Pleasant Valley, NY Homes

• 

  

  

  /23

  $799,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft

  991 Freedom Rd, Pleasant Valley, NY 12569

  TO BE BUILT – The Vanderbilt Model Colonial on Over 3 Acres!This stunning 4-bedroom, 2.5-bath colonial offers the perfect blend of elegance and functionality. The thoughtfully designed main level features a formal living room and dining room, a spacious family room that showcases a gas fireplace and a wall of windows, seamlessly opening to the kitchen with quartz counters, a center island,

  John Gabriel Jr KW MidHudson

  991 Freedom Rd, Pleasant Valley, NY 12569
• 

  $640,000

  Sold Mar 18, 2026

  2 English Way, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $243/SF
  • 34 Days On Market

  Current Estimated Value $654,411

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  2 English Way, Pleasant Valley, NY 12569
• 

  Est $801,764

  Not Listed For Sale

  45 Cider Mill Ct, Pleasant Valley, NY 12569

  • 4 Beds
  • 3 Baths
  • 2,566 Sq Ft
  • Built 2007

  45 Cider Mill Ct, Pleasant Valley, NY 12569

  Last Sold Summary

  • 91 Days On Market

  Last Listing Agent Lori Roell BHHS Hudson Valley Properties
• 

  

  

  /27

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,780 Sq Ft

  27 Patricia Dr, Pleasant Valley, NY 12569

  Welcome to this spacious 4-bedroom, 2-bathroom contemporary home offering 2,780 square feet of thoughtfully designed living space on 2.24 picturesque acres within the Arlington Central School District. Blending timeless architecture with an inviting layout, this home offers the perfect balance of comfort, functionality, and privacy. A long driveway leads to the home, where mature trees, expansive

  Justin LaFalce KW MidHudson

  27 Patricia Dr, Pleasant Valley, NY 12569
• 

  $371,000

  Sold Aug 11, 2026

  430 North Ave, Pleasant Valley, NY 12569

  • 3 Beds
  • 1 Bath
  • 1,666 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Above List Price
  • $223/SF
  • 34 Days On Market

  Current Estimated Value $358,857

  Last Listing Agent Michael Strutt BHHS Hudson Valley Properties

  430 North Ave, Pleasant Valley, NY 12569
• 

  Est $715,508

  Not Listed For Sale

  57 Cider Mill Ct, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,199 Sq Ft
  • Built 2005

  57 Cider Mill Ct, Pleasant Valley, NY 12569

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Justin LaFalce KW MidHudson
• 

  

  /50

  $1,495,000

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

  49 Barkit Kennel Rd, Pleasant Valley, NY 12569

  Rare and extraordinary custom built private estate nestled on 43 private acres in the heart of Pleasant Valley. Surrounded by rolling woodlands and breathtaking natural beauty, this exceptional residence offers an unparalleled blend of timeless elegance, refined craftsmanship, and resort-style living. Whether you're seeking a luxurious full-time residence, an executive retreat, or a secluded

  Justin Phillips United RE Hudson Valley Edge

  49 Barkit Kennel Rd, Pleasant Valley, NY 12569
• 

  $630,000

  Sold Mar 19, 2026

  404 Gretna Rd, Hyde Park, NY 12538

  • 5 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Below List Price
  • $210/SF
  • 112 Days On Market

  Current Estimated Value $657,756

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  404 Gretna Rd, Hyde Park, NY 12538
• 

  Est $725,867

  Not Listed For Sale

  78 Parksville Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,561 Sq Ft
  • Built 1998

  78 Parksville Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Jaime Thomas CBC Realty Services LLC
• 

  

  /49

  $799,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,438 Sq Ft

  44 Eleanor Dr, Salt Point, NY 12578

  Tucked away on 3.66 private acres in the heart of Salt Point, this custom contemporary home offers a rare combination of seclusion, character, and functionality. Surrounded by mature trees and natural landscape, the property provides a peaceful setting while remaining conveniently located to nearby amenities and commuter routes. Designed with a unique architectural style, the home features 2,438

  STEVEN WROBEL JR. Serhant LLC

  44 Eleanor Dr, Salt Point, NY 12578
• 

  $675,000

  Sold Jul 22, 2026

  343 North Ave, Pleasant Valley, NY 12569

  • 3 Beds
  • 3.5 Baths
  • 3,041 Sq Ft
  • Built 2005

  Last Sold Summary

  • $222/SF
  • 46 Days On Market

  Current Estimated Value $673,946

  Last Listing Agent John Durso Keller Williams Realty Partner

  343 North Ave, Pleasant Valley, NY 12569
• 

  /2

  Est $712,268

  Not Listed For Sale

  28 Mill Ln, Pleasant Valley, NY 12569

  • 4 Beds
  • 3 Baths
  • 3,040 Sq Ft
  • Built 1976

  28 Mill Ln, Pleasant Valley, NY 12569
• 

  

  /50

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 3,106 Sq Ft

  100 Rockledge Dr, Pleasant Valley, NY 12569

  Roof is brand new. Perfectly positioned just two miles from the Taconic State Parkway, this exceptional home offers an easy commute north or south while being only five minutes from Overlook Elementary School and nine minutes from Arlington High School.Designed with both comfort and functionality in mind, the home features hardwood floors and elegant crown molding throughout, hydro-air

  Peggy Santamorena Houlihan Lawrence Inc.

  100 Rockledge Dr, Pleasant Valley, NY 12569
• 

  $625,000

  Sold May 26, 2026

  303 Freedom Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 4 Baths
  • 4,160 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $150/SF
  • 19 Days On Market

  Current Estimated Value $645,700

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  303 Freedom Rd, Pleasant Valley, NY 12569
• 

  Est $503,855

  Not Listed For Sale

  38 Parksville Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft
  • Built 2011

  38 Parksville Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Joseph Lukic Compass Greater NY, LLC
• 

  

  /37

  $695,000

  $100K PRICE DROP

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

  41 Meddaugh Rd, Pleasant Valley, NY 12569

  Welcome to 41 Meddaugh Road, a beautifully transformed 4 bedroom, 2.5 bathroom contemporary home with Hudson Valley historic farmhouse charm. Setback from the road, this turnkey home is sited on 1.84 acres and has undergone an extensive ground-up renovation. This property was previously under contract. The buyer was unable to close due to a contingency on their own home sale -- not any issue with

  Kyle Irwin Corcoran Country Living

  41 Meddaugh Rd, Pleasant Valley, NY 12569
• 

  $310,000

  Sold Jan 19, 2026

  201 Rossway Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 1 Bath
  • 998 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $311/SF
  • 35 Days On Market

  Current Estimated Value $327,961

  Last Listing Agent Heather Bragg River to Ridge Rlty Associates

  201 Rossway Rd, Pleasant Valley, NY 12569
• 

  Est $471,553

  Not Listed For Sale

  236 Lakeshore Dr, Pleasant Valley, NY 12569

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1850

  236 Lakeshore Dr, Pleasant Valley, NY 12569

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Jake Garay Serhant LLC
• 

  

  /41

  $1,100,000

  $50K PRICE DROP

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

  129 Clinton Corners Rd, Salt Point, NY 12578

  Set behind a sweeping driveway canopied by pear trees in bloom, this extraordinary post-and-beam contemporary is a study in what privacy truly looks like — 18.5 acres of curated landscape, forest trails, and open sky, ten minutes from the Taconic State Parkway. The architecture announces itself immediately: soaring 25-foot cathedral ceilings, a commanding central stone fireplace, and grand

  Ryan Arket Compass Greater NY, LLC

  129 Clinton Corners Rd, Salt Point, NY 12578
• 

  $220,000

  Sold Feb 02, 2026

  453 Pine Hill Rd, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 846 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $260/SF
  • 63 Days On Market

  Current Estimated Value $228,818

  Last Listing Agent Ronald Green KW MidHudson

  453 Pine Hill Rd, Pleasant Valley, NY 12569
• 

  Est $419,513

  Not Listed For Sale

  47 Arbor Hill Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • Built 1965

  47 Arbor Hill Dr, Pleasant Valley, NY 12569

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Patricia Hogan BHHS Hudson Valley Properties
• 

  

  /15

  $184,900

  • 2 Beds
  • 1 Bath
  • 1,098 Sq Ft

  4 Wilbur Rd, Pleasant Valley, NY 12569

  DIAMOND IN THE ROUGH! HUGE POSSIBILITIES! RANCH HOME TWO BEDROOM, OFFICE OR NURSERY, DEN, LIVINGROOM. EAT IN KITCHEN WITH SLIDERS TO HUGE DECK. SPACIOUS ROOMS. BASEMENT AND WORKSHOP. PRIVATE YARD. ENJOY BACK YARD CREEK VIEWS.MATURE LANDSCAPING. CONVENIENT TO EASTDALE VILLAGE AND ALL AMENITIES. MIN. TOTSP AND TRAIN. WAPPINGERS CREEK FOR FISHING. KAYAKING AND SUMMER FUN.

  Angela Kern BHHS Hudson Valley Properties

  4 Wilbur Rd, Pleasant Valley, NY 12569
• 

  $630,000

  Sold Nov 13, 2025

  129 Barkit Kennel Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 3.5 Baths
  • 2,716 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Above List Price
  • $232/SF
  • 35 Days On Market

  Current Estimated Value $701,311

  Last Listing Agent Kimberlee Markarian BHHS Hudson Valley Properties

  129 Barkit Kennel Rd, Pleasant Valley, NY 12569
• 

  Est $388,238

  Not Listed For Sale

  1771 Route 44, Pleasant Valley, NY 12569

  • 4 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1966

  1771 Route 44, Pleasant Valley, NY 12569

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Susan Stevens BHHS Hudson Valley Properties
• 

  

  /49

  $699,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  394 Smith Rd, Hyde Park, NY 12538

  Welcome to 394 Smith Rd. A sprawling Mid-Century Ranch on Nearly 10 Acres with Pond & Panoramic Views. Set on nearly 10 private acres, this picturesque sprawling ranch offers true one-level living with breathtaking 360-degree views, including stunning sunrises and sunsets. Tucked back from the road and elevated for maximum privacy, this special property blends natural beauty and charm.The

  LISA WOHLMUTH KW MidHudson

  394 Smith Rd, Hyde Park, NY 12538
• 

  $443,500

  Sold Oct 10, 2025

  113 Rossway Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $243/SF
  • 27 Days On Market

  Current Estimated Value $470,772

  Last Listing Agent Stephenie DiMase Exit Realty Connections

  113 Rossway Rd, Pleasant Valley, NY 12569
• 

  Est $463,066

  Not Listed For Sale

  34 Briar Patch Ln, Pleasant Valley, NY 12569

  • 4 Beds
  • 1.5 Baths
  • 1,776 Sq Ft
  • Built 1981

  34 Briar Patch Ln, Pleasant Valley, NY 12569

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Umesh Shrestha BHHS Hudson Valley Properties
• 

  

  /38

  $549,500

  • 4 Beds
  • 2.5 Baths
  • 2,469 Sq Ft

  34 Contour Ln, Salt Point, NY 12578

  Welcome to 34 Contour Lane. Situated on a small cul-de-sac and nestled on almost 4 private acres in the heart of Salt Point, equidistant between the Villages of Rhinebeck and Millbrook. This beautifully maintained 4-bedroom, 2.5-bath Colonial offers the perfect blend of timeless charm, modern updates, and peaceful country living. Offering almost 2500 finished SQFT, this home welcomes you with

  Justin LaFalce KW MidHudson

  34 Contour Ln, Salt Point, NY 12578
• 

  $575,000

  Sold Aug 06, 2026

  66 Gretna Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,384 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Above List Price
  • $241/SF
  • 82 Days On Market

  Current Estimated Value $570,246

  Last Listing Agent Karen Volino Houlihan Lawrence Inc.

  66 Gretna Rd, Pleasant Valley, NY 12569
• 

  Est $389,194

  Not Listed For Sale

  768 Traver Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 1.5 Baths
  • 2,040 Sq Ft
  • Built 1957

  768 Traver Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent KARINA POZZA Rich Brenner Realty, LLC
• 

  $635,000

  Sold Mar 31, 2026

  366 Overlook Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 3 Baths
  • 2,668 Sq Ft
  • Built 1975

  Last Sold Summary

  • 2% Above List Price
  • $238/SF
  • 33 Days On Market

  Current Estimated Value $639,995

  Last Listing Agent Joseph Lukic Compass Greater NY, LLC

  366 Overlook Rd, Pleasant Valley, NY 12569
• 

  Est $687,485

  Not Listed For Sale

  48 Briar Patch Ln, Pleasant Valley, NY 12569

  • 4 Beds
  • 2.5 Baths
  • 3,550 Sq Ft
  • Built 1982

  48 Briar Patch Ln, Pleasant Valley, NY 12569

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Omar Harper Epique Realty
• 

  $500,000

  Sold Aug 17, 2026

  25 Mcallister Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Above List Price
  • $278/SF
  • 20 Days On Market

  Current Estimated Value $474,905

  Last Listing Agent Emmanuel Jimenez Compass Greater NY, LLC

  25 Mcallister Dr, Pleasant Valley, NY 12569
• 

  Est $395,151

  Not Listed For Sale

  774 Traver Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1952

  774 Traver Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.
• 

  $555,000

  Sold Oct 20, 2025

  844 Salt Point Turnpike, Poughkeepsie, NY 12601

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1983

  Last Sold Summary

  • 1% Above List Price
  • $241/SF
  • 84 Days On Market

  Current Estimated Value $565,199

  Last Listing Agent Brian Woolsey BHHS Hudson Valley Properties

  844 Salt Point Turnpike, Poughkeepsie, NY 12601
• 

  Est $621,189

  Not Listed For Sale

  779 Traver Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,940 Sq Ft
  • Built 1984

  779 Traver Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Ellen 'Ellie' Savoy Houlihan Lawrence Inc.
• 

  $430,000

  Sold Apr 06, 2026

  6 Swain Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft
  • Built 1950

  Last Sold Summary

  • 10% Below List Price
  • $256/SF
  • 309 Days On Market

  Current Estimated Value $431,454

  Last Listing Agent Thomas Klug HV Premier Properties Realty

  6 Swain Dr, Pleasant Valley, NY 12569
• 

  Est $474,634

  Not Listed For Sale

  64 Creek Rd, Pleasant Valley, NY 12569

  • 1 Bed
  • 1 Bath
  • 870 Sq Ft
  • Built 1952

  64 Creek Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Philip Messina BHHS Hudson Valley Properties
• 

  $381,000

  Sold Apr 16, 2026

  1245 Salt Point Turnpike, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 1,648 Sq Ft
  • Built 1951

  Last Sold Summary

  • 1% Below List Price
  • $231/SF
  • 28 Days On Market

  Current Estimated Value $390,601

  Last Listing Agent Susan Whalen George T Whalen Real Estate

  1245 Salt Point Turnpike, Pleasant Valley, NY 12569
• 

  Est $645,253

  Not Listed For Sale

  106 Stream Ln, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,678 Sq Ft
  • Built 1964

  106 Stream Ln, Pleasant Valley, NY 12569

  Last Sold Summary

  • 137 Days On Market

  Last Listing Agent Sharon Pehush HomeSmart Homes & Estates

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