Chester Homes with Private Parking features

Welcome to Chester, New York – a hidden gem nestled in the heart of Orange County. Known for its breathtaking landscapes and vibrant community, Chester offers a perfect blend of small-town charm and modern amenities. With its picturesque views of the nearby mountains and serene lakes, this area is ideal for those who appreciate nature and an active lifestyle. Whether you’re exploring the scenic hiking trails, indulging in local eateries, or enjoying community events, Chester has something for everyone.

One of the standout features of homes in Chester is the availability of private parking. In a world where convenience is key, having your own designated parking space is a significant advantage. Many properties in this charming town come equipped with private parking options, allowing residents to enjoy the peace of mind that comes with secure and accessible parking. Imagine returning home after a long day, knowing you have a dedicated spot waiting just for you – it’s a luxury that enhances your living experience.

Chester’s real estate market offers a diverse range of homes, from cozy cottages to spacious family residences, all designed to suit various lifestyles and budgets. With private parking as a common feature, homeowners can relish the ease of coming and going without the hassle of street parking or crowded lots.

If you're searching for a place that combines natural beauty, a warm community atmosphere, and the practicality of private parking, Chester, NY, is the perfect destination. Discover your dream home in this enchanting town today!

Newest Chester Homes with Private Parking features

$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

$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

$575,000

6 Beds ⋅ 2 Baths ⋅ 992189 MLS

Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The Second beautiful structure offers hardwood floors, as seen, 2 bedrooms, a kitchen, a living room, and 1 full bath. In addition, there is a garage about 750 sq that can be rented out for another few hundred dollars a month. Enjoy the beautiful 1.1-acre property. This unique property has multiple opportunities!

68 Conklingtown Road Unit #1&2, Chester

$1,195,000

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

22 Goshen Road, Chester

$875,000

4 Beds ⋅ 3 Baths ⋅ 1011165 MLS

Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by nature. The soaring great room creates a dramatic first impression, while the beautifully updated kitchen serves as the heart of the home with its oversized island and bright, modern finishes. Outside, the expansive grounds provide endless possibilities—from entertaining and recreation to simply enjoying the peaceful surroundings. With 4 bedrooms, 2.5 baths, and over 3,600 square feet of living space, this property offers room to spread out while enjoying the privacy and beauty of its remarkable setting.

49 Stone Mountain Trail, Chester

$525,000

4 Beds ⋅ 3 Baths ⋅ 1004369 MLS

Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange Heritage Trail, local dining, and easy commuter access, this property is as practical as it is inviting. The main residence spans three spacious bedrooms and 1.5 baths, offering comfortable everyday living with room for the whole family. The private secondary suite features a bright one-bedroom, one-bath layout, ideal for in-laws, extended family, an au pair, or a long-term rental opportunity. Whether you're seeking to offset your mortgage or keep loved ones close while preserving everyone's privacy, this thoughtful configuration checks every box. With a 2,698 sq ft footprint, a full basement, attached garage, hardwood floors, central air, and a sweeping 0.56-acre lot with park views, this home combines classic charm with everyday function. Located in the Chester Union Free School District and just a short drive to Legoland, the Capelli Sports Complex, and Coach USA transit to NYC — 24 Walnut Street isn't just a home. It's a lifestyle. Opportunity like this doesn't last. Schedule your private showing today.

24 Walnut Street, Chester

$749,999

4 Beds ⋅ 3 Baths ⋅ 995624 MLS

Looking for a spacious home that has everything? Look no more! Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial offers over 3,300sqft of living space! The property offers four spacious sleeping areas and 2.5 baths. Endless possibilities for additional use continue on the 3rd floor with a 15 x 42 climate-controlled walk-up attic, offering approximately 630 additional square feet of space. Whether envisioned as a media lounge, home gym, creative studio, guest suite, game room, or finished living area, this expansive attic provides an incredible opportunity to customize the home to fit your lifestyle and needs. On the main level sun-filled living spaces showcase hardwood floors, recessed lighting, a striking stone fireplace, and an expansive family room with a pellet stove capable of heating the entire home. The spacious kitchen serves as the heart of the home, complete with granite countertops, abundant cabinetry, stainless steel appliances, double ovens, and direct access to the backyard for seamless indoor-outdoor living. Spectacular views, a fenced backyard, brand-new Trex deck, above-ground pool, and potential home office, make this property truly stand out. Abundant living space, flexible rooms, exceptional storage, newer major systems, outstanding outdoor amenities and exceptional curb appeal make this property the rare combination of comfort, functionality, and room to grow.

58 Nancy Lane, 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

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