Chester Homes with Parking Lot Parking features

Chester Homes with Parking Lot Parking features

Welcome to Chester, New York—a charming town nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its stunning views of the Shawangunk Mountains and beautiful lakes, Chester offers a perfect blend of natural beauty and suburban convenience. With its rich history and friendly atmosphere, residents enjoy a quality of life that is both relaxed and engaging.

Chester is an outdoor enthusiast's paradise, featuring numerous parks, hiking trails, and recreational areas. The nearby Greenwood Lake provides ample opportunities for boating, fishing, and swimming, making it a cherished spot for families and individuals alike. The town also hosts various community events throughout the year, fostering connections among neighbors and creating a warm, welcoming environment.

When it comes to real estate, Chester has a diverse selection of homes to suit every lifestyle. One of the standout features of many properties in this area is the availability of parking lot parking. This practical amenity ensures that residents have easy access to their vehicles, providing convenience and peace of mind. Whether you’re looking for a cozy cottage or a spacious family home, Chester’s real estate market has something for everyone.

With its stunning scenery, friendly community, and practical amenities like parking lot parking, Chester, NY, is the perfect place to call home. Discover the charm of this delightful town and find your dream home today!

Newest Chester Homes with Parking Lot Parking features

$389,900
3 Beds 2 Baths 1027245 MLS
WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door) perfect for outdoor enjoyment and relaxation overlooking the pretty landscape. The kitchen has been thoughtfully renovated with new modern cabinetry, quartz countertops, updated backsplash, newer appliances (dishwasher, gas range and microwave), dedicated pantry with roll outs and ample shelving, new sink and pull out garbage drawer. Through the main entry level you have immediate access to the 1 car garage, which also has a dedicated storage space. This home has its own private entrance and the two story foyer offers a warm welcome to the unit. Notice how well maintained this home is as you tour. The primary bedroom is spectacular. This room is spacious and it has a large walk in closet and a gorgeous newly designed on suite full bathroom that feels like a "spa". Throughout the home, new flooring and window blinds have been installed, along with recessed lighting and a modern dining room chandelier. An added perk is that the entire condo was freshly painted in 2023. Further, additional significant updates offering peace of mind for years to come include: New furnace (2022) and new air conditioning unit (2023). There is also a smart thermostat system. This property is located in the Chester school district. Whispering Hills is an in-demand location - just minutes from shopping, restaurants, parks and more. Also, you'll love the easy access to main routes while enjoying the peaceful setting this development has to offer! Within Whispering Hills is the community pool for Summer fun, tennis court and sidewalks. Call for your private tour. Welcome home! *Special features sheet with more details and a floor-plan are available*

4114 Whispering Hills, Chester

$389,000
3 Beds 1 Baths 1019170 MLS
Welcome to 185 Oxford Road, Chester! •••••This charming 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral ceiling, natural woodwork, recessed lighting, and a welcoming breakfast bar in the open kitchen. The kitchen is equipped with a cooktop, oven, refrigerator, washer, and dryer (with both electric and gas dryer hookups right in the kitchen). You'll also appreciate the bow window, casement and double-pane windows that fill the home with loads of natural light. •••••The unfinished basement provides plenty of storage, conveniently accessed using Bilco doors. Outside, the level, landscaped lot offers front and backyard space and is partly wooded for privacy. •••••Highlights include: • Brand New Boiler • Brand New Gravel Driveway • Entire House Painted and Refreshed • Central Air plus Ductless Cooling in the Living Room • Propane hot water baseboard heating system • 2 Drilled Wells • Septic system (pumped every 4 years) • 100-amp electric service •••••Located in the highly rated Monroe-Woodbury School District, this home has annual taxes of $6,831 (after STAR discount for primary home-owners). •••••This affordable, single-level Ranch home combines classic appeal with modern improvements and a spacious lot — ideal for comfortable living with room to enjoy the outdoors. •••••Discover the Perfect Blend of Peaceful Country Living and Modern Convenience •••••Escape to this serene rural retreat that offers the best of both worlds: a tranquil, private country setting paired with unmatched accessibility. Nestled in a quiet, picturesque location, this home provides a true sense of peace and privacy while placing everyday essentials and major transportation routes just minutes away. •••••A Paradise for Outdoor Enthusiasts This property is an outdoor lover’s dream. Step outside and immerse yourself in abundant recreational opportunities, with excellent hiking, cycling, and rollerblading right at your doorstep. World-class natural destinations surround you, including Goosepond Mountain State Park, Harriman State Park, and Bear Mountain State Park — all offering miles of scenic trails, stunning lakes, and breathtaking vistas. •••••Just minutes away, the renowned Heritage Trail awaits — a beautifully paved 19.5-mile multi-use path along the historic Erie Railroad corridor, stretching from Middletown to Harriman. Whether you enjoy walking, running, cycling, or rollerblading, this scenic trail delivers peaceful countryside views and year-round enjoyment. •••••Effortless Commuting & Everyday Convenience Commuters will love the easy access to major routes: • Less than 3 miles to Route 17 (The Quickway) • Just 4 miles to the Monroe Park & Ride at Twin Lakes • Approximately 8 miles to the New York State Thruway (I-87) • About 10 miles to the Harriman Metro-North train station •••••Whether heading into the Hudson Valley or New York City, commuting is seamless and efficient. Shopping, dining, top-rated schools, healthcare, and all modern amenities are conveniently close, allowing you to enjoy a relaxed rural lifestyle without ever feeling isolated. •••••This rare combination of peaceful country charm, endless outdoor adventures, and superior location makes this home an exceptional opportunity for those seeking tranquility without compromise. Welcome home to your perfect sanctuary. •••••Reach out for a private showing today and discover all that 185 Oxford Road, Chester has to offer !!

185 Oxford Road, Chester

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