Dutchess Homes with Detached Parking features

Welcome to Dutchess County, New York—a picturesque gem nestled in the heart of the Hudson Valley. Known for its stunning landscapes, rich history, and vibrant communities, Dutchess County offers a unique blend of suburban charm and rural tranquility. With its rolling hills, scenic rivers, and lush parks, this area is perfect for outdoor enthusiasts and families alike. Whether you’re hiking the trails of the Appalachian Trail or enjoying a leisurely afternoon at one of the county’s many wineries, there’s always something to explore.

Dutchess County is home to a diverse array of towns and villages, each with its own distinct personality. From the historic streets of Poughkeepsie to the quaint charm of Rhinebeck, you’ll find a welcoming atmosphere and a strong sense of community. The county boasts excellent schools, abundant recreational opportunities, and a rich cultural scene, making it an ideal place to call home.

For those seeking a new residence, Dutchess County offers a variety of homes, many featuring the highly sought-after detached parking option. Imagine coming home to a beautiful property with ample space for your vehicles, providing convenience and peace of mind. Detached garages not only offer protection from the elements but also create additional storage options, enhancing your living experience.

Explore the enchanting neighborhoods of Dutchess County and discover your dream home today. With its beautiful scenery, vibrant culture, and homes that cater to your lifestyle needs, you’ll find that Dutchess County is not just a place to live—it’s a place to thrive.

Newest Dutchess Homes with Detached Parking features

$5,750,000

4 Beds ⋅ 3 Baths ⋅ 1048609 MLS

In a premier location on a quiet road in Millbrook Hunt country, this unique property of 100 acres has been in the same family for 44 years. Proudly maintained, protected and in conservation, Shooter’s Hill is an exceptional offering and an unparalleled opportunity to own and enjoy the tranquility of this magical sanctuary, yet only minutes from Millbrook Village, clubs, schools and other amenities. Nestled on a hillside, this four bedroom, three bath home overlooks beautiful meadows, farm fields, three masterly designed stepping ponds, and protected woodlands laced with extensive trails. Completing the homestead is a two story barn with an artist studio and a two-room office building with a three-car garage. Contiguous to Bontecou Wildlife Conservation Preserve of 1258 acres.

81-85 Fraleigh Hill Road, Millbrook

$199,900

3 Beds ⋅ 2 Baths ⋅ 1049221 MLS

Nestled against NYS Taconic Park land, this older single-family home offers unlimited potential in an irreplaceable setting. Surrounded by 1.4 acres of lush, mature landscaping, the backyard borders a scenic trail linking the historic Ogden Mills Estate to the Norrie Point Environmental Center and Marina. Whether you are looking to create a lucrative short-term rental or craft a private retreat for buyers who appreciate nature and historic Hyde Park, the possibilities are endless. Enjoy year-round outdoor recreation right from your doorstep. Located in the quaint hamlet of Staatsburg—featuring a vibrant local library, basketball and pickleball courts, a renowned golf course, local dining, and a 10-minute drive to the train station. Unique location. Property is being sold as-is and awaits your vision!

10 Cedar Street, Staatsburg

$475,000

3 Beds ⋅ 1 Baths ⋅ 1048856 MLS

Welcome home to this charming 3-bedroom, 1-bath Cape, offering a wonderful blend of classic character and everyday comfort. The updated kitchen has plenty of cabinets and features a wall-mounted pot-filler faucet above the range so you can fill pots directly on the cooktop without carrying them from the sink. The six-burner range is heated by propane. The living room and bedrooms all have hardwood flooring. A full unfinished basement offers plenty of storage and potential for future use. Enjoy additional living space in the inviting enclosed porch—perfect for morning coffee, relaxing, or enjoying the seasons. Outside, a level yard provides plenty of room for gardening, play, or outdoor gatherings, while the detached garage offers convenient parking and additional storage. A delightful home in a welcoming setting—come see all it has to offer!

3 Kinderhook Drive, Poughkeepsie

$1,375,000

3 Beds ⋅ 2 Baths ⋅ 1049518 MLS

Built in 1787, this wonderfully preserved Hudson Valley farmhouse carries more than two centuries of history with an ease that feels remarkably livable today. Original details remain at the heart of the three-bedroom, two-bath home, set on just shy of 5 acres: wood floors, period hardware, a Dutch door with distinctive patty-pan hinges, exposed structural elements and a generous fireplace anchoring the main living space. These early details are complemented by a thoughtfully updated kitchen that feels clean and understated while remaining sympathetic to the architecture. Light moves beautifully through the house, while a generous screened porch extends the living space outdoors—a relaxed place for summer dinners, morning coffee and long afternoons overlooking the surrounding landscape. Outside, mature trees and established plantings frame the farmhouse, while an impressive original three-bay barn adds another layer of history, character and possibility. And while the setting feels wonderfully removed, it is anything but remote. Bard College and the center of Red Hook are just minutes away, with Rhinebeck and Hudson both within easy reach and Amtrak service from Rhinecliff providing a convenient connection to New York City. What makes this property particularly compelling is what hasn’t been erased. The craftsmanship, patina and wonderful irregularities of an 18th-century farmhouse remain, balanced by the comfort and simplicity of a home meant to be lived in now. A rare opportunity to become the next steward of a Hudson Valley farmhouse dating to 1787—Dutch door, patty-pan hinges, original barn and all.

101 Spring Lake Road, Red Hook

$289,000

3 Beds ⋅ 2 Baths ⋅ 1049009 MLS

Brand-New 2026 Living in Pleasant Valley. Welcome to 9 Odell Lane, a brand-new 2026 model offering modern finishes, generous living space, and effortless low-maintenance living. The bright, open-concept interior features a spacious kitchen with center island, contemporary cabinetry, recessed lighting, new appliances, and a clean, neutral design throughout. Outside, enjoy a generous yard framed by mature trees, providing plenty of space to relax, entertain, garden, or simply enjoy the outdoors. A spacious rear deck extends your living space outside, while the detached garage offers valuable additional parking, storage, or workspace. Located in a well-maintained community, the $838/month lot fee includes snow removal, garbage pickup, water & taxes, all while keeping you minutes from Pleasant Valley, Millbrook & LaGrange. New construction, modern comfort, and outdoor space—all without the maintenance of a traditional property. Schedule your private tour of 9 Odell Lane today!

9 Odell, Pleasant Valley

$895,000

3 Beds ⋅ 2 Baths ⋅ 1047613 MLS

Situated along Millbrook’s main avenue, this 1900s traditional home offers character and comfort, in an exceptional location. The first floor features a spacious kitchen, a light-filled living room with fireplace and an inviting dining room. A mudroom with laundry and a full bathroom completes this main level. Upstairs, you’ll find three bedrooms and a full bathroom. A walk-up attic and full basement provide abundant space for storage. Outside, a wonderful wraparound porch offers the perfect vantage point for enjoying the energy and charm of village life, including seasonal events and community gatherings. A rear deck overlooks the beautifully landscaped yard and gardens, creating a lovely setting for relaxing or entertaining. A detached garage and additional parking are conveniently accessed from a service road at the rear of the property, preserving the home’s pristine curb appeal along Franklin Avenue. Located just steps from the best of Millbrook, this home is an easy stroll to outdoor summer concerts, the Farmers’ Market, library, public tennis courts, parks, shops and restaurants. With convenient access to the nearby Metro-North station and Taconic Parkway, this could be the perfect weekend getaway or full time residence.

3315 Franklin Avenue, Millbrook

$1,125,000

4 Beds ⋅ 3 Baths ⋅ 1044719 MLS

This exceptional log home offers a tranquil retreat on 8.8 acres, featuring a private pond and a park-like setting. The property emphasizes privacy and includes an inground pool with a deck for outdoor enjoyment. Additionally, it boasts a substantial workshop with a one-bedroom guest quarters located above it, providing versatile extra space. Another run-in shed offers further utility storage. The location is highly desirable, offering the serenity of a private estate while remaining just minutes from the charming Rhinebeck village and convenient access to the Taconic Parkway.

331 Mountain View Road Unit #325, Rhinebeck

$695,000

4 Beds ⋅ 2 Baths ⋅ 1047901 MLS

Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$680,000

3 Beds ⋅ 2 Baths ⋅ 1047398 MLS

A little bit of magic lives at 16 Carlson Road. Built in 1850, this charming home feels like something out of a fairytale, surrounded by nearly nine acres of mature gardens and old-growth trees. Walking paths wind through the acreage, and the beautifully established landscape gives the property a character all its own. While the history of the home is felt throughout, recent thoughtful updates have been made, creating comfortable, beautifully considered spaces while preserving the character that makes it so special. Inside, natural light fills the rooms, with skylights overhead and windows framing views of the surrounding gardens. The main level unfolds through a series of inviting spaces, including a sunroom, formal and informal dining rooms, and a living room anchored by a wood-burning stove. A deck just off the dining room sits beneath an extraordinary mature hydrangea, creating a natural canopy for long summer lunches and dinners outside. The primary suite is on the main level, with radiant floor heating extending through both the bedroom and spacious bathroom. Two generously sized walk-in closets provide ample storage, while French doors open directly onto a bluestone patio. Just off the bedroom, a charming home office with built-ins makes working from home feel decidedly less like work. Upstairs, two sun-filled bedrooms share a bathroom with a clawfoot tub, with ample storage throughout. The property also includes two outbuildings: a one-car garage and a separate garage/workshop with a loft above, ready for projects, studio space, or whatever creative pursuits the property inspires. Just five minutes from the Harlem Valley Metro-North station, the property offers easy access to New York City, with Grand Central just over two hours away. Wassaic Metro-North is 20 minutes away, with Kent, Connecticut just 10 minutes away and Millbrook approximately 25 minutes. It’s a rare kind of Hudson Valley retreat, where beautiful gardens, a sense of history, and just a little everyday magic come together.

16 Carlson Road, Wingdale

$519,990

4 Beds ⋅ 3 Baths ⋅ 1047097 MLS

This beautiful Victorian is located in the sought after Hamlet of Staatsburg. It has been completely updated and has all its original charm along with many modern updates. The home features its original hardwood floors throughout. The whole house has been freshly painted inside and out. Gorgeous updated kitchen with granite countertops and center island. All 3 bathrooms have been beautifully renovated. All new energy efficient windows in every room. Each and every bedroom is nicely sized. Fantastic 2 car detached garage behind the home. Full unfinished basement. Large deck off of the kitchen is great for entertaining your guests. You can walk to restaurants, the library, Dinsmore Golf Course, and the historic site at Mills Mansion. You will not find a true Victorian home for this price anywhere in Dutchess County and especially not in the Hamlet of Staatsburg.

46 Old Post Road, Staatsburg

$575,000

6 Beds ⋅ 6 Baths ⋅ 1036859 MLS

Welcome to a truly special piece of Poughkeepsie history. Built in 1877 and set within the Historic District, this striking Victorian residence offers an exceptional opportunity to restore and reimagine a grand historic home while preserving its remarkable architectural character. From the gracious curved staircase and soaring ceilings to original hardwood floors, intricate moldings, pocket and French doors, multiple fireplaces, and a distinctive glass-enclosed cupola, the craftsmanship and scale of this home are rarely found today. With approximately 4,831 square feet, three levels, 8 plus bedrooms (tax indicate 6), 6 baths (3 full 3 half), a spacious kitchen with cherry cabinetry, granite countertops and multiple work areas, plus a butler's pantry, the possibilities are extensive. A full basement, detached garage, private yard, and rooftop garden area with views add even more potential. Recent improvements provide a foundation for the next chapter, while the property's historic details invite thoughtful restoration. Whether envisioned as a magnificent private residence, a thoughtfully restored historic property, or another permitted use subject to municipal approval, 8 Garfield Place is an extraordinary opportunity to bring a landmark-quality home back to its full glory.

8 Garfield Place, Poughkeepsie

$650,000

3 Beds ⋅ 3 Baths ⋅ 1044510 MLS

Set beautifully near the center of almost 8 private acres, this cherished home has been owned by the same family for nearly 50 years and offers a setting that invites you to slow down and enjoy the natural beauty that surrounds you. A picturesque pond, meandering stream and waterfalls create a peaceful backdrop, while thoughtfully positioned gardens and mature landscaping offer something beautiful to enjoy in every season. Spend quiet mornings listening to the sounds of the water, relax on the screened-in porch with your morning coffee or evening cocktail, or gather with family and friends on the stone patio. Inside, warmth and character continue with hardwood floors throughout, two wood-burning stoves and distinctive wood details that give the home its inviting feel. The kitchen is appointed with quartz countertops and a custom island with seating, while the dining room provides the perfect setting for everything from intimate dinners to holiday gatherings and entertaining. Designed for the ease of one-level living, the home offers three bedrooms and two full baths on the main level, including a primary bedroom with private en-suite bath, along with additional rooms offering flexibility for a den, home office, in-law space, guest accommodations or whatever best suits your lifestyle. A conveniently located laundry area just off the kitchen leads directly to the stone patio, making indoor-outdoor living easy. The lower level provides convenient access to the two-car garage, while an additional carport is ideal for storing equipment and machinery or providing a dedicated exterior workspace. Located in the Millbrook School District and just five minutes from the Taconic State Parkway, this special property offers a rare combination of privacy, natural beauty, character and convenience. After nearly five decades with one family, this much-loved home and property are ready for their next chapter.

2800 Route 82, Pleasant Valley

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