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$599,900

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.

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

$575,000

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.

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

$349,000

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

4 Beds ⋅ 2 Baths ⋅ 1019365 MLS

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

137 N Clinton Street, Poughkeepsie

$1,250,000

Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on 0.21 acres just steps from Millbrook's boutiques, restaurants, galleries, and everyday conveniences, the property offers an increasingly rare combination of village living and income-producing potential. Originally built in 1910, the main residence was extensively renovated in 2002 with new windows, updated heating systems, a new oil tank, and two-zone central air conditioning, blending modern comfort with historic character. The guest apartment was constructedin 2018 and provides excellent flexibility for rental income, guests, or extended family. The private fenced backyard serves as a peaceful retreat, featuring two bluestone patios ideal for outdoor dining, entertaining, or relaxing. Ideally located near highly regarded public and private schools, summer camps, and premier sporting clubs, including the Millbrook Golf & Tennis Club, Tamarack Preserve, and Mashomack Preserve Club. The region is renowned for its equestrian lifestyle, with access to horse shows, fox hunting, riding trails, and top-tier equestrian facilities. Hiking, fly-fishing, polo, and skiing are all nearby. Millbrook's central location provides convenient access to Rhinebeck, Red Hook, Pine Plains, Millerton, Hudson, Litchfield County, and the Berkshires, home to Tanglewood and a wealth of cultural attractions. Just 1¾ hours from Manhattan by car or via Metro-North Railroad, this unique property offers the perfect blend of village convenience, country charm, and income-producing flexibility.

4 Beds ⋅ 3 Baths ⋅ 967644 MLS

Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire property! Set on 0.21 acres just steps from Millbrook's boutiques, restaurants, galleries, and everyday conveniences, the property offers an increasingly rare combination of village living and income-producing potential. Originally built in 1910, the main residence was extensively renovated in 2002 with new windows, updated heating systems, a new oil tank, and two-zone central air conditioning, blending modern comfort with historic character. The guest apartment was constructedin 2018 and provides excellent flexibility for rental income, guests, or extended family. The private fenced backyard serves as a peaceful retreat, featuring two bluestone patios ideal for outdoor dining, entertaining, or relaxing. Ideally located near highly regarded public and private schools, summer camps, and premier sporting clubs, including the Millbrook Golf & Tennis Club, Tamarack Preserve, and Mashomack Preserve Club. The region is renowned for its equestrian lifestyle, with access to horse shows, fox hunting, riding trails, and top-tier equestrian facilities. Hiking, fly-fishing, polo, and skiing are all nearby. Millbrook's central location provides convenient access to Rhinebeck, Red Hook, Pine Plains, Millerton, Hudson, Litchfield County, and the Berkshires, home to Tanglewood and a wealth of cultural attractions. Just 1¾ hours from Manhattan by car or via Metro-North Railroad, this unique property offers the perfect blend of village convenience, country charm, and income-producing flexibility.

3311 Franklin Avenue, Millbrook