Poughkeepsie City Homes with On Street Parking features

Welcome to Poughkeepsie City, a vibrant gem nestled in the heart of Dutchess County, New York. Known for its rich history and scenic views along the Hudson River, Poughkeepsie offers a unique blend of urban convenience and suburban charm. One of the standout features of this area is its exceptional school district, which is dedicated to providing a well-rounded education for all students. The Poughkeepsie City School District prides itself on its commitment to academic excellence, innovative programs, and a supportive community environment. With a variety of educational opportunities, including advanced placement courses and specialized programs, parents can feel confident that their children are receiving a top-tier education.

In addition to its educational offerings, Poughkeepsie City boasts a diverse range of homes, many of which feature the convenience of on-street parking. This is a significant advantage for residents who appreciate easy access to their vehicles without the hassle of dedicated parking spaces. Whether you’re looking for a charming historic home or a contemporary residence, the availability of on-street parking makes life a little easier, especially in a bustling city environment.

Living in Poughkeepsie means enjoying a dynamic lifestyle with access to parks, cultural attractions, and a thriving downtown area, all while being part of a community that values education and growth. Explore the possibilities of making Poughkeepsie City your home, where comfort, convenience, and quality education come together seamlessly.

Newest Poughkeepsie City Homes with On Street Parking features

$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

$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

$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

$599,900

5 Beds ⋅ 4 Baths ⋅ 964091 MLS

Historic Elegance in the Heart of Poughkeepsie Step back in time while enjoying generous modern living in this remarkable 1880 single-family home, nestled within the Poughkeepsie Historic District. Offering an impressive 3,640 sq/ft of living space, this stately residence features 5 spacious bedrooms and 4 bathrooms, ideal for both comfortable family living and elegant entertaining. Rich in character, the home showcases period details throughout— ornate moldings, high ceilings, and original hardwood floors—all reflecting the craftsmanship of a bygone era. Large, light-filled rooms provide flexible spaces for gatherings, home offices, or creative studios. A detached two-car garage with convenient entry from 21 S Bridge St adds practicality and value, while the central location offers walkability to shops, dining, and the vibrant culture that makes Poughkeepsie so beloved. Don’t miss this rare opportunity to own a distinguished piece of Hudson Valley history, blending classic architecture with everyday comfort.

181 Union Street, Poughkeepsie

$460,000

3 Beds ⋅ 2 Baths ⋅ 1035889 MLS

Welcome to 8 Mitchell Avenue, where charm, convenience, and thoughtful updates come together in the heart of Poughkeepsie. Ideally located in a highly walkable area, this home provides easy access to local shops, dining, and everyday conveniences, complemented by municipal water, sewer, and natural gas utilities. Inside, you’ll find a beautifully updated bathroom and kitchen featuring stainless steel appliances including two ovens, seamlessly blending modern functionality with classic style. This home offers three comfortable bedrooms, plus a finished third floor that provides the perfect flexible space ideal for a game room, home office, or entertaining area. Rich natural wood accents and custom built-ins throughout the home create a warm, inviting atmosphere that highlights its true Colonial character. The welcoming front entryway functions as a practical mudroom, while the screened-in porch leads to a second entry that doubles as an additional mudroom and pantry space, perfect for everyday living! While the quaint, tree-lined street offers convenient on-street parking, the property also includes a private garage and driveway located behind the home, giving you the best of both worlds. A perfect blend of charm, space, and location. This is one you won’t want to miss!

8 Mitchell Avenue, Poughkeepsie

$450,000

3 Beds ⋅ 3 Baths ⋅ 1029480 MLS

Exceptional investment opportunity in the heart of Poughkeepsie! Offered for the first time since 1981, this well-maintained triplex near Market Street presents an outstanding opportunity for investors or owner-occupants. Over the years, the property has undergone significant updates, including replacement of the original plaster walls, electrical, plumbing, insulation, and windows, providing peace of mind for years to come. Unit 1, located on the main level, has been recently updated and is currently vacant, offering immediate rental income potential or the perfect option for an owner-occupant. Unit 2 is located on the upper level and is occupied by a long-term tenant. Unit 3, with its own private entrance at the rear of the property, spans two levels and offers access to a spacious, fenced backyard, also occupied by a long-term tenant. In addition to ample on-street parking, the property features a newly paved driveway with space for three vehicles. Conveniently located just minutes from the Mid-Hudson Bridge, Metro-North, Vassar Brothers Medical Center, Marist University, the Culinary Institute of America, The Bardavon, restaurants, shopping, and all that downtown Poughkeepsie has to offer, this is a rare opportunity to own a solid income-producing property in a prime location. Schedule your private showing today!

25 Conklin Street, Poughkeepsie

$750,000

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

$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

$379,900

4 Beds ⋅ 2 Baths ⋅ 1017704 MLS

Fully Rented Is This Affordable Two Family Home For Sale. Each Unit Has Living Room, Kitchen, Two Bedrooms And Separate Utilities (Gas And Electric). This One Is Within Walking Distance To Restaurants, Beauty And Na.il Salons And Other General Services. Prior Day's Notice Is Needed For Showings. Agents Please See Other Remarks.

18 Grant Street, Poughkeepsie

$490,000

4 Beds ⋅ 2 Baths ⋅ 1017057 MLS

Turnkey Investment Opportunity – Fully Renovated Two-Family Home with Strong Rental Income Don't miss this exceptional opportunity to own a fully renovated two-family property generating approximately $43,000 in annual rental income. Both apartments are currently occupied by tenants under annual lease agreements, providing immediate and reliable cash flow for investors. This well-maintained multi-family home features two spacious apartments, each offering: • 2 Bedrooms • 1 Full Bathroom • Bright Living Room • Functional Kitchen • Separate Living Space for Privacy and Comfort The property has undergone extensive renovations designed to create a modern, welcoming, and low-maintenance living environment. Recent improvements include: • Complete renovation of the first and second-floor apartments • Updated bathrooms • New flooring throughout • New energy-efficient windows • New water heater installed in June 2026 • Professionally improved front and backyard landscaping • Attractive shared backyard area for tenant enjoyment With strong rental income already in place, major capital improvements completed, and a desirable two-family layout, this property offers an excellent opportunity for investors seeking immediate returns or owner-occupants looking to offset mortgage costs with rental income. A true turnkey property—collect rent from day one and enjoy the benefits of extensive renovations and stable tenancy.

17 Carroll Street, Poughkeepsie

$675,000

6 Beds ⋅ 6 Baths ⋅ 1016201 MLS

Four Family Multi Unit Building For Sale Consisting Of (3) Two Bedroom Apartments And (1) Studio. Property Hosts A Total Of Six Bedrooms And Six Full Bathrooms With Each Apt Having Its Own Individual Level As Well As Separate Utilities. Added Bonus: Two Apartments Feature Two Full Bathrooms The Convenience Of Being Inner City With Amenities Such As On The Bus Routes, Close To Eateries/Restaurants/Delis, Hair & Nail Salons, Major Highways, Train Station, Riverfront, Educational Facilties, Hospitals And More Could Make This An Ideal Investment. This Is An As Is Sale. Agents, please see other remarks.

67 Academy Street, Poughkeepsie

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