning for year-round comfort. Additional improvements include a Marathon non-metallic electric water heater and a whole-house water filtration and softening system with UV treatment. With its renovated interior, spacious layout, finished walk-out lower level, private wooded setting, pool and extensive major-system improvements, 101 Beverly Road offers the space and amenities to enjoy from day one—all within the Warwick Valley School District.

101 Beverly Road, Chester

$459,000

4 Beds ⋅ 2 Baths ⋅ 1047996 MLS

Welcome to this charming 4-bedroom, 2-bath bilevel, ideally situated on a quiet dead-end street. The inviting open floor plan offers a seamless flow for everyday living and entertaining, with beautiful hardwood floors throughout the main level and a spacious kitchen featuring stainless steel appliances. Enjoy year-round comfort with central air and take advantage of the large deck overlooking a flat, fully fenced backyard, providing the perfect space for outdoor entertaining, relaxing and play. With Monroe-Woodbury Schools, low taxes, and an excellent commuter location, this home offers the ideal combination of comfort, convenience, and value. Don’t miss the opportunity to make this wonderful home your own!

8 Townsend Place, Chester

$99,900

PADE2123436 MLS

Investment opportunity in Chester! This triplex features two 2-bedroom units and one 1-bedroom unit, offering a versatile setup with strong income-producing potential. Whether you're looking to expand your rental portfolio or take on your next investment project, this multi-unit property presents plenty of possibilities. Conveniently located near local shopping, transportation, and major roadways. Schedule your showing today and explore the potential this triplex has to offer! Please note : Property is being sold as-is. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification, research and inspections and are relying solely on the results thereof. Buyer to pay all closing costs and transfer tax.

2024 Edgmont Ave, Chester

$99,900

5 Beds ⋅ 3 Baths ⋅ PADE2123422 MLS

Discover a prime investment opportunity with this traditional twin/semi-detached home, built in 1920 and offering 1,744 sq. ft. of potential. With 5 spacious bedrooms and 3 full bathrooms, this property is well-suited for rental income or a flip project. The full basement provides additional storage or potential for conversion into livable space, enhancing overall value. Situated on a compact 0.05-acre lot, this property requires minimal maintenance while maximizing rental yield. The brick construction ensures durability and low upkeep costs. On-street parking adds convenience for tenants, while the absence of a homeowners association means no additional fees. With the local market showing steady growth, this property presents an excellent opportunity for cash flow and appreciation. Whether you're a seasoned investor or looking to expand your portfolio, this home is a solid choice for generating returns. Don't miss out on this chance to capitalize on a promising asset! Please note : Property is being sold as-is. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification, research and inspections and are relying solely on the results thereof. Buyer to pay all closing costs and transfer tax.

2024 Edgmont Ave, Chester

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