Dutchess County NY Homes for Sale with Acreage

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  /33

  $1,150,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 5,809 Sq Ft

  59 Spy Glass Hill, Hopewell Junction, NY 12533

  Welcome to the Legends ! This elegantly appointed, four-bedroom, four-and-a-half-bathroom home stands as a testament to exceptional craftsmanship and bespoke millwork. Intricate details such as decorative wood inlays, framing, wainscoting, and crown molding enhance the sophistication of every room.In the colder months, gather around the impressive two-story stone fireplace, which

  Ashley Hamedi Compass Greater NY, LLC

  59 Spy Glass Hill, Hopewell Junction, NY 12533
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  /45

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 3,504 Sq Ft

  93 Widmer Rd, Wappingers Falls, NY 12590

  Built in 1788 this home is one of the original homes in Wappinger Falls. It has been stated that one of President George Washingtons friend built the original home. This has been a family owned property for some 62 years. Wide board floors are throughout as well as original beams. There is a total of 5 large fireplaces, including one in the basement. That fireplace was used for the

  Joan Sanford BHHS Hudson Valley Properties

  93 Widmer Rd, Wappingers Falls, NY 12590
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  /30

  $875,000

  • 2 Beds
  • 1 Bath
  • 1,784 Sq Ft

  202 Bundy Hill Rd, Holmes, NY 12531

  This spectacular property is available for the first time in 2 decades. Currently owned and loved by a cook, artist and true Renaissance Man this home is sure to appeal to those with a sharp eye for design as well as a love for the outdoors. The house sits about a half mile from the road at the end of a gravel driveway. It is situated so as to afford seasonal 360 degree mountain views. The

  Daniel Balassone VYLLA Home

  202 Bundy Hill Rd, Holmes, NY 12531
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  /48

  $1,399,000

  • 4 Beds
  • 4.5 Baths
  • 4,500 Sq Ft

  145 Whalesback Rd, Red Hook, NY 12571

  Welcome to this stunning colonial-style residence, beautifully situated on 6.26 acres in the scenic HudsonValley. This exceptional home greets you with a grand entrance, as pink cherry blossoms line thedriveway leading to a spacious three-car garage, while elegant Japanese Red Maples frame the street.Zoned for up to four horses, this private estate offers a perfect blend of charm and

  Chelsea Pollard-Seiler Mondello Upstate Properties

  145 Whalesback Rd, Red Hook, NY 12571
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  /50

  $839,000

  • 4 Beds
  • 2 Baths
  • 1,784 Sq Ft

  280 Pitcher Ln, Red Hook, NY 12571

  A/O 8/4/2025 Step into timeless elegance with this beautifully maintained and thoughtfully updated 2-story, Craftsman style home, perfectly situated on 1.06 acres of mature, landscaped grounds in the heart of the Hudson Valley. This 4-bedroom, 2-bath residence blends original charm with modern conveniences, offering the perfect balance of character and comfort.From the moment you arrive, you

  Vincenza Seche Howard Hanna Rand Realty

  280 Pitcher Ln, Red Hook, NY 12571
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  /48

  $799,000

  • 3 Beds
  • 1.5 Baths
  • 2,650 Sq Ft

  267 Smith Rd, Pleasant Valley, NY 12569

  This one is for the car enthusiast and hobby farmer. Welcome to this well-maintained two-bedroom raised ranch, featuring numerous updates and exceptional amenities. Enjoy peace of mind with a newer roof, insulated windows and doors, and vinyl siding that enhance energy efficiency and curb appeal. The home is equipped with central air, a new air conditioner and handler, security system, and an

  Melissa Pettinella Century 21 Alliance Realty Grp

  267 Smith Rd, Pleasant Valley, NY 12569
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  /33

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 5,654 Sq Ft

  27 Sommerset Rd, Poughkeepsie, NY 12603

  Welcome to 27 Sommerset Road, a beautifully maintained Colonial located in the highly desirable Hills at Lagrange subdivision in the Town of Poughkeepsie, within the Arlington Central School District. This breathtaking 4-bedroom, 2.5-bath home offers over 5,600 sq ft of finished living space and sits on a private 6.67-acre lot, providing the perfect balance of space, privacy, and elegance. Enter

  ABBY JOSIAH KW MidHudson

  27 Sommerset Rd, Poughkeepsie, NY 12603
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  /25

  $774,999

  • 3 Beds
  • 3.5 Baths
  • 4,400 Sq Ft

  2117 Route 82, Lagrangeville, NY 12540

  Welcome to 2117 Route 82 – A Private Retreat in the Heart of Dutchess CountyLocated in the sought-after Arlington School District, this beautifully updated home sits on 3 private acres and backs up to 78 acres of protected farmland, offering peace, privacy, and panoramic views.Recently upgraded with all-new electrical and HVAC systems, and featuring a thoughtfully designed

  Ryan McGrath McGrath Realty Inc

  2117 Route 82, Lagrangeville, NY 12540
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  /17

  $975,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  14 Akindale Rd, Pawling, NY 12564

  TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better

  Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
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  /50

  $850,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  8 Hamlet Way, Hopewell Junction, NY 12533

  Welcome to 8 Hamlet Way – Peaceful Living with Expansive Mountain ViewsSet on a sprawling 1.74-acre lot with breathtaking mountain views, this beautifully maintained 4-bedroom, 3.5-bath colonial offers a rare combination of comfort, space, and serene surroundings. Nestled in one of Hopewell Junction’s most sought-after neighborhoods, this home delivers timeless charm and modern

  Natalia Fonte Distinguished Realty Services

  8 Hamlet Way, Hopewell Junction, NY 12533
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  $950,000 Open Sun 12PM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  58 Salisbury Turnpike, Rhinebeck, NY 12572

  Welcome to your own private paradise. This stunning 20’ x 40’ heated saltwater pool is the centerpiece of nearly five level, park-like acres, surrounded by mature trees, lush landscaping, and a serene spring-fed pond. It’s a resort-style setting that offers peace, privacy, and extended swimming seasons.The contemporary ranch home strikes the perfect balance of style and comfort. Step into

  Judah Fried Elegran LLC

  58 Salisbury Turnpike, Rhinebeck, NY 12572
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  /38

  $875,000

  • 4 Beds
  • 1.5 Baths
  • 2,709 Sq Ft

  7668 Route 82, Pine Plains, NY 12567

  Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an

  Susan Whalen George T Whalen Real Estate

  7668 Route 82, Pine Plains, NY 12567
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  /11

  $900,000

  • 5 Beds
  • 2.5 Baths
  • 2,413 Sq Ft

  2365 Route 83, Pine Plains, NY 12567

  Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing

  Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
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  $865,000

  • 4 Beds
  • 2.5 Baths
  • 3,256 Sq Ft

  176 Old Peckslip Rd, Holmes, NY 12531

  Welcome to this spectacular custom-built Colonial—the move-in ready home you’ve been dreaming of. Privately set back from the road, a long, picturesque driveway leads you to this serene oasis, impeccably maintained by these owners. No detail was overlooked in the careful selection of finishes and the superior quality throughout.Step inside to a gracious double-height foyer that sets the

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  176 Old Peckslip Rd, Holmes, NY 12531
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  /22

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  1104 Cold Spring Rd, Clinton Corners, NY 12514

  Discover a rare opportunity with these two separate expansive lots totaling 78.4 acres, less than 2 hours from NYC. Turn right on to the Taconic and be in NYC in less than 2 hours. Winding gated driveway leads to the A-Frame house, and another driveway leads to a pond site and an open field. Excellent development opportunity with cleared areas, pond sites, wetlands, roads and utilities in place,

  Shana Altstaetter Halter Associates Realty Inc

  1104 Cold Spring Rd, Clinton Corners, NY 12514
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  $825,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  1104 Cold Spring Rd, Red Hook, NY 12571

  Discover a rare opportunity with these two separate expansive lots totaling 78.4 acres, less than 2 hours from NYC. Turn right on to the Taconic and be in NYC in less than 2 hours. Winding gated driveway leads to the A-Frame house, and another driveway leads to a pond site and an open field. Excellent development opportunity with cleared areas, pond sites, wetlands, roads and utilities in place

  Shana Altstaetter Halter Associates Realty

  1104 Cold Spring Rd, Red Hook, NY 12571
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  /5

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  Beilke Road Beilke Rd, Millerton, NY 12546

  4 Bedroom 3 Bath Barn style home To Be Built on 21 acre hilltop property in the town of Northeast bordering the Village of Millerton. Super energy efficient home with low cost heat pump technology that will provide heating and cooling. Geo thermal and Solar are also possibilities for this home. 21 acre parcel residential zoning allows for further sub-division if buyer wishes to do so. A current

  Brad Rebillard DUTCHESS COUNTRY REALTY INC. M

  Beilke Road Beilke Rd, Millerton, NY 12546
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  /38

  $775,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1220 Hunns Lake Rd, Pine Plains, NY 12567

  1220 Hunns Lake Rd is perfect as a full-time family home or a weekend escape, ideally located for both tranquility and convenience. This charming early 1900's farmhouse in the serene Shekomeko Valley offers 4 bedrooms, 2 bathrooms, and 1,344 square feet on 1.52 bucolic acres. The property boasts views of the surrounding countryside and stunning sunsets. Enter the home through the light-drenched

  Marina Tatistcheff Compass Greater NY, LLC

  1220 Hunns Lake Rd, Pine Plains, NY 12567
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  /16

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  59 Corbin Rd, Dover Plains, NY 12522

  Welcome to your brand-new, beautifully renovated ranch in the peaceful and sought-after Town of Dover. This isn't just a house; it's a golden opportunity to own a piece of tranquility. Situated on over an acre of lush land, this home offers the perfect escape from the everyday hustle.Step inside and be captivated by the stunning new kitchen, complete with sleek stainless steel appliances. The

  Daniel Deutsch eRealty Advisors, Inc

  59 Corbin Rd, Dover Plains, NY 12522
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  /20

  $260,000

  • Land
  • 5.00 Acres
  • $52,000 per Acre

  TBD Deer Run, Red Hook, NY 12571

  Beautiful mostly level wooded 5 acre lot to build your dream home. Located on Deer Run road which is a horseshoe shaped road coming out to Spring lake road in 2 areas. The homes on Deer Run are on 3 to 5 acre lots and the house prices range from the 700,000s probably into the millions. The utilities are underground so aesthetically beautiful without wires. To the right of the wooded parcel

  Randy Spiesman Weichert REALTORS

  TBD Deer Run, Red Hook, NY 12571
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  /20

  $260,000

  • Land
  • 5.00 Acres
  • $52,000 per Acre

  Tbd Deer Run Rd(off Spring Lake Rd, Red Hook, NY 12571

  Beautiful mostly level wooded 5 acre lot to build your dream home. Located on Deer Run road which is a horseshoe shaped road coming out to Spring lake road in 2 areas. The homes on Deer Run are on 3 to 5 acre lots and the house prices range from the 700,000s probably into the millions. The utilities are underground so aesthetically beautiful without wires. To the right of the wooded parcel

  Randy Spiesman Weichert, REALTORS The Spiesma

  Tbd Deer Run Rd(off Spring Lake Rd, Red Hook, NY 12571
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  $550,000

  • 3 Beds
  • 2.5 Baths
  • 2,094 Sq Ft

  27 Woodland Dr, Salt Point, NY 12578

  Enjoy this Sunlit Salt Point retreat with pool and custom charm! Welcome to this dream escape in the heart of Salt Point! this beautifully crafted 3-bedroom, 2.5 bath home offers the perfect blend of natural beauty and thoughtful design. Nestled on a peaceful property the home features a heated inground pool, ideal for summer relaxation, and a blue stone driveway that adds timeless charm from

  LAUREN VONDERAU Inspire Realty

  27 Woodland Dr, Salt Point, NY 12578
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  /35

  $13,500,000

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

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522

  Privately sited at the end of a tree-lined drive, this architectural estate enjoys panoramic views over the Hudson Valley and Catskill Mountains. Designed by AD100 architect Gil Schafer, with landscape architecture by Warren Byrd, the home is a Greek Revival masterpiece that blends timeless elegance with modern sophistication. As featured in Elle Decor, the interiors showcase meticulous

  OLIVER BROWN Houlihan Lawrence Inc.

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522
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  $529,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,735 Sq Ft

  45 Sun up Rd, Stormville, NY 12582

  Welcome to 45 Sun Up Rd! This stunning 3 bedroom 2.5 bath cape has so much to offer! Situated on 1.2 acres of serene property in the Arlington Central School District, this home has classic curb appeal and room for everyone! When you walk through the front door you are greeted by a sun filled living room. Also on the main floor is a formal dining room, a family room with wood burning fireplace

  Nicole Magro eXp Realty

  45 Sun up Rd, Stormville, NY 12582
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  $2,200,000

  • 4 Beds
  • 4 Baths
  • 5,064 Sq Ft

  2461 Salt Point Turnpike, Clinton Corners, NY 12514

  Nestled in the quaint hamlet of Clinton Corners, this rare and tasteful 18th-century Georgian stone house offers classic proportions and timeless charm on beautifully established, landscaped grounds. The home seamlessly blends original architectural details—including preserved woodwork, deep sill windows, six fireplaces, refinished floors, and classic Georgian symmetry—with modern updates such as

  OLIVER BROWN Houlihan Lawrence Inc.

  2461 Salt Point Turnpike, Clinton Corners, NY 12514
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  /14

  $350,000

  • Land
  • 6 Acres
  • $56,634 per Acre

  0 Bangall Rd Unit KEY898387, Washington, NY 12545

  An attractive 6.18 acres of gently rolling meadow minutes from the quaint Village of Millbrook. This is a wonderful opportunity for a new owner to build a home in Millbrook Hunt Country.

  Susan Whalen George T Whalen Real Estate

  0 Bangall Rd Unit KEY898387, Washington, NY 12545
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  /22

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  5760 Route 82, Clinton Corners, NY 12514

  Discover the potential of tranquil living at 5760 Route 82 in Clinton Corners. This 3-bedroom, 2-full bath raised ranch is set on over 5 private acres with a long driveway offering peace, privacy, and space to grow. This home has been beautifully renovated with all new kitchen appliances, new floors, new deck, updated bathrooms as well as new mini splits coming soon for heating and cooling. The

  Alan Amerman Coldwell Banker Realty

  5760 Route 82, Clinton Corners, NY 12514
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  /45

  $750,000

  • 4 Beds
  • 2.5 Baths
  • 3,019 Sq Ft

  41 Meddaugh Rd, Pleasant Valley, NY 12569

  Why settle for basic new construction when you can enjoy more space, privacy, and luxurious finishes in this beautifully renovated 4-bedroom, 2.5-bathroom home in the Arlington Central School District? From the moment you enter, you're welcomed by wide-plank white oak hardwood floors and an abundance of natural light pouring in through oversized picture windows that seamlessly connect the indoors

  Gregory Pikor Inspire Realty

  41 Meddaugh Rd, Pleasant Valley, NY 12569
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  /48

  $649,000

  • 4 Beds
  • 4 Baths
  • 1,976 Sq Ft

  16 Pellbridge Dr, Hopewell Junction, NY 12533

  Welcome to this beautifully maintained 4-bedroom Colonial nestled in the heart of Dutchess County, NY. This inviting home offers the perfect blend of classic charm and modern convenience, featuring a spacious layout ideal for both everyday living and entertaining.Enjoy a living room, family room with fireplace, formal dining room, and a well-appointed kitchen with ample cabinetry and counter

  Tom Consaga RE/MAX Ace Realty

  16 Pellbridge Dr, Hopewell Junction, NY 12533
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  /23

  $260,000

  • 2 Beds
  • 1 Bath
  • 916 Sq Ft

  1253 Salt Point Turnpike, Pleasant Valley, NY 12569

  This move-in ready 1949 traditional cottage sits on 1.3 picturesque acres in the heart of the Hudson Valley. Thoughtfully preserved with original wood flooring, trim, and a charming wooden scalloped eave awning, the home offers timeless character and warm curb appeal. Inside, you'll find two bedrooms plus an additional laundry room that could flex as a home office. Exterior features include

  Susan Whalen George T Whalen Real Estate

  1253 Salt Point Turnpike, Pleasant Valley, NY 12569
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  /18

  $375,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,606 Sq Ft

  6 Beaver Rd, Lagrangeville, NY 12540

  Set on a spacious lot in a prime commuter location, 6 Beaver Road offers a blend of comfort, versatility, and room to grow. The main level features a bright, open flow from the living room, framed by a large bay window, into the kitchen and dining area perfect for everyday living. Three bedrooms and 1.5 baths provide functional space, while the finished basement offers additional room for

  Corinna Deigan Compass Greater NY, LLC

  6 Beaver Rd, Lagrangeville, NY 12540
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  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,580 Sq Ft

  143 Ryan Rd, Pine Plains, NY 12567

  This 4 Bedroom, 2.5 Bath Classy Contemporary Colonial emulates "Pride of Ownership" and has so much to offer anyone looking for a turnkey home in a wonderful town. As you enter the airy Center Hall you will immediately fall in love with the gleaming Cherry Hardwood Floors that run abundantly through the whole home. Appreciate the Crown Molding that accentuates each room. Marvel at the lofty

  Catherine Mondello Mondello Upstate Properties

  143 Ryan Rd, Pine Plains, NY 12567
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  /38

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,487 Sq Ft

  900 S Anson Rd, Stanfordville, NY 12581

  Let's meet country and contemporary together in this extremely unique 3 bedroom, 1.5 bath home with legal accessory apartment that includes another 867 finished square feet with a walkout. You will truly not be disappointed when you view this one of kind, tri-level home that also offers separate porches, balconies and decks. The main level offers open floor plan with a gorgeous floor to

  Monica Whitney Exit Realty Connections

  900 S Anson Rd, Stanfordville, NY 12581
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  /22

  $399,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  3889 Route 82, Millbrook, NY 12545

  Welcome to 3889 Route 82 — the perfect starter home or peaceful retirement retreat!This beautifully maintained brick ranch sits on a level one-acre lot just outside the charming Village of Millbrook, a place that feels like stepping back in time. In this close-knit community, neighbors know each other by name, the local school is small and welcoming, taxes are low, and the pace of life

  Ginalea Healy K. Fortuna Realty, Inc.

  3889 Route 82, Millbrook, NY 12545
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  /50

  $498,000

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft

  93 Sylvan Lake Rd, Hopewell Junction, NY 12533

  Peace, Privacy & Park-Like Perfection on 3.2 Acres. Discover comfort, privacy, and serenity in this charming 3-bedroom, 2-bathroom home, perfectly situated on 3.2 acres of beautiful, park-Like property. Tucked far back from the road and surrounded by nature, this inviting property offers the ideal blend of indoor and outdoor living. A welcoming rocking chair front porch leads into a spacious

  Ann Scarano Realty Center Hudson Valley

  93 Sylvan Lake Rd, Hopewell Junction, NY 12533
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  /36

  $650,000

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

  178 Sylvan Lake Rd, Hopewell Junction, NY 12533

  Very rare opportunity to own TWO IMPECCABLY MAINTAINED HOMES on a stunning 11.9-Acre parcel with breathtaking mountain views. The primary residence, nestled on a private hill, affords a tranquil setting with 2 bedrooms, 1 full bathroom, an additional den or office, a full basement, and a one-car garage, complete with washer and dryer. The well-appointed kitchen includes a propane stove for

  Michael Dunstan RE/MAX Town & Country

  178 Sylvan Lake Rd, Hopewell Junction, NY 12533
• 

  

  /15

  $499,999

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  9 Gretna Park Rd, Pleasant Valley, NY 12569

  NEW CONSTRUCTION!! Welcome to this beautifully crafted, new construction ranch-style home nestled on nearly 2 peaceful acres in a private cul-de-sac, offering the perfect blend of tranquility and convenience. Located in the highly regarded Arlington School District, this home is just minutes from shopping, dining, parks, and commuter routes — yet feels like your own secluded

  Rita White Keller Williams Realty Partner

  9 Gretna Park Rd, Pleasant Valley, NY 12569
• 

  

  /8

  $225,000

  • Land
  • 5 Acres
  • $44,643 per Acre

  L510455 Creek Rd, Pleasant Valley, NY 12569

  Situated on Creek Rd, along Wappinger Creek in the desirable town of Pleasant Valley, this 5.04 acres site is ready for your site improvements and building. The driveway has already been rough cut in with the location for the house accessible for further clearing and site preparation. Current BOH approved with proposed site location for house, well, and septic. Bring your contractor and architect

  Gary Martin Compass Greater NY LLC

  L510455 Creek Rd, Pleasant Valley, NY 12569
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  /8

  $225,000

  • Land
  • 5 Acres
  • $44,643 per Acre

  0 Creek Rd Unit KEY896908, Pleasant Valley, NY 12569

  Situated on Creek Rd, along Wappinger Creek in the desirable town of Pleasant Valley, this 5.04 acres site is ready for your site improvements and building. The driveway has already been rough cut in with the location for the house accessible for further clearing and site preparation. Current BOH approved with proposed site location for house, well, and septic. Bring your contractor and architect

  Gary Martin Compass Greater NY, LLC

  0 Creek Rd Unit KEY896908, Pleasant Valley, NY 12569
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  /30

  $599,000

  • 4 Beds
  • 3 Baths
  • 3,422 Sq Ft

  333 Cary Rd, Fishkill, NY 12524

  Massive Fishkill raised ranch perfectly situated on 1.43 acre parcel. Versatile floor plan features main level living room w/cathedral ceiling and fireplace, which flows seamlessly to formal dining room w/cathedral ceiling & spacious sunroom. Huge eat-in kitchen w/center island, two pantries and deck access. Large master bedroom suite includes two walk-in closets & ensuite bathroom with jetted

  Dan Axtmann BHHS Hudson Valley Properties

  333 Cary Rd, Fishkill, NY 12524

Showing Results 41 - 80, Page 2 of 14