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$375,000
6 Beds ⋅ 2 Baths ⋅ 1051383 MLS
Attention Investors! Turnkey duplex offering an excellent opportunity to add a strong, low-maintenance asset to your portfolio. The property features two spacious 3-bedroom apartments, each offering over 1,000 square feet of living space with comfortable, functional layouts. Move-in ready and positioned for immediate rental income, this property offers an attractive cap rate with minimal anticipated capital expenditures. A great opportunity for investors seeking cash flow, or an owner-occupant looking to offset their housing costs with rental income.

144 Winnikee Avenue, Poughkeepsie
$289,000
2 Beds ⋅ 2 Baths ⋅ 1048974 MLS
Welcome to 152 N Clinton Street, a beautifully renovated home in the heart of Poughkeepsie offering the perfect blend of modern style, comfort, and convenience. This move-in-ready 2-bedroom, 2 full bathroom home has been thoughtfully updated from top to bottom with contemporary finishes and functional living spaces throughout. Step inside to find a bright open-concept layout featuring brand-new flooring, recessed lighting, fresh paint, and a stunning modern kitchen complete with sleek cabinetry, stainless steel appliances, and stylish countertops. The spacious living area is filled with natural light and centered around a charming decorative fireplace that adds warmth and character to the space. Both full bathrooms have been tastefully redesigned with modern tilework and updated fixtures, while the generously sized bedrooms offer comfort, flexibility, and ample closet space. Additional upgrades include updated mechanicals, and off-street parking with a private driveway. Outside, enjoy a manageable yard space perfect for relaxing, entertaining, or gardening. Conveniently located near downtown Poughkeepsie, the waterfront, restaurants, shopping, colleges, hospitals, and the Metro-North train station, this property is ideal for commuters, first-time buyers, or anyone looking for a low-maintenance home with modern appeal in a prime Hudson Valley location.

152 N Clinton Street, Poughkeepsie
$375,000
3 Beds ⋅ 2 Baths ⋅ 977482 MLS
Welcome home to this charming and beautifully maintained 3 bedroom, 2 bath colonial nestled in Poughkeepsie’s Southside neighborhood. From the moment you arrive, the adorable front porch offers the perfect place to enjoy your morning coffee or unwind at the end of the day. Rich hardwood floors throughout add warmth and timeless character, while thoughtful updates provide comfort for today’s lifestyle The updated kitchen features contemporary appliances and an inviting space for cooking, gathering, and creating everyday memories. A walk-up attic provides abundant storage and flexible space for future possibilities Step outside to enjoy the fully fenced backyard is ideal for relaxing, gardening, entertaining, or simply enjoying the outdoors in your own private setting. Additional highlights include central air, a whole-house humidifier for added year round comfort, and the convenience of off-street parking with a private driveway Conveniently located near shopping, dining, parks, colleges, medical facilities, and Metro-North access, this home combines classic charm with everyday convenience in the heart of the Hudson Valley. Don’t miss the opportunity to make this special property your own. Furniture can be negotiated.

10 Oakwood Boulevard, Poughkeepsie
$350,000
3 Beds ⋅ 2 Baths ⋅ 1042187 MLS
Step inside through the welcoming foyer and discover a comfortable, light-filled living room perfect for relaxing, gathering with loved ones, or enjoying a quiet evening at home. Rich wood trim and classic French doors add character, while the adjoining formal dining room creates a beautiful setting for holiday celebrations, dinner parties, and everyday meals. The bright eat-in kitchen offers abundant cabinetry, plenty of workspace, a dedicated dining area, and convenient access to the backyard, making indoor-outdoor entertaining a breeze. Full updated first floor bathroom finishes the first floor living area. Upstairs you will find two spacious bedrooms, spacious primary bedroom featuring a walk-in closet, and a full updated bathroom. A finished walk-up attic provides even more possibilities and can easily serve as a recreation room, creative studio, work-from-home space, or additional storage. A full unfinished basement offers further storage and utility space. Outside, the home continues to impress with a rear deck overlooking a level, fenced-in backyard, a wonderful setting for summer barbecues, outdoor dining, gardening, play, pets, or simply enjoying the fresh air. A blue stone patio, storage shed, private driveway, and charming picket-fenced front yard complete the property. With municipal water, sewer, natural gas and a convenient location minutes to the Walkway over the Hudson, Marist University, Culinary Institute of America, amazing restaurants, shopping, dining, schools, parks, transportation, and more, come make 25 Taylor your own! PRICED TO SELL!

25 Taylor Avenue, Poughkeepsie
$575,000
6 Beds ⋅ 6 Baths ⋅ 1036859 MLS
Welcome to a truly special piece of Poughkeepsie history. Built in 1877 and set within the Historic District, this striking Victorian residence offers an exceptional opportunity to restore and reimagine a grand historic home while preserving its remarkable architectural character. From the gracious curved staircase and soaring ceilings to original hardwood floors, intricate moldings, pocket and French doors, multiple fireplaces, and a distinctive glass-enclosed cupola, the craftsmanship and scale of this home are rarely found today. With approximately 4,831 square feet, three levels, 8 plus bedrooms (tax indicate 6), 6 baths (3 full 3 half), a spacious kitchen with cherry cabinetry, granite countertops and multiple work areas, plus a butler's pantry, the possibilities are extensive. A full basement, detached garage, private yard, and rooftop garden area with views add even more potential. Recent improvements provide a foundation for the next chapter, while the property's historic details invite thoughtful restoration. Whether envisioned as a magnificent private residence, a thoughtfully restored historic property, or another permitted use subject to municipal approval, 8 Garfield Place is an extraordinary opportunity to bring a landmark-quality home back to its full glory.

8 Garfield Place, Poughkeepsie
$425,000
7 Beds ⋅ 2 Baths ⋅ 1046143 MLS
Welcome to this beautifully renovated rental in the heart of Downtown Poughkeepsie! Offering a comfortable blend of modern updates and inviting living spaces, this spacious second-floor residence is ready to welcome you home. Step inside to find updated flooring and hardwood-style finishes throughout, complemented by abundant natural light. The thoughtfully designed layout features separate living and dining rooms, providing plenty of room to relax, entertain, and make the space your own. The fully renovated kitchen offers a fresh, modern feel with stainless-steel appliances and updated finishes. The renovated bathroom continues the contemporary style with new tilework and fixtures. The home offers a flexible bedroom layout, with one bedroom conveniently located on the main floor and three additional cozy bedrooms in the finished attic, providing versatility for bedrooms, guests, a home office, or additional living space. Outside, enjoy a spacious fenced backyard complete with a patio area—an ideal setting for summer gatherings, outdoor dining, gardening, or simply enjoying some fresh air. Located in Downtown Poughkeepsie, this rental puts you close to local shops, restaurants, entertainment, transportation, and the many amenities the area has to offer. A recently renovated home, generous living spaces, multiple bedrooms, and a private outdoor area make this a wonderful opportunity to enjoy comfortable living in a convenient Poughkeepsie location. Additional Information: Heating Fuel: Oil (Above Ground).

81 Washington St, Poughkeepsie
$439,000
4 Beds ⋅ 3 Baths ⋅ 1045625 MLS
RARE OWNER OCCUPANT OPPORTUNITY in the City of Poughkeepsie, NY. This two building property features a spacious 2BR/1BA owner's unit currently rented at $1,875/mo with an attached 2-car garage, abundant storage and in unit washer/dryer. IDEAL for a buyer with a business or hobby — plus a second building with two long-term-tenanted 1BR/1BA units renting for $1,135 and $1,250/mo with off street parking and leases running through Aug 31, 2027. Perfect for an owner-occupant looking to live on-site while collecting rental income from day one. All municipal services and natural gas. Buildings are in good condition with newer features such as electrical, boiler/HVAC and roof. This unique two building opportunity offers something increasingly hard to find: a private owner's residence with serious garage and storage space, paired with a second building generating steady rental income. Whether you're a contractor, tradesperson, artist, collector, or hobbyist who needs real workspace — or simply an investor looking to live on-site while building equity — this property delivers flexibility that's tough to match. Easy access to train stations, Vassar College, Marist College, Walkway Over the Hudson and all the dining and cultural opportunities in the City of Poughkeepsie.

11 S White Street, Poughkeepsie
$735,000
1045579 MLS
Investment Opportunity – High Cash Flow Property in the Heart of Poughkeepsie Presenting 40 S. Hamilton Street, a rare opportunity to acquire a proven income-producing property in the City of Poughkeepsie. This well-established rooming house consists of nine private single-occupancy rooms, seven bathrooms, providing affordable and independent living accommodations that serve a critical role in the local housing market. This property is a grandfathered rooming house (meaning no other property can be zoned as a rooming house without a special permit). Coin operated laundry also included in the basement. The property has demonstrated strong and consistent performance, currently generating approximately $100,000 in annual gross rental income with a current NOI of $49,315. Residents enjoy access to shared common areas including a communal kitchen, lounge, and hallway facilities on each floor, creating a practical and cost-effective housing solution for tenants. Situated on a generous lot, the property features a large rear driveway with ample off-street parking, a valuable amenity for both tenants and management. A substantial basement provides additional storage space and operational flexibility. For investors seeking immediate cash flow, this property is generating income from day one. Beyond its current performance, there are multiple avenues for future upside. Four apartment conversion is allowed by right. If you split the lot, you can build eight apartments on a knockdown. Student housing is also permitted outright (with Marist, Vassar, Dutchess Community College, and CIA nearby). You can also continue operating as a successful rooming house rental property. The combination of strong in-place income, parking, storage, and future value-add potential makes this an attractive acquisition for both experienced and aspiring investors. Additionally, there is a small parking lot in the rear of the building. Whether you're looking to expand your portfolio with a stabilized asset or capitalize on redevelopment and repositioning opportunities, 40 S. Hamilton Street offers a compelling blend of cash flow, flexibility, and long-term potential in a growing rental market.

40 S Hamilton Street, Poughkeepsie
$375,000
3 Beds ⋅ 2 Baths ⋅ 1027873 MLS
Welcome to 30 Glenwood Avenue, a charming Cape Cod offering comfortable living spaces and a well-maintained, move in ready interior. The home features a functional layout, vinyl flooring, an enclosed front porch, and a rear porch overlooking a spacious, level backyard, perfect for relaxing, entertaining, or enjoying time outdoors. Set on approximately a quarter-acre lot, the property offers plenty of outdoor space along with convenient off-street parking. A full basement provides additional space for storage. Solar panels are owned and will tranfer ownership along with the sale of home. Conveniently located in the City of Poughkeepsie with easy access to local shopping, dining, parks, schools, and major commuter routes. Well cared for and ready for its next owner, 30 Glenwood Avenue is a wonderful place to call home.

30 Glenwood Avenue, Poughkeepsie
$439,000
5 Beds ⋅ 2 Baths ⋅ 1041152 MLS
A great opportunity for investors or owner-occupants! This two-family property offers two completely renovated apartments. A 2-bedroom first-floor unit and a 3-bedroom second-floor unit. Both units feature newer appliances along with new HVAC systems and new hot water heaters, and tenants pay their own utilities. Both apartments are currently occupied by attentive tenants, providing immediate rental income. The first-floor unit rents for $1,800 per month, currently below market value, while the second-floor unit rents for $2,300 per month. With renovated interiors, separate utilities, new mechanicals and strong rental potential, this is a turnkey income producing property with plenty to offer!

193 N Hamilton Street, Poughkeepsie
$299,950
3 Beds ⋅ 1 Baths ⋅ 1040492 MLS
Welcome to this well-maintained Colonial offering over 1,200 square feet of comfortable living space with 3 bedrooms and 1 full bathroom. Blending classic charm with tasteful updates, this home features a spacious and inviting living room highlighted by a beautiful brick fireplace and abundant natural light. The updated eat-in kitchen features beautiful vaulted ceilings, white cabinetry, stainless steel appliances, ample counter space, and room for dining, creating the perfect space for everyday living and entertaining. A full bathroom is conveniently located on the main level, while the second floor offers three bedrooms, including a generously sized primary bedroom with a walk-in closet. Recent updates and improvements throughout the home provide a move-in ready feel while still maintaining character and warmth. Outside, enjoy a large level backyard with patio space, mature trees, and plenty of room for outdoor gatherings, gardening, or recreation. Conveniently located near shopping, restaurants, schools, parks, and major commuter routes, this charming home offers both comfort and convenience.

194 Smith Street, Poughkeepsie
$286,000
3 Beds ⋅ 2 Baths ⋅ 1040444 MLS
Welcome to 173 S. Cherry Street, a charming 3-bedroom, 1.5-bath home ideally situated on the sought-after South Side of Poughkeepsie. Offering approximately 1,464 square feet of living space on a manageable 0.17-acre lot, this property presents an excellent opportunity for buyers seeking comfort, convenience, and the potential to make a home truly their own. The traditional layout provides comfortable living spaces, while the second floor features three generously sized bedrooms offering privacy and flexibility for family, guests, or a home office. A walk-up attic provides valuable storage and exciting potential for future expansion, subject to the appropriate approvals. The property continues to offer versatility with an unfinished basement, providing ample space for a workshop, home gym, hobby area, or additional storage. Outside, the spacious backyard creates a wonderful setting for family gatherings, entertaining, gardening, or simply enjoying your own private outdoor space. Additional features include oil heat and a classic floor plan with plenty of opportunity to add your personal style and vision. Whether you're a first-time buyer, investor, or homeowner looking for a property with room to grow, this home offers a compelling combination of location, space, and potential. Conveniently located just minutes from Route 9, shopping, restaurants, everyday amenities, and the Metro-North train station, this home offers an ideal balance of neighborhood living and commuter convenience. Bring your vision and unlock the possibilities at 173 S. Cherry Street. This South Side Poughkeepsie opportunity is ready for its next chapter — schedule your showing today! Please note: The property is being sold strictly “AS IS.”

173 S Cherry Street, Poughkeepsie
$399,900
2 Beds ⋅ 3 Baths ⋅ 1039912 MLS
Welcome to 303 Bridgeview! Experience elevated Hudson River living in this beautifully maintained 2 bedroom, bonus loft, 2.5 baths, almost 2200 finished SQFT, thoughtfully designed living space in one of Poughkeepsie's most desirable waterfront communities, Hudson Pointe. This multi-level home combines modern comfort, spacious interiors, and an unbeatable location just moments from the riverfront, Poughkeepsie train station, restaurants, and waterfront attractions. Step inside to discover an inviting open-concept main level featuring gleaming hardwood floors, recessed lighting, abundant natural light throughout, slider egress to the rear patio, perfect for entertaining. The spacious living room flows seamlessly into the kitchen and dining area, creating the perfect setting for both everyday living and entertaining. The well-appointed kitchen offers leathered quartz countertops, tiled backsplash, wood cabinetry, stainless steel appliances, generous cabinet space, and a breakfast bar. Upstairs, the impressive primary suite serves as a private retreat with soaring vaulted ceilings, a walk-in closet, and a luxurious en-suite bathroom complete with a custom tiled shower and double vanity. A spacious second bedroom, additional updated full bathroom, and ample closet space provide comfort and flexibility for family or guests. The finished third-floor bonus room offers endless possibilities as a home office, media room, fitness space, or guest retreat. Downstairs, the finished lower level expands your living space as a possible rec room, office or flex space. Additional highlights include central air, natural gas forced-air heat, automatic window shades, an attached one-car garage, and maintenance-free living with exterior maintenance, snow removal, landscaping, and pool maintenance all included through the HOA. Residents also enjoy access to community amenities including a clubhouse, pool, and park. Perfectly situated near the Hudson River waterfront, this exceptional townhouse offers easy access to the Walkway Over the Hudson, Metro-North, Vassar Hospital, Marist University, Culinary Institute of America, restaurants, marinas, and all that the vibrant Poughkeepsie waterfront has to offer. Come see this beautiful unit today and all that the Hudson Valley has to offer!

303 Bridgeview Drive, Poughkeepsie
$525,000
2 Beds ⋅ 2 Baths ⋅ 1039739 MLS
Charming Two-Family Home located just off Hooker Avenue, this exceptional two-family property presents a fantastic opportunity for both owner-occupants and investors alike. Situated on a desirable, beautifully landscaped corner lot, this versatile home combines convenience, charm, and functional living spaces. First Floor Main Unit Step inside the spacious first-floor apartment to discover classic comfort and warm character. Living Space: Features gorgeous hardwood floors and a striking stone fireplace as the room's centerpiece, creating a cozy and inviting atmosphere. Kitchen & Dining: A well-appointed eat-in kitchen designed for everyday meal prep and casual dining. Bedrooms & Storage: Includes two comfortable bedrooms, ceramic tile flooring in designated areas, and a convenient walk-in hallway closet. Lower Level: A full, unfinished basement provides ample storage space and features a dedicated laundry area. Climate Control: Enjoy year-round comfort with central air conditioning. Second Floor Efficiency Apartment A bright and private upstairs efficiency apartment offering an independent living setup. Equipped with its own convenient washer and dryer. Comfortably climate-controlled using an efficient heat pump for both heating and air conditioning. Exterior & Grounds The outdoor space is a private oasis, meticulously landscaped and designed for easy relaxation or entertaining. Yard & Garden: Features an open shed, a dedicated garden area, and a lovely cement patio surrounded by lush landscaping. Parking & Storage: Includes a rare two-car garage under, offering secure parking and extra storage capability. Conveniently located close to local dining, shopping, and commuter routes, this unique Poughkeepsie gem is a must-see. Schedule your private tour today!

69 Cedar Avenue, Poughkeepsie
$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
$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
$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
$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
$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
$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
$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
$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
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