Dutchess, NY Homes

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  /46

  $599,500

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

  89 Birch Dr, Pleasant Valley, NY 12569

  Welcome Home!This spacious and impeccably maintained oversized raised ranch offers comfort, flexibility, and pride of ownership in every room.With a thoughtfully designed layout, this home features two bedrooms on the lower level and a primary suite with a private bath on the main floor, along with an additional bedroom—ideal for guests, family, or a home office.The heart of

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 681-2247

  89 Birch Dr, Pleasant Valley, NY 12569
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  /2

  Call for Price

  14 Arbor Hill Drive

  2 Beds

  12 Arbor Hill Dr, Pleasant Valley, NY 12569

  Residential

  12 Arbor Hill Dr, Pleasant Valley, NY 12569
• 

  $900,000 Sold Aug 07, 2025

  • 3,770 Sq Ft
  • $239/SF
  • 161 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  422 Rossway Rd, Pleasant Valley, NY 12569

  Discover the elegance and charm of this stunning residence located in the Town of LaGrange, within the esteemed Arlington School District. Nestled on nearly 11 acres of land, this enchanting stone-clad and stucco ranch home offers a perfect blend of sophistication and comfort.As you approach the property, a wooded path leads you to a scenic setting enhanced by stacked stone walls and

  Kaye Saglibene

  422 Rossway Rd, Pleasant Valley, NY 12569
• 

  Est $604,346 Not Listed For Sale

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

  664 Plass Rd, Pleasant Valley, NY 12569

  664 Plass Rd, Pleasant Valley, NY 12569
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  /22

  $499,900 Open Sun 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  166 Hibernia Rd, Salt Point, NY 12578

  Nestled In The Hamlet Of Salt Point NY, In The Town Of Pleasant Valley Is This Remodeled Home Offering Four Bedrooms And Two Baths. The Front Exterior Has Dual Entry Access To Various Locations Within The Home Which Displays A Combination Of Engineered Wood And Ceramic Tiled Floors. Each Room Has Been Thoughtfully Updated. Here You Will Find The Kitchen With State Of The Arts Stainless Steel

  

  Joyce Stanton

  Century 21 Hudson Valley Rlty.

  (845) 599-8106

  166 Hibernia Rd, Salt Point, NY 12578
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  /40

  $8,000 per month

  • 3 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • House for Rent

  209 Route 343, Millbrook, NY 12545

  A great opportunity to escape to your own private retreat in Millbrook. This property is for rent on an annual basis and offers 3200 sq ft of living space on 10 acres of beautiful land. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this residence provides ample room for comfortable living. The first floor creates an inviting atmosphere for gatherings, with spacious formal and informal

  Susan Whalen George T Whalen Real Estate

  209 Route 343, Millbrook, NY 12545
• 

  $1,817,500 Sold Jul 31, 2025

  • 4,777 Sq Ft
  • $380/SF
  • 19 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1850

  3925 Route 82, Millbrook, NY 12545

  Wake up to birdsong in this spacious and sunny renovated historic Millbrook farmhouse. Situated on over 13 acres in an enchanted setting of old growth trees, a year-round running stream, natural landscaping, moss and stonework, this inviting home is perfect for the weekender or full-time resident. A recent architectural addition seamlessly bridges this home's 19th century pedigree with modern

  E. ELIZABETH PETERS Corcoran Country Living

  3925 Route 82, Millbrook, NY 12545
• 

  Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft

  62 Elm Ln, Pleasant Valley, NY 12569

  62 Elm Ln, Pleasant Valley, NY 12569
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  /39

  $2,550,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 9,150 Sq Ft

  216 Barmore Rd, Lagrangeville, NY 12540

  This wonderful country retreat is a balance of modern design, a wellness mindset, and timeless craftsmanship with every attention to detail. Milling trees from the property to construct the barn using the masterful post-and-beam construction method, creating intricate joints without nails.The current owner has meticulously updated the home in Union Vale which offers notably lower school

  Marc Maclean William Pitt Sothebys Int Rlty

  216 Barmore Rd, Lagrangeville, NY 12540
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  /20

  $1,999 - $2,509 per month

  Village Park Apartments

  1 - 2 Beds

  5 Park Dr, Pleasant Valley, NY 12569

  Enjoy all the pleasures of country living by renting at Village Park Apartments. We are located in the heart of the beautiful, historic land of Pleasant Valley, NY, only minutes away from all the conveniences of village life. With our scenic atmosphere and quick access to New York City or the beautiful Queen City of the Hudson River Poughkeepsie, you have the best of both worlds here at Village

  5 Park Dr, Pleasant Valley, NY 12569
• 

  $1,900,000 Sold Jul 30, 2025

  • 5,086 Sq Ft
  • $374/SF
  • 101 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1999

  59 Bangall Rd, Millbrook, NY 12545

  Welcome to Field House, an inviting country home nestled in the midst of 6+ acres in beautiful Millbrook. Remodeled and enlarged in 2017, this captivating home boasts a stunning open and flowing design of dining and living space, perfect for entertaining family and friends. Hosting is easy with an incredible chef's kitchen that flows seamlessly into a sun-filled family room and dining room.

  Susan Whalen George T Whalen Real Estate

  59 Bangall Rd, Millbrook, NY 12545
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  65 Elm Ln, Pleasant Valley, NY 12569

  65 Elm Ln, Pleasant Valley, NY 12569
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  /32

  $247,000

  • Land
  • 25 Acres
  • $9,860 per Acre

  00WP Rossway Rd, Pleasant Valley, NY 12569

  Welcome to your idyllic escape in the beautiful Hudson Valley town of Pleasant Valley, NY! This exceptional piece of property is a hidden gem, offering unmatched privacy and an abundance of natural beauty. Spanning acres of mixed hardwood and softwood species, the land is a harmonious blend of lush greenery and scenic vistas, providing the perfect backdrop for your dream project. Whether

  Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00WP Rossway Rd, Pleasant Valley, NY 12569
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  /10

  $2,500 per month

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

  15 Quaker Hill Rd Unit 1, Pleasant Valley, NY 12569

  Immaculate rental opportunity available in Pleasant Valley, NY. Two bedroom apartment is brand new, complete with spectacular eat-in kitchen, with granite countertops, new appliances and cabinetry lighting. New carpets throughout rest of the home, figuring two spacious bedrooms, brand new stunning full bathroom, and plenty of storage. Quiet and serine, but close to shops, schools, parks, and

  Dominick Passafiume Houlihan Lawrence Inc.

  15 Quaker Hill Rd Unit 1, Pleasant Valley, NY 12569
• 

  $535,000 Sold Jul 25, 2025

  • 1,500 Sq Ft
  • $357/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  65 O' Halloran Cir, Pleasant Valley, NY 12569

  This newly constructed gem sits perched at the top of O'Halloran Circle boasting an over 7.8 acre lot, both private and tranquil with so much possibility. This cottage was over engineered at every step and saw meticulous oversight by the owner/builder during the entire process. No expenses were sparred in making this home as solid as possible with an extra 2" of concrete reinforcement used on

  Andre Aivazians HomeSmart Homes & Estates

  65 O' Halloran Cir, Pleasant Valley, NY 12569
• 

  Est $501,440 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,408 Sq Ft

  1847 Route 44, Pleasant Valley, NY 12569

  1847 Route 44, Pleasant Valley, NY 12569
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  /45

  $750,000 Open Sat 12PM - 2PM

  • 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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  /31

  $1,960 - $3,095 per month

  Brookside Meadows Luxury Rental Community

  1 - 3 Beds

  10100 Brookside Rd, Pleasant Valley, NY 12569

  Welcome to Brookside Meadows, where timeless elegance meets modern convenience in the heart of Pleasant Valley, NY. This sought-after luxury gated rental community offers a serene, park-like setting with beautifully landscaped grounds, walking trails, and scenic views just minutes from the vibrant Hudson Valley lifestyle.Each residence is thoughtfully designed with upscale finishes,

  10100 Brookside Rd, Pleasant Valley, NY 12569
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  $112,000 Sold Jul 24, 2025

  • 1,000 Sq Ft
  • $112/SF
  • 49 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1989

  14 Hilltop Ln, Pleasant Valley, NY 12569

  Don't miss this beautifully updated 2-bedroom, 2-bathroom home located in the heart of Pleasant Valley and the highly desirable Arlington School District. With recent upgrades including a new roof, water heater, furnace, flooring, and fully renovated bathrooms, this home offers peace of mind and modern comfort. The underbelly has been spray-foamed for added insulation—ideal for year-round energy

  Ivan Carvalho Exit Realty Connections

  14 Hilltop Ln, Pleasant Valley, NY 12569
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  Not Listed For Sale

  0 Verbank Rd, Millbrook, NY 12545

  0 Verbank Rd, Millbrook, NY 12545
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  /37

  $749,000

  • 3 Beds
  • 4 Baths
  • 3,633 Sq Ft

  30 Eddy Rd, Verbank, NY 12585

  Welcome to 30 Eddy Road, a stunning contemporary residence nestled on a generous 1.17-acre lot in the serene Town of Union Vale. This meticulously maintained home boasts gleaming hardwood floors throughout, creating a warm and inviting atmosphere from the moment you step inside.The open-concept living and dining areas feature soaring ceilings accented by rustic wooden beams and expansive

  Robert Chiappone Century 21 Hire Realty

  30 Eddy Rd, Verbank, NY 12585
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  /2

  $1,495 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  29 Quaker Hill Rd Unit 4, Pleasant Valley, NY 12569

  Available for September 1st move-in! Spacious one bedroom located right in the heart of the Village in Pleasant Valley. Plenty of room for 2-car parking, large yard, conveniently located near the shopping center and local restaurants in walking distance. Great price for this unit!!! Utilities included; heat, hot water, garbage, snow plowing and lawn maintenance. Available Immediately. Well

  Kirk Rotger Millennium Realty Solutions

  29 Quaker Hill Rd Unit 4, Pleasant Valley, NY 12569
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  /8

  $52,000 Sold Jul 23, 2025

  • Land
  • 0.56 Acre
  • $92,857 per Acre

  • 77 Days On Market

  1443 Route 44, Pleasant Valley, NY 12569

  Build Your Dream Home - BOH Approved Lot in Arlington School DistrictThis rare find offers a .56-acre approved building lot in the highly sought-after Arlington School District. With Board of Health approval already in place for a 3-bedroom single-family residence, and a recent survey completed, this property is primed for immediate action.A spacious 3-bay garage is already on

  Lawrence Gregory Gilcrest Properties

  1443 Route 44, Pleasant Valley, NY 12569
• 

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,584 Sq Ft

  29 Merrit Ave, Millbrook, NY 12545

  29 Merrit Ave, Millbrook, NY 12545
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  /49

  $689,000

  • 4 Beds
  • 4 Baths
  • 3,088 Sq Ft

  28 Hurley Rd, Salt Point, NY 12578

  Perched at the crest of a pillared drive, this stunningly reimagined contemporary home masterfully fuses modern design with inviting warmth and everyday comfort. Set on a peaceful, wooded lot and drenched in natural light, this home offers a rare balance of modern elegance and everyday livability.The main level is open, light-filled and airy with soaring ceilings and thoughtful

  Craig Smith Compass Greater NY, LLC

  28 Hurley Rd, Salt Point, NY 12578
• 

  /2

  $1,600 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  359 Masten Rd, Pleasant Valley, NY 12569

  Charming Cottage for Rent in Pleasant Valley Nestled on a serene and private property in Pleasant Valley, this delightful cottage offers a unique opportunity for individuals or couples looking for a cozy and convenient living space. Perfect for those planning to purchase a home in the future, this charming residence combines all the essentials with the warmth of a welcoming community. The cottage

  359 Masten Rd, Pleasant Valley, NY 12569
• 

  $745,000 Sold Jul 23, 2025

  • 2,686 Sq Ft
  • $277/SF
  • 98 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1968

  16 Shunpike, Clinton Corners, NY 12514

  You will fall in love with this spacious, open layout in this cape style home that is overflowing with natural light and brand new hardwood floors throughout. This home has an outstanding flow and surreal views (that include your pond) and just call for you to relax and unwind. The main level offers an open floor plan with a beautiful kitchen, dining, and living space with sliding glass doors

  Monica Whitney Exit Realty Connections

  16 Shunpike, Clinton Corners, NY 12514
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  /2

  Est $1,330,594 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 450 Sq Ft

  1612 Main St, Pleasant Valley, NY 12569

  1612 Main St, Pleasant Valley, NY 12569
• 

  

  /50

  $799,999

  • 4 Beds
  • 3.5 Baths
  • 3,420 Sq Ft

  50 Grist Mill Ln, Pleasant Valley, NY 12569

  Welcome to your dream home in the prestigious Mill Valley Estates, located within the highly-sought-after Arlington Central School District. This stunning colonial, nestled on over 2 private acres, offers an exquisite blend of luxury, comfort, and functionality. As you approach, a picturesque setting the lush landscaping greets you. Step inside to discover a meticulously maintained interior

  Jennifer Lappe Keller Williams Realty

  50 Grist Mill Ln, Pleasant Valley, NY 12569
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  /18

  $1,550 per month

  • 1 Bed
  • 1 Bath
  • 684 Sq Ft
  • Apartment for Rent

  2582 Route 44 Unit 1, Salt Point, NY 12578

  Located in the highly sought-after town of Millbrook, this fully furnished 1-bedroom apartment offers a clean, comfortable living space with both heating and air conditioning for year-round comfort. Thoughtfully outfitted with everything you need to settle in right away, the unit combines convenience and ease in a peaceful setting. Just a short drive from the village, local shops, and scenic

  Kason Fearon Serhant LLC

  2582 Route 44 Unit 1, Salt Point, NY 12578
• 

  $600,000 Sold Jul 22, 2025

  • 2,678 Sq Ft
  • $224/SF
  • 137 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  106 Stream Ln, Pleasant Valley, NY 12569

  Serene Oasis Just Minutes from Town – Your Dream Home Awaits! Welcome to your very own slice of paradise! Nestled on a sprawling 2.3 acres, this stunning 3400 sqft + living space is a true retreat, boasting everything you need for a life filled with comfort, charm, and endless adventures. Discover a home imbued with character and bright, airy spaces. The open-concept living area features

  Sharon Pehush HomeSmart Homes & Estates

  106 Stream Ln, Pleasant Valley, NY 12569
• 

  Not Listed For Sale

  0 Milewood Rd Unit KEYH6305719, Washington, NY 12545

  0 Milewood Rd Unit KEYH6305719, Washington, NY 12545
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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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  /2

  $2,200 - $2,500 per month

  Apartment for Rent

  2 Beds

  7 Oswego Rd, Pleasant Valley, NY 12569

  Rental is a two bedroom newly remodeled cottage adjacent to the main apartment building.

  7 Oswego Rd, Pleasant Valley, NY 12569
• 

  $508,000 Sold Jul 08, 2025

  • 1,600 Sq Ft
  • $318/SF
  • 41 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2015

  57 Whiteford Dr, Pleasant Valley, NY 12569

  PICTURESQUE RANCH STYLE HOME WITH 3 BEDROOMS, 1.5 BATHS ON AN ACRE OF BEAUTIFULLY LANDSCAPED LAND, COMPLETE WITH A LARGE SHED. ENTER THE HOME THROUGH A CUSTOM MADE DOOR & BE AMAZED AT THE OPEN & LIGHT LARGE LIVING AREA COMPLETE WITH CATHEDRAL CEILINGS & FOUR DORMERS ACTING AS SKYLIGHTS. THE CUSTOM KITCHEN, WITH A 10 FOOT ISLAND, WAS DESIGNED TO PLEASE ANY CHEF & OPENS INTO THE LIVING ROOM &

  SUSAN FEIT BHHS Hudson Valley Properties

  57 Whiteford Dr, Pleasant Valley, NY 12569
• 

  Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  323 Masten Rd Unit 325, Pleasant Valley, NY 12569

  323 Masten Rd Unit 325, Pleasant Valley, NY 12569
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  /44

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,024 Sq Ft

  12 Wolf Ln, Pleasant Valley, NY 12569

  Tucked away on over 14 acres of total privacy and tranquility, 12 Wolf Lane is a contemporary retreat offering 4,000+ square feet of beautifully designed living space and every amenity you could ask for. From the moment you arrive, you’ll feel the calm, surrounded by nature, fieldstone walls built with stone from the land itself, and the kind of seclusion that’s increasingly hard to

  Jake Garay Serhant LLC

  12 Wolf Ln, Pleasant Valley, NY 12569
• 

  

  /13

  $1,650 per month

  • 1 Bed
  • 1 Bath
  • 350 Sq Ft
  • Apartment for Rent

  1613 Main St Unit 1, Pleasant Valley, NY 12569

  Nearby shops, dining and an outdoor park.

  Mordchai Stern eRealty Advisors, Inc

  1613 Main St Unit 1, Pleasant Valley, NY 12569
• 

  $560,000 Sold Jul 07, 2025

  • 2,200 Sq Ft
  • $255/SF
  • 115 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2025

  60 Obrien Hill Rd, Union Vale, NY 12585

  Welcome to this beautifully designed newly built ranch-style home, offering modern comfort and timeless appeal. This spacious 3-bedroom, 3-full-bathroom home features an inviting open floor plan with high ceilings and gorgeous hardwood flooring throughout. The kitchen is a chef’s dream, complete with granite countertops, stainless steel appliances, and ample cabinet space.The energy-efficient

  Gina Tapia Guaman Keller Williams Realty Partner

  60 Obrien Hill Rd, Union Vale, NY 12585
• 

  Est $750,024 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,920 Sq Ft

  938 Freedom Rd Unit 965, Pleasant Valley, NY 12569

  938 Freedom Rd Unit 965, Pleasant Valley, NY 12569

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