Dutchess Homes with On Street Parking features

Welcome to Dutchess County, New York – a picturesque blend of natural beauty, vibrant communities, and rich history. Nestled in the heart of the Hudson Valley, Dutchess County is renowned for its stunning landscapes, charming towns, and a lifestyle that perfectly balances tranquility with accessibility. With the Hudson River winding through its heart, residents enjoy a plethora of outdoor activities, from hiking the scenic trails of the Appalachian Mountains to leisurely strolls along the riverbanks.

Dutchess County boasts a diverse array of neighborhoods, each with its unique character and charm. Whether you are drawn to the historic streets of Poughkeepsie, the quaint shops in Rhinebeck, or the family-friendly atmosphere of Fishkill, there’s a perfect home waiting for you. One of the appealing features of many homes in this area is the availability of on-street parking. This convenience not only enhances the ease of daily living but also reflects the welcoming community spirit that defines Dutchess County.

Imagine returning home after a day of exploring local wineries, farmers' markets, or art galleries, and finding a convenient spot right outside your door. With on-street parking, you can easily welcome friends and family, making gatherings effortless and enjoyable.

In Dutchess County, you’ll find a place that feels like home, where the beauty of nature meets the warmth of community. Discover your dream home today and embrace the vibrant lifestyle that awaits you in this enchanting part of New York!

Newest Dutchess Homes with On Street Parking features

$426,500

3 Beds ⋅ 3 Baths ⋅ 1050260 MLS

Super central location! Charming, 3-4 bedroom home better than new inside and out. Close to the Arlington schools, town shopping, trains, public transportation, hospitals and more. This home has been well cared for. First level is a spacious open floor plan of the kitchen, dining area and living room. Beautiful custom kitchen and appliances are a cooks delight. main level all ne lighting, windows and flooring. Second floor has 3 bedroom and a full bath all renovated. Easy access to attic or loft area. Large family room down from kitchen with all custom wood work and windows, with cathedral ceiling and skylights. Bonus rooms and so much to offer along with manicured grounds.

88 Innis Avenue, Poughkeepsie

$695,000

4 Beds ⋅ 3 Baths ⋅ 1046889 MLS

Move right into this like-new 4-bedroom, 2.5-bath Colonial on a corner lot, in the Arlington School District, built in 2022 and offering over 2,685sq ft of beautifully maintained living space. A welcoming rocking-chair front porch leads inside to rich dark hardwood floors, light neutral tones, and an open, elegant layout. The main level features a formal dining room, an expansive two-story family room with fireplace and dramatic windows, and a stunning kitchen with stainless steel appliances, and center island. Sliding glass doors open to a back deck overlooking the yard. An office/den/playroom, large half bath, and garage access complete the first floor. Upstairs, hardwood floors open hallway overlooking the family room. Four spacious bedrooms, a full bath with double sinks, and a large laundry room add convenience. The primary suite offers a generous walk-in closet and bathroom with double vanity, and oversized walk-in shower. A full basement provides exceptional storage or future finishing potential. Additional highlights include natural gas, municipal water, community sewer, window treatments and power blinds. Ideally located minutes from the Taconic Parkway. A rare opportunity to enjoy like-new construction without the wait.

16 Kensington Lane, Poughkeepsie

$585,000

3 Beds ⋅ 1 Baths ⋅ 1043794 MLS

Welcome home to this charming, ranch beautifully situated in a very desirable location in Beacon with scenic mountain views and inviting curb appeal. The well-maintained front yard features lovely, mature landscaping and a welcoming bay window that adds character and natural light to the home. The fenced in backyard also includes a separate contained garden section for your flowers , herbs or vegetables! Enjoy the convenience of a wide sidewalk-lined street and a pleasant neighborhood setting. This well-loved and cared for home includes an ample living room , dining room and eat-in kitchen with 3 bedrooms and hardwood floors throughout. Double hung windows, updated bathroom and a 5 year old roof add to your piece of mind. Last, but certainly not least, this home has a PRIME location that can't be beat - 4 blocks from Main St. with all its restaurants and shops and a 4 minute drive from the Beacon train station or I-84. Picture yourself on the deck enjoying a cup of coffee or a cocktail while enjoying your views. This home is a Must See!!!

67 E Willow Street, Beacon

$524,000

4 Beds ⋅ 3 Baths ⋅ 1046416 MLS

PRICE REDUCED! BACK ON MARKET! Spackenkill Town of Poughkeepsie NY welcome to this beautifully renovated multi-level home 4BR 3 Baths on plush grounds w/mature trees. Quiet peaceful 1/2 acre setting, attached 2 car-garage, new paved driveway. Highly sought-after Spackenkill schools in community of well kept homes. You can walk kids to nearby schools. Clean, turn-key, move-in ready. Foyer w/large windows, new Anderson storm door, new lighting, new wood flooring, double sliding closet doors. Den on entry level off Foyer w/Half Bath and;addtl hot/cold valves for potential Shower or alternate Washer/Dryer location, and access to rear of house. Main Floor presents spacious Living Rm w/Brick Fireplace for warm; Winter nights. Brand new Kitchen w/White Cabinetry, Marble Countertops, Stainless Steel appliances, new fixtures, new lighting, new wood flooring. Formal Dining Rm w/new lighting and Anderson double sliding glass doors leading out to large Upper and Lower Decks. Large Backyard great for entertaining or just listening to sounds of nature. Upper Floor presents roomy Primary BR w/Ensuite Bath and generous closets, 3 addtl BRs, Hallway;Main Bath;and Linen Closet.;All Baths feature new vanities, new fixtures, new mirrors, new lighting, new flooring. Freshly refinished natural oak hardwood floors like-new throughout, and freshly painted home. New windows, new extra large roof gutters, new AC w/Wi-Fi features. Clean Dry Finished;Bsmt w/all;new Windows, hook-up for;Washer/Dryer, Utilities, and space for your imagination. Oil Heat, Town Sewer, your choice of Well or Town Water. New Owned Security and Fire System 24/7 live-monitoring w/many features. 2,067sf Total. Close to schools, shopping centers, restaurants, entertainment, health facilities, walking trails, main roads, bus routes, Rte 9, Rte 55, Rte 44, bridges over Hudson River, Taconic State Pkwy, convenient commuter location. All taxes $7,914. Make this home your dreamhouse!

31 Old Farms Road, Poughkeepsie

$540,000

1044674 MLS

Two Story, Mixed Use Brick Commercial Bldg For Sale In The Business District Of Poughkeepsie. This Property Comes As Turnkey With An Established Convenience Store Included In The Sale And With A Separate Additional Level On The Second Floor Offering More Opportunity For Additional Income. Allow The Photos Included To Give You A Glimpse Of The Vast Amount Of Diverse Inventory Incorporated Into This Sale, And There's More! Although The Present Owner Is Not Participating, The Store Had Been And Can Be Licensed For A Deli Plus Lotto And EBT Can Be Added To Paint A More Profitable Picture. Here You Can Purchase Not Only The Bldg In A High Foot And Vehicle Traffic Area., But Also The Business Already Set Up For Instant Income Plus Owning Land, The Building And Your Own Business. Feel Free To Have Your Agent Of Choice Make Your Appointment To View.....Perhaps, Your Future Earning Possibilities. Serious Inquiries Only. Agents, Please See Other Remarks.

352 Main Street, Poughkeepsie

$185,000

1 Beds ⋅ 1 Baths ⋅ 1042178 MLS

Welcome to this spacious 925-square-foot, second-floor condominium in the Cherry Hill community. Offering more room than many one-bedroom units, this move-in-ready home features true Central Air throughout, an open living and dining area, a convenient walk-through kitchen, and a generously sized bedroom with a large walk-in closet. Step outside onto the private balcony and enjoy comfortable, low-maintenance living. The monthly HOA fee includes heat, hot water, exterior maintenance, snow removal and garbage service. Ideally located just minutes from the popular Adams Fairacres Farms, as well as additional shopping, dining, commuter routes and Metro-North. An excellent opportunity for an owner-occupant or investor.

210 Cherry Hill Drive, Poughkeepsie

$1,550,000

4 Beds ⋅ 4 Baths ⋅ 1034392 MLS

This gorgeous Four Bedroom Colonial welcomes you with exceptional curb appeal & an elegant presence from the street. Offering Three full floors of beautifully appointed living space. The home blends timeless architectural character with thoughtful custom design throughout. The main living spaces are ideal for both everyday living and entertaining, featuring a gourmet kitchen, formal dining room, & an impressive entertainers room with a dramatic floor to ceiling stone wood burning fireplace. A sun filled home office surrounded by windows provides an inspiring workspace, while custom designed bathrooms & expansive crown molding, personally designed by the current owner add sophistication and detail throughout. Tucked throughout the home are numerous charming nooks, perfect for reading, relaxing, or enjoying a quiet moment. Every space reflects the care & craftsmanship of the original owners, who continue to reside in the home. The outdoor setting is truly an entertainers dream. The expansive yard features multiple seating areas, an in-ground pool, Trex Decking & mature, hand selected plantings that create a private & beautifully landscaped retreat. Hand picked flowering stone beds add even more character & color throughout the grounds. The custom finished basement extends the living & entertaining possibilities, offering a full bathroom, guest room, entertainment room, gym, & additional office space. A walk out leads directly to the pool & patio, creating an effortless connection between indoor & outdoor living. A large 2 car garage is conveniently located beneath the home, adding valuable parking & storage. A rare combination of timeless Colonial elegance, exceptional craftsmanship, custom finishes, & resort like outdoor living, this extraordinary home is designed for those who appreciate beauty, comfort, & the art of entertaining. Situated privately on a no outlet Street within close distance to restaurants & all the local shopping. Take a stroll down to the dead end of your Road for a short trip to the center of the Village of Fishkill for all the amazing dining experiences.

61 High View Road, Fishkill

$99,999

3 Beds ⋅ 2 Baths ⋅ 1039019 MLS

COMPLETELY RENOVATED 3-BEDROOM, 2-BATH HOME IN DESIRABLE CAMELOT VILLAGE! Welcome to move-in-ready living in Camelot Village! This beautifully renovated 3-bedroom, 2-bath home has been thoughtfully updated from top to bottom, offering the perfect blend of modern style, comfort, space, and convenience. Step inside to a bright, open and inviting floor plan featuring new flooring throughout and a beautifully updated eat-in kitchen showcasing gorgeous granite countertops and brand-new appliances—the perfect space for everyday living and entertaining. The extensive improvements continue with a new heating system, new hot water tank, brand-new exterior skirting, and numerous additional updates throughout, giving the next owner the opportunity to simply unpack and enjoy. The the low-maintenance lifestyle makes this home an attractive alternative to traditional homeownership. Conveniently located near shopping, dining, everyday conveniences, and major commuter routes, Camelot Village offers the opportunity to enjoy community living while remaining close to everything the Hudson Valley has to offer. Beautifully renovated, spacious, affordable, and truly move-in ready—this is one you won't want to miss. Schedule your private showing today!

567 Sheafe Road Unit #3, Poughkeepsie

$399,999

4 Beds ⋅ 2 Baths ⋅ 1038824 MLS

For those who believe a home should have a story to tell, this character-filled 1925 semi-attached townhouse is something truly special. Behind its exposed brick façade and welcoming front porch, four spacious bedrooms and one-and-a-half baths are surrounded by the craftsmanship and architectural details that make older homes so captivating. Soaring ceilings, hardwood floors, rich natural woodwork, crown moldings, built-in storage, pocket doors, and a fireplace create warmth and personality throughout, while oversized windows fill the formal living and dining rooms with beautiful natural light. At the heart of the home, the original walkthrough pantry remains intact, a charming reminder of another era. The kitchen was thoughtfully remodeled in 2017, pairing restored original woodwork with Carrara marble imported from Italy, updated appliances, and modern finishes, while the bathrooms carry the same Carrara marble detailing and updated vanities. Outside, an unusually expansive city backyard offers space to garden, entertain, or simply escape, complete with a back porch and outdoor brick fireplace. A partially finished lower level provides a comfortable family room, while the full walkable attic offers exceptional storage and the possibility of creating an inspiring studio, workspace, or additional finished space. Updated electrical and a modern heating system with on-demand hot water add everyday convenience without sacrificing the home's century-old character. Just five minutes from downtown Poughkeepsie, with restaurants, coffee shops, shopping, supermarkets, and Metro-North nearby, this is a home for those who appreciate architecture, creativity, and the beauty of something that simply cannot be recreated today.

111 S Hamilton Street, Poughkeepsie

$379,900

1039885 MLS

Great opportunity to own a charming brick two-family home in the City of Poughkeepsie. Both units offer sizable layouts with two bedrooms and comfortable living areas, making this an excellent option for investors or owner-occupants looking to offset expenses with rental income. The property generated $31,600 in rental income in 2025. Additional highlights include hardwood floors, basement laundry, and a spacious backyard. Conveniently located near shops, restaurants, major roadways, and the Poughkeepsie Metro-North station, offering easy access to New York City.

46 S Bridge Street, Poughkeepsie

$73,000

2 Beds ⋅ 1 Baths ⋅ 1040424 MLS

Welcome to 16 Jennifer Court, an affordable opportunity to own a home in the Poughkeepsie/Hyde Park area! Offered at just $80,000, this well-maintained 2-bedroom, 1-bath manufactured home offers approximately 980 square feet of comfortable, single-level living. The functional layout provides a welcoming living area, comfortable bedrooms, and plenty of potential to make the space your own. Conveniently located near shopping, dining, schools, major roadways, and other local amenities. Enjoy the benefits of community living while remaining close to everything the Hudson Valley has to offer. Whether you're looking to downsize or simply searching for an affordable place to call home, this property is worth a look. Schedule your showing today

16 jennifer Court, Poughkeepsie

$435,000

2 Beds ⋅ 2 Baths ⋅ 1038744 MLS

Welcome to 69 Montgomery Street, a beautifully maintained circa 1849 Colonial Victorian set in the heart of Poughkeepsie’s historic district, where original character and thoughtful modern updates come together. Step inside to soaring ceilings, gleaming red oak floors, and oversized, sun-filled rooms that immediately showcase the scale and craftsmanship of this historic home. The main level offers a spacious living room that flows naturally into the grand dining room—an inviting setting for everything from quiet dinners to holiday gatherings. The well-appointed kitchen features an induction cooktop and Sub-Zero refrigerator, combining modern function with the home’s timeless surroundings. One of the most special spaces is the screened-in porch, accessible from both the kitchen and dining room. Tucked away from the street and overlooking the private backyard toward Garfield Place, it’s the kind of space made for morning coffee, summer dinners, and slow evenings at home. Upstairs, beautiful wide-plank pine floors continue throughout two generously sized bedrooms and a flexible third room that can easily serve as a home office, den, nursery, or additional bedroom. A full bathroom completes this level. The walk-up attic offers even more possibilities. With impressive ceiling height and generous space, it provides an opportunity to create a dramatic primary suite, studio, or additional living area while preserving the architectural character of the home. The lower level adds another layer of flexibility, featuring a newly renovated full bathroom, separate entrance, and space perfectly suited for guests, a recreation room, home office, or private retreat. Rich in 19th-century character yet thoughtfully updated for modern living, 69 Montgomery Street offers the space, history, and architectural details that simply cannot be replicated today—all within convenient reach of shopping, transportation, universities, medical centers, and everything Poughkeepsie and the Hudson Valley have to offer.

69 Montgomery Street, Poughkeepsie

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