Homes in ZIP Code 12569

• 

  Est $509,953

  Not Listed For Sale

  13 Birch Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1986

  13 Birch Dr, Pleasant Valley, NY 12569

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Michele Rios BHHS Hudson Valley Properties
• 

  

  

  /47

  $569,900

  • 2 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  145 Drake Rd, Pleasant Valley, NY 12569

  What if your backyard came with its own pond? Welcome to 145 Drake Road, a charming, meticulously kept Hudson Valley Colonial farmhouse where timeless character, natural beauty, and the pleasures of country living come together on 1.33 beautifully maintained acres in the Arlington School District. Tucked into a peaceful Pleasant Valley setting, this lovingly cared-for home offers 1,488 square

  Ian Pinckney Curasi Realty, Inc.

  145 Drake 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

  Current Estimated Value $456,827

  Last Listing Agent Dominick DiFilippo Keller Williams Realty Partner

  19 Gleason Blvd, Pleasant Valley, NY 12569
• 

  Est $524,624

  Not Listed For Sale

  22 Tyrell Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • Built 1969

  22 Tyrell Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 106 Days On Market

  Last Listing Agent Curtis Darragh Legacy Land & Homes LLC
• 

  

  

  /32

  $449,900

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  1078 Salt Point Turnpike, Pleasant Valley, NY 12569

  PEACEFUL AND PRIVATE newly renovated 3BR home in the Town of Pleasant Valley. Brand new kitchen with granite counters and new stainless appliances. Bright, spacious sunroom overlooking the peaceful yard and woods in the rear of the property. Large, open living/dining room and an additional family room. Beautifully refinished original hardwood floors and fresh paint throughout. Large 2nd floor

  RENATE POGGE Century 21 Alliance Rlty Group

  1078 Salt Point Turnpike, Pleasant Valley, NY 12569
• 

  $277,850

  Sold Jul 13, 2026

  163 Bower Rd, Poughkeepsie, NY 12603

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft
  • Built 1931

  Last Sold Summary

  • 7% Below List Price
  • $300/SF
  • 38 Days On Market

  Current Estimated Value $288,612

  Last Listing Agent Myriam Ramos Keller Williams Realty Partner

  163 Bower Rd, Poughkeepsie, NY 12603
• 

  Est $494,626

  Not Listed For Sale

  53 Masten Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 1974

  53 Masten Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Margaret Labozzetti BHHS Hudson Valley Properties
• 

  

  /26

  $1,395,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  625 Traver Rd, Pleasant Valley, NY 12569

  QUICK DELIVERY NEW CONSTRUCTION! Welcome to your own private retreat in the heart of Pleasant Valley. A Modern Scandinavian Ranch style home nestled on an extraordinary 25-acre parcel surrounded by nature, this custom Den Barnhouse Plan seamlessly blends timeless Scandinavian design with a highly efficient, thoughtfully crafted floor plan. Offering the perfect balance of modern simplicity and

  Justin LaFalce KW MidHudson

  625 Traver 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

  Current Estimated Value $235,823

  Last Listing Agent Brian Smith River Realty Services, Inc.

  11 Demelis Dr, Pleasant Valley, NY 12569
• 

  Est $498,464

  Not Listed For Sale

  193 Rossway Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 2,226 Sq Ft
  • Built 1991

  193 Rossway Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Andrew Moore Daniel Gale Sothebys Intl Rlty
• 

  

  /21

  $799,999

  • Land
  • 93 Acres
  • $8,602 per Acre

  46 South Ave, Pleasant Valley, NY 12569

  3 PARCELS 93.3 ACRES! Discover a rare opportunity in the heart of Pleasant Valley with this expansive offering of three contiguous parcels totaling approximately 93 acres. Whether you're looking to build a private estate, establish a compound, invest in land, or explore development potential, this property offers exceptional flexibility with subdivision possibilities (subject to municipal

  MICHAEL SANTARPIA K. Fortuna Realty, Inc.

  46 South Ave, Pleasant Valley, NY 12569
• 

  $2,795,000

  Sold May 29, 2026

  165 Drake Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 7 Baths
  • 6,412 Sq Ft
  • Built 2010

  Last Sold Summary

  • 24% Below List Price
  • $436/SF
  • 347 Days On Market

  Last Listing Agent E. ELIZABETH PETERS Corcoran Country Living

  165 Drake Rd, Pleasant Valley, NY 12569
• 

  Est $738,896

  Not Listed For Sale

  75 Grist Mill Ln, Pleasant Valley, NY 12569

  • 4 Beds
  • 2.5 Baths
  • 3,099 Sq Ft
  • Built 2004

  75 Grist Mill Ln, Pleasant Valley, NY 12569

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent MariaElaina Cirone Keller Williams Realty Partner
• 

  

  /28

  $779,000

  New Construction $20K PRICE INCREASE Pending

  • 4 Beds
  • 2.5 Baths
  • 2,434 Sq Ft

  989 Freedom Rd, Pleasant Valley, NY 12569

  TO BE BUILT: Introducing the wildly-popular Jefferson model, a colonial-style home in Arlington School District on almost 2 acres! Highlights of this 4 BR 2.5 bath include: 9' first floor ceilings, an expansive open concept kitchen, breakfast area and family room with a fireplace, home office, master bedroom suite with tray ceiling, second floor laundry and 2 car garage. Generous-sized bedrooms,

  John Gabriel Jr KW MidHudson

  989 Freedom Rd, Pleasant Valley, NY 12569
• 

  $645,000

  Sold Jan 05, 2026

  244 Rombout Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 4 Baths
  • 3,159 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Above List Price
  • $204/SF
  • 30 Days On Market

  Current Estimated Value $660,759

  Last Listing Agent Lynn Angelo BHHS Hudson Valley Properties

  244 Rombout Rd, Pleasant Valley, NY 12569
• 

  Est $701,224

  Not Listed For Sale

  303 Davis Rd, Salt Point, NY 12578

  • 4 Beds
  • 3.5 Baths
  • 2,688 Sq Ft
  • Built 1988

  303 Davis Rd, Salt Point, NY 12578

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Craig Smith Compass Greater NY, LLC
• 

  

  /17

  $304,900

  • 3 Beds
  • 1 Bath
  • 904 Sq Ft

  37 Shady Creek Rd, Pleasant Valley, NY 12569

  Welcome to 37 Shady Creek Road, a beautifully renovated ranch nestled in the sought-after Shady Creek community. Blending modern upgrades with cozy character, this turnkey home offers comfortable single-level living in a peaceful setting. Inside you'll find an inviting open layout featuring three bedrooms, stylish new flooring, fresh paint, and abundant natural light. The thoughtfully updated

  Kristina Mancini BHHS Hudson Valley Properties

  37 Shady Creek Rd, Pleasant Valley, NY 12569
• 

  $579,900

  Sold Aug 06, 2026

  55 O Halloran Cir, Pleasant Valley, NY 12569

  • 4 Beds
  • 2.5 Baths
  • 3,240 Sq Ft
  • Built 2003

  Last Sold Summary

  • $179/SF
  • 90 Days On Market

  Current Estimated Value $638,278

  Last Listing Agent EDWIN MCNIFF JR. McNiff Real Estate LTD

  55 O Halloran Cir, Pleasant Valley, NY 12569
• 

  Est $455,763

  Not Listed For Sale

  574 Creek Rd, Pleasant Valley, NY 12569

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft
  • Built 1954

  574 Creek Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Anne Negrin Houlihan Lawrence Inc.
• 

  

  /31

  $460,000

  $122K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  176 Downing Rd, Pleasant Valley, NY 12569

  The Ultimate Hudson Valley Retreat: Private Living Meets an Enthusiast’s DreamEscape to your own private, tree-lined sanctuary in Pleasant Valley. Tucked away in the highly desirable Arlington School District, this custom-built, 1.7-story residence offers the perfect blend of country living, efficiency, and unmatched mechanical utility. From the moment you arrive, the towering trees and

  Christine Hamilton Keller Williams Realty Partner

  176 Downing Rd, Pleasant Valley, NY 12569
• 

  $2,650,000

  Sold Dec 30, 2025

  189 Freedom Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 4.5 Baths
  • 6,452 Sq Ft
  • Built 1986

  Last Sold Summary

  • 21% Above List Price
  • $411/SF
  • 118 Days On Market

  Current Estimated Value $2,142,839

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.

  189 Freedom Rd, Pleasant Valley, NY 12569
• 

  /2

  Est $480,921

  Not Listed For Sale

  689 North Ave, Salt Point, NY 12578

  • 4 Beds
  • 3 Baths
  • 3,080 Sq Ft
  • Built 1963

  689 North Ave, Salt Point, NY 12578
• 

  

  /45

  $975,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 4,135 Sq Ft

  125 Frost Hill Rd, Pleasant Valley, NY 12569

  Welcome to 125 Frost Hill Road, a spectacular Colonial offering over 4,000 square feet of beautifully finished living space on more than four private acres. Perfectly positioned atop a knoll, this exceptional home captures sweeping panoramic views while providing the ideal balance of luxury, comfort, and privacy. Step into the impressive foyer and immediately appreciate the home's bright, open

  Blake Michaud BHHS Hudson Valley Properties

  125 Frost Hill Rd, Pleasant Valley, NY 12569
• 

  $760,000

  Sold Aug 14, 2026

  2 Brenner Hollow Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,776 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $274/SF
  • 15 Days On Market

  Current Estimated Value $747,586

  Last Listing Agent Margaret Kozlark Berkshire Hathaway HS NE Prop.

  2 Brenner Hollow Rd, Pleasant Valley, NY 12569
• 

  Est $652,517

  Not Listed For Sale

  2109 Route 44, Pleasant Valley, NY 12569

  • 4 Beds
  • 3.5 Baths
  • 2,400 Sq Ft
  • Built 1949

  2109 Route 44, Pleasant Valley, NY 12569

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Nicole Porter Houlihan Lawrence Inc.
• 

  

  /3

  $68,000

  • Land
  • 2.87 Acres
  • $23,693 per Acre

  0 Frost Hill Rd Unit KEY978887, La Grange, NY 12569

  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 Frost Hill Rd Unit KEY978887, La Grange, NY 12569
• 

  $292,000

  Sold Jan 13, 2026

  15 Barbara Ln, Pleasant Valley, NY 12569

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1960

  Last Sold Summary

  • 17% Below List Price
  • $234/SF
  • 102 Days On Market

  Current Estimated Value $358,635

  Last Listing Agent Joseph Kuhl River Realty Services, Inc.

  15 Barbara Ln, Pleasant Valley, NY 12569
• 

  Est $624,505

  Not Listed For Sale

  72 Barkit Kennel Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 2,612 Sq Ft
  • Built 1986

  72 Barkit Kennel Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Mariola Jedynasty Belvedere Partners Corp
• 

  

  /30

  $340,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  1666 Main St, Pleasant Valley, NY 12569

  Welcome to 1666 Main Street, a beautifully renovated classic early-1900s home in the heart of Pleasant Valley. This move-in ready property offers 3–4 bedrooms, 2 full baths, and over 2,000 square feet of living space on a low-maintenance .20-acre lot in the Arlington School District with low taxes.Inside, you’ll find refinished 100+ year-old Maple and Douglas Fir hardwood floors, upgraded

  Kiyoshi Henson RE/MAX Town & Country

  1666 Main St, Pleasant Valley, NY 12569
• 

  $680,000

  Sold Jul 01, 2026

  3 Brenner Ridge Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 2.5 Baths
  • 2,606 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $261/SF
  • 16 Days On Market

  Current Estimated Value $680,575

  Last Listing Agent Geraldine Brucale BHHS Hudson Valley Properties

  3 Brenner Ridge Rd, Pleasant Valley, NY 12569
• 

  Est $377,802

  Not Listed For Sale

  45 Barkit Kennel Rd, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Built 1952

  45 Barkit Kennel Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Nicole Porter Houlihan Lawrence Inc.
• 

  

  /41

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  809 Traver Rd, Pleasant Valley, NY 12569

  809 Traver is a stunning Dutch Colonial, maintained with uncommon discipline and enduring craftsmanship. Built in 1764 as the Peter Flagler House, it was the town’s central tavern and meeting House.Set on just over an acre of mature landscaping, enjoy your heated swimming pool - or walk steps to the lovely town of Pleasant Valley.The home’s layout is classic in its proportions. A Dutch

  Kelli Williams The Machree Group, LLC

  809 Traver Rd, Pleasant Valley, NY 12569
• 

  $670,000

  Sold Jul 13, 2026

  64 Travis Rd, Hyde Park, NY 12538

  • 3 Beds
  • 2.5 Baths
  • 2,750 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $244/SF
  • 37 Days On Market

  Current Estimated Value $697,148

  Last Listing Agent Arij Kurzum Houlihan Lawrence Inc.

  64 Travis Rd, Hyde Park, NY 12538
• 

  Est $481,749

  Not Listed For Sale

  48 Valley View Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft
  • Built 1965

  48 Valley View Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Dominick DiFilippo Keller Williams Realty Partner
• 

  

  /24

  $510,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,736 Sq Ft

  38 Forest Valley Rd, Pleasant Valley, NY 12569

  Welcome to 38 Forest Valley Road a beautifully maintained and thoughtfully updated 4-bedroom, 2-bath home set on a scenic, level one-acre lot in the Arlington Central School District.The main level features an updated kitchen with granite counter tops, wood cabinetry, and stainless steel appliances. Comfortable dining area that opens to the deck overlooking the private backyard and

  Debra Tarpey RE/MAX Town & Country

  38 Forest Valley Rd, Pleasant Valley, NY 12569
• 

  $562,500

  Sold Dec 16, 2025

  185 Forest Valley Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Above List Price
  • $281/SF
  • 22 Days On Market

  Current Estimated Value $581,140

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  185 Forest Valley Rd, Pleasant Valley, NY 12569
• 

  Est $452,269

  Not Listed For Sale

  330 Creek Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Built 1965

  330 Creek Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties
• 

  

  /9

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  71 O Halloran Cir, Pleasant Valley, NY 12569

  Welcome to 71 O’Halloran Circle, where space, privacy, and possibility come together on 3.74 scenic acres in Pleasant Valley. This inviting raised ranch offers 4 bedrooms, 2 and a half bathrooms, and a versatile layout designed for comfortable everyday living and effortless entertaining.Inside, generous living spaces provide plenty of room to gather, unwind, work from home, or create the

  Anna Traina BERKSHIRE HATHAWAY

  71 O Halloran Cir, Pleasant Valley, NY 12569
• 

  $650,000

  Sold Mar 27, 2026

  261 Freedom Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft
  • Built 1982

  Last Sold Summary

  • 8% Above List Price
  • $278/SF
  • 41 Days On Market

  Current Estimated Value $628,047

  Last Listing Agent Ronald Green KW MidHudson

  261 Freedom Rd, Pleasant Valley, NY 12569
• 

  Est $708,954

  Not Listed For Sale

  186 Creek Rd, Pleasant Valley, NY 12569

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

  186 Creek Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent LISA WOHLMUTH KW MidHudson

Showing Results 81 - 120, Page 3 of 18