Chester Homes with Off Street Parking features

Welcome to Chester, New York – a hidden gem nestled in the picturesque Hudson Valley, within the heart of Orange County. This charming town offers a delightful blend of small-town charm and vibrant community spirit, making it an ideal place for families, retirees, and everyone in between. With its stunning landscapes, rich history, and outdoor recreational opportunities, Chester is a haven for nature lovers and those seeking a tranquil lifestyle.

One of the standout features of homes in Chester is the availability of off-street parking. In a town where outdoor adventures beckon, having your own dedicated parking space is a true luxury. Imagine returning home after a day of exploring the scenic trails of the nearby Harriman State Park or enjoying a leisurely afternoon at the local farmers market, knowing that you can park your vehicle conveniently and safely right at your doorstep.

Chester's real estate market boasts a variety of homes, from cozy cottages to spacious family residences, all equipped with the convenience of off-street parking. This feature not only enhances your living experience but also adds value to your property. Whether you’re hosting a summer barbecue or simply returning from a busy day, the ease of off-street parking allows you to enjoy your home without the hassle of street congestion.

With its welcoming community, beautiful surroundings, and the practical advantage of off-street parking, Chester is more than just a place to live – it’s a place to thrive. Come discover your new home in Chester, where comfort and convenience meet the beauty of nature!

Newest Chester Homes with Off Street Parking features

$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

$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

$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

$299,000

2 Beds ⋅ 1 Baths ⋅ 1042658 MLS

Welcome to Whispering Hills! This inviting end-unit home offers a comfortable blend of everyday living, privacy, and convenience. Enjoy easy access to major commuter routes and highways, making this an ideal choice for commuters seeking the comfort of home without sacrificing convenience. Come home to a welcoming community and enjoy all that this convenient location has to offer.

2124 Whispering Hills, 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

$360,000

3 Beds ⋅ 3 Baths ⋅ 1032618 MLS

Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways. Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace, providing a welcoming space to relax or entertain with a new HVAC system. The kitchen boasts modern stainless-steel appliances, ample cabinetry, and a functional layout, making it a delight for cooking and meal prep. Living in Whispering Hills comes with a wealth of amenities. Enjoy sunny days by the community pool, play a match on the tennis courts, or hit the gym for your daily workout. There are also handball courts and beautifully landscaped surroundings that make everyday living feel like a getaway. With a prime location, you’re never far from shopping, dining, and recreation options.

3409 Whispering Hills, Chester

$469,000

3 Beds ⋅ 3 Baths ⋅ 1034449 MLS

Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural character with generous living spaces and modern convenience. The main residence features an inviting floor plan with bright, sunlit rooms and comfortable living areas throughout. A standout highlight of this property is the separate detached barn/garage, featuring a private loft perfect for an artist studio, or a dedicated work-from-home space. Enjoy classic Village of Chester living with walkable access to schools, local dining, boutique shopping, parks, and effortless commuter routes. A rare find offering space and charm.

70 Main Street, Chester

$449,000

3 Beds ⋅ 2 Baths ⋅ 1033721 MLS

Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

66 Whitetail Run, Chester

$349,999

4 Beds ⋅ 2 Baths ⋅ 1024779 MLS

Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship. Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming atmosphere that highlights the home's authentic farmhouse appeal. Rich with historic charm and original details, this property is ready for its next owner to restore and make it their own. Enjoy peaceful, scenic views of the surrounding greenery while benefiting from a highly convenient commuter friendly location. Just minutes from the highway, downtown Chester, Goshen, Monroe, and Warwick, you'll have easy access to local shops, restaurants, parks, wineries, farmers markets, and everything the Hudson Valley has to offer. Priced with the home's restoration needs in mind, this is a rare opportunity to invest in a property with incredible potential, generous outdoor space, and an unbeatable location. Whether you're searching for a primary residence, weekend retreat, or renovation project, this farmhouse is ready to be brought back to life. Schedule your private tour today and imagine the possibilities!

241 Meadow Avenue, Chester

$3,400,000

4 Beds ⋅ 4 Baths ⋅ 988789 MLS

Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise. Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional. What truly sets this property apart is the lifestyle it delivers. A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence. Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home. Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley’s most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that is both active and refined. This is more than a residence. It is a fully realized compound, private, efficient, and architecturally significant, built for someone who values time, discretion, and a level of living that cannot be replicated.

19 Greentree Lane, Chester

$875,000

3 Beds ⋅ 3 Baths ⋅ 974429 MLS

The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the Sears & Roebuck catalogue and delivered by rail, this "pre-fab" pioneer was famously the first electrified home in the area. The current owner has meticulously performed a full-scale reconstruction, ensuring the home is entirely turn-key while honoring its heritage. The home features modern infrastructure with all-new mechanical systems, walls, and energy-efficient windows. Its preserved character is astounding. Every period molding, the original grand staircase, panel doors and authentic flooring have been salvaged and restored. The architectural heritage is monumental as it features its signature steeply pitched hipped roof and a dominant front-facing gable that defines its Victorian silhouette. Built for Howard Conklin—the local postmaster/general store owner—and later by his son, Dr. Roger Howard Conklin, this residence has been a cornerstone of the community for over a century. It represents a rare opportunity to own a piece of Hudson Valley history without the burden of historic maintenance. The lifestyle in Sugar Loaf and Chester, NY is refreshing, especially to New Yorkers getting away from the city. Nestled in a tight-knit arts and crafts hamlet, one is steps away from 18th-century buildings housing artisan studios, galleries, and boutique eateries. And there is rich Outdoor Adventure to take advantage of too! The area has direct access to the 18-mile Heritage Trail for biking and walking, plus proximity to Goosepond Mountain State Park and the Birnberg Nature Preserve. Its rural serenity offers a quiet, creative lifestyle surrounded by majestic mountains and rolling meadows, all while being part of a bustling weekend destination. Driving to and from the Conklin House to NYC is about 1 hour and 15 minutes and using mass transit a little longer. This is more than a house; it is a storied landmark reimagined for the modern connoisseur. Nothing compares to the character, lifestyle and wilderness that the Conklin House has to offer.

2 Pine Hill Road, Chester

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