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

$530,000

3 Beds ⋅ 2 Baths ⋅ 1031124 MLS

What a fantastic home on this corner lot with views looking straight up Mt Beacon. This home has been loved for many years by its current owners. The manicured yard offers a fully fenced rear with a concrete patio, raised beds for your vegetables or fruits, shed to store the tools in and a 2 sided driveway with a carport for your vehicle. The raised beds and mature plantings make this have such a homey feel. Step inside to your 3 bedroom 1 bath, kitchen & large living room all on the 1st floor. The middle bedroom is currently used as an office & has a sliding glass door to a trex & vinyl rear porch & entry to the back yard. The other 2 bedrooms are spacious and have corner windows which bring in such great light. The basement offers so much storage space with 2 large rooms, a utility room and bath including a shower. This home has been wonderfully maintained and is offered in as-is condition. There is central air, central vac & a whole house generator which remains.

76 Phillips Street, Beacon

$79,999

2 Beds ⋅ 2 Baths ⋅ 1025338 MLS

SEASONAL May 1 to October 31. NO short term rentals or subleasing. Pleasant View Acres private coop community on over 15 acres. Double unit, 2 bedroom, 2 bath. Recently renovated, electric upgraded approx. 5 years ago. Lovingly cared for over 19 years. It's like summer camp for the whole family! Put your vacation anxieties to rest! Cute summer bungalow for sale in a long established cooperative bungalow colony in lovely suburban area of Dutchess. Open and available for use from May 1 to October 31. Fully Furnished. Includes use of beach @ Red Wing Park Common room includes laundry and recreation room.The property is located just a short distance to TSP, Beekman Golf, Taconic Tennis Club (world class tennis/pool). Centrally located to Beacon, Millbrook, Hyde Park, Cold Spring and the Culinary Institute. HOA fees conveniently include electric, water, trash, taxes, insurance, common area grounds and plumbing to open and close units. May 1 through October 31 allowing for an extended season of enjoyment. Don’t miss this rare opportunity to own a seasonal home. Just over an hour to NYC

7 Brodie Road Unit #27 & 28, Hopewell Junction

$1,200,000

5 Beds ⋅ 3 Baths ⋅ 1028375 MLS

Welcome to 37 North Cedar Street, Beacon, NY, where modern updates meet flexible living in one of the Hudson Valley's most sought-after communities. Ideally located just minutes from Beacon's vibrant Main Street, Metro-North, local shops, restaurants, and outdoor recreation, this beautifully maintained home offers the perfect balance of comfort, convenience, and versatility. Inside, you'll find a thoughtfully updated interior featuring three fully renovated bathrooms with stylish finishes and all brand-new appliances, allowing you to move right in with confidence. The spacious layout provides plenty of room for everyday living, entertaining, or working from home. The finished basement offers exceptional added value with two legally converted bedrooms, complete with the proper permits and documentation from the sellers, ideal for guests, extended family, or additional living space. The former garage has also been converted into a bonus room, providing even more flexibility as a home office, gym, playroom, or studio, while still offering the option to be easily converted back into a garage if desired. Whether you're looking for extra space, modern upgrades, or a prime Beacon location, this home checks all the boxes. Don't miss the opportunity to make this move-in-ready property your next home.

37 N Cedar Street, Beacon

$299,900

4 Beds ⋅ 2 Baths ⋅ 1027461 MLS

STOP RENTING & START OWNING! COMPLETELY TURN-KEY 4-BEDROOM COLONIAL! Why pay a landlord when you can own this spacious, updated 4-bedroom, 1.5-bathroom single-family Colonial for less than the cost of local rent? Boasting 1,600 square feet of vibrant, sun-drenched living space, 20 Grant Street is the definition of "move-in ready." THE LAYOUT YOU WANT: Say goodbye to cramped quarters! The flexible 7-room floor plan features a highly coveted main-level bedroom option—perfect for a home office, guest space, or playroom—plus three additional oversized bedrooms upstairs. INTERIOR HIGHLIGHTS: Enjoy modern, seamless flooring throughout, natural gas cooking, and a floor plan built for everyday living. Out back, a private backyard space and balcony offer the perfect retreat for summer BBQs or morning coffee. Need storage? The partial basement has you covered. ULTRA-CONVENIENT CITY LIVING: Say goodbye to utility headaches. This home features high-efficiency natural gas forced-air heating, city water, city sewer, and low-maintenance on-street parking right at your front door. Located seconds from downtown shopping, hospitals, local parks, and major commuter routes. THE BOTTOM LINE: Whether you are a first-time homebuyer looking for space to grow or a savvy investor hunting for a high-yield, turn-key rental with zero renovations needed—this is the property you’ve been waiting for.A property this clean at this price point will not last. Don't wait—schedule your private tour today!

20 Grant Street, Poughkeepsie

$420,000

6 Beds ⋅ 2 Baths ⋅ 1025819 MLS

Excellent investment opportunity in the City of Poughkeepsie! This vacant two-family property features two spacious 3-bedroom units, providing strong rental income and immediate cash flow for investors. Each apartment offers bright living spaces, large bedrooms, eat-in kitchens, and separate entrances for added privacy and convenience. The property is well maintained with separate utilities, making it an ideal low-maintenance addition to any investment portfolio. Roof 12 years old, Windows 8 Years old, Furnace 5 years old and Water Heater 2 years old. Conveniently located near Metro-North, Vassar College, Marist College, shopping, restaurants, hospitals, and major commuter routes, this property is positioned in a high-demand rental area. Whether you’re looking to expand your portfolio or secure a solid income-producing property, this multi-family home offers excellent long-term potential.

37 Delano Street, Poughkeepsie

$799,990

6 Beds ⋅ 4 Baths ⋅ 1023883 MLS

Welcome to Academy House. Built in 1881, this distinguished Victorian residence is set along one of Poughkeepsie’s most admired tree-lined streets within the city’s Historic District. A gracious front porch introduces a home where original craftsmanship has been thoughtfully preserved while modern infrastructure provides the comfort and reliability expected today. The main level unfolds through a welcoming foyer into a collection of light-filled living and entertaining spaces, where generous proportions and beautifully preserved architectural details create a natural sense of flow. The dramatic horseshoe window in the grand living room is elegantly echoed in a remarkable set of pocket doors leading to the family room, a distinctive design feature that showcases the exceptional craftsmanship found throughout the home. A gracefully curved ceiling above the gathering area and the home’s signature curved glass windows further highlight its architectural character. Newly updated kitchen blends historic charm with modern function, featuring quartz countertops, stainless steel appliances, and abundant workspace designed for everyday living and entertaining. Extensive infrastructure improvements provide confidence behind the walls while allowing the home’s original character to remain the focal point. Recent updates include an upgraded electrical system, replacement PVC plumbing throughout, updated main sewer piping, a newer roof, storm windows throughout the home, and a new water heater. Together, these improvements deliver the convenience and efficiency of modern living without compromising the home’s historic integrity. The second level is accessible by both the main staircase and a secondary staircase off the kitchen, offering a layout that reflects the home’s original design while enhancing everyday functionality. Six bedrooms are thoughtfully arranged across the upper floors, including two spacious primary suites with beautifully renovated custom bathrooms. The remaining bedrooms are filled with natural light and enriched by original architectural details that continue the home’s timeless appeal. The finished and insulated third level offers exceptional flexibility, featuring an additional family room, two bedrooms, and a full updated bathroom. Whether used as guest accommodations, a home office, creative studio, or private retreat, this level provides versatile living space while maintaining the home’s historic character. Outside, the fully fenced backyard extends the living experience with space for outdoor dining, gardening, or quiet afternoons in a private setting. A detached two-car garage and newly paved driveway provide everyday convenience while complementing the property’s classic streetscape. Meticulously maintained throughout, Academy House offers the rare opportunity to enjoy the beauty and craftsmanship of a historic Victorian without the extensive restoration projects often associated with homes of this era. Positioned just minutes from Metro-North, Vassar College, Marist University, local hospitals, restaurants, cafés, and the growing cultural and dining destinations of downtown Poughkeepsie, the location offers exceptional convenience while remaining rooted in one of the city’s most architecturally significant neighborhoods. Academy House captures the elegance of 1881 with the infrastructure and functionality expected today, creating a residence where historic craftsmanship and modern living exist in effortless harmony.

112 Academy Street, Poughkeepsie

$430,000

3 Beds ⋅ 3 Baths ⋅ 1023350 MLS

Better Than new! Charming home move in ready! Totally renovated. Beautiful Cooks kitchen, 2 full baths and 1 half. Open floor plan for LR,DA, and kitchen Recessed lighting and so much more. New flooring,Lighting, windows . Large Family room 2 steps down off Kitchen. Cathedral ceilings, has its own AC,. conditioning. Tile flooring, walls and cathedral ceiling of beautiful natural back wood and lots of windows. with ground floor access to exterior and back yard. Surprise space, the basement is fully finishd. 4th bedroom and or bonus room,LDRY, full bathroom, finished storage room .Fitness area and furnace room and utilitie room. Secon floor has 3 bedrooms and a full bath with easy access to the large attic whichcould be loft area. The new fornt porch is made of stone will last for ever over looks new landscaped side walk to front door. Super cental location to shopping,trains, bus line, 2 hospitals, 3 major colleges and the CIA. minjutes to

88 Innis Avenue, Poughkeepsie

$299,900

3 Beds ⋅ 2 Baths ⋅ 1022816 MLS

2 Family within walking distance to Metro North, the Main Street Restaurant District and the waterfront. Solid rental history with very low turnover. This home features separate utilities and a driveway for off street parking. Perfect for the investor or a live in one unit and rent out the other unit type situation.

10 Charles Street, Poughkeepsie

$22,000

1 Beds ⋅ 1 Baths ⋅ 1020166 MLS

SEASONAL May 1 to October 31 NO short term rentals or sub leasing Pleasant View Acres private coop community on over 15 acres. Don’t miss this charming seasonal bungalow located in the desirable Pleasant View Estates! This well-maintained getaway offers numerous updates, making it the perfect place to enjoy the warmer months. Features include: Updated electrical with a newer interior panel and approximately $2,000 in electrical upgrades completed 4–5 years ago. Roof replaced just 3 years ago. New screen door with a sliding glass insert for added convenience and ventilation. Functional kitchen featuring a microwave, compact refrigerator, and two-burner countertop cooktop. Spacious attic offering additional storage. Convenient access enclosure beneath the bungalow for easy access to utilities. Storage shed with a new door, which also houses the propane tank. Whether you’re looking for a relaxing summer retreat or a low-maintenance seasonal escape, this adorable bungalow is ready for its next owner.

7 Brodie Road Unit #26, Hopewell Junction

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 1011843 MLS

This brand new Two story traditional Beacon home awaits you. Situated on a tree lined Street in an established neighborhood with the convenience of all Beacon's amenities. Construction is beginning so now is the perfect time to get into a home just blocks off Main St, a stone's throw from the train station & conveniently close to Mt Beacon for an amazing hike. This will become a 4 bedroom 2.5 bath home. The Primary suite is located on the first floor along with the Primary bath & laundry. The exterior is being finished with Composite Siding, stone details, Trex decking & a metal porch roof. Spacious rooms, gorgeous wide hardwood flooring, heated full bath flooring & original details name a few of the amenities going into this well thought out designed home.

222 Rombout Avenue, Beacon

$319,900

3 Beds ⋅ 2 Baths ⋅ 1020109 MLS

Opportunity in hand for the private 3 bedroom 2 full bath home set back off of Violet Avenue in the Town of Hyde Park. An easy commute to the train station, restaurants, Marist University, Dutchess Community College, The Walkway Over The Hudson, along with various waterfront parks in the Town of Hyde Park and City of Poughkeepsie. Priced to move in an market where buyers struggle to find affordable homes. The home features a new septic, new flooring, paint and insulated windows.

431 Violet Avenue, Poughkeepsie

$349,000

4 Beds ⋅ 2 Baths ⋅ 1019365 MLS

Perched high above the City of Poughkeepsie on desirable North Clinton Street, this classic home offers timeless character in an exceptional setting adjacent to College Hill Park. Rich with original architectural details, the residence showcases beautiful hardwood floors, original woodwork, decorative moldings, solid wood doors, and other period features that reflect its historic charm. Enjoy seasonal views, abundant natural light, and the convenience of being just minutes from Vassar College, the Poughkeepsie waterfront, Metro-North, Walkway Over the Hudson, restaurants, shopping, and the city's vibrant arts and dining scene. The park next door provides open green space, walking paths, and recreation right outside your door. Whether you're searching for a distinctive residence or a property with enduring architectural character, this home presents an opportunity to own a piece of Poughkeepsie's history in one of its most desirable hillside neighborhoods. Bring your vision and make this charming home your own.

137 N Clinton Street, Poughkeepsie

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