Dutchess, NY Homes

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  /37

  $1,799,000 Pending

  • 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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  Explore Red Hook

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  /10

  $1,350 per month

  • 1 Bath
  • 350 Sq Ft
  • Apartment for Rent

  8068 Albany Post Rd Unit 4, Red Hook, NY 12571

  This clean and efficient studio apartment offers approx. 350 sq ft of living space with a private bathroom, off-street parking, and on-site laundry. Located in a quiet, well-kept building in Upper Red Hook, it’s perfect for anyone seeking low-maintenance, affordable living.Tenant pays for heat, landlord covers electric.

  William Schunk Schunk Realty Group

  8068 Albany Post Rd Unit 4, Red Hook, NY 12571
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  $250,000 Sold Jul 29, 2025

  • 1,609 Sq Ft
  • $155/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  155 Metzger Rd Unit 19, Red Hook, NY 12571

  This immaculate Ranch style manufactured home is 2 years young. Enter the front door from the wonderful front covered Porch and you will marvel at the huge open floor plan with fabulous modern Kitchen with loads of cabinets and a beautiful peninsula with great workspace. The classy plank floors run throughout the home. The Living room holds a full suite of furniture, and the formal Dining Area

  Catherine Mondello Mondello Upstate Properties

  155 Metzger Rd Unit 19, Red Hook, NY 12571
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  Est $1,021,947 Not Listed For Sale

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

  57 Pondview Dr, Red Hook, NY 12571

  57 Pondview Dr, Red Hook, NY 12571
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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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  /22

  $3,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • House for Rent

  593 Field Rd Unit 601, Red Hook, NY 12571

  Originally a 19th-century homestead, this two-bedroom cottage overlooking Little Wappinger Creek has been thoughtfully renovated by an interior designer, adding modern comfort to it's historic charm. The home features two bedrooms, one full bath, one half bath, and a spacious eat-in kitchen with both a breakfast bar and dining area.Interior highlights include memory foam beds, quality

  Zev Eisenberg Hudson Modern Co

  593 Field Rd Unit 601, Red Hook, NY 12571
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  $400,000 Sold Jul 28, 2025

  • 1,325 Sq Ft
  • $302/SF
  • 27 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1958

  2 Princeton St, Red Hook, NY 12571

  Stylish and move-in ready, this beautifully updated 3-bedroom, 1-bath ranch is located in a lovely Red Hook community, just minutes from top-rated schools, Bard College, and shopping. Set on a fenced corner lot perfect for pets, children, or added privacy, this home offers the ease of one-level living with a bright, open floor plan and cathedral ceilings in the living room. New, stylish laminate

  Margaret Niekrewicz Margaret Mondello Real Estate

  2 Princeton St, Red Hook, NY 12571
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  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,165 Sq Ft

  7328 S Broadway, Red Hook, NY 12571

  7328 S Broadway, Red Hook, NY 12571
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  /35

  $795,000

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

  216 Starbarrack Rd, Red Hook, NY 12571

  Privacy abounds at this custom-built post & beam Colonial. Situated upon a hilltop with 3+ acres, there is a wonderful blend of woods in the front and a serene, landscaped meadow in the back. The rear deck is the perfect spot for enjoying the wildlife & the lovely views. Featured are 3 bedrooms, 2.5 baths, a fireplace w woodstove, a perfect window seating area, and amazing post & beam

  Elizabeth Barrett Dachs Chris Barrett Realty

  216 Starbarrack Rd, Red Hook, NY 12571
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  /33

  $7,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,810 Sq Ft
  • House for Rent

  49 Rocky Rd, Red Hook, NY 12571

  This unique dwelling provides all the reasons people are moving to the Hudson Valley.... 20 Acres set off at the end of a private road with a 3 acres pond with a floating dock and two kayaks, walking trails, and two large gardens filled with vegetables, herbs, and flowers (including 50 dahlia plants. Truly a rural residence with a wall of windows allowing you to spend as much time

  Doreen De Carolis Upstate Down

  49 Rocky Rd, Red Hook, NY 12571
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  /41

  $900,000 Sold Jul 24, 2025

  • 2,556 Sq Ft
  • $352/SF
  • 16 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1937

  293 Linden Ave, Red Hook, NY 12571

  Welcome to The Robin's Nest — a graceful retreat tucked beneath a canopy of mature trees, where timeless style meets natural serenity. This sophisticated residence is enveloped by nature, offering an atmosphere of quietude and privacy, with enchanting views from nearly every room.Inside, the home unfolds with an intuitive, flowing layout that balances openness and warmth. Whether entertaining

  Leslie Foti Coldwell Banker Village Green

  293 Linden Ave, Red Hook, NY 12571
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  Est $226,000 Not Listed For Sale

  23 Guski Rd, Red Hook, NY 12571

  23 Guski Rd, Red Hook, NY 12571
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  /42

  $900,000

  • 4 Beds
  • 2.5 Baths
  • 3,500 Sq Ft

  98 Mill Rd, Red Hook, NY 12571

  Live in resort-style luxury year-round in this exceptional 3,500 sq ft waterfront residence tucked away on 1.2 private acres in the heart of Red Hook, NY. Designed for comfort, elegance, and versatility, this lives-like-5-bedroom (legal 4), 3.5-bath home feels like your own private retreat. With direct access to the serene Mill Road Pond, you'll enjoy kayaking, paddle boarding, birdwatching, or

  Christopher Ferraro RE/MAX Town & Country

  98 Mill Rd, Red Hook, NY 12571
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  /15

  $2,850 per month

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft
  • Apartment for Rent

  35 Old Route 199, Red Hook, NY 12571

  Welcome to this beautifully updated apartment, located in the charming town of Red Hook. With three spacious bedrooms an d two full baths, this thoughtfully designed unit offers both comfort and convenience on one of the Hudson Valley's most desirable communities. The primary bedroom features a private en suite bathroom and generous closet, creating a perfect retr4eat within the home. Two

  TRACY DOBER Rouse + Co Real Estate LLC

  35 Old Route 199, Red Hook, NY 12571
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  $2,336,940 Sold Jul 24, 2025

  • 4,024 Sq Ft
  • $581/SF
  • 379 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2023

  0 Yantz Rd Unit 411430, Red Hook, NY 12571

  (To-be-built) The Elm residence is a study in understated sophistication, in perfect context with the Hudson Valley. The architecture is comprised of two intersecting gable roof wood clad volumes creating inviting indoor and outdoor living spaces. Elm is sited on 6 private primarily wooded acres accessible from a quiet country road and surrounding bucolic farm landscapes. The property inspires

  Sean Eidle BHHS Hudson Valley Properties

  0 Yantz Rd Unit 411430, Red Hook, NY 12571
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  Est $924,960 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  133 Country Club Dr, Red Hook, NY 12571

  133 Country Club Dr, Red Hook, NY 12571
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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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  /25

  $5,000 per month

  • 3 Beds
  • 3 Baths
  • 1,320 Sq Ft
  • House for Rent

  116 Torre Rock Rd, Red Hook, NY 12571

  Looking for privacy and quiet? This adorable chalet has that and so much more. Totally renovated and updated, outside is tranquil country, inside is stylish and serene. The kitchen is to die for and overlooks part of the almost 17 acres of nature, which includes a pond. Partially fenced in, so no deer, but room for your dog. The open floor plan includes living room with fireplace, dining area and

  Leigh Bahnatka BHHS Hudson Valley Properties

  116 Torre Rock Rd, Red Hook, NY 12571
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  $110,000 Sold Jul 18, 2025

  • 1,240 Sq Ft
  • $89/SF
  • 131 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  127 Spring Lake Rd, Red Hook, NY 12571

  Knock-Down Property in Upper Red Hook Prime Location with Endless Potential!Welcome to this charming ranch-style home located in the picturesque town of Upper Red Hook, NY. This 3-bedroom, 1-bathroom property sits on a spacious corner lot, offering ample privacy and room for outdoor possibilities. The home presents an exciting opportunity for those looking to start fresh and build their dream

  Jeanne Rakowski Corcoran Country Living

  127 Spring Lake Rd, Red Hook, NY 12571
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  /35

  Est $1,336,698 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,850 Sq Ft

  48 Eastview Ln, Red Hook, NY 12571

  48 Eastview Ln, 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

  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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  /19

  $3,300 per month

  • 3 Beds
  • 1.5 Baths
  • 1,524 Sq Ft
  • House for Rent

  12 Elizabeth St, Red Hook, NY 12571

  FOR RENT – UPDATED 3 BEDROOM 1 1/2 BATH HOME in the Village of Red Hook. Walking distance to restaurants, coffee shops, etc. Living room, formal dining room, enclosed porch, washer/dryer, split unit. Nice size fenced backyard. Ample parking for 4 cars. One year minimum lease. Good credit and references. No smoking. Tenant pays all utilities (electric, heat/oil, water, garbage, cable/internet)

  Julie Goldberg HomeSmart Homes & Estates

  12 Elizabeth St, Red Hook, NY 12571
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  $610,000 Sold Jul 15, 2025

  • 1,670 Sq Ft
  • $365/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  161 Camp Rd, Red Hook, NY 12571

  A cozy, light-filled cottage tucked away at the end of a quiet country cul-de-sac in Columbia County. Surrounded by trees, a meandering stream, and the gentle sounds of birds chirping in the woods - this adorable cottage is the kind of place you settle into and never want to leave.This home lives simply and beautifully, with natural sunlight pouring in through every window. The main floor

  Craig Smith Compass Greater NY, LLC

  161 Camp Rd, Red Hook, NY 12571
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  Est $632,588 Not Listed For Sale

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

  38 Blue Echo Rd, Red Hook, NY 12571

  38 Blue Echo Rd, Red Hook, NY 12571
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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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  /8

  $1,950 per month

  • 2 Beds
  • 1 Bath
  • 500 Sq Ft
  • Apartment for Rent

  62 E Market St, Red Hook, NY 12571

  Cozy 2 bedroom apartment located in the village of red hook. Close to restaurants, stores, public transportation and bard collage shuttle. Please no smoking and no pets.

  Neal Kightlinger LeGrand Real Estate, Inc.

  62 E Market St, Red Hook, NY 12571
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  $585,000 Sold Jul 15, 2025

  • 1,323 Sq Ft
  • $442/SF
  • 13 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1987

  48 Vosburgh Rd, Red Hook, NY 12571

  Tucked away in a quiet, private setting in Red Hook, this log-sided ranch offers warmth, character, and comfort. The property is set on three open and usable acres and provides ample space for gardens, recreation, or simply enjoying the outdoors. The home features 3 bedrooms and 1.5 bathrooms, with an inviting interior and an open kitchen and dining area that flows seamlessly to the outside. A

  Kyle Irwin Corcoran Country Living

  48 Vosburgh Rd, Red Hook, NY 12571
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  Est $909,365 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,020 Sq Ft

  89 Fairway Ln, Red Hook, NY 12571

  89 Fairway Ln, 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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  /62

  $18,000 per month

  • 5 Beds
  • 2.5 Baths
  • 3,112 Sq Ft
  • House for Rent

  5 Fulton Homestead Rd, Red Hook, NY 12571

  Discover Fulton Homestead, an exceptional Hudson Valley seasonal retreat, where historic charm meets idyllic upstate living. Set on 85 private acres, this beautifully renovated 1790s historic homestead offers the perfect setting to enjoy the region's peak season in comfort, style, and privacy.The property comes alive during the warm-weather months with abundant forsythia and peonies, verdant

  Jennifer Enloe Four Seasons Sotheby's Int.

  5 Fulton Homestead Rd, Red Hook, NY 12571
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  /26

  $680,000 Sold Jul 03, 2025

  • 2,000 Sq Ft
  • $340/SF
  • 28 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  1315 Annandale Rd, Red Hook, NY 12571

  This rare residential offering in Annandale-on-Hudson is encompassed by the beautiful Bard College campus, while privately set back from the road on a forested lot that backs onto hundreds of acres protected lands.The house is well proportioned with over two-thousand square feet of living space with four bedrooms on the second floor, one en-suite, and each with charming dormer windows. The

  Susan Lyne HOUSE Hudson Valley Realty

  1315 Annandale Rd, Red Hook, NY 12571
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  Est $633,601 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 4,200 Sq Ft

  421 Feller Newmark Rd, Red Hook, NY 12571

  421 Feller Newmark 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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  $129,921 Sold Jul 02, 2025

  • 1,008 Sq Ft
  • $129/SF
  • 147 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  155 Metzger Rd Unit 46, Red Hook, NY 12571

  Easy living in this 5-year young 3 Bedroom, 2 Bath Manufactured Home in quiet well-maintained park. Some Features include Open Floor Plan with bright and sunny Kitchen with great workspace and abundant cabinetry. Dining Area looks out on front yard and Living room is a cozy place to entertain guests. The Primary Bedroom has a large en-suite with a large shower and pretty vanity. Two guest

  Catherine Mondello Mondello Upstate Properties

  155 Metzger Rd Unit 46, Red Hook, NY 12571
• 

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  155 Metzger Rd, Red Hook, NY 12571

  155 Metzger Rd, Red Hook, NY 12571
• 

  

  /31

  $749,000

  • 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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  $395,000 Sold Jul 01, 2025

  • 1,100 Sq Ft
  • $359/SF
  • 26 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1971

  15 Spencer Dr, Red Hook, NY 12571

  Welcome to 15 Spencer, Red Hook — this 2-bedroom, 1.5-bath ranch-style home offers the ease of single-level living with over 1,400 sq ft of well-maintained space, all set on a serene 1+ acre private lot. Tucked back from the road with a long driveway, this home combines peaceful seclusion with convenient access to shopping, transportation, and major highways.Designed for comfort and

  Howard Payson RE/MAX Town & Country

  15 Spencer Dr, Red Hook, NY 12571
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  Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 3,885 Sq Ft

  667 Budds Rd, Red Hook, NY 12571

  667 Budds Rd, Red Hook, NY 12571
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  /30

  $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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  $1,250,000 Sold Jul 01, 2025

  • 2,900 Sq Ft
  • $431/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1945

  76-77 E Lake Ln, Red Hook, NY 12571

  Set on four wooded acres, Red Hook Lake Retreat is a three-cottage lakeside compound just 10 minutes from Red Hook Village—one of the Hudson Valley’s most charming towns—and two hours from New York City. With a total of 4 bedrooms and 3.5 bathrooms, each cottage has its own personality, private lake access, and dedicated outdoor space. Together, they offer flexibility for personal use, creative

  Divya Jayachandran Rouse + Co Real Estate LLC

  76-77 E Lake Ln, Red Hook, NY 12571

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