5-Bedroom Homes for Sale in Dutchess County NY

• 

  

  

  /23

  $799,900

  • 5 Beds
  • 3 Baths
  • 3,600 Sq Ft

  5 Douglas Dr, Wappingers Falls, NY 12590

  Endless Opportunities Await at This Unique 9-Acre Estate! Check out this sprawling 9-acre property offering **endless opportunities** for living, income, and whatever else you can dream up. This multi-family home, all on one level, features two separate units: a 2-bedroom, 1-bath and a larger **3-bedroom, 2-bath with an updated kitchen**. It's set up for multi-generational living, rental income,

  Lynn Fronckowiak K. Fortuna Realty, Inc.

  5 Douglas Dr, Wappingers Falls, NY 12590
• 

  

  

  /23

  $390,000

  • 5 Beds
  • 2 Baths
  • 2,100 Sq Ft

  30 S White St, Poughkeepsie, NY 12601

  Excellent Investment Opportunity! Welcome to this charming 2-family home on a beautiful, fenced corner lot with a large detached 2 car garage. Next to the garage is a vacant lawn area also part of the property.The first-floor unit is vacant, fully renovated, and ready to rent or move in and let the upstairs tenant help pay your mortgage. Renovations include new LVP flooring, vanity, toilet,

  Michael Dunstan RE/MAX Town & Country

  30 S White St, Poughkeepsie, NY 12601
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  /39

  $599,000

  • 5 Beds
  • 2 Baths
  • 1,825 Sq Ft

  67 Jennifer Hill Rd, Lagrangeville, NY 12540

  Welcome to this charming Cape/Colonial-style home, perfectly set on a private and impeccably maintained 1.3-acre property. Thoughtfully renovated by the current owner in 1997 and 2004, this residence showcases quality craftsmanship and timeless character throughout. The home features an expanded second floor with a distinctive gambrel roof and a stunning sun-filled family room boasting a vaulted

  JEANNE BURKE BHHS Hudson Valley Properties

  67 Jennifer Hill Rd, Lagrangeville, NY 12540
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  /30

  $995,000

  • 5 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  7441 S Broadway, Red Hook, NY 12571

  Village of Red Hook renovation projected epitomizes the modern farmhouse. Thoughtful and tasteful design creates an enticing open floor plan with a designer kitchen as the focal point. Kitchen includes center island, quartz counters & stainless appliances. Massive family room/dining room combo flows seamlessly to living room w/adjacent powder room. Two primary suites, one on each floor makes this

  Dan Axtmann BHHS Hudson Valley Properties

  7441 S Broadway, Red Hook, NY 12571
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  /50

  $815,000

  • 6 Beds
  • 4.5 Baths
  • 3,974 Sq Ft

  82 Thornhill Dr, Pleasant Valley, NY 12569

  Stunning Pleasant Valley Colonial in park-like setting: This wonderful 6 bedroom home can be your personal oasis; close enough to civilization to have convenience, yet just rural enough to also have serenity. The acre and a half property features stately, landscaped front & side yards with walkways & mature trees - and a more private, fenced & wooded backyard that is all about relaxing and/or

  Christopher Hanson Hanson Real Estate Partners

  82 Thornhill Dr, Pleasant Valley, NY 12569
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  /35

  $665,000

  • 5 Beds
  • 3 Baths
  • 1,884 Sq Ft

  40 Old Glenham Rd, Beacon, NY 12508

  This beautifully updated Craftsman-style 5 bedroom 3 bath home combines timeless architecture with modern comfort. Inside, an updated kitchen, newly refinished floors, and an energy-efficient all-electric heat pump system enhance everyday living. The first-floor primary suite provides ease and privacy, while preserved original details showcase the home’s character throughout. Freshly painted

  Angela Ingham BHHS Hudson Valley Properties

  40 Old Glenham Rd, Beacon, NY 12508
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  /42

  $13,500,000

  • 5 Beds
  • 8 Baths
  • 5,867 Sq Ft

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522

  A singular and exceedingly rare residence, this exquisite home was masterfully designed by renowned AD100 architect Gil Schafer, featuring interiors by Antony Todd and landscape architecture by Warren Byrd, all set against panoramic views of the Hudson Valley and Catskill Mountains. This home is a Greek Revival masterpiece that blends timeless elegance with modern sophistication. As featured in

  OLIVER BROWN Houlihan Lawrence Inc.

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522
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  /40

  $699,900

  • 5 Beds
  • 3.5 Baths
  • 3,640 Sq Ft

  181 Union St, Poughkeepsie, NY 12601

  Historic Elegance in the Heart of PoughkeepsieStep back in time while enjoying generous modern living in thisremarkable 1880 single-family home, nestled within the PoughkeepsieHistoric District. Offering an impressive 3,640 sq/ft of living space, thisstately residence features 5 spacious bedrooms and 3 full bathrooms,ideal for both comfortable family living and elegant

  Randy Florke Rural Connection Inc.

  181 Union St, Poughkeepsie, NY 12601
• 

  

  /20

  $429,000

  • 6 Beds
  • 3 Baths
  • 2,848 Sq Ft

  34 Luty Dr, Hyde Park, NY 12538

  Welcome to this spacious and versatile detached multi-family home nestled in the charming town of Hyde Park, just minutes from the world-renowned Culinary Institute of America, Marist University, National Parks, shops, restaurants and the beautiful Hudson Valley waterfront. This 2-family home offers incredible potential for owner-occupants, extended families, or savvy investors seeking a strong

  JAIME WOLLMAN BHHS Hudson Valley Properties

  34 Luty Dr, Hyde Park, NY 12538
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  /36

  $699,000

  • 5 Beds
  • 4 Baths
  • 3,384 Sq Ft

  83-85 Old Post Rd, Staatsburg, NY 12580

  A great 3-family property in the heart of Staatsburg offering strong rental income and versatile living options. The main home features over 2,000 sqft with 3 bedrooms and 2 bathrooms. A detached second home features two private 1-bedroom, 1-bath units, ideal for maximizing rental income or accommodating extended family with ease. Each unit has its own entrance, creating privacy and flexibility

  STEVEN WROBEL JR. Serhant LLC

  83-85 Old Post Rd, Staatsburg, NY 12580
• 

  

  /50

  $3,995,000

  • 5 Beds
  • 7 Baths
  • 3,500 Sq Ft

  401 Woodmont Rd, Hopewell Junction, NY 12533

  Welcome to Cloud Walk Estate, a once-in-a-lifetime opportunity to own the entire summit of a private mountain in East Fishkill, NY. Encompassing nearly 120 acres across three parcels, this extraordinary estate offers panoramic views stretching close to 150 miles — a setting that simply cannot be replicated.Perfectly positioned just 90 minutes from NYC, this legacy property features five

  JORDAN VACCARO Serhant LLC

  401 Woodmont Rd, Hopewell Junction, NY 12533
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  /30

  $699,000

  • 8 Beds
  • 4 Baths

  77 Academy St, Poughkeepsie, NY 12601

  Welcome to 77 Academy Street, a stately brick three-unit building located in Poughkeepsie’s historic Academy Street District. This beautifully maintained property features two spacious 3-bedroom apartments and one 2-bedroom unit, each offering a blend of classic charm and modern updates including hardwood floors, decorative fireplaces, and renovated kitchens. Just over a mile from the

  Hamar Clarke Clarke Realty & Associates LLC

  77 Academy St, Poughkeepsie, NY 12601
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  /47

  $549,000

  • 6 Beds
  • 4 Baths

  29 Lake St, Poughkeepsie, NY 12601

  Prime Investment Opportunity!! Spacious 3-Family in High-Demand Location. This is your chance to own a versatile, income generating multi-family property in one of the area’s most sought after neighborhoods! Whether you’re a seasoned investor looking to expand your portfolio or a buyer seeking to live in one unit while renting the others, this solid 3-family home offers the perfect blend of

  Marie Savage Curasi Realty, Inc.

  29 Lake St, Poughkeepsie, NY 12601
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  /31

  $550,000

  • 5 Beds
  • 4.5 Baths
  • 3,225 Sq Ft

  8 Rock Garden Way, Poughkeepsie, NY 12603

  A rare opportunity for someone with vision to transform this expansive property into something truly special. Nestled in the heart of the Spackenkill School District, this home offers over 4,000 total square feet, including a legal accessory apartment, ideal for multi-generational living, guests, or future rental potential. Located on a quiet cul-de-sac, the property also features a detached

  DAVID DEBERARDINIS Serhant LLC

  8 Rock Garden Way, Poughkeepsie, NY 12603
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  /40

  $485,000

  • 6 Beds
  • 2 Baths
  • 4,026 Sq Ft

  788 788 Dutchess Turnpike, Poughkeepsie, NY 12603

  Welcome to 788 Dutchess Turnpike – a high-visibility property located in the heart of Poughkeepsie with 200 feet of road frontage in a bustling commercial and residential corridor. This versatile property offers outstanding potential for investors and entrepreneurs looking to possibly live and work in one central location. This converted residence is now a Commercial building with town permission

  Ann Scarano Realty Center Hudson Valley

  788 788 Dutchess Turnpike, Poughkeepsie, NY 12603
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  /33

  $750,000

  • 5 Beds
  • 3 Baths
  • 4,124 Sq Ft

  49 Flower Rd, Hopewell Junction, NY 12533

  Spacious contemporary nestled in a peaceful cul-de-sac within one of the area's most desirable neighborhoods, this expansive 4,200 sq ft open concept residence offers room to grow and endless potential. Featuring 5 generous bedrooms and 3 full baths, this home is perfect for multi-generational living or those seeking extra space for work and play. House also offer outdoor speakers in the family

  Zuzana Dankova HomeSmart Homes & Estates

  49 Flower Rd, Hopewell Junction, NY 12533
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  /48

  $11,750,000

  • 5 Beds
  • 6 Baths
  • 9,684 Sq Ft

  Unlisted Address

  Exquisite Shekomeko Estate with Panoramic Catskill Mountain views. Nestled on 50 private acres in the heart of the Hudson Valley, this country estate offers timeless sophistication, refined comfort, and breathtaking views of the Catskills. Designed by architect Jimmy Crisp and completed in 2004, the residence spans over 9,684 finished square feet of thoughtfully curated living space. A tree-lined

  PAULA REDMOND Corcoran Country Living

  Unlisted Address
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  /13

  $375,000

  • 7 Beds
  • 2 Baths
  • 2,000 Sq Ft

  117 Talmadge St, Poughkeepsie, NY 12601

  Duplex in the heart of Poughkeepsie on a quiet street. Unit 1 renovated in 2018 with stainless steel appliances. Unit 2 is newly renovated with new kitchen cabinets, quartz countertops, new bathroom, vynl flooring and carpet in the bedrooms. Property line goes down the middle of the shared driveway. The backyard could be used as private parking if needed. Unit 1 has direct access to backyard but

  Maritza Soto eXp Realty

  117 Talmadge St, Poughkeepsie, NY 12601
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  /36

  $3,500,000

  • 5 Beds
  • 4.5 Baths
  • 4,972 Sq Ft

  0 Wing Rd, Washington, NY 12545

  The artistry of Coole Park is in the way it unfolds from the center. Two gracious wings on either side of the original 1888 house create an architectural triptych that conveys elegance and comfort in equal measure. Warm wide board floors, soaring French doors, six working fireplaces, and numerous demi-lune windows create a sense of space and style as well as history. To the right of the entryway,

  Candy Anderson Compass Greater NY, LLC

  0 Wing Rd, Washington, NY 12545
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  /50

  $2,150,000

  • 7 Beds
  • 7.5 Baths
  • 7,720 Sq Ft

  143 Bedell Rd, Poughkeepsie, NY 12603

  Hilltop Retreat, built in the Millenium Mansion style, provides an incomparable experience of country living. This gracious residence is approached via a meandering driveway past stone walls and a pond and is secluded within 66 acres of curated lawns w/ majestic trees, a shimmering pond, old growth forest, and year-round Catskill mountain views. Casually formal, w/over 7,000sqft of living space

  Eliane Abramoff Four Seasons Sothebys Intl

  143 Bedell Rd, Poughkeepsie, NY 12603
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  /34

  $389,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  95 Worrall Ave, Poughkeepsie, NY 12603

  Lovingly maintained by the same family for more than sixty years, find this 5 bedroom, 2 bathroom colonial situated on the City of Poughkeepsie's desirable south side. Floor plan offers tremendous potential and flexibility with large kitchen, formal dining room, living room w/fireplace, two first floor bedrooms and full bathroom plus mudroom. Second floor layout includes three bedrooms and full

  Dan Axtmann BHHS Hudson Valley Properties

  95 Worrall Ave, Poughkeepsie, NY 12603
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  /51

  $19,995,000

  • 7 Beds
  • 9 Baths
  • 11,970 Sq Ft

  309 Woodstock Rd, Millbrook, NY 12545

  Presenting Canoe Hill, a remarkable 63-acre estate and vineyard in the heart of Millbrook, New York. This extraordinary property stands as a testament to architectural evolution, where a storied mid-1700s colonial core has been thoughtfully expanded to create a remarkable 12,650 SF main residence that seamlessly marries Colonial, Georgian and Greek Revival influences. Two significant expansions,

  Jason Karadus Corcoran Country Living

  309 Woodstock Rd, Millbrook, NY 12545
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  /26

  $699,000

  • 5 Beds
  • 3 Baths
  • 2,808 Sq Ft

  47 Main St, Wappingers Falls, NY 12590

  This beautifully renovated two-unit apartment building is situated in the charming hamlet of New Hamburg, offering a prime investment opportunity in a highly desirable location. Just a short walk from the Metro-North train station, tenants enjoy an effortless commute while benefiting from the area’s peaceful, small-town atmosphere.Apartment 1: Is a charming 2-bedroom, 2-bathroom apartment

  Daniel Staley Staley Real Estate, LLC

  47 Main St, Wappingers Falls, NY 12590
• 

  

  /22

  $455,000

  • 10 Beds
  • 3 Baths
  • 3,052 Sq Ft

  77 Carroll St, Poughkeepsie, NY 12601

  Three family home located on a quiet street in the desirable South Side of Poughkeepsie. This home is in good condition and has been nicely maintained throughout the years. Improvements include replacement windows, exterior & interior painting, and new floors in some rooms. Gas boilers, municipal water and sewer. The heating systems and electric meters are fully separated for each unit so the

  Mark Snyder eXp Realty

  77 Carroll St, Poughkeepsie, NY 12601
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  /33

  $479,999

  • 6 Beds
  • 2 Baths
  • 5,016 Sq Ft

  89 S Cherry St, Poughkeepsie, NY 12601

  PRIME 2-FAMILY INVESTMENT offers a Epic Opportunity for passive income or leverage into commercial. This 2-Family investment opportunity is sited on a huge double lot just shy of a quarter of an acre on the south side of Poughkeepsie. Perfect for the Owner Investor who lives in one unit while the rental income pays your mortgage. Unique property features that add value include private off street

  Latanya Frazier Oxford Property Group USA

  89 S Cherry St, Poughkeepsie, NY 12601
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  /30

  $610,000

  • 6 Beds
  • 3 Baths

  27 Hooker Ave, Poughkeepsie, NY 12601

  Discover the perfect investment opportunity in the heart of Poughkeepsie's Vibrant South Side! This recently renovated 3-unit apartment building offers a turnkey experience for both tenants and investors. Each unit is designed for comfort and functionality, featuring contemporary finishes and ample light ideally located within walking distance to schools, parks, and convenient shopping

  Jennifer Martini K. Fortuna Realty, Inc.

  27 Hooker Ave, Poughkeepsie, NY 12601
• 

  

  /18

  $549,000

  • 6 Beds
  • 3 Baths
  • 3,249 Sq Ft

  86 S Hamilton St, Poughkeepsie, NY 12601

  Great find! Three family fully rented. Located on the Southside of Poughkeepsie. The set up is 2 Bedrooms and 1 bath on each floor. All apartments have gas stoves and refrigerators; Flooring is mixed with some hardwood and laminate. There is only 1 heating system and 1 electric meter. All apartments have baseboard /radiator hot water heat. Separation can be done with 2 apartments by adding the

  Michelle Ayala BHHS Hudson Valley Properties

  86 S Hamilton St, Poughkeepsie, NY 12601
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  /50

  $2,200,000

  • 7 Beds
  • 7 Baths
  • 11,222 Sq Ft

  3893 Route 82, Millbrook, NY 12545

  Set on 11.1 private acres in the heart of Millbrook, this stately brick Colonial estate offers over 11,222 square feet of refined living space, combining timeless elegance with exceptional versatility. A true legacy property, it delivers the scale, design, and amenities expected by the most discerning buyers.A dramatic two-story granite foyer welcomes you with a sweeping double staircase and a

  Howard Payson RE/MAX Town & Country

  3893 Route 82, Millbrook, NY 12545
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  /33

  $769,000

  • 5 Beds
  • 4 Baths
  • 3,252 Sq Ft

  61 Sherwood Heights, Wappingers Falls, NY 12590

  Home is fully available! Discover timeless elegance in this beautifully landscaped 5 bedroom custom colonial, perfectly sited in a peaceful, sought after neighborhood. The perfect home for a large or extended family. This home offers the ideal blend of classic architecture and contemporary updates, providing both space and sophistication for modern living. Stone pillars grace the entrance to

  Jan Kaplan BHHS Hudson Valley Properties

  61 Sherwood Heights, Wappingers Falls, NY 12590
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  /19

  $359,900

  • 7 Beds
  • 3 Baths
  • 2,200 Sq Ft

  94 South Ave, Poughkeepsie, NY 12601

  Rare opportunity to acquire this legal rooming house on the City of Poughkeepsie's desirable south side. Featuring seven rooms, shared kitchen & three full bathrooms. Natural gas for heating, hot water & cooking. Unfinished basement & walkup attic for abundant storage. Large covered front porch & huge backyard for outdoor enjoyment. Centrally located just minutes from hospitals, colleges, bus

  Dan Axtmann BHHS Hudson Valley Properties

  94 South Ave, Poughkeepsie, NY 12601
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  /24

  $399,000

  • 5 Beds
  • 1,062 Sq Ft

  215 Little Pond Rd, Pawling, NY 12564

  Private Lake House on a Private Lake!Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and

  Jillian Pajer Douglas Elliman Real Estate

  215 Little Pond Rd, Pawling, NY 12564
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  /44

  $649,000

  • 5 Beds
  • 3 Baths
  • 1,900 Sq Ft

  11 Queen Anne Ln, Wappingers Falls, NY 12590

  Charming Home with Income Potential in the Heart of East FishkillWelcome to this beautifully maintained 4-bedroom, 2-bathroom home nestled on a level, landscaped one-acre parcel. From the moment you step onto the inviting covered front porch, you’ll picture yourself enjoying coffee at sunrise or relaxing with evening sunsets.Inside, you’ll find warm and welcoming living spaces,

  Bernadette Smyth Coldwell Banker Realty

  11 Queen Anne Ln, Wappingers Falls, NY 12590
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  /36

  $699,000

  • 7 Beds
  • 5 Baths
  • 4,353 Sq Ft

  2 Hunns Lake Rd, Stanfordville, NY 12581

  Calling all investors! A great opportunity to acquire an income-producing asset with value-add potential, featuring two buildings on one parcel in the heart of Standfordville. The site is over an acre with great frontage on NYS Rt 82. This property has four units consisting of one vacant space that was used as a commercial office in years past (with potential for residential conversion), and

  Ryan Arket Compass Greater NY, LLC

  2 Hunns Lake Rd, Stanfordville, NY 12581
• 

  

  /20

  $340,000

  • 5 Beds
  • 2 Baths
  • 2,272 Sq Ft

  320 Mansion St, Poughkeepsie, NY 12601

  Excellent investment opportunity in the City of Poughkeepsie! This legal 2-family offers a spacious 3-bedroom, 1 bath unit upstairs and a 2-bedroom, 1-bath unit on the main level. Both units are separately metered and currently leased, providing immediate income with value-add potential through future updates. Tenants pay their own utilities. Recent updates include a new roof just one year ago!

  Michael Cahill HomeSmart Homes & Estates

  320 Mansion St, Poughkeepsie, NY 12601
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  /38

  $3,000,000

  • 9 Beds
  • 5 Baths
  • 7,500 Sq Ft

  3412 Route 52, Stormville, NY 12582

  Former Mount Storm Ski Area – 88 Acres with Stunning Views & Rich History This unique property, once the site of the iconic Mount Storm Ski Area, is now available for sale. A total of 5 parcels, spanning 88 acres, it offers breathtaking 180-degree panoramic views from the mountaintop, where you can see for miles and experience the natural beauty of the region. The property features a main

  Christopher Galli Century 21 Elite Realty

  3412 Route 52, Stormville, NY 12582
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  /28

  $1,999,999

  • 5 Beds
  • 2 Baths
  • 2,618 Sq Ft

  148 Creek Rd, Staatsburg, NY 12580

  Welcome to 148 N creek, a stunning property boasting 136 acres of preserved farmland. The sale features a charming 5 bedroom 2 bath farmhouse from the 1800s, several restored and updated barns, . This property is also home to an active farm brewery and agrotourism center. The acreage is protected by the Winnakee Land Conservancy, with future upgrades in mind. Upgraded electric, septic, and well

  EUGENE VALOY BHHS Hudson Valley Properties

  148 Creek Rd, Staatsburg, NY 12580
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  /39

  $649,000

  • 6 Beds
  • 2 Baths
  • 3,100 Sq Ft

  11-13 Eldridge Ln, Red Hook, NY 12571

  Red Hook Village Compound! Once in a generation a property offering like this is available. Tucked in at the end of Eldridge lane in the village walkable to parks, shoppes, and restaurants. This is composed of a lovely four bedroom home, with 2 sunrooms, large living room with stone fireplace, massive bathroom with skylights, new roof with warranty, new skylights and carpets. The home is light

  Chelsea Pollard-Seiler Mondello Upstate Properties

  11-13 Eldridge Ln, Red Hook, NY 12571
• 

  

  /22

  $635,000

  • 5 Beds
  • 3 Baths
  • 2,524 Sq Ft

  27 Mill St, Wappingers Falls, NY 12590

  Prime Multi-Family Investment in the Heart of the Village of Wappingers Falls!Don’t miss this exceptional opportunity to own a well-maintained and income-generating three-family home in the vibrant Village of Wappingers Falls. Ideal for investors or savvy owner-occupants, this versatile property features three fully independent units—each with private entrances, separate utilities, and

  Virginia Corbett eXp Realty

  27 Mill St, Wappingers Falls, NY 12590
• 

  

  /45

  $3,750,000

  • 5 Beds
  • 7 Baths
  • 6,050 Sq Ft

  33 Pells Rd, Rhinebeck, NY 12572

  This magnificent Modern Farmhouse, sheltered in an elegant landscape of rolling hills, mature trees, colorful gardens and a 7-acre lake, is the quintessential Hudson Valley retreat on 43+ picturesque acres. Located an easy five minutes from historic, cultural-rich Rhinebeck Village, it’s the country destination for the sophisticated buyer who values privacy, property and proximity. The striking

  Peggy Santamorena Houlihan Lawrence Inc.

  33 Pells Rd, Rhinebeck, NY 12572
• 

  

  /49

  $1,175,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 3.5 Baths
  • 4,356 Sq Ft

  1035 Noxon Rd, Lagrangeville, NY 12540

  Discover timeless charm blended with modern comfort in this Classic Circa 1810 Historical Beauty, set on 7-acres in the heart of the Hudson Valley! (Also, an additional 7 acres are available!) There's space galore featuring 4,356 sq. ft. of finished living space with 5 bedrooms, 3.5 baths, and an additional 1,435 sq. ft. full, unfinished basement. All rooms are generously sized, with 3

  Susan Stevens BHHS Hudson Valley Properties

  1035 Noxon Rd, Lagrangeville, NY 12540

Showing Results 41 - 80, Page 2 of 3