Homes in ZIP Code 12569

• 

  Est $772,581 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
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• 

  

  

  /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
• 

  $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
• 

  Est $753,880 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
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  /6

  $240,000

  • Land
  • 29.2 Acres
  • $8,219 per Acre

  0 James Way Unit ONEH6325454, Pleasant Valley, NY 12569

  Attention builders. 2 parcels totaling 29.2 acres with approximately 18 acres of level cleared land. Definitely worth taking a look at this wonderful property with subdivision possibilities. Located at the end of the road. Property includes parcel 1344006363033554200000. Assessment and taxes are the total for both parcels.

  Judy Lancia

  0 James Way Unit ONEH6325454, 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

  Last Listing Agent Ronald Green KW MidHudson

  33 Stirrup Ln, Pleasant Valley, NY 12569
• 

  Est $836,172 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
• 

  $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 $769,444 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
• 

  

  /50

  $799,000

  • 6 Beds
  • 4.5 Baths
  • 3,974 Sq Ft

  82 Thornhill Dr, Pleasant Valley, NY 12569

  Stunning Pleasant Valley Colonial in park-like setting: This wonderful 6 bedroom home can be your personal oasis; close enough to civilization to have convenience, yet just rural enough to also have serenity. The acre and a half property features stately, landscaped front & side yards with walkways & mature trees - and a more private, fenced & wooded backyard that is all about relaxing and/or

  Christopher Hanson Hanson Real Estate Partners

  82 Thornhill Dr, 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

  Last Listing Agent Susan Whalen George T Whalen Real Estate

  1253 Salt Point Turnpike, Pleasant Valley, NY 12569
• 

  Est $391,556 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
• 

  

  /13

  $229,900

  • Land
  • 4.81 Acres
  • $47,796 per Acre

  0 Freedom Rd Unit KEY913491, La Grange, NY 12569

  4.81 Acre Parcel in the Heart of Lagrange Discover the perfect blend of privacy and convenience with this 4.81-acre wooded parcel in the heart of Lagrange. Nestled in a peaceful natural setting, yet just minutes to everything the Hudson Valley has to offer, this location is ideal for your dream home—or for a potential small subdivision. Commuters will appreciate the easy access to the Taconic

  Michael Tellerday Houlihan Lawrence Inc.

  0 Freedom Rd Unit KEY913491, La Grange, 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 $678,803 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
• 

  /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 $903,047

  Last Listing Agent Kaye Saglibene

  422 Rossway Rd, Pleasant Valley, NY 12569
• 

  Est $460,098 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
• 

  

  /47

  $625,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,159 Sq Ft

  244 Rombout Rd, Pleasant Valley, NY 12569

  Plenty of room for everyone! Picture perfect 4 bedroom, 3.5 bath Contemporary Raised Ranch tucked away on 2.77 private acres. Main floor features include large living room with wood burning fireplace and gleaming wide plank floors, eat in kitchen with ceramic tiled floors, granite countertops and new appliances, formal dining room, Expansive primary en-suite with gas fireplace. 3 additional

  Lynn Angelo BHHS Hudson Valley Properties

  244 Rombout 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 $459,043 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
• 

  

  /38

  $2,195,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 6,452 Sq Ft

  189 Freedom Rd, Pleasant Valley, NY 12569

  An Enchanting Stone Manor-First Time Offered. Set amidst exquisitely landscaped grounds in the heart of the Hudson Valley, this extraordinary stone manor is a triumph of design, craftsmanship, and setting—gracefully secluded, yet just minutes from the bucolic village of Millbrook. Meticulously conceived and built to the highest standards, the estate is being offered for the very first

  Jill Rose Houlihan Lawrence Inc.

  189 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 $531,890

  Last Listing Agent JOHN SCARANO Keller Williams Realty

  49 North Ave, Pleasant Valley, NY 12569
• 

  Est $595,365 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,636 Sq Ft

  69 Birch Dr, Pleasant Valley, NY 12569

  69 Birch Dr, Pleasant Valley, NY 12569
• 

  

  /50

  $2,995,000

  • 4 Beds
  • 7 Baths
  • 6,412 Sq Ft

  165 Drake Rd, Pleasant Valley, NY 12569

  Welcome to Timber Lake Farm, a stunning property in the heart of Dutchess County horse country. This Adirondack-style estate offers a harmonious blend of rustic elegance and modern luxury, set on 33.26-acre lot with a pristine 9-acre pond that flows over a waterfall at one end. The bespoke stone and wood home boasts 6,412 square feet of living space sited at the highest elevation point on the

  Kyle Irwin Corcoran Country Living

  165 Drake 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 $563,494

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  4 Straub Dr, Pleasant Valley, NY 12569
• 

  Est $589,782 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,028 Sq Ft

  31 Birch Dr, Pleasant Valley, NY 12569

  31 Birch Dr, Pleasant Valley, NY 12569
• 

  

  /4

  $287,100 Pending

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  15 Barbara Ln, Pleasant Valley, NY 12569

  A New Chapter Awaits in Pleasant Valley!Welcome to this charming 3-bedroom, 1-bathroom split-level home, perfectly situated on a beautiful half-acre lot in Pleasant Valley, NY. This 1250 sq ft residence offers a fantastic opportunity for those seeking to create their dream home in Dutchess County.Step inside and discover the potential. The main living area provides a comfortable space for

  Joe Kuhl River Realty Services, Inc.

  15 Barbara Ln, Pleasant Valley, NY 12569
• 

  $685,000 Sold Jul 11, 2025

  22 Gretna Woods Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 3 Baths
  • 3,400 Sq Ft
  • Built 1965

  Last Sold Summary

  • 14% Below List Price
  • $201/SF
  • 22 Days On Market

  Current Estimated Value $681,449

  Last Listing Agent JOAN PEDATELLA BHHS Hudson Valley Properties

  22 Gretna Woods Rd, Pleasant Valley, NY 12569
• 

  Est $451,540 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,447 Sq Ft

  22 Tyrell Rd, Pleasant Valley, NY 12569

  22 Tyrell Rd, 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
• 

  $345,000 Sold Sep 11, 2025

  16 Nied Dr, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 1,184 Sq Ft
  • Built 1960

  Last Sold Summary

  • 8% Below List Price
  • $291/SF
  • 77 Days On Market

  Current Estimated Value $351,927

  Last Listing Agent ABBY JOSIAH KW MidHudson

  16 Nied Dr, Pleasant Valley, NY 12569
• 

  Est $364,050 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,530 Sq Ft

  237 Masten Rd, Pleasant Valley, NY 12569

  237 Masten Rd, Pleasant Valley, NY 12569
• 

  

  /40

  $1,815,000

  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
• 

  $155,000 Sold Jan 24, 2025

  47 View Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1980

  Last Sold Summary

  • $155/SF
  • 82 Days On Market

  Last Listing Agent ANDREA SOTOMAYOR K Fortuna Lighthouse Realty

  47 View Dr, Pleasant Valley, NY 12569
• 

  Est $483,298 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft

  53 Masten Rd, Pleasant Valley, NY 12569

  53 Masten Rd, Pleasant Valley, NY 12569
• 

  

  /23

  $215,000

  • Land
  • 5.04 Acres
  • $42,659 per Acre

  L510455 Creek Rd, Pleasant Valley, NY 12569

  Situated on Creek Rd, along Wappinger Creek in the desirable town of Pleasant Valley, this 5.04 acres site is ready for your site improvements and building. The driveway has already been rough cut in with the location for the house accessible for further clearing and site preparation. Current BOH approved with proposed site location for house, well, and septic. Bring your contractor and architect

  Gary Martin Compass Greater NY LLC

  L510455 Creek Rd, Pleasant Valley, NY 12569
• 

  $625,000 Sold Feb 07, 2025

  186 Creek Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,744 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $228/SF
  • 40 Days On Market

  Current Estimated Value $688,173

  Last Listing Agent LISA WOHLMUTH

  186 Creek Rd, Pleasant Valley, NY 12569
• 

  Est $479,242 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,226 Sq Ft

  193 Rossway Rd, Pleasant Valley, NY 12569

  193 Rossway Rd, Pleasant Valley, NY 12569

Showing Results 41 - 80, Page 2 of 18