Chester Homes with Driveway Parking features

Welcome to Chester, New York—a picturesque gem nestled in the heart of Orange County. Surrounded by the breathtaking beauty of the Hudson Valley, Chester is a charming town that perfectly blends small-town allure with modern conveniences. With its rolling hills, lush greenery, and vibrant community spirit, Chester offers a serene escape while still being just a stone's throw away from the bustling cities of New York and New Jersey.

Chester is known for its rich history and welcoming atmosphere, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle. The town boasts a variety of recreational activities, including hiking trails, parks, and local events that foster a strong sense of community. From farmers' markets to seasonal festivals, there's always something happening in Chester to engage residents and visitors alike.

When it comes to finding your dream home in Chester, you'll be delighted to discover a range of properties featuring driveway parking. Imagine arriving home to your own private space, where you can easily park your vehicle without the hassle of street parking. Homes with driveway parking not only provide convenience but also add an extra layer of comfort and security.

Whether you’re looking for a cozy cottage, a family-sized home, or a luxurious retreat, Chester's real estate market offers a diverse selection of properties to suit your needs. Embrace the charm of Chester, where community, nature, and modern living harmoniously coexist. Your dream home awaits in this idyllic town!

Newest Chester Homes with Driveway Parking features

$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

$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

$679,000

4 Beds ⋅ 4 Baths ⋅ 1046418 MLS

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester

$374,900

3 Beds ⋅ 2 Baths ⋅ 1044316 MLS

UNLOCK UNLIMITED POTENTIAL IN WARWICK VALLEY SCHOOLS! Are you ready to stop renting, build instant equity, and design your dream home from the ground up? This hidden gem off Gibson Hill Road is your golden ticket into one of Orange County’s most desirable school districts at a rare and unbeatable entry-level price! Whether you are a savvy investor looking for your next high-margin flip, a contractor seeking a prime project, or a first-time homebuyer eager to earn serious sweat equity, the upside potential here is off the charts! Nestled in a peaceful setting with a shared private access setup off well-maintained Speranza Ct, you get the perfect balance of serene rural living with easy access to regional commuter routes, local dining, shopping, and wineries. Set on an acre of private, flat land, this 3 bedroom bi-level is a handyman special. Bring your contractor, bring your measuring tape, and bring your inspiration—roll up your sleeves and transform this structure into a showstopping countryside retreat! Property is being sold AS-IS. Bring your offers and turn your homeownership vision into reality today! No gov't loans due to condition.

260 Gibson Hill Road, Chester

$1,685,000

6 Beds ⋅ 8 Baths ⋅ 1043860 MLS

Welcome to 69 Cedar Pond Lane. Perched to capture panoramic mountain views, this expansive Chester estate offers an extraordinary combination of multi generational living, proven Airbnb and rental income potential, and top tier infrastructural upgrades across three fully finished levels. The first floor and its bright living & seamless entertaining sun drenched interiors greet you with soaring skylights and massive picture windows framing panoramic mountain views. The open living and dining layout centers on a wood-burning fireplace, flowing into a chef’s kitchen featuring new countertops, custom tile backsplash, breakfast bar, dining nook, built in wine rack, new refrigerator, dedicated beverage fridge and so much more. This floor features two bedrooms and 2.5 bathrooms, with direct walkout access to an expansive outdoor patio outfitted with an outdoor bar, fireplace, and lounge seating. On the second floor you're greeted to a luxury primary suite & a private in law apartment. The upper level hosts three bedrooms, highlighted by a primary suite with mountain vistas, a walk in closet, and a spa bath with dual vanities, a deep soaking tub, stand up shower, and private water closet. This floor also features a dedicated second kitchen, living room, and private patio access. Thoughtfully updated with new countertops, a built in electric fireplace, and an integrated media center, this wing easily functions as an independent, fully equipped apartment. Downstairs is a guest suite & hidden speakeasy. Designed for recreation and flexible guest accommodations, the walkout lower level features a large open playroom created by opening the main space, complemented by a kitchenette, new carpeting, and updated tile. This level includes an Airbnb ready bedroom, finished laundry room, a newly added half bath, and an additional versatile flex room ideal for a home gym, private office, extra bedroom, or mudroom. Concealed discreetly behind a custom bookshelf lies a finished secret room with an adjacent full bathroom, perfect for a private lounge, speakeasy, or creative studio. Unwind in the private hot tub positioned to the right of the home, gather around the backyard fire pit, or enjoy the upper driveway area landscaped with a dedicated children's playset and seating area. The backyard has already been scoped for a custom in ground pool, with renderings available by seller. Additionally, the lower lot can be subdivided and built on, with electrical infrastructure already set up. The property includes a high efficiency HVAC system, commercial grade well pump, and dual water heaters installed in 2025. The roof was replaced around 2022. Ceiling fans and skylights are installed throughout, and all interior wallpaper is high quality peel and stick for effortless design customization. Whether you are looking for a spacious family home, a turn key rental retreat, or a property with room to build and expand, 69 Cedar Pond Lane has it all. Schedule your private tour today and see everything this one of a kind home has to offer.

69 Cedar Pond Lane, Chester

$290,000

2 Beds ⋅ 2 Baths ⋅ 1043197 MLS

Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors. Additional updates include a newer furnace, central air conditioning and water heater! Enjoy country club-style living with fantastic community amenities including clubhouses, swimming pools, tennis courts, basketball courts, playgrounds, walking areas and a dog run. An excellent commuter location with NYC bus service right in the complex, plus convenient access to major highways, shopping, restaurants and everyday necessities. Comfort, convenience and community amenities all in one—this is one you won’t want to miss!

1005 Whispering Hills, Chester

$749,000

4 Beds ⋅ 3 Baths ⋅ 1042913 MLS

Imagine coming home to a beautifully maintained and upgraded property designed for comfort, entertaining, and enjoying the outdoors. This home features a high-ceiling foyer flooded with natural sunlight, a granite kitchen with a tiled backsplash, a gas fireplace, extra living and dining room space, 9-foot ceilings, hardwood flooring, and central AC throughout. Step outside to an oversized double deck offering a breathtaking view from the 1.4-acre property, complete with an above-ground pool and cozy hot tub. Recent updates include new flooring in 3 bedrooms. A two-car garage and driveway provide ample parking. The home CURRENTLY OPERATING AS AN AIRBNB with approximately $70,000 in annual revenue after Airbnb fees. The sale includes all furniture, appliances, kitchen housewares, and all TVs, offering a truly move-in-ready opportunity with the option to seamlessly continue the existing rental use. Conveniently located near Lowe’s, ShopRite, The Castle Fun Center, and major highways, and very close to Legoland. Don’t miss this unique opportunity!

121 Conklingtown Road, Chester

$550,000

3 Beds ⋅ 2 Baths ⋅ 1042882 MLS

Welcome to this charming ranch style home set on 4 picturesque acres, featuring beautiful flowing hardwood floors and a peaceful, private setting. The inviting kitchen offers gorgeous marble countertops, an abundance of cabinetry, a sink positioned beneath the windows, and stainless-steel appliances. From the living room, double sliding doors open onto the expansive wraparound porch, creating an effortless connection to the serene backyard perfect for relaxing, entertaining, or enjoying the surrounding nature. The spacious primary suite features a huge closet and a private master bath. Two additional bedrooms offer generous closet space, providing plenty of room for family, guests, or a home office. Step outside and cross the charming bridge over the stream to access the enlarged backyard, offering even more space to enjoy the outdoors. A spacious 24' x 28' detached garage with a 10' x 10' garage door provides ample room for large vehicles, ATVs, a workshop, equipment, and storage. Conveniently located just minutes from Route 17, shopping, restaurants, and everyday amenities, this property offers the perfect blend of country tranquility and convenient access to town.

50 Hambletonian Avenue, Chester

$649,999

3 Beds ⋅ 3 Baths ⋅ 1041906 MLS

If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of finished living space, offering room for everyone and every lifestyle. Set on approximately 2 acres and conveniently located near schools, shopping, and transportation, this home delivers the perfect combination of space, flexibility, privacy, and convenience! Step inside to a bright, open-concept main level with soaring vaulted ceilings, a welcoming living room with fireplace, and a dining area featuring custom lighting. The beautifully appointed kitchen offers granite countertops, breakfast island, stainless steel appliances, and direct access to the spacious back deck—perfect for effortless indoor/outdoor entertaining. Three bedrooms are located on the main level, including a spacious primary suite with vaulted ceiling, wall-to-ceiling closets, hardwood floors, and abundant natural light. Two additional bedrooms and convenient main-level laundry complete the first floor. The fully finished lower level is a true bonus, offering endless possibilities with LVP flooring, custom built-in shelving, walk-out access, entertainment space, family room/den, and a bonus room currently used as an office that could easily serve as a guest room or additional sleeping space. A full bath with custom vanity and tiled shower makes this level ideal for guests, extended living, hobbies, or working from home. Outside, enjoy a sprawling yard, mature landscaping, circular driveway, and plenty of room to play, relax, and entertain. The spacious back deck and hot tub create the perfect private retreat. Space, style, flexibility, and location—all in one exceptional property. This is the one you’ve been waiting for!

3561 Rte 94, Chester

$699,000

5 Beds ⋅ 4 Baths ⋅ 1041722 MLS

Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful, wooded setting. From the inviting covered front porch, step inside to spacious, light-filled rooms that blend comfort and elegance. Rich hardwood floors, soaring ceilings, abundant windows, and a beautiful stone fireplace create a warm and welcoming atmosphere. The heart of the home is the expansive open kitchen, featuring modern appliances, generous cabinetry, and plenty of counter space, making it ideal for everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, offering both open gathering spaces and cozy nooks. Five generously sized bedrooms provide flexibility and room for everyone. Enjoy the outdoors from the extensive decks overlooking the mature, wooded surroundings, complete with a charming koi pond that adds to the property's peaceful, natural setting. Whether enjoying morning coffee, entertaining guests, or simply unwinding, this outdoor space offers a tranquil retreat. Adding exceptional versatility, a separate approximately 800-square-foot building offers endless possibilities as an art studio, workshop, private office, creative space, or whatever best suits your needs. With its combination of generous living space, distinctive character, privacy, and flex outbuilding space, this property offers a truly special place to call home.

65 Oxford Springs Road, Chester

$669,000

3 Beds ⋅ 3 Baths ⋅ 1040801 MLS

Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities. Conveniently located near shopping, restaurants, and all that the Hudson Valley has to offer, and located in the Warwick School District. A wonderful opportunity to make this colonial your new home!

173 Creamery Pond Road, Chester

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