5-Bedroom Homes for Sale in Dutchess County NY

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  /31

  $2,875,000

  • 5 Beds
  • 6 Baths
  • 7,600 Sq Ft

  26 Mountain Farm Rd, Millerton, NY 12546

  Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring &

  Graham Klemm GRAHAM T. KLEMM LIC. RE BROKER

  26 Mountain Farm Rd, Millerton, NY 12546
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  /19

  $519,999

  • 5 Beds
  • 4 Baths

  185 Creek Rd, Pleasant Valley, NY 12569

  Welcome to your own private retreat! This two-family home offers a peaceful, park-like setting with a creek right in your backyard—perfect for fishing or simply unwinding by the water. The home is set back from the road, offering privacy and serenity, with stairs leading down to the creek and multiple decks for relaxing or entertaining.Inside, you'll find an open floor plan that features

  Anthony Melella Vision Alliance Realty Inc.

  185 Creek Rd, Pleasant Valley, NY 12569
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  /27

  $849,000

  • 5 Beds
  • 5 Baths
  • 3,456 Sq Ft

  45 Manor Dr W, Poughkeepsie, NY 12603

  New construction Colonial in the city of Lagrange, and the Arlington School District and close proximity to NYC. This contemporary/Colonial home has charm and elegance, with open concept floorplan. Gourmet kitchen with quartz countertops and ample cabinets space and pantry a chef's dream is just one the many upgrades in this home. Enjoy a bright and sunlit living room, plus the vaulted ceilings

  Joseph Brown RE/MAX Real Property Group

  45 Manor Dr W, Poughkeepsie, NY 12603
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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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  /9

  $700,000

  • 9 Beds
  • 3 Baths

  108 Winnikee Ave, Poughkeepsie, NY 12601

  Turnkey three-family investment opportunity in the heart of the City of Poughkeepsie! Each unit features three bedrooms and one bathroom, all currently rented with consistent cash flow and a solid NOI of $61,309—with room for upside, as insurance costs can be optimized. The property has been thoughtfully updated: Unit 1 was fully renovated in April 2025 with a brand-new range and fridge; Unit 2

  Savannah Miceli Century 21 Alliance Rlty Group

  108 Winnikee Ave, Poughkeepsie, NY 12601
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  /45

  $4,950,000

  • 5 Beds
  • 5.5 Baths
  • 6,310 Sq Ft

  310 Carpenter Hill Rd, Pine Plains, NY 12567

  Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double

  PAULA REDMOND Corcoran Country Living

  310 Carpenter Hill Rd, Pine Plains, NY 12567
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  /4

  $460,000

  • 6 Beds
  • 3 Baths
  • 2,475 Sq Ft

  69 Glenwood Ave, Poughkeepsie, NY 12603

  Fully rented 3-unit triplex, Southside Poughkeepsie location! Newer Roof. Unit #3 recently renovated. Unit #1... 3 bedroom, 1 bath. Unit #2... 2 bedroom, 1 bath. Unit #3... 1 bedroom, 1 bath. Live in one and let the other 2 units pay your mortgage! This city of Poughkeepsie triplex is located just minutes from Vassar College, Vassar Hospital, parks, Poughkeepsie train station, restaurants

  Gregory Pikor Inspire Realty

  69 Glenwood Ave, Poughkeepsie, NY 12603
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  /38

  $699,000

  • 5 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  5 Red Tail Ct, Pawling, NY 12564

  Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining.Step inside to find a sun-filled living room with a cozy

  Julius Cooper eXp Realty

  5 Red Tail Ct, Pawling, NY 12564
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  /22

  $349,000

  • 6 Beds
  • 2 Baths
  • 2,452 Sq Ft

  1 Gray St, Poughkeepsie, NY 12603

  PERFECT CHOICE FOR OWNER OR INVESTOR! GROUND FLOOR APARTMENT IS VACANT, MOVE IN AND COLLECT THE RENT ON THE UPSTAIRS LEASED UNIT.BOTH UNITS FEATURE 3 NICE SIZE BEDROOMS, AN EAT IN KITCHEN, LIVING ROOM AND FULL BATH. SECOND STAIRCASE IN THE BACK GIVES DIRECT ACCESS TO A FENCED IN BACKYARD. AMPLE PARKING IN THE DRIVEWAY PLUS ONE CAR GARAGE. HOUSE HAS FULL WALK-OUT BASEMENT AND A WALK-UP

  Hana Kogan Mark One Real Estate

  1 Gray St, Poughkeepsie, NY 12603
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  /43

  $1,175,000

  • 5 Beds
  • 3 Baths
  • 2,482 Sq Ft

  303 Hicks Hill Rd, Stanfordville, NY 12581

  Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

  HOMER STALEY JR. Staley Real Estate, LLC

  303 Hicks Hill Rd, Stanfordville, NY 12581
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  /4

  $525,000

  • 9 Beds
  • 3 Baths
  • 3,576 Sq Ft

  58 Lincoln Ave, Poughkeepsie, NY 12601

  High-Yield 3-Unit Investment Property Near Vassar Brothers Medical Center. *1031 Exchange Buyers - ask about our 13 Door Package deal with this property. Investors, take advantage of this prime multi-family opportunity at 58 Lincoln Avenue, Poughkeepsie, NY 12601. This fully occupied 3-unit property features three spacious 3-bedroom apartments, currently generating $57,000 in gross annual

  Curtis Darragh Legacy Land & Homes LLC

  58 Lincoln Ave, Poughkeepsie, NY 12601
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  /49

  $730,000

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

  12 S Parsonage St, Rhinebeck, NY 12572

  FABULOUS 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 directly across the street, it’s an

  Robyn Tricinelli Century 21 Alliance Realty Grp

  12 S Parsonage St, Rhinebeck, NY 12572
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  /45

  $825,000

  • 6 Beds
  • 2 Baths
  • 2,154 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 Seiler MONDELLO UPSTATE PROPERTIES LLC

  11-13 Eldridge Ln, Red Hook, NY 12571
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  /29

  $575,000

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  7 Hujay Terrace, Wappingers Falls, NY 12590

  Welcome to 7 Hujay Terrace in Wappinger Falls – a home that perfectly blends modern upgrades with functional amenities, offering a luxurious lifestyle and an ideal in-law suite.Step inside to find an updated kitchen featuring granite countertops, new cabinets, a new undermount kitchen sink, and new double wall ovens. The home's exterior is equally impressive, showcasing a new roof, new

  Ramanjit Dhanoa eXp Realty

  7 Hujay Terrace, Wappingers Falls, NY 12590
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  /19

  $425,000

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

  94 Academy St, Poughkeepsie, NY 12601

  Centrally located City of Poughkeepsie multi-family featuring two spacious 3 bedroom units. Second floor unit includes renovated kitchen & bathroom, new flooring throughout & new furnace. Separate utilities w/gas furnaces & electric water heaters. Front porches and fenced backyard for outdoor enjoyment. Located just minutes from schools, shopping, dining, commuter routes, Poughkeepsie waterfront

  Dan Axtmann BHHS Hudson Valley Properties

  94 Academy St, Poughkeepsie, NY 12601
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  /47

  $2,700,000

  • 7 Beds
  • 6.5 Baths
  • 5,486 Sq Ft

  20 Orchard Hill Dr, Millbrook, NY 12545

  Modern Country Retreat with Iconic Hudson Valley Views Proven Investment or Private Escape Seconds from MillbrookExperience refined country life in this beautifully updated Hudson Valley home, nestled on 12+ private acres with sweeping views of the Catskill Mountains. Surrounded by lush lawns, open meadows and a fenced paddock, the property offers a sense of serenity, space, and

  Kathryn Johnson William Pitt Sothebys Int Rlty

  20 Orchard Hill Dr, Millbrook, NY 12545
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  /9

  $1,100,000

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

  51 Estate Dr, Pawling, NY 12564

  Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

  Tony Zaccardo Coldwell Banker Realty

  51 Estate Dr, Pawling, NY 12564
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  /35

  $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
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  /36

  $6,750,000

  • 6 Beds
  • 9 Baths
  • 8,177 Sq Ft

  465 Shunpike, Millbrook, NY 12545

  Be transcended into refined elegance. This stately home is an entertainer's dream. Set at the end of a picturesque, tree-lined drive on 40 serene acres, it offers a harmonious blend of historic elegance and contemporary living. The main house, which dates back to the late 1800s, has been thoughtfully updated and retains much of its period detail and charm with an updated twist. The four barns

  Kyle Irwin Corcoran Country Living

  465 Shunpike, Millbrook, NY 12545
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  /45

  $4,250,000

  • 6 Beds
  • 4.5 Baths
  • 4,208 Sq Ft

  570 Pumpkin Ln, Clinton Corners, NY 12514

  Sited on one of the most beautiful parcels in the Hudson Valley, this idyllic estate on a quiet country lane offers endless possibilities with the features of a mini-resort. Set on a knoll overlooking a gorgeous, spring-fed pond complete with gazebo, swing and swim-up dock, this historic country retreat includes the circa 1860 main house, a separate guest apartment with views of an additional

  Kyle Irwin Corcoran Country Living

  570 Pumpkin Ln, Clinton Corners, NY 12514
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  /45

  $3,900,000

  • 6 Beds
  • 7.5 Baths
  • 7,460 Sq Ft

  259 Woodstock Rd, Millbrook, NY 12545

  Peace and tranquility await at this sprawling country retreat. A stream meanders through the 15.37 acre property forming two waterfalls and flows into a deep water pond creating a beautiful lush landscape viewed from many vantage points. This amazing and expansive 7,460 square foot home is comprised of three 18th century structures that were dismantled and brought together. At the center of the

  PAULA REDMOND Corcoran Country Living

  259 Woodstock Rd, Millbrook, NY 12545
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  /39

  $1,050,000

  • 5 Beds
  • 3.5 Baths
  • 3,664 Sq Ft

  3715 Route 44 Unit 37, Millbrook, NY 12545

  This historic 1800s home of James Mabbett sits on 4 plus acres with a pristine pond and extensive outbuildings. The main house with its fine architectural details has been newly renovated and updated with new baths and kitchen, appliances, fixtures, mechanicals, gleaming hardwood floors, moldings and coffered ceilings. Enter the high ceiling elegant foyer which leads to a living room with a

  ANN WILKINSON Compass Greater NY, LLC

  3715 Route 44 Unit 37, Millbrook, NY 12545
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  /36

  $6,785,000

  • 5 Beds
  • 5.5 Baths
  • 5,162 Sq Ft

  47 Crescent Rd, Millbrook, NY 12545

  Exquisitely restored 1822 farmhouse on 50+ acres in Millbrook, NY, blending historic charm and modern luxury. This stunning home features sun-filled rooms, original hardwood floors, and six fireplaces. The gourmet kitchen is equipped with marble countertops, high-end appliances, a butler's pantry, and a fireplace. A beautiful sunroom with floor-to-ceiling windows and marble floors connects

  William Melnick Elyse Harney Real Estate

  47 Crescent Rd, Millbrook, NY 12545
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  /36

  $589,000

  • 6 Beds
  • 2.5 Baths
  • 3,402 Sq Ft

  10 Greenwood Dr, Beacon, NY 12508

  This expansive (3,400 sq. ft.) split-level ranch is on 1.6 acres and features 6 bedrooms, 2.5 baths, and a 2-bedroom accessory apartment with a private entrance bordering numerous hiking trails. THREE additional adjoining lots are sold separately and require BOHA approval although municipal water is provided by the town (.58 acres MLS H6321787, .57 acres MLS H6321777, & 1.02 acres MLS H6325550).

  TIMOTHY TURNER Keller Williams Hudson Valley

  10 Greenwood Dr, Beacon, NY 12508
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  /36

  $6,995,000

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

  20 Smithfield Way, Amenia, NY 12501

  Set on 118 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
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  /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
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  /32

  $10,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,170 Sq Ft

  292 Wood Duck Rd, Amenia, NY 12501

  In a coveted position on the lake, 292 Wood Duck Road presents an extraordinary opportunity to own a turnkey property just two hours from Manhattan. The pristine estate spans approximately 5,000+ square feet of interior space, complimented by more than 1,800+ square feet of outdoor terrace and covered porch.The home includes five beautifully appointed ensuite bedrooms and two half baths.

  Jonathan Stein Douglas Elliman Real Estate

  292 Wood Duck Rd, Amenia, NY 12501
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  /32

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 3,820 Sq Ft

  67 Myers Corners Rd, Wappingers Falls, NY 12590

  Welcome To 67 Myers Corners Rd...This Unique Meticulously Cared For One Of A Kind Colonial Home Sprawled Out In A Country Setting Awaits You To Call Home. Nestled On More Than 2 Acres Is Guaranteed To Provide Peace & Tranquility. Step Inside To A Boasting 3800sqft Of Living Space That Has Plenty Of Charm And Character. Tastefully Updated Throughout With Hardwood Floors, Granite/Marble

  Owais Khan OXM Realty Group LLC

  67 Myers Corners Rd, Wappingers Falls, NY 12590
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  /36

  $610,000

  • 5 Beds
  • 2 Baths
  • 2,304 Sq Ft

  22 Hunns Lake Rd, Stanfordville, NY 12581

  Charming country farm house, circa 1772, in the heart of Stanfordville Ny. Spacious 5 bedroom, 2 bath with bonus room for your office/studio. Picturesque views. Close to Wineries, dining, antiques and Polo. Close to Taconic State Parkway and trains. Additional Information: Amenities:Pedestal Sink,Stall Shower,HeatingFuel:Oil Above Ground,

  Christina Coughlin Hudson Valley Home Connection

  22 Hunns Lake Rd, Stanfordville, NY 12581
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  /36

  $5,500,000

  • 17 Beds
  • 13 Baths
  • 15,000 Sq Ft

  618 Quaker Hill Rd, Pawling, NY 12564

  25.5-acre equestrian estate with a 43-room Elizabethan Style manor house, two caretaker homes, a carriage house with groom’s quarters, a yoga studio, a 12,000 sq. ft. stable, greenhouse and more. Situated on the crest of Quaker Hill, Elmwood Farm has stunning views and endless possibilities. The 3-story, 17-bedroom (7 of which are in the nursery wing and the caretakers' wing) 9-bath (plus 4

  Harriet Norris Douglas Elliman Real Estate

  618 Quaker Hill Rd, Pawling, NY 12564
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  /12

  $1,950,000

  • Land
  • 164 Acres
  • $11,890 per Acre

  5 Homestead Farm Ln, Millerton, NY 12546

  Once in a lifetime opportunity to acquire one of the last remaining unrestricted working farms in Northern Dutchess County, NY. Choice building sites, panoramic views and seclusion yet convenient to New York City, Metro North commuter train and nearby area amenities including Millerton, NY, Litchfield County, CT, Troutbeck Inn, Millbrook, NY and Silo Ridge. This property is totally unrestricted

  Andrew Gates Houlihan Lawrence, Inc.

  5 Homestead Farm Ln, Millerton, NY 12546
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  /30

  $2,495,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  474 Route 199, Red Hook, NY 12571

  Welcome to NOOK architecturally designed.Perched gracefully atop a natural saddle in the land, this architecturally crafted residence embodies refined contemporary living in perfect harmony with its surrounding landscape. Designed with both beauty and purpose, the home integrates modern aesthetics with eco-conscious principles, creating a sanctuary that is as enduring as it is

  Pamela King-Belfor Four Seasons Sotheby's Int.

  474 Route 199, Red Hook, NY 12571
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  /61

  $360,800

  • 5 Beds
  • 2 Baths
  • 2,088 Sq Ft

  2470 Route 55, Hopewell Junction, NY 12533

  This is an online auction listing ending 7/16. List price reflects full market value on public record, No Minimum Starting Bid! Mid-Century style 2,088+/- sq. ft. single family home on 1.30 +/- acres, in the Arlington Central School District. Ready for your renovation! Built in 1964 with five bedrooms, two full baths. Main floor has kitchen, three bedrooms, full bath and a family room. The

  Philip Gableman ABSOLUTE AUCTION AND REALTY INC

  2470 Route 55, Hopewell Junction, NY 12533

Showing Results 81 - 113, Page 3 of 3