Poughkeepsie Homes with On Street Parking features

Welcome to Poughkeepsie, a vibrant city nestled in the heart of Dutchess County, New York. Known for its rich history, stunning Hudson River views, and a burgeoning cultural scene, Poughkeepsie is a place where urban convenience meets natural beauty. With its charming neighborhoods, diverse dining options, and a plethora of outdoor activities, it’s no wonder that Poughkeepsie has become a sought-after destination for homebuyers.

One of the appealing features of homes in Poughkeepsie is the availability of on-street parking. This amenity adds a layer of convenience for residents, especially in a city known for its bustling downtown and vibrant community events. Imagine coming home to a picturesque street lined with trees, where you can easily find parking right outside your door, allowing for seamless access to all that the city has to offer.

Poughkeepsie boasts a variety of homes, from historic Victorian houses to modern townhouses, catering to diverse tastes and lifestyles. Many of these properties are situated in friendly neighborhoods, making it easy to connect with neighbors and enjoy a sense of community. The city is also home to several parks, walking trails, and the scenic Walkway Over the Hudson, perfect for those who appreciate outdoor adventures.

Whether you're a first-time homebuyer or looking to settle down in a vibrant community, Poughkeepsie offers a unique blend of charm, convenience, and opportunity. Discover your new home in this delightful city and experience all the warmth and character it has to offer!

Newest Poughkeepsie Homes with On Street Parking features

$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

$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

$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

$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

$500,000

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

$460,000

3 Beds ⋅ 3 Baths ⋅ 1015343 MLS

Turnkey 3-family investment opportunity in the City of Poughkeepsie! This income-producing property features two fully renovated units, one vacant, one recently rented, and a third with long term tenant! Recent improvements include new kitchens, updated bathrooms, modern fixtures, fresh paint, updated flooring, and contemporary finishes throughout. The rent ready vacant unit offers an excellent opportunity for an owner-occupant looking to offset expenses or an investor seeking immediate lease-up and increased cash flow. Additional features include a beautiful rear deck, on-site coin operated laundry, and attractive updates that minimize deferred maintenance and make this property a strong addition to any portfolio. Conveniently located near Metro-North, Vassar Brothers Medical Center, Marist University, the Culinary Institute of America, the Poughkeepsie waterfront, restaurants, shopping, and major commuter routes. Whether you're a seasoned investor or looking for your first multifamily property, this is a rare opportunity to acquire a largely turnkey asset with immediate upside and strong rental demand.

32 N Bridge Street, Poughkeepsie

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