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$489,000
2 Beds ⋅ 3 Baths ⋅ 1039925 MLS
Welcome to effortless, resort-style living in one of the most desirable gated communities in the Hudson Valley! Welcome to Hudson Pointe! This beautifully designed townhouse offers spacious, light-filled living across multiple levels, featuring two generously sized bedrooms, two-and-a-half bathrooms, and a versatile open loft—perfect for a home office, den, guest space, or reading retreat. The finished lower-level flex space provides even more room for a family room, media room, playroom, or entertaining area. Enjoy the privacy and security of a gated setting along with exceptional community amenities, including a private in-ground pool with cabana, beautifully appointed clubhouse, and fully equipped fitness center. The location is equally impressive—within walking distance of Vassar Brothers Medical Center and just minutes from Metro-North, shopping, dining, colleges, and everyday conveniences. Explore everything the Hudson Valley has to offer, including the Poughkeepsie waterfront, Walkway Over the Hudson, scenic parks, hiking and biking trails, wineries, breweries, historic destinations, acclaimed restaurants and all that the Hudson Valley has to offer! With generous living space, a flexible layout, maintenance-free convenience, and an outstanding commuter location, this exceptional home combines the comfort of a private residence with the amenities of a year-round retreat. This is more than a townhouse—it’s a lifestyle! Stop clicking and start dialing!

308 Bridgeview Drive, 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
$495,000
4 Beds ⋅ 2 Baths ⋅ 1038224 MLS
Charming 1920 Colonial featuring original details throughout. High ceilings & doors, classic woodwork, stained glass windows, ornamental fireplaces and generously sized rooms showcase the charm and craftsmanship of the era. A welcoming foyer features beautiful woodwork and pocket doors opening to the formal living room. The first floor offers convenient laundry area and spacious living area. The ornamental fireplaces are non-functioning and add architectural character. Relax on the covered front porch, the deck off the second-floor bedroom or in the semi-private fenced-in backyard. Recent updates include furnace, hot water heater, roof and chimney insulation. A wonderful opportunity to enjoy the character of a classic colonial with inviting outdoor spaces and plenty of room to make the home your own. Please try and look past the clutter. Definitely worth taking a look at this wonderful city home.

11 Balding Avenue, Poughkeepsie
$425,000
4 Beds ⋅ 2 Baths ⋅ 1037125 MLS
Welcome to 170 Hooker Avenue! A charming 1930s Colonial offering tasteful updates preserving the timeless character in the heart of the Southside of Poughkeepsie. Step inside to discover beautiful gleaming hardwood floors throughout, classic architectural details, arched openings, built-in shelving, and a welcoming living room surrounding a wood burning fireplace. The spacious formal dining room is a standout, featuring a striking decorative ceiling and French doors that lead to the enclosed three-season room that is an inviting space surrounded by windows, perfect for relaxing, reading, or enjoying your morning coffee. (not included in the finished sq ft) The kitchen blends classic charm with modern convenience, featuring rich wood cabinetry, granite countertops, newer stainless steel appliances, a tiled backsplash, and generous storage. A convenient half bath and additional flex space complete the main level. Upstairs you'll find four bedrooms and a full bath, including a generously sized primary bedroom. The home also offers a full basement for additional storage and utility space and 1 car garage under. Outside, mature landscaping, a stone retaining wall, and classic Colonial curb appeal create a welcoming first impression. Additional features include a brand new roof with transferable warranty, sleek black gutters, private driveway, municipal water, sewer and access to natural gas on the street. With just over 1,800 square feet of finished living space, plus the three-season room, this home offers a wonderful combination of character, functionality, and opportunity. 170 Hooker Avenue is ready for its next chapter, come experience the warmth and character of this classic Poughkeepsie home. Excellent location, minutes to Route 9, the Walkway over the Hudson, Marist University, Culinary Institute of America, great restaurants, shopping, schools and more! Come see all that the beautiful Hudson Valley has to offer!

170 Hooker Avenue, Poughkeepsie
$795,000
5 Beds ⋅ 4 Baths ⋅ 1037519 MLS
Timeless architecture, exceptional character, and remarkable craftsmanship define this distinctive 4-bedroom, 3.5-bath Tudor Revival, beautifully set on .41 acres among mature trees and established landscaping. From its steeply pitched gables and decorative half-timbering to its expansive covered porch and intricate exterior detailing, this is a home with a presence all its own. Step inside and the character continues with rich hardwood floors, beautiful original millwork, graceful arched openings, oversized windows, and an impressive sweeping staircase. Generously proportioned rooms and abundant natural light create an inviting sense of openness while preserving the warmth and charm that make homes of this era so special. The expansive main living room is a true centerpiece, featuring a grand fireplace, built-in bookcases, and exceptional scale with plenty of room for multiple seating areas and even a grand piano. An adjoining sun-filled room wrapped in windows offers a wonderful connection to the outdoors, while the dedicated library is one of the home's most memorable spaces, lined with floor-to-ceiling bookshelves and complete with a rolling library ladder. Throughout the home, thoughtfully preserved architectural details, multiple fireplaces, large windows, and an abundance of flexible living space provide character at every turn. Four bedrooms and three-and-a-half baths offer plenty of room for everyday living, guests, home offices, and more. Outside offers mature trees, lush lawn, established plantings, stone patios, and brick terraces providing multiple places to relax and entertain. Rich in history, warmth, and architectural interest, this is far more than simply a place to live—it's a home with a story, offering the craftsmanship and character of a bygone era with the space and versatility to be enjoyed for years to come.

83 Hooker Avenue, 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
$435,000
4 Beds ⋅ 2 Baths ⋅ 1036556 MLS
Great turnkey opportunity for investors or owner-occupants looking to have a rental income potential! This multi-family property on Mansion Street offers two units with separate utilities to minimize investor overhead expenses. There is a walk up attic with potential for an added unit or additional storage. Enjoy a level, manageable .23 acre yard, off-street parking and a garage for storage. A convenient location that is just a short drive from local higher education campuses, transit hubs (Poughkeepsie Train Station 1.7 miles), medical centers and area restaurants! Minutes from the Hudson Valley's iconic Walkway Over The Hudson, the world's longest elevated pedestrian bridge. If you are an investor looking to expand your portfolio with a turnkey multi-family or seeking strong immediate cash flow, 362 Mansion Street delivers the ideal blend of location, convenience and long-term ROI!

362 Mansion Street, Poughkeepsie
$495,000
5 Beds ⋅ 3 Baths ⋅ 1034549 MLS
Excellent opportunity for investors or owner-occupants! This fully vacant triplex offers a flexible 2-bedroom/1-bathroom over 2-bedroom/1-bathroom over a fully renovated studio layout. The first-floor studio has been completely renovated and is move-in ready, while the two upper-level apartments provide additional income potential. All three units are currently vacant, allowing a new owner the opportunity to establish market rents from day one or occupy one unit while generating rental income from the others. Separate utilities, including landlord metering, provide added convenience for managing expenses. Additional highlights include a new roof, a new Certificate of Occupancy at closing. The property also features a rear garage/storage area and attic space for additional storage. Whether you're looking to expand your portfolio, house-hack, or take advantage of a fully vacant multi-family property, this is an opportunity worth exploring!

54 Gifford Avenue, Poughkeepsie
$950,000
1030135 MLS
Income-producing multifamily opportunity delivering an 8.5% current cap rate, with potential to reach approximately 10.5% at pro forma rents. This 5-unit property features (1) 1-bedroom apartment, (2) 3-bedroom apartments, and (2) 4-bedroom apartments, generating $117,480 in current gross annual income. All tenants pay for heat, hot water, and electricity, while the landlord is responsible for water and sewer. The sale also includes a separately deeded 9-car parking lot, with one parking space for each unit, and every apartment has an in-unit washer/dryer hookup. Located near major anchors such as Route 9, the Mid-Hudson Bridge, Marist College, Vassar College, Dutchess Community College, and the Culinary Institute of America, the property offers strong in-place income with meaningful room for future upside. An ideal opportunity for investors seeking a stable, income-producing asset in a prime Poughkeepsie location. Income & expense information available upon request.

10 Eastman Terrace, 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
$359,000
4 Beds ⋅ 2 Baths ⋅ 1032080 MLS
Welcome to this spacious 4-bedroom, 2-full-bath home offering 2,192 square feet of living space. The open floor plan provides an easy flow between the living areas, while the fireplace adds warmth and character. A first-floor bedroom and full bath offer added flexibility. Step outside to the deck overlooking a spacious backyard with plenty of room for outdoor enjoyment, gardening and entertaining. A full unfinished walk-out basement provides additional storage and possibilities. Conveniently located near shopping, dining, transportation and local amenities.

33 Fitchett Street, 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
$450,000
3 Beds ⋅ 3 Baths ⋅ 1007852 MLS
Timeless Mid-Century Modern brick home offering enduring quality and incredible potential. Featuring hardwood floors, classic architectural details, and a spacious walk-up attic with a variety of potential uses, this solid home is ready for its next chapter. While it would benefit from updating, its exceptional location and quality construction present an outstanding investment opportunity in the Hudson Valley at an attractive value. A wonderful opportunity to personalize and restore a well-built home. Conveniently located near shopping, restaurants, parks, and the Poughkeepsie Tennis Club, and approximately a five-minute drive to the Poughkeepsie Metro-North and Amtrak station, this home combines timeless charm with everyday convenience in an established neighborhood.

13 Osborne Road, Poughkeepsie
$575,000
6 Beds ⋅ 2 Baths ⋅ 1030768 MLS
Step into the rich history of this circa 1865 home, located in the City of Poughkeepsie's Historic District. Offering approximately 3,876 square feet across three finished levels, this residence showcases a distinctive Mansard roof, pocket doors, original millwork, bay windows, extensive built-ins, decorative fretwork, and other preserved architectural details that reflect its history and craftsmanship, such as plaster ceilings and walls throughout. A grand staircase with ornate woodwork and a built-in hall settle welcomes you upon entry, while hardwood floors, high ceilings, and ornate cast-iron radiators continue throughout much of the home. Spacious rooms provide flexibility for everyday living, entertaining, home office space, or creative pursuits. The kitchen complements the home's period appeal with custom wood cabinetry, built-in hutches, exposed brick, granite countertops, a movable center island, and a bright bay-window dining area. A freestanding wood stove set on a decorative mosaic tile hearth adds warmth and architectural interest. Additional features include a covered front porch, three finished levels, a full unfinished basement, municipal water and sewer, oil heat, and mature landscaping. Conveniently located near Route 9, Metro-North, the Mid-Hudson Bridge, the Poughkeepsie waterfront, restaurants, shopping, parks, Vassar Brothers Medical Center, Marist University, Vassar College, and other Hudson Valley amenities. A rare opportunity to own a substantial historic home in the City of Poughkeepsie's Historic District, offering preserved architectural details, generous living space, and a convenient Hudson Valley location. Don't miss out! **Some photos have been virtually staged**

129 Academy Street, Poughkeepsie
$449,500
4 Beds ⋅ 3 Baths ⋅ 1028671 MLS
Steeped in history and rich in architectural significance, The James D. Keith House is one of Poughkeepsie's most recognizable residences. Gracefully positioned within the coveted Academy Street Historic District, this extraordinary c.1900 Colonial Revival masterpiece—designed by acclaimed local architect Percival M. Lloyd, this home beautifully blends timeless Colonial elegance with Victorian-inspired details. Offering almost 3,400 finished SQFT, 4 bedrooms, 2 full and 1 half baths, three fireplaces, and an additional unfinished third floor and expansive basement, this is a rare opportunity to own one of the Hudson Valley's architectural treasures. From the moment you step through the crystal-lined vestibule, you're welcomed by breathtaking period craftsmanship. A dramatic central foyer showcases a sweeping grand staircase illuminated by an impressive cathedral-height stained-glass window, while original woodwork, intricate moldings, soaring ceilings, hardwood floors, built-in cabinetry, oversized pocket doors, and elegant fireplaces highlight the home's remarkable character throughout. The main level was designed for both grand entertaining and comfortable everyday living. Multiple formal gathering spaces include an elegant living room with a wood-burning stove insert, a gracious formal parlor tucked into the home's iconic rounded tower, an expansive formal dining room, and an inviting wraparound covered porch that seamlessly extends the living space outdoors. The spacious eat-in kitchen, complete with adjoining butler's pantry and separate laundry room, overlooks the peaceful backyard beneath the canopy of a magnificent copper beech tree, providing the perfect opportunity to create a dream chef's kitchen while honoring the home's historic integrity. The second floor offers four generously sized bedrooms, two full bathrooms, and a flexible den or sitting room ideal for a home office, library, or nursery. The primary suite is warmed by a recently relined Rumford fireplace, while the spectacular tower bedroom captures sweeping western views and unforgettable Hudson River sunsets beneath its distinctive domed ceiling and beautifully arched architectural detailing. Above it all, the unfinished third floor presents approximately 1,500 square feet of untapped potential. Featuring soaring cathedral ceilings, abundant natural light, and charming architectural details, this incredible space is ready to become a luxurious primary retreat, artist's loft, guest quarters, home office, or creative studio. The expansive full basement offers an additional level of opportunity with room for workshops, storage, recreation, or future finished space. Outside, the stately wraparound porch, Juliet balconies, mature landscaping, and classic Colonial Revival facade create unforgettable curb appeal while honoring the home's historic pedigree. Situated on a quarter-acre lot in one of Poughkeepsie's most distinguished neighborhoods, the property is just moments from Vassar Brothers Medical Center, the vibrant downtown waterfront, restaurants, shops, Metro-North, and all that the Hudson Valley has to offer from hiking at Mohonk Preserve to weekend escapes in the Catskills. Whether you're an architectural enthusiast, preservationist, or visionary homeowner, 151 Academy Street offers a once-in-a-generation opportunity to restore, personalize, and preserve one of Poughkeepsie's most celebrated historic homes. Offered AS-IS, this remarkable residence is ready for its next chapter, to be restored and for someone who appreciates the craftsmanship, scale, and timeless beauty that simply cannot be replicated. Municipal water, sewer and natural gas! Excellent location, minutes to Route 9, Downtown Poughkeepsie, Walkway over the Hudson, Culinary Institute of America, Marist University, schools, all things shopping and more! Come be a part of History and see all that the Hudson Valley has to offer! *SOME INTERIOR PHOTOS HAVE BEEN VIRTUALLY STAGED WITH FURNITURE*

151 Academy Street, Poughkeepsie
$599,900
3 Beds ⋅ 3 Baths ⋅ 1028071 MLS
Welcome home to this meticulously maintained Colonial, completely renovated in 2024 and offering the perfect blend of modern style, comfort, and convenience. Step inside to discover a light filled, open floor plan designed for today's lifestyle. The stunning chef's kitchen features KraftMaid cabinetry, beautiful Quartz countertops, abundant workspace, and seamlessly flows into the dining area and spacious living space, perfect for everyday living and entertaining. A sliding glass door opens to a brand-new Trex deck with a retractable awning overlooking the level, fully fenced backyard. Working from home is effortless with the private first-floor office, complete with elegant French doors, providing a quiet and comfortable workspace. Upstairs, the primary suite offers an en-suite bath and generous closet space. Two additional bedrooms with another full bath and an oversized bonus room providing incredible flexibility as a playroom media room, home gym, or even a potential fourth bedroom. Additional features included a second floor laundry attaehed two car garage, generator, and countless updates throughout, making this truly move-in. Ideally located on the sought-after Southside of Poughkeepsie, this exceptional home is just minutes from shopping, restaurants, schools, major commuter routes, and approximately 3.5 miles from the metro-North train station. Furniture is negotiable.

24 Whittier Boulevard, Poughkeepsie
$220,000
2 Beds ⋅ 1 Baths ⋅ 1027329 MLS
A rare opportunity to own what feels like brand-new construction in an established community. Completely gut renovated from the inside out, this exceptional co-op combines designer finishes, energy-efficient upgrades, and an unbeatable location just moments from the Hudson River. Every inch of this home has been thoughtfully reimagined with a modern yet timeless design, quality craftsmanship, and attention to detail. The open-concept floor plan creates a bright, welcoming atmosphere, centered around a beautifully designed kitchen with warm cream cabinetry, elegant hardware and faucet, and an elevated breakfast bar that seamlessly connects the kitchen and living space—perfect for entertaining or everyday living. Luxury vinyl plank flooring, tasteful lighting, and a soft, modern color palette flow throughout the home, creating a sophisticated yet inviting feel. What truly sets this residence apart is what you don't see. The renovation extended far beyond cosmetic updates, with newer electrical and plumbing systems, plus all-new insulation installed to today's energy-efficient building standards. Combined with a high-efficiency mini-split heating and cooling system, these upgrades provide year-round comfort while helping reduce energy costs. The spacious primary bedroom offers a peaceful retreat, while the second bedroom provides flexibility for guests, a home office. The beautifully renovated bathroom features contemporary finishes and a clean design that complements the rest of the home. Outside, enjoy amenities including a community swimming pool, clubhouse, and grilling area. Even better, the monthly HOA fee INCLUDES both property and school taxes, offering exceptional value and predictable monthly ownership costs. Perfectly positioned just around the corner from the scenic Hudson River waterfront, marinas, and walking areas, this home is also conveniently located near shopping, restaurants, and major commuter routes, making it easy to enjoy everything the area has to offer. With every major system already updated, designer finishes throughout, and absolutely nothing left to do, this is a truly turnkey home that stands out from anything else on the market.

164 Rinaldi Boulevard Unit #C, Poughkeepsie
$500,000
4 Beds ⋅ 2 Baths ⋅ 1022089 MLS
Great Investment Opportunity! This 2-family home has one leased unit and one vacant. Live in one unit and use the rent to help with expenses or rent out both units for maximum income. It has been generating $52,800 annually. Included in the sale is the lot next door (3 Park Place, 131300-6162-71-320192-0000). Solar panels will be paid off by seller at closing. Solar panels were installed in 2022 and keep electricity costs to the bare minimum of $60/month. Separate natural gas meters allow tenants to pay, which saves on the owner's monthly cost. The roof was replaced in 2022 when the panels were installed. Each unit offers 2 bedrooms, 1 bath, large kitchen, dining room, living room, and unit 2 has a den/office that leads to the balcony. With a shared washer and dryer, basement storage, plenty of parking, and a convenient location close to shopping, dining, schools, and major commuter routes, this property is designed for both tenant appeal and long-term value.

1 Park Place, Poughkeepsie
$465,000
4 Beds ⋅ 3 Baths ⋅ 1026339 MLS
Welcome to 149 Washington street, where beauty, functionality and affordability meet. Featuring 4 bedrooms, 2.5 bathrooms, a fully renovated kitchen, formal dining room, semi finished basement and beautiful livingroom fitted with a timeless stone fireplace. An additional flexible living space is offered as a fully finished attic boasts a huge amount of addition square footage. This home offers detailed finishes you don't often see today including stained glass windows, and craftsman style wood features. As a bonus, a split heating system allows each floor its own comfortable living temperature. Located directly across the street from the community pool, a half mile from major educational institutions, and less than a block from the renowned Walkway Over the Hudson. Imagine yourself sipping sweet tea as you relax on your porch swing after a day at the community pool. The perfect opportunity to own as a home or turnkey rental property. Truly a must see.

149 Washington Street, Poughkeepsie
$529,000
5 Beds ⋅ 3 Baths ⋅ 1026212 MLS
Investment or owner-occupant opportunity at 17 North Clover Street, a spacious three-unit property offering flexibility, recent exterior improvements, and a convenient location. The building features two vacant units, each offering two bedrooms and one full bathroom, allowing a new owner to select tenants, establish current rental terms, or occupy one unit while generating income from the others. The third unit is an occupied one-bedroom, one-bathroom apartment, providing immediate rental income. Recent improvements include new roofs on both the main house and detached three-car garage, a freshly painted exterior, and an upgraded common foyer that creates an inviting entrance for residents and guests. Additional highlights include off-street parking and a three-car garage offering space for vehicles, storage, or other income generating possibilities. Ideally positioned within close proximity of the Poughkeepsie Metro-North and Amtrak station, the property provides convenient rail access to New York City, Albany, and surrounding Hudson Valley destinations. It is also close to Route 9, Routes 44/55, the Mid-Hudson Bridge, downtown restaurants and shops, the Poughkeepsie waterfront, parks, and the Walkway Over the Hudson. With two vacant apartments, an occupied income-producing unit, major exterior upgrades, and a highly accessible location, this is a great opportunity to build or expand a real estate portfolio.

17 N Clover Street, Poughkeepsie
$100,000
1 Beds ⋅ 1 Baths ⋅ 1026011 MLS
Nestled in the heart of Poughkeepsie’s vibrant Executive Towers, Unit 3P is a bright and inviting 1-bedroom, 1-bathroom co-op offering a perfect blend of comfort and convenience. Step out onto your private balcony, ideal for savoring morning coffee or unwinding in the evening while enjoying sweeping views of the surrounding cityscape. This residence comes with a host of premium amenities: a 24-hour doorman ensures security and ease, laundry rooms on every floor eliminate the hassle of in-unit appliances, and assigned gated parking provides peace of mind for your vehicle. The building’s large in-ground pool invites you to relax and socialize during warm months, while elevators and on-site management make daily living effortless. Location couldn’t be better, just steps from Poughkeepsie’s best shops, dining, and transportation. Local favorites like Lola’s Cafe and The Poughkeepsie Grind are within easy reach, and the Metro-North station is nearby for seamless commuting. Schedule your private showing today and experience everything Unit 3P has to offer. Don’t miss this opportunity to make this inviting home yours!

160 Academy Street Unit #3P, Poughkeepsie
$349,900
2 Beds ⋅ 3 Baths ⋅ 1021925 MLS
Welcome to this beautiful 2-bedroom townhouse in the desirable Fox Hill community located on the South Side of Poughkeepsie. Offering a spacious layout, comfortable living spaces and a prime location, this home is perfect for those seeking low-maintenance living without sacrificing space. The main level features an inviting living room, a dining area ideal for entertaining, and a functional kitchen with plenty of cabinet and counter space. In addition, you’ll find two generously sized bedrooms, including a spacious primary bedroom with a private ensuite bathroom and ample closet space. Both bedrooms offer direct access to a private deck, creating the perfect spot to enjoy your morning coffee or unwind while overlooking the peaceful surroundings. The partially finished basement adds valuable living space and endless possibilities. Whether you need a family room, home office, exercise area, or recreation room, this flexible space can easily adapt to your needs, as well as a walk out to an inviting patio. Fox Hill is a well-maintained community known for its attractive setting and convenient location. Enjoy easy access to shopping, restaurants, parks, schools, medical facilities, and major commuter routes. Metro-North train service and nearby highways make traveling throughout the Hudson Valley or commuting to New York City simple and convenient. Whether you’re purchasing your first home, downsizing, or looking for a move-in-ready property with room to grow, this townhouse checks all the boxes. This exceptional Fox Hill home offers comfort, convenience, and an outstanding opportunity to enjoy everything the South Side of Poughkeepsie has to offer.

702 Scenic Lane, 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
$299,900
3 Beds ⋅ 2 Baths ⋅ 1024789 MLS
Welcome home to 100 Rinaldi Blvd., this beautifully updated 3BR,1.5 Bath end unit townhome offers the perfect blend of modern luxury and effortless urban living. From the moment you step inside, You will be captivated by the bright, inviting atmosphere and the thoughtful, top-to-bottom updates that make this home completely move-in ready. Very reasonable common fees only $70 monthly. The updates featured are a new architectural shingle roof with a transferable warranty, brand-new kitchen complete with sparkling new countertops and pristine cabinetry, designed to make everything from quick morning coffees to hosting intimate dinner parties an absolute joy. With three nice, sunlit bedrooms with new carpeting and one and a half beautifully refreshed baths. There is plenty of room to comfortable unwind, grow, or design the perfect dedicated work-from-home space. This charming property places Poughkeepsie’s finest lifestyle right at your doorstep with partial views of the Mid-Hudson Bridge, from your private backyard. There is also additional storage space with a pull down stairs for access to a large attic and more possible storage in the crawl space beneath the home. You will love the unbeatable convenience of being just minutes away from local shopping, a flourishing culinary scene, and walking distance to a nearby train station for effortless commuting. It is a rare opportunity to enjoy easy, turn-key townhome living without sacrificing the vibrant Hudson Valley culture you love—schedule your tour today and welcome home!

100 Rinaldi Boulevard, Poughkeepsie
$445,000
3 Beds ⋅ 2 Baths ⋅ 1020961 MLS
South side extremely well cared for home is looking for its next long term owner. Looking for a home that will offer you everything you're looking for? Stop the search is over. A solidly built brick cape style home situated above the quiet street it sits on. Plenty of off street parking and a backyard made for gatherings. A whole house basement with two root cellars and the ceiling hight to do whatever you would like. Game room, home gym, plenty of storage or whatever else you may think of. Access the garage and your car without going outside, no more hot sun, cold snow or wet rain to hinder you from comfortably entering or exiting your car. The house offers a warm welcoming entry from the front door where hardwood floors through out the home lead to a very generous sized living room with fireplace. A formal dinning room to enjoy any celebration or holiday you like. A large eat in kitchen with more counter top space then you could use. A counter top stove and double wall oven to prepare culinary delights and snacks alike. You can also enjoy a cold drink, warm cup of morning coffee or just unwind in the screened in porch right of the eating area of this incredible kitchen. Down the hallway leads to two generous sized bedrooms with closets for plenty of clothes. Your first full bath rounds off the first floor of this home. Then up the stairs to the second floor where you will find space for even more storage if you need it, your second full bathroom and a third spacious bedroom with closets. A large walk in cedar closet is also there for anything you'd like to store in it. At the end of the home is a large space currently used for even more storage or can be finished to become an incredible work from home office that would be extremely private or a sitting area for relaxing and unwinding with tv away from it all steps away from your slumber. Close to everything the city and town has to offer, minutes to Raymond ave farmers market and restaurants. A few more minutes to the main street corridor, waterfront, train station and the Walkway over the Hudson state park. Home was so well cared for that any updating you may like to do can be done when you would like as you like in time if you decided. The pride of ownership is blinding in this home. Easy to show but confirmation is required.

10 Degarmo Place, Poughkeepsie
$450,000
4 Beds ⋅ 3 Baths ⋅ 1023576 MLS
Welcome to 17 Coughlin Street, a value-packed three-unit investment property offering immediate rental income and additional upside in the heart of Poughkeepsie. Two of the three apartments have been fully renovated and are currently rented, featuring updated kitchens and bathrooms, new appliances, modern flooring, fresh finishes, and bright, comfortable living spaces. The ground-level unit is under construction and has been thoughtfully set up for the next owner to complete, providing an excellent opportunity to customize the space and further increase the property’s income potential. Major improvements include a new roof, renovated siding, updated electrical and plumbing systems, separate water heaters, and a fire-alarm system. Outside, the property offers valuable off-street parking, a spacious rear area, and a rare three-car garage with excellent potential for parking, storage, or additional rental income. Conveniently located near downtown Poughkeepsie, shopping, restaurants, public transportation, the Metro-North train station, Route 9, Routes 44/55, the Mid-Hudson Bridge, and the Walkway Over the Hudson, this property combines updated living spaces, strong income potential, and a commuter-friendly location. A great opportunity for investors or owner-occupants looking to complete the final unit while collecting income from the two renovated apartments.

17 Conklin Street, Poughkeepsie
$344,999
3 Beds ⋅ 2 Baths ⋅ 1021691 MLS
This fully renovated colonial blends modern updates with timeless charm. Move in ready 3-bedroom, 2-bathroom light filled open living space that is cozy and inviting. The beautifully updated kitchen features sleek countertops, contemporary cabinetry, and stainless-steel appliances, a functional space perfect for everyday living and entertaining. Both full bathrooms have been refreshed with clean, modern finishes, and each bedroom provides comfortable space for relaxation. The partial finished attic would make a great space for a primary suite or Rec room. Outside the expansive lot offers endless possibilities-gardens, play area and outdoor entertaining on a new patio installed in 2024. New water and Sewer line completed 2023. Owners will consider a rent to own situation.

146 Smith Street, Poughkeepsie
$575,000
1021090 MLS
Position yourself in the heart of Downtown Poughkeepsie with this exceptional mixed use investment opportunity at 381 Main Street. This well-maintained commercial property offers the rare combination of immediate cash flow, long term upside, and one of the most valuable amenities in the city: dedicated off street parking with approximately 10 exclusive spaces. The first floor is occupied by a successful, high-end salon whose owner is offering the property for sale and is interested in remaining as a long-term tenant, providing investors with immediate occupancy and rental income from an established business. The second floor is currently leased on a month-to-month basis to a nail salon, offering flexibility to maintain the existing tenant, negotiate new lease terms, or reposition the space to maximize future income. Investment potential extends well beyond the existing rental stream. With approximately 10 dedicated parking spaces, this property offers an uncommon advantage in Downtown Poughkeepsie, where neighboring commercial buildings often lack private parking. The lot itself presents an additional revenue opportunity through leased parking spaces for nearby businesses, employees, or residents, creating another potential income source. Located within an area benefiting from ongoing public and private investment, Downtown Poughkeepsie continues to experience significant revitalization, making this an ideal time to secure a commercial asset with both current income and future appreciation potential. Investors seeking stable cash flow may appreciate the opportunity to retain the existing businesses while strategically increasing rental income over time to improve overall returns. Whether you are completing a 1031 Exchange, expanding your commercial portfolio, or seeking a mixed-use asset with multiple income streams, 381 Main Street offers a compelling combination of location, flexibility, parking, and long-term investment potential. Opportunities to acquire a property of this caliber with established tenants, dedicated parking, and multiple avenues for increased revenue are increasingly rare in the City of Poughkeepsie.

381 Main Street, Poughkeepsie
$249,000
2 Beds ⋅ 1 Baths ⋅ 1021054 MLS
This is a cute cottage type house with 2 Bedrooms, 1 bath, dining room, a good size living room and bonus room. It does need TLC but can be livable while fixing it to your taste. There are 3 levels. First floor has access from a large covered porch and front door. From the porch you enter the kitchen and have access to a full Bath, dining room, linving room and bedroom. Also access to the second floor and basement. Second floor has a good size bedroom. Basement has access to the street and consist of laundry room, utility room and bonus room. This a great starter home at a great price. Make it you home!

149 South Avenue, Poughkeepsie
$2,300,000
1020300 MLS
THE DERBY BAR/RESTAURANT PROPERTY LOCATED AT 96 MAIN STREET, A LANDMARK IN THE CITY OF POUGHKEEPSIE SINCE 1902 ACCORDING TO THE JOURNAL, IS AVAILABLE FOR SALE. RECENTLY CLOSED, NEW OWNERSHIP CAN STEP IN AND CONTINUE THE GOOD FORTUNE OF PREVIOUS OWNERS WITH THE HELP OF SEVEN RESIDENTIAL RENTAL UNITS ON THE SECOND AND THIRD FLOORS. THE BRICK BUILDING TOTALS 8,064 SQUARE FEET ON THREE FLOORS. BAR/RESTAURANT ON THE FIRST FLOOR CONSIST OF 3,328 SQUARE FEET WITH AN ADDITIONAL 2,368 SQAURE FEET IN THE BASEMENT WITH INTERIOR STAIRWELL ACCESS. FRONT DOOR ACCESS FROM MAIN STREET, KITCHEN ACCESS FROM SOUTH CLOVER STREET AND THE 18 CAR PARKING LOT. LARGE 36 FOOT BAR WITH HIGH-TOP TABLES AND 24 BAR STOOLS. THREE DINING ROOMS WITH 16 FOUR-TOP TABLES AND 5 TWO-TOP TABLES. SECOND AND THIRD FLOORS CONSIST OF SEVEN ONE-BEDROOM APARTMENTS UNITS TOTALING 4,736 SQAURE FEET WITH SEPARATE ACCESS FROM MAIN STREET. BEING LESS THAN .2 MILES FROM POUGHKEEPSIE TRAIN STATION KEEPS THE APARTMANTS UNITS FULLY RENTED.

96 Main Street, Poughkeepsie
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