Homes for Sale in Dutchess County NY with 5-Bedrooms

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  /46

  $39,000,000

  • 9 Beds
  • 15 Baths
  • 55,000 Sq Ft

  104 N Garden Dr, Pawling, NY 12564

  Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

  Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

  104 N Garden Dr, Pawling, NY 12564
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  /32

  $2,950,000

  • 9 Beds
  • 5 Baths

  3412 Route 52, Stormville, NY 12582

  Former Mount Storm Ski area - 88 acres with stunning views & rich history. Once the site of the iconic Mount Storm Ski area. Total of 5 parcels spanning 88 acres offering 180 degree panoramic views from the mountaintop where you can see for miles. The property features a main building the includes three, 3bedroom apartments, studio office and basement. The basement holds a nostalgic piece of

  Christopher Galli Ginnel Real Estate

  3412 Route 52, Stormville, NY 12582
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  /43

  $710,000

  • 5 Beds
  • 2.5 Baths
  • 2,406 Sq Ft

  45 Old Farms Rd, Poughkeepsie, NY 12603

  A beautifully updated and maintained large property with lots of possibilities. Five large bedrooms with a beautiful open floor plan. 3 full bathrooms. Beautiful living room and a family room. The house has lots of closets and storage space. The marble is amazing! A grand finished basement with room to possibly add another bath and bedroom. An oversized heated two car garage. A large master

  James Young YOUNG & ASSOCIATES REAL ESTATE LLC

  45 Old Farms Rd, Poughkeepsie, NY 12603
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  /40

  $600,000

  • 6 Beds
  • 3 Baths
  • 2,520 Sq Ft

  12 Parker Ave, Poughkeepsie, NY 12601

  Excellent 3 family investment opportunity with a potential of 4-5 total units and oversized garage . This well maintained fully occupied multi-family house offers 3 - 2 bedroom apartments with current CO in place for 3 units and full basement for potential additional unit . Many updates include high efficiency natural gas boilers, water heaters , electric service, fireproof entry doors and

  John Costanzo BHHS Hudson Valley Properties

  12 Parker Ave, Poughkeepsie, NY 12601
• 

  

  

  /20

  $425,000

  • 6 Beds
  • 2 Baths
  • 2,034 Sq Ft

  26 Taylor Ave, Poughkeepsie, NY 12601

  Now is the time to own a very well maintained 2-family home. The first floor apartment offers a living room, dining room, 3 bedrooms, full bath & updated kitchen w/ a loft area. The second floor offers a living room, eat in kitchen, 3 bedrooms. Updates include roof ( yrs old), electric wall heaters, kitchens & baths, insulated basement & vinyl siding (level 1). The driveway allows for 4

  Nancy Martinelli Century 21 Alliance Rlty Group

  26 Taylor Ave, Poughkeepsie, NY 12601
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  /49

  $559,900

  • 5 Beds
  • 5.5 Baths
  • 4,800 Sq Ft

  113 Hooker Ave, Poughkeepsie, NY 12601

  Discover the timeless charm of this 1915 Grand Colonial Estate on Poughkeepsie’s desirable Southside—an exceptional opportunity for investors or residents. Offering over 4,800 sq ft, it includes an attached professional suite (5 rooms/2 baths), separate from the main residence, ideal for doctors, lawyers, or remote professionals, with potential to generate income. Set on nearly half an acre, the

  Matthew Gibbs Keller Williams Hudson Valley

  113 Hooker Ave, Poughkeepsie, NY 12601
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  /27

  $10,995,000

  • 9 Beds
  • 9.5 Baths
  • 13,737 Sq Ft

  121-125 Butts Hollow Rd, Millbrook, NY 12545

  Perched above the rolling hills of Millbrook Hunt Country with sweeping Catskill Mountain views, this idyllic retreat and exceptional equestrian estate spans 185 ultra-private acres. Once the beloved property of Margaret Carnegie, only child of Andrew Carnegie, the estate preserves a rich legacy of elegance and prestige. Originally built in 1865, it has been thoughtfully expanded to blend

  John Oliveira Douglas Elliman of Connecticut

  121-125 Butts Hollow Rd, Millbrook, NY 12545
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  /21

  $454,900

  • 6 Beds
  • 2 Baths
  • 2,708 Sq Ft

  324-326 Church St, Poughkeepsie, NY 12601

  INCOME PRODUCING OPPORTUNITY! MORE PHOTOS TO COME...PLEASE DON’T WAIT TO TOUR. THIS MIGHT BE GONE SOON! AMAZING DUPLEX OPPORTUNITY OFFERING ATTACHED TOWNHOUSE STYLE RESIDENCE THAT IS PERFECT FOR OWNER-OCCUPANTS OR INVESTORS ALIKE. EACH UNIT IS PRESENTLY UNDERGOING ITS INDIVIDUAL REFRESH AND UPDATES. ENJOY THE COMFORT OF HOME AND PRIVACY AS EACH UNIT IS OFFERING ITS OWN PRIVATE ENTRANCE, LIVING

  Roadman Etienne BHHS Hudson Valley Properties

  324-326 Church St, Poughkeepsie, NY 12601
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  /27

  $2,399,000

  • 5 Beds
  • 3.5 Baths
  • 5,016 Sq Ft

  12 Monell Place, Beacon, NY 12508

  Welcome to “Eustatia” — one of Beacon’s most historically significant and architecturally remarkable homes. Built in 1867 for Judge John Monell and Caroline Downing, widow of celebrated architect Andrew Jackson Downing, this High Victorian Gothic estate was designed by Frederick Clarke Withers and published in the 1873 edition of Cottage Residences as Design XXV. Set on nearly five acres

  Liudmila Lobeeva eXp Realty

  12 Monell Place, Beacon, NY 12508
• 

  

  /29

  $1,310,000

  • 7 Beds
  • 4.5 Baths
  • 4,365 Sq Ft

  105 & 107 E Market St, Rhinebeck, NY 12572

  A rare opportunity to own .66 acres in the heart of historic Rhinebeck Village. Currently divided into two adjoining parcels, the property is ready for restoration and new life. Once a late 19th century homestead, this special property retains its rich character with the original Victorian residence, barn, and blacksmith's open barn still standing. Imagine creating your own village compound — the

  Paula Redmond Corcoran Country Living - Mill

  105 & 107 E Market St, Rhinebeck, NY 12572
• 

  

  /49

  $730,000

  • 5 Beds
  • 4 Baths
  • 3,444 Sq Ft

  12 S Parsonage St, Rhinebeck, NY 12572

  CALLING ALL INVESTORS! FABULOUS RHINEBECK INVESTMENT OPPORTUNITY! Rare three family rental property in the Village of Rhinebeck! Fully occupied by long term tenants. Washer and Dryer in every unit! Separate electric meters. This three-family home in the charming Village of Rhinebeck presents a fantastic investment opportunity. Located in a quiet, family-friendly neighborhood with a park

  Robyn Tricinelli Century 21 Alliance Realty Grp

  12 S Parsonage St, Rhinebeck, NY 12572
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  /50

  $750,000

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

  5028-5030 Rt-82, Millbrook, NY 12578

  Rare Find!!! Charming Property with detached cottage, Discover an exceptional opportunity in the heart of Salt Point set on 0.68 well maintained acre lot surrounded by Hudson Valley charm. This versatile home features multiple living spaces ideal for extended families, Investors, or those seeking additional rental income. Adding to the property's appeal is a detached cottage, featuring 2

  Jennifer Roberts Curasi Realty, Inc.

  5028-5030 Rt-82, Millbrook, NY 12578
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  /4

  $600,000

  • 7 Beds
  • 3 Baths
  • 2,844 Sq Ft

  18 S Clinton St, Poughkeepsie, NY 12601

  Tastefully updated and well maintained City of Poughkeepsie three family. Featuring two 3 bedroom units and unique 1 bedroom unit w/cathedral ceiling & loft. Apartments featuring recent interior updates plus updated mechanicals including three newer gas boiler & three newer electric water heaters. Separate utilities, off street parking and spacious backyard. Central location with easy access to

  Dan Axtmann BHHS Hudson Valley Properties

  18 S Clinton St, Poughkeepsie, NY 12601
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  /50

  $4,500,000

  • 6 Beds
  • 5.5 Baths
  • 4,546 Sq Ft

  926 Turkey Hill Rd, Red Hook, NY 12571

  Nearly 30 secluded acres of rolling meadows and woodlands unfold into breathtaking panoramic views of the Catskill Mountains. This is a place to slow down and reconnect. Reminiscent of the Adirondack Great Lodges, this home is a masterful blend of rustic elegance and timeless craftsmanship. Soaring, strap-and-beam ceilings create a dramatic sense of space, while a custom-crafted staircase and a

  Harry Hill Houlihan Lawrence Inc.

  926 Turkey Hill Rd, Red Hook, NY 12571
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  /45

  $825,000

  • 5 Beds
  • 4 Baths
  • 4,100 Sq Ft

  7 Ferris Ln, Poughkeepsie, NY 12601

  Situated on Poughkeepsie's prestigious south side, find this rare opportunity of a single family home w/supplemental office space zoned for home occupation. Incredibly unique mid century modern features attractive open floor plan ideal for entertaining. Huge center island kitchen w/custom maple & cherry cabinetry, granite counters & stainless appliances. Kitchen flows seamlessly to family room

  Dan Axtmann BHHS Hudson Valley Properties

  7 Ferris Ln, Poughkeepsie, NY 12601
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  /42

  $11,200,000

  • 8 Beds
  • 6 Baths
  • 8,280 Sq Ft

  40 Morton Rd, Rhinebeck, NY 12572

  Stonecrest on the Hudson is a stunningly designed home on 16 inspiringly landscaped acres with extensive views of the river and the Catskills. A creation of stone, metal, and glass, the home, though imposing, inhabits its environment with seamless grace and is curated for comfort and meditative living. Many exquisite features make Stonecrest one-of-a-kind, impossible to duplicate. Upon approach,

  Jill Rose Houlihan Lawrence Inc.

  40 Morton Rd, Rhinebeck, NY 12572
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  /30

  $679,000

  • 6 Beds
  • 4 Baths
  • 3,983 Sq Ft

  2748 W Main St, Wappingers Falls, NY 12590

  Great investment opportunity. Mixed-use property with a small clothing store and two three-bedroom apartments. Each unit has three bedrooms and two bathrooms along with a kitchen, living room and dining room. The driveway is large enough for three cars. Close to transportation, stores, restaurants, and more.

  Emilexis Medina Houlihan Lawrence Inc.

  2748 W Main St, Wappingers Falls, NY 12590
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  /50

  $1,399,999

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  57 Cedar Berry Ln, Dover Plains, NY 12522

  Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living. The moment you

  Lindsay Stevens eXp Realty

  57 Cedar Berry Ln, Dover Plains, NY 12522
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  /12

  $950,000

  • 5 Beds
  • 3 Baths
  • 3,684 Sq Ft

  38 Dartmouth Dr, Poughkeepsie, NY 12603

  The Grand Harley boasts an impressive first floor featuring a stunning open floor plan that offers enchanting views of the spacious great room and the inviting casual dining area, seamlessly extending to a desirable 16x20 TREX Deck—perfect for outdoor living. The well-appointed kitchen is a culinary dream, complete with a large center island and a breakfast bar that invites gatherings and casual

  David Bartolone Christie's Int. Real Estate

  38 Dartmouth Dr, Poughkeepsie, NY 12603
• 

  

  /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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  /50

  $11,750,000

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

  147 Moadock Rd, Millerton, NY 12546

  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

  147 Moadock Rd, Millerton, NY 12546
• 

  

  /26

  $1,750,000

  • 6 Beds
  • 3.5 Baths
  • 4,248 Sq Ft

  11 Brown Rd, Pleasant Valley, NY 12569

  Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: Sarah famously sent cheese from her dairy to George Washington's encampment nearby. Over the years, the home has flown both British

  Daniel Colomban Skyler Realty LLC

  11 Brown Rd, Pleasant Valley, NY 12569
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  /51

  $19,995,000

  • 7 Beds
  • 9 Baths
  • 12,659 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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  /36

  $630,000

  • 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 that

  Daniel Staley Staley Real Estate, LLC

  47 Main St, Wappingers Falls, NY 12590
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  /33

  $12,500,000

  • 5 Beds
  • 6.5 Baths
  • 6,054 Sq Ft

  129 W Meadow Ln, Millbrook, NY 12545

  Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance

  Candy Anderson Compass Greater NY, LLC

  129 W Meadow Ln, Millbrook, NY 12545
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  /37

  $11,250,000

  • 5 Beds
  • 7.5 Baths
  • 14,800 Sq Ft

  46 Ledgerock Ln, Hyde Park, NY 12538

  Ledgerock, the riverfront masterpiece by modern architect Lee Ledbetter is back on the market after undergoing significant infrastructure improvements. This one-of-a-kind estate offers the finest Hudson River and Catskill Mountain views on the market today and is set on 5 private acres. Constructed from the finest materials available, this gorgeous fossilized French limestone & glass compound

  Jason Karadus Corcoran Country Living

  46 Ledgerock Ln, Hyde Park, NY 12538
• 

  

  /36

  $5,500,000

  • 7 Beds
  • 5 Baths
  • 6,019 Sq Ft

  20 Smithfield Way, Amenia, NY 12501

  Set on 53+ Bucolic acres in the heart of the Hudson Valley, Smithfield Farm is an exquisite estate, offering breathtaking, sweeping western views of the Smithfield Valley and the Catskill mountains. The centerpiece of the estate is a meticulously preserved 1790 Colonial main house with a stately brick exterior and a grand center hall. Inside, you will find four woodburning fireplaces, central air

  OLIVER BROWN Houlihan Lawrence Inc.

  20 Smithfield Way, Amenia, NY 12501
• 

  

  /31

  $65,000,000

  • 10 Beds
  • 8 Baths
  • 14,706 Sq Ft

  45 Hitchcock Ln, Millbrook, NY 12545

  The Hitchcock Estate is an exceptional property in size, location and history. The property has 2078 acres intact since the first owner assembled it from 5 area farms in 1889. Located in the heart of Millbrook, NY it has remained undeveloped, shrouded in mystique, the subject of curiosity and imagination providing now and then a glimpse into its elegant and storied past. Beginning as a summer

  HEATHER CRONER William Pitt Sothebys Int Rlty

  45 Hitchcock Ln, Millbrook, NY 12545
• 

  

  /23

  $665,000 Coming Soon

  • 9 Beds
  • 4 Baths
  • 3,952 Sq Ft

  276 Old Route 22, Wassaic, NY 12592

  Whether you’re seeking an investment property, multi-generational living, or the opportunity to live in one unit while generating rental income from the other two, this versatile property is ready to meet your needs. This well-designed triplex features three townhome-style apartments, each offering three bedrooms, a welcoming front porch, a private rear patio, and a one-car attached garage. Every

  Stacey Cronin Houlihan Lawrence Inc.

  276 Old Route 22, Wassaic, NY 12592
• 

  

  /27

  $995,000 Coming Soon

  • 8 Beds
  • 4 Baths
  • 3,478 Sq Ft

  762 Old Route 22, Amenia, NY 12501

  Whether you're seeking a property with positive cash flow, a multigenerational living setup, or the ability to live on-site while generating rental income, this unique offering delivers exceptional versatility. The property features two separate duplex buildings along with an adjacent lot, providing added privacy and future expansion possibilities. Each duplex consists of two well-appointed

  Stacey Cronin Houlihan Lawrence Inc.

  762 Old Route 22, Amenia, NY 12501
• 

  

  /38

  $525,000

  • 5 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  6 Reggie Dr, Wappingers Falls, NY 12590

  Spacious 5-bedroom, 2-bath single-family home offering 2,256 sq ft of living space on .39 acres in a desirable Wappingers Falls location. This home offers great potential and is ready for your personal touch and imagination.The layout includes a possible all-season room, granite countertops, a finished basement with a fireplace, additional living space, and a bedroom, providing flexibility

  Angela Chenery Century 21 Alliance Rlty Group

  6 Reggie Dr, Wappingers Falls, NY 12590
• 

  

  /44

  $299,900

  • 5 Beds
  • 4 Baths
  • 2,790 Sq Ft

  6 Laurel Dr, Holmes, NY 12531

  Fantastic 3-Family Opportunity in Holmes, NY!Discover the potential in this unique multifamily property, featuring a single-family home plus an additional 2-family house on one parcel. Whether you're a homeowner looking for a fixer-upper with rental income potential or an investor seeking a high-demand rental property, this is the one you’ve been waiting for. Both homes need repairs and

  Arafat Ibrahim AI Realty Brokerage LLC

  6 Laurel Dr, Holmes, NY 12531
• 

  /2

  $397,400

  • 5 Beds
  • 2.5 Baths
  • 2,714 Sq Ft

  34 Brookland Farms Rd, Poughkeepsie, NY 12601

  Auctioned Property. Situated in the community of Country Club Estates in the heart of the Town of Poughkeepsie, this large 5-bedroom, 2.5 bath, raised ranch home has 2,714 square feet of living space and sits on 17,424square foot lot. Property is sold "as is" with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or

  Neven Spralja REALHome Services & Solutions

  34 Brookland Farms Rd, Poughkeepsie, NY 12601

Showing Results 41 - 73, Page 2 of 2