Annandale On Hudson, NY Homes for Sale

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  /37

  $1,799,000

  • 5 Beds
  • 4.5 Baths
  • 5,490 Sq Ft

  161 Whalesback Rd, Red Hook, NY 12571

  Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury.Originally built in 1900, the barn has been thoughtfully transformed to

  

  Ann Stettner

  Neil Charles Real Estate, LLC

  (845) 448-2559

  161 Whalesback Rd, Red Hook, NY 12571
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  /39

  $659,000

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  412 Sepasco Center St, Rhinebeck, NY 12572

  Fall in love with this charming 3 bedroom, 2.5 bathroom custom built home situated in the quaint Sepasco Lake community. Enjoy water access from the park/picnic area just down the street. This home features a large living room with a woodstove, dining room and bright and airy eat-in kitchen. There is one bedroom, a full bathroom and half bathroom all located on the first level. Beautifully

  

  Amy Hawks

  Berardi Realty

  (845) 552-0731

  412 Sepasco Center St, Rhinebeck, NY 12572
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  /16

  $399,925

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  10 Aspinwall Rd, Red Hook, NY 12571

  Upgraded one level living ranch in wonderful location, close to Route 9 and all amenities. This home has been freshly painted, new carpeting installed, new doors, new bathrooms and is ready for its next owner. Perfect for first time home buyer or anyone downsizing.Large Country kitchen with sizeable eating area and sliding glass doors to large deck overlooking large level backyard, walk into

  

  Patricia Cannizzaro

  Century 21 Alliance Rlty Group

  (845) 377-2559

  10 Aspinwall Rd, Red Hook, NY 12571
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  /40

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,016 Sq Ft

  23 Briarpatch Ln, Clinton Corners, NY 12514

  Down a long private drive, tucked into the trees and lying perfectly on your five acre retreat is the Briarpatch home. Original builders, this cape cod is a dream. Welcoming you home is a covered front porch, perfect for sitting on your porch swing and listening to the birds while you sip your coffee in the sweet Hudson valley air. Your living room greets you when you walk in with wood stove and

  Chelsea Pollard-Seiler Mondello Upstate Properties

  23 Briarpatch Ln, Clinton Corners, NY 12514
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  /50

  $839,000

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

  280 Pitcher Ln, Red Hook, NY 12571

  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 will be

  Vincenza Seche Howard Hanna Rand Realty

  280 Pitcher Ln, Red Hook, NY 12571
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  /28

  $745,000

  • 3 Beds
  • 2 Baths
  • 2,348 Sq Ft

  49 Old Farm Rd, Rhinebeck, NY 12572

  LIVING IS EASY in this low maintenance luxury ranch on almost 8 acres of privacy and tranquility. If you are looking for a full time base, a weekend escape, or just solitude with room to roam, 49 Old Farm Road in Rhinebeck delivers. This no-nonsense property offers the freedom of open land, the privacy of woods and a home built for real living, not just for show. This 3 bedroom, 2 bath

  MARY ANNE HARVEY BHHS Hudson Valley Properties

  49 Old Farm Rd, Rhinebeck, NY 12572
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  /47

  $729,000

  • 4 Beds
  • 3 Baths
  • 2,559 Sq Ft

  7432 S Broadway, Red Hook, NY 12571

  Take a step back to a simpler time in this charming Circa 1920 4 bed 3 bath Victorian home. Located in the beautiful village of Red Hook, Dutchess county. The town once named Hardscrabble offers all the convenience of modern day life. Multiple excellent restaurants, supermarket, juice bar, a health food shop, art galleries, a Pilates studio and much more. The 2,559 square foot stately

  Anthony Winters Upstate Down

  7432 S Broadway, Red Hook, NY 12571
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  /50

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,345 Sq Ft

  172 Shields Rd, Red Hook, NY 12571

  Set along a quiet, picturesque dirt road, this private escape delivers the kind of peace you didn’t know you needed—until now. A wide, grassy yard flows to a meandering stream, while a heated saltwater pool turns every day into a vacation. Whether you're seeking a full-time sanctuary or a weekend retreat, this home strikes the perfect balance between comfort, privacy, and style.Inside,

  Michael Kahns Compass Greater NY, LLC

  172 Shields Rd, Red Hook, NY 12571
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  /50

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  7641 N Broadway, Red Hook, NY 12571

  Discover the charm of Red Hook, New York, with this inviting ranch-style residence at 7641 N Broadway. Nestled in one of the Hudson Valley’s most desirable communities, this beautifully maintained single-family home offers 2,657 sq. ft. across two levels—featuring 1,992 sq. ft. on the main floor and a full finished basement below.Inside, you’ll find four generously sized bedrooms and two

  Ryan Sylvestri RE/MAX Town & Country

  7641 N Broadway, Red Hook, NY 12571
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  /29

  $950,000

  • 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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  /31

  $799,999

  • 4 Beds
  • 2.5 Baths
  • 3,370 Sq Ft

  117 Deer Run Rd, Red Hook, NY 12571

  Welcome to this elegant four bedroom, two and a half-bath Colonial gracefully set on three beautifully manicured acres in one of Red Hook’s most desirable executive neighborhoods. Thoughtfully designed for both comfort and style, this home offers timeless curb appeal with its charming rocking chair front porch and classic architectural lines.Step inside to a spacious and light-filled layout

  Peggy Santamorena Houlihan Lawrence Inc.

  117 Deer Run Rd, Red Hook, NY 12571
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  /46

  $998,000 Open Wed 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,763 Sq Ft

  345 Metzger Rd, Rhinebeck, NY 12572

  Escape with us to Red Hook, NY! Hidden amongst a canopy of trees, down a long, meandering, private drive, sits this spacious Cape Cod overlooking 10+ acres of the most beautiful, organic gardens and orchards. Enjoy having the convenience of both Rhinebeck and Red Hook Villages at your fingertips, but the feeling of being in your own little piece of Hudson Valley paradise. Head out in the morning

  Miranda Alger Mondello Upstate Properties

  345 Metzger Rd, Rhinebeck, NY 12572
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  /31

  $759,900

  • 4 Beds
  • 4 Baths
  • 3,858 Sq Ft

  37 Pine Ln, Tivoli, NY 12583

  Get ready to have the summer of your dreams in this impeccably cared for turnkey Center Hall Colonial style home in serene country setting. Tucked away at the end of a private road, you instantly feel welcomed as you enter a spacious and bright Living Room with a pellet stove. You will love to dine in the eat in Kitchen with brand new appliances and multitude of counter space. Formal Dining Room

  ANGELINA POLLARD Mondello Upstate Properties

  37 Pine Ln, Tivoli, NY 12583
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  /42

  $759,900

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft

  224 Fraleigh Ln, Red Hook, NY 12571

  Country Cape on near end cul-de-Sac situate on 6 private acres , country kitchen with dining area ,LR with mason chimney pellet stove. double dutch door lead to4 season room, access to L shaped decking with jacuzzi, overlooking fire pit and landscaped yard and fenced in pool 16x36 area.Hardwd floors on main floor, and tile flrd baths ,4 Bedrooms,( 2 up, 2 down) 2 updated full baths (1

  Karen Vetere Vetere, Karen Real Estate

  224 Fraleigh Ln, Red Hook, NY 12571
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  /38

  $799,000

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

  12 Broadview Ln, Red Hook, NY 12571

  Tucked right outside the village of Red Hook, is the lovely neighborhood on Broadview Lane, where you have the unique luxury of extensive private acreage but also enjoy the community setting. This custom colonial is both elegant and cozy; it has been carefully curated with immaculate details featuring crown moldings, recessed lighting, and beautiful hardwood floors. Welcome your guests into the

  Chelsea Pollard-Seiler Mondello Upstate Properties

  12 Broadview Ln, Red Hook, NY 12571
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  /49

  $1,200,000

  • 3 Baths
  • 4,000 Sq Ft

  573 E Kerley Corners Rd, Elizaville, NY 12523

  Welcome to the Elizaville Diner & Deli, a Hudson Valley roadside treasure with a lakeside backdrop. Set on just over two picturesque acres, this mixed-use commercial property includes a restored vintage diner, a renovated deli, ample parking, and grassy fields overlooking a spring-fed quarry.Originally built in 1956, the Elizaville Diner is the last surviving example of a Kullman Dutchess

  Shaina Marron Houlihan Lawrence Inc.

  573 E Kerley Corners Rd, Elizaville, NY 12523
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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
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  /34

  $749,000

  • 4 Beds
  • 4 Baths
  • 2,300 Sq Ft

  8 Orlich Rd, Red Hook, NY 12571

  Welcome to 8 Orlich Road - a beautifully designed home offering endless possibility! This property is perfect for those seeking both space and versatility, with features that cater to a wide range of needs and lifestyles. The main level boasts four bedrooms including a private primary suite with large en-suite bath and plenty of closet space. The heart of the home includes an open-plan living and

  Hayes Clement Compass Greater New York, LLC

  8 Orlich Rd, Red Hook, NY 12571
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  /36

  $734,900

  • 3 Beds
  • 2.5 Baths
  • 2,864 Sq Ft

  7 Glen View Dr, Red Hook, NY 12571

  Begin each morning in tranquil serenity at this 1993 Cape Cod style residence, positioned at the end of a peaceful country lane just two miles from the center of Red Hook Village. The country kitchen and dining room flow seamlessly into a screened porch, creating an ideal setting for both daily moments and memorable gatherings. Sip your morning coffee while watching wildlife in the wooded

  Linda Lindsay Upstate Down

  7 Glen View Dr, Red Hook, NY 12571
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  /25

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft

  81 W Market St, Red Hook, NY 12571

  The A.J. Davis Mid- 19th Century Gardener's Cottage -A rare opportunity to own a piece of Hudson Valley history, The Gardener's Cottage, once part of Maizefield. This property was built in the mid- 19th century and the architect commissioned was Alexander Jackson Davis, a very prominent man of his time. It is a two story, three-by-one-bay timber frame cottage, on an exposed stone foundation, with

  Brock Anderson Four Seasons Sotheby's Int.

  81 W Market St, Red Hook, NY 12571
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  /30

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  79 Torre Rock Rd, Red Hook, NY 12571

  79 Torre Rock Rd. in Red Hook NY is a charming Cape Cod home sitting quietly on 12.25 very private acres of serene land in the town of Milan. Built in 1976 this retro home welcomes you with a spacious screened-in front porch, perfect for enjoying nature’s symphony at any hour, this retreat boasts three bedrooms and 2.5 baths. The main floor features a generous primary bedroom with an en suite

  Rebecca Hanlon Corcoran Country Living

  79 Torre Rock Rd, Red Hook, NY 12571
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  /64

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,235 Sq Ft

  100 White Schoolhouse Rd, Temple, ME 04984

  Calling All Preppers and Homesteaders: Your Off-Grid Paradise Awaits! 🌲🏡 If you're dreaming of total privacy, escaping the chaos of the world, and embracing nature without sacrificing modern comforts—this TURN KEY FURNISHED mountaintop gem in Maine is your dream come true!🛖 Surrounded by thousands of acres of pristine forest, this home offers nothing but peace,

  Wendy Pelletier Meservier & Associates

  

  100 White Schoolhouse Rd, Temple, ME 04984
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  /26

  $639,000

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

  297 Turkey Hill Rd, Red Hook, NY 12571

  First time on the market in a generation, this Turkey Hill Charmer has it all. When you pull in, a lovely rocking chair covered porch welcomes you; begging you to spend your summer evenings listening to the birds and enjoying the upstate air here. Walk in to a formal entry way to an open living room with 20 foot ceilings, primary bedroom with en-suite bath off living room and 2 great sized guest

  Chelsea Pollard-Seiler Mondello Upstate Properties

  297 Turkey Hill Rd, Red Hook, NY 12571
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  /50

  $619,000

  • 3 Beds
  • 2.5 Baths
  • 2,462 Sq Ft

  43 Overlook Dr, Rhinebeck, NY 12572

  Come home to this country colonial, located just 2 minutes to the Rhinecliff Bridge for easy access to Kingston shopping. This home is at the end of a dead-end road and minutes to Rhinebeck and Red Hook, this is truly a central location in the Red Hook school district. Take in the local farms and restaurants the area has to offer and enjoy easy access to events held at the Rhinebeck fairgrounds,

  Adrienne Volpe Keller Williams Hudson Valley

  43 Overlook Dr, Rhinebeck, NY 12572
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  /2

  $325,000

  • Land
  • 18 Acres
  • $18,362 per Acre

  0 Sawmill Rd, Milan, NY 12571

  Fantastic Opportunity to own 17.7 prime acres featuring multiple potential building sites and Catskill mountain views with light clearing. This lightly wooded property includes walking trails throughout, offering easy access and a serene natural setting. Build your dream home in a private haven surrounded by nature and wildlife, all while being just minutes from Red Hook Village and the Taconic

  Margaret Niekrewicz Margaret Mondello Real Estate

  0 Sawmill Rd, Milan, NY 12571
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  /25

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  3 Holt Rd, Red Hook, NY 12571

  Looking for a completely updated, stunning home with great yard to expand? Look no further! Enter into the spacious living room with vaulted ceilings brand new windows, and life proof flooring. Dining room and stunning open chefs kitchen including high end appliances, marble counter tops and island, gas stove and endless cabinets for ample storage. You will love spending your evenings making

  Chelsea Pollard-Seiler Mondello Upstate Properties

  3 Holt Rd, Red Hook, NY 12571
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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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  /34

  $629,000

  • 3 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  35 Rowe Rd, Red Hook, NY 12571

  Set on 2.2 scenic acres, this spacious Raised Ranch offers a perfect blend of comfort and versatility. The main level features a primary bedroom with en-suite bathroom, two additional bedrooms, and a full hall bathroom. The living room with woodburning stove flows into the dining area with sliders to the deck—ideal for indoor-outdoor entertaining. The kitchen includes a center island and plenty

  Rita Longo Howard Hanna Rand Realty

  35 Rowe Rd, Red Hook, NY 12571
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  /35

  $9,450,000

  • 3 Beds
  • 4.5 Baths
  • 6,216 Sq Ft

  151 Rowe Rd, Red Hook, NY 12571

  Crestline is a visionary to-be-built residence with 6,216 finished square feet of meticulously designed living space, including three bedroom suites and four-and-a-half luxurious baths. Perched atop a 41-acre hilltop with commanding 360-degree views of the Catskills, Stissing Mountain, and the rolling agricultural valleys below, this architectural masterpiece harmonizes with its natural

  Sean Eidle BHHS Hudson Valley Properties

  151 Rowe Rd, Red Hook, NY 12571
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  /37

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  11 Tribune Ln, Red Hook, NY 12571

  Picture-perfect vintage vibe meets endless possibilities on 1.6 private acres. This warm, enchanting 3-bed, 2-bath cottage combines nostalgic character with cozy, peaceful country living. From its inviting porch to the sprawling, sunlit yard full of mature trees, every corner of this property whispers warmth and charm. Here you can cultivate charming gardens of flowers and shrubs or grow herbs

  Bettina Louise Sturm Howard Hanna Rand Realty

  11 Tribune Ln, Red Hook, NY 12571
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  /29

  $625,000

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

  110 Read Rd, Red Hook, NY 12571

  This well-maintained Cape Cod Style exemplifies a "pride of ownership". You will enjoy relaxing in the comfortable Living Room with its vaulted ceilings, skylights and hardwood floors. The Eat in Kitchen has been upgraded with stainless appliances and is abundant with cabinetry and conveniently accesses a two-car Garage with a loft for storage or other potential. The "Crown Jewel" of the home is

  Catherine Mondello Mondello Upstate Properties

  110 Read Rd, Red Hook, NY 12571
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  /41

  $459,000

  • 4 Beds
  • 1.5 Baths
  • 1,672 Sq Ft

  252 Route 199, Red Hook, NY 12571

  This well-loved property has been owned by the same family for almost 65 years! Hardwood floors & natural woodwork are throughout. More recent 2 rm addition features a 3-season room w vaulted wood ceiling & propane stove, plus an additional bedroom or family room w 3 closets. Dry basement features a 4th BR or FR, utility room, plus room for 3 cars. This space could easily be finished for extra

  Elizabeth Barrett Dachs Chris Barrett Realty

  252 Route 199, Red Hook, NY 12571
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  /25

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,097 Sq Ft

  1601 Route 199, Red Hook, NY 12571

  Charming Renovated Ranch with Scenic Views and Endless Potential, l with extra additional side lot!! Welcome to this beautifully renovated ranch-style home offering 1,200 square feet of comfortable, single-level living. Featuring 3 spacious bedrooms and 2 full baths, this thoughtfully updated home boasts a functional and versatile layout with multiple private entrances—perfect for

  Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
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  /30

  $365,000

  • 3 Beds
  • 1 Bath
  • 1,160 Sq Ft

  9 Roger Ct, Red Hook, NY 12571

  Nestled on a private road shared with just two other homes, this recently renovated ranch offers an out-of-the-way location, minutes from the heart of Red Hook.A newly built front deck welcomes you home, providing the perfect spot to enjoy your morning coffee or entertain guests. Step inside to a light-filled living room featuring large windows and warm wood wainscoting, seamlessly connected

  KIMBERLEY MILLER BHHS Hudson Valley Properties

  9 Roger Ct, Red Hook, NY 12571
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  /50

  $2,350,000

  • 3 Beds
  • 4 Baths
  • 4,220 Sq Ft

  1202 Jackson Corners Rd, Red Hook, NY 12571

  Exquisite Mid-Century Home with scenic water views and luxury amenities. Nestled on the banks of the picturesque Roe Jansen Kill, this stunning three bedroom home offers an open, flowing floor plan perfect for modern living. The spacious great room features a custom kitchen with a Garland gas stove, double ovens, large pantry and s/s refrigerator. Relax by the stone wood burning fireplace or step

  Sharon Farley Corcoran Country Living

  1202 Jackson Corners Rd, Red Hook, NY 12571
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  /2

  $75,000

  • Land
  • 3.00 Acres
  • $25,000 per Acre

  0 County Route 2, Elizaville, NY 12523

  Welcome to Blackberry Hill Road! Nice 3 acre corner lot on Blackberry Hill Road, 5 minutes to Taconic, 10 min to Red Hook or Pine Plains. Nice flat piece of land on lovely residential road ready for you to build your perfect home. Low Taxes and Pine Plains schools, this is a great opportunity to get an affordable homestead.

  Chelsea Pollard-Seiler Mondello Upstate Properties

  0 County Route 2, Elizaville, NY 12523
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  /22

  $434,900

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft

  18 Amherst Rd, Red Hook, NY 12571

  Beautiful town of Red Hook home that has been lived in and loved for years. With many updates and additions this 5 bedroom home is priced to sell quickly. Private 1st floor main bedroom with ensuite bathroom plus 2 more bedrooms and another full bath on the first floor. Downstairs has been fully finished with a bedroom, full bath, storage room and a tv/work out area. Walk into town to enjoy

  MARIE MONROE BHHS Hudson Valley Properties

  18 Amherst Rd, Red Hook, NY 12571
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  /38

  $595,000

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

  22 Beacham Rd, Rhinebeck, NY 12572

  Charming and Secluded Home in Highly Sought-After Location - First Time on Market in 36 YearsNestled in a quiet, serene setting just 7-10 minutes from the heart of Rhinebeck, this beautifully maintained one-owner home offers comfort, privacy, and timeless charm. Built in 1988, the property has been lovingly cared for over the decades and is now ready for its next chapter.Charming

  Margaret Williams Coldwell Banker Advisor Realty

  22 Beacham Rd, Rhinebeck, NY 12572
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  /35

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,425 Sq Ft

  9 Lakeside Dr, Rhinebeck, NY 12572

  Charming Cape Cod Cottage with Private Round Lake Access! Nestled on 2 secluded acres, this well-maintained Cape Cod-style cottage offers 1,425 sq ft of inviting living space and exclusive access to pristine Round Lake—a non-motorized lake ideal for swimming, fishing, canoeing, paddle boarding, and kayaking. The main level features a spacious living room, a sunny kitchen with a dinette area, two

  Sean Eidle BHHS Hudson Valley Properties

  9 Lakeside Dr, Rhinebeck, NY 12572
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  /11

  $399,000

  • Land
  • 9 Acres
  • $43,370 per Acre

  0 Willow Glen Rd Unit KEY879400, Milan, NY 12571

  Here it is your own private slice of heaven. Set high on a mountain with beautiful Hudson valley views and gorgeous sunsets. Perfect for a weekend retreat or everyday enjoyment. Search no more your dream home can be built here. The property backs up to 118 acres of wooded land. Serene, peaceful and private yet only a short drive to Rhinebeck and Red Hook and a two hour drive to the city. You

  MARIE MONROE BHHS Hudson Valley Properties

  0 Willow Glen Rd Unit KEY879400, Milan, NY 12571

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