Pleasant Valley, NY Homes

• 

  

  

  /39

  $625,000

  • 5 Beds
  • 3 Baths
  • 2,668 Sq Ft

  366 Overlook Rd, Pleasant Valley, NY 12569

  Welcome to 366 Overlook Road in Pleasant Valley—an exceptional raised ranch offering refined updates, thoughtful design, and outstanding flexibility. This spacious 5-bedroom, 3.5-bath home features two full kitchens with stainless steel appliances, ideal for versatile living arrangements, extended household needs, or guest accommodations. Additional highlights include a cozy fireplace, dedicated

  Joseph Lukic Compass Greater NY, LLC

  366 Overlook Rd, Pleasant Valley, NY 12569
• 

  $985,000 Sold Oct 20, 2025

  22 Tannen Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 3 Baths
  • 2,844 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $346/SF
  • 33 Days On Market

  Current Estimated Value $857,942

  Last Listing Agent JOAN PEDATELLA K. Fortuna Realty, Inc.

  22 Tannen Dr, Pleasant Valley, NY 12569
• 

  Est $686,015 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,625 Sq Ft

  50 Forest Meadow Dr, Salt Point, NY 12578

  50 Forest Meadow Dr, Salt Point, NY 12578
• 

  

  

  /30

  $609,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,048 Sq Ft

  112 Pleasant View Rd, Pleasant Valley, NY 12569

  Sprawling 3000+ square foot contemporary privately nestled on 1.65 acres in the desirable Arlington School District, just minutes from the Taconic State Parkway. Enter through the front door and into the formal foyer featuring a beautifully tiled floor, oversized coat closet, custom lighting and tucked in the corner, a private half bath. Relax in the massive living room accented by vaulted

  Dave Longbard KW MidHudson

  112 Pleasant View Rd, Pleasant Valley, NY 12569
• 

  $499,999 Sold Oct 16, 2025

  7 Gretna Park Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 2024

  Last Sold Summary

  • $298/SF
  • 44 Days On Market

  Last Listing Agent Rita White Keller Williams Realty Partner

  7 Gretna Park Rd, Pleasant Valley, NY 12569
• 

  Est $422,878 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 2,148 Sq Ft

  22 Promise Ln, Salt Point, NY 12578

  22 Promise Ln, Salt Point, NY 12578
• 

  /2

  $99,000 Pending

  • Land
  • 6.2 Acres
  • $15,968 per Acre

  Lot 748535 Hollow Crest Ln, Millbrook, NY 12545

  Some properties don’t need hype—they need context. Lot 748513 on Hollow Crest Lane is one of those rare pieces of land where the hard work has already been done and the setting speaks for itself. Set on 6.2 acres in the heart of Millbrook, this parcel comes with a current 4-bedroom Board of Health Approval, removing one of the biggest hurdles buyers face when considering vacant land. The

  Thomas Santore Coldwell Banker Realty

  Lot 748535 Hollow Crest Ln, Millbrook, NY 12545
• 

  $290,000 Sold Aug 13, 2025

  1358 Route 44, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1930

  Last Sold Summary

  • $264/SF
  • 40 Days On Market

  Current Estimated Value $293,426

  Last Listing Agent Richard Brenner Rich Brenner Realty, LLC

  1358 Route 44, Pleasant Valley, NY 12569
• 

  Est $470,145 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  43 Denise Ct, Salt Point, NY 12578

  43 Denise Ct, Salt Point, NY 12578
• 

  

  /8

  $289,500 Pending

  • 3 Beds
  • 1 Bath
  • 1,384 Sq Ft

  1680 Main St, Pleasant Valley, NY 12569

  This house set in one of the most desirable areas of Pleasant Valley with Arlington schools, this 3BR is close to shops and all the major highways. It offers a two car detached garage, back porch, hardwood floors, an original fireplace, and a large backyard for entertaining. House needs some TLC but, is a great first time home or investment property. ***Accepted Offer*** please show for backup.

  Sean McPhail Next Level Property Management

  1680 Main St, Pleasant Valley, NY 12569
• 

  $470,000 Sold Dec 11, 2025

  26 Carter Rd, Pleasant Valley, NY 12569

  • 2 Beds
  • 2 Baths
  • 1,518 Sq Ft
  • Built 1974

  Last Sold Summary

  • 14% Below List Price
  • $310/SF
  • 111 Days On Market

  Last Listing Agent Shawn Pitcher KFortuna All Aspects Realty

  26 Carter Rd, Pleasant Valley, NY 12569
• 

  

  /35

  Est $578,000 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,544 Sq Ft

  47 Eleanor Dr, Salt Point, NY 12578

  47 Eleanor Dr, Salt Point, NY 12578
• 

  

  /4

  $95,000 Pending

  • Land
  • 3.4 Acres
  • $27,941 per Acre

  0 New York 82, Pleasant Valley, NY 12569

  This 3.4 acre wooded lot in the Town of LaGrange offers a great opportunity to build your dream home. With approximately 145 feet of frontage on Cole Road and 720 feet along Route 82, this property provides multiple access points and design flexibility. Board of Health Approval (BOHA) is needed, making this an ideal blank canvas for your custom home project. Enjoy proximity to popular local spots

  Debra Allan BHHS Hudson Valley Properties

  0 New York 82, Pleasant Valley, NY 12569
• 

  $540,000 Sold Sep 26, 2025

  33 Stirrup Ln, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1979

  Last Sold Summary

  • 3% Above List Price
  • $311/SF
  • 23 Days On Market

  Current Estimated Value $537,253

  Last Listing Agent Ronald Green KW MidHudson

  33 Stirrup Ln, Pleasant Valley, NY 12569
• 

  Est $792,727 Not Listed For Sale

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

  422 Masten Rd, Pleasant Valley, NY 12569

  422 Masten Rd, Pleasant Valley, NY 12569
• 

  

  /26

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  62 Netherwood Plaza, Salt Point, NY 12578

  Discover your private retreat at the end of a peaceful dead end street with this enchanting, move-in-ready home. This charming 3-bedroom, 2-bathroom residence seamlessly blends cozy cabin vibes with tasteful, modern updates throughout. An abundance of windows floods the entire home with natural light, highlighting the warm and inviting atmosphere. The well-appointed kitchen is a chef's delight,

  Samantha McCrory Exit Realty Connections

  62 Netherwood Plaza, Salt Point, NY 12578
• 

  $45,000 Sold Aug 22, 2025

  30 Elm Ln, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1979

  Last Sold Summary

  • 50% Below List Price
  • $46/SF
  • 99 Days On Market

  Last Listing Agent Steven Collier BHHS Hudson Valley Properties

  30 Elm Ln, Pleasant Valley, NY 12569
• 

  Est $609,741 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,783 Sq Ft

  359 Masten Rd, Pleasant Valley, NY 12569

  359 Masten Rd, Pleasant Valley, NY 12569
• 

  

  /12

  $1,300,000

  • Land
  • 90.32 Acres
  • $14,393 per Acre

  0 Gretna Rd, Pleasant Valley, NY 12569

  Own one of the last legacy parcels in this coveted corridor of Dutchess County. Seldom does a property of this caliber come to market with over 90 acres of serene rural land, gently rolling fields and woodland, tucked away among historic farms and long-established estates.The property reflects a well-established equestrian legacy, shaped over time across gently rolling fields and wooded

  Rob Buyakowski RBR Real Estate Solutions LLC

  0 Gretna Rd, Pleasant Valley, NY 12569
• 

  $282,500 Sold Oct 31, 2025

  1253 Salt Point Turnpike, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 916 Sq Ft
  • Built 1949

  Last Sold Summary

  • 9% Above List Price
  • $308/SF
  • 40 Days On Market

  Current Estimated Value $280,936

  Last Listing Agent Susan Whalen George T Whalen Real Estate

  1253 Salt Point Turnpike, Pleasant Valley, NY 12569
• 

  Est $820,027 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,209 Sq Ft

  2153 Route 44, Pleasant Valley, NY 12569

  2153 Route 44, Pleasant Valley, NY 12569
• 

  

  /38

  $254,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  445 Creek Rd, Pleasant Valley, NY 12569

  - This small cottage is situated on a private 1.75 acre lot that includes a variety of flowering plants and trees including a rare, but beautiful Mimosa tree. The back yard leads you to the creek which is an ideal area to relax and enjoy a cup of coffee and a favorite book. This home as it currently sits is ideal for a couple, but there is room for expansion. The town currently has this home

  Susan Budai BROCKTON DAVIS REAL ESTATE CONSULTANTS INC

  445 Creek Rd, Pleasant Valley, NY 12569
• 

  $440,000 Sold Nov 20, 2025

  19 Gleason Blvd, Pleasant Valley, NY 12569

  • 3 Beds
  • 1.5 Baths
  • 1,702 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $259/SF
  • 48 Days On Market

  Last Listing Agent Dominick DiFilippo Keller Williams Realty Partner

  19 Gleason Blvd, Pleasant Valley, NY 12569
• 

  Est $236,418 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 484 Sq Ft

  2562 Route 44, Salt Point, NY 12578

  2562 Route 44, Salt Point, NY 12578
• 

  /2

  $85,000

  • Land
  • 2.7 Acres
  • $31,481 per Acre

  0 Freedom Rd, Pleasant Valley, NY

  Board of Health approved lot in beautiful Pleasant Valley. Just minutes to the Lagrange Town Center, and to the Taconic State Parkway. This is a fantastic location to build a home in the heart of Dutchess County.

  Ryan LaLuna McGrath Realty Inc

  0 Freedom Rd, Pleasant Valley, NY
• 

  $900,000 Sold Aug 07, 2025

  422 Rossway Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 3,770 Sq Ft
  • Built 2004

  Last Sold Summary

  • $239/SF
  • 161 Days On Market

  Current Estimated Value $906,453

  Last Listing Agent Kaye Saglibene

  422 Rossway Rd, Pleasant Valley, NY 12569
• 

  Est $761,243 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,816 Sq Ft

  491 Masten Rd, Pleasant Valley, NY 12569

  491 Masten Rd, Pleasant Valley, NY 12569
• 

  

  /26

  $1,750,000

  • 6 Beds
  • 3.5 Baths
  • 4,248 Sq Ft

  11 Brown Rd, Pleasant Valley, NY 12569

  Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: Sarah famously sent cheese from her dairy to George Washington's encampment nearby. Over the years, the home has flown both British

  Daniel Colomban Skyler Realty LLC

  11 Brown Rd, Pleasant Valley, NY 12569
• 

  $185,250 Sold Nov 26, 2025

  11 Demelis Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 1 Bath
  • 1,520 Sq Ft
  • Built 1963

  Last Sold Summary

  • 32% Below List Price
  • $122/SF
  • 72 Days On Market

  Last Listing Agent Brian Smith River Realty Services, Inc.

  11 Demelis Dr, Pleasant Valley, NY 12569
• 

  Est $401,155 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,196 Sq Ft

  2322 Route 44, Pleasant Valley, NY 12569

  2322 Route 44, Pleasant Valley, NY 12569
• 

  

  /27

  $349,000 Pending

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft

  387 Freedom Rd, Pleasant Valley, NY 12569

  Discover the potential at 387 Freedom Road—a 3-bed, 1-bath in the highly sought after Arlington School District. This well maintained home is set back off the road on an acre of land and offers peace, privacy, and charm. A welcoming front porch is the perfect spot to take in the natural surroundings, while enjoying your morning coffee. Inside features include luxury vinyl plank flooring

  John Gabriel Jr KW MidHudson

  387 Freedom Rd, Pleasant Valley, NY 12569
• 

  $740,000 Sold Sep 16, 2025

  28 Hurley Rd, Salt Point, NY 12578

  • 4 Beds
  • 4 Baths
  • 3,088 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Above List Price
  • $240/SF
  • 24 Days On Market

  Current Estimated Value $691,996

  Last Listing Agent Craig Smith Compass Greater NY, LLC

  28 Hurley Rd, Salt Point, NY 12578
• 

  Est $708,041 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,930 Sq Ft

  21 Trillium Rd, Pleasant Valley, NY 12569

  21 Trillium Rd, Pleasant Valley, NY 12569
• 

  

  /40

  $1,815,000 Pending

  380 Freedom Rd, Pleasant Valley, NY 12569

  PRICE REDUCED!! The sellers are also willing to negotiate terms for seller financing. This is your opportunity to own a slice of history and pastoral beauty in the heart of Pleasant Valley, NY. This 138.4-acre dairy farm combines fertile land with panoramic views and endless possibilities, making it an ideal investment for farming, recreation, or development. The land has not had any in organic

  Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  380 Freedom Rd, Pleasant Valley, NY 12569
• 

  $532,500 Sold Jun 11, 2025

  49 North Ave, Pleasant Valley, NY 12569

  • 4 Beds
  • 3 Baths
  • 3,596 Sq Ft
  • Built 1850

  Last Sold Summary

  • 8% Below List Price
  • $148/SF
  • 134 Days On Market

  Current Estimated Value $537,215

  Last Listing Agent JOHN SCARANO Keller Williams Realty

  49 North Ave, Pleasant Valley, NY 12569
• 

  Est $458,375 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,694 Sq Ft

  234 Rossway Rd, Pleasant Valley, NY 12569

  234 Rossway Rd, Pleasant Valley, NY 12569
• 

  

  /20

  $399,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  63 Parksville Rd, Pleasant Valley, NY 12569

  Fully rented two-family home in Pleasant Valley offering a strong opportunity for investors or future owner-occupants, set on a creekside lot backing directly to the Wappingers Creek. The upper unit has been updated, both units are currently occupied and producing income, and the property offers plenty of off-street parking for tenants. Conveniently located just minutes to the Town of Pleasant

  STEVEN WROBEL JR. Serhant LLC

  63 Parksville Rd, Pleasant Valley, NY 12569
• 

  $552,000 Sold Jun 02, 2025

  4 Straub Dr, Pleasant Valley, NY 12569

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $230/SF
  • 155 Days On Market

  Current Estimated Value $569,921

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  4 Straub Dr, Pleasant Valley, NY 12569
• 

  Est $457,995 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  224 Rossway Rd, Pleasant Valley, NY 12569

  224 Rossway Rd, Pleasant Valley, NY 12569
• 

  

  /27

  $325,000 Pending

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  38 Marshall Rd, Hyde Park, NY 12538

  Welcome to this charming 3-bedroom, 1-bath ranch on a half-acre. Inside you’ll find hardwood floors that bring warmth and character throughout, along with recent updates including the boiler, windows, and roof so you can move right in with ease. The single-level layout makes everyday living simple and convenient, while the spacious yard offers plenty of room for gardening, play, or relaxing

  STEVEN WROBEL JR. Serhant LLC

  38 Marshall Rd, Hyde Park, NY 12538

Showing Results 41 - 80, Page 2 of 18