Wassaic, NY Homes

• 

  $525,000

  Sold Dec 09, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft
  • Built 1949

  Last Sold Summary

  • 10% Above List Price
  • $223/SF
  • 12 Days On Market

  Current Estimated Value $493,401

  Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

  Unlisted Address
• 

  Est $821,235

  Not Listed For Sale

  2153 Route 44, Pleasant Valley, NY 12569

  • 4 Beds
  • 3.5 Baths
  • 3,209 Sq Ft
  • Built 2007

  2153 Route 44, Pleasant Valley, NY 12569

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Jill Doppel Jill Doppel Real Estate, LLC
• 

  

  

  /25

  $650,000

  • 3 Beds
  • 1.5 Baths
  • 3,193 Sq Ft

  59-61 Valley Farm Rd, Millbrook, NY 12545

  Step back in time and bring your vision to this classic 1870s Colonial, featuring original details throughout, perfectly situated on a lovely one + acre lot on a quiet country road. Flanked by mature pines and Flowering Hibiscus. The property offers a serene setting while being conveniently located near the charming village of Millbrook, NY. A unique opportunity for those looking to restore a

  Sarah Sartorini-Yarmoluk William Pitt Sothebys Int Rlty

  59-61 Valley Farm Rd, Millbrook, NY 12545
• 

  $445,000

  Sold Mar 04, 2026

  3406 Route 82, Verbank, NY 12585

  • 2,784 Sq Ft
  • Built 1940

  Last Sold Summary

  • $160/SF
  • 50 Days On Market

  Current Estimated Value $468,088

  Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

  3406 Route 82, Verbank, NY 12585
• 

  Est $225,854

  Not Listed For Sale

  2562 Route 44, Salt Point, NY 12578

  • 2 Beds
  • 1 Bath
  • 484 Sq Ft
  • Built 1953

  2562 Route 44, Salt Point, NY 12578

  Last Sold Summary

  • 95 Days On Market

  Last Listing Agent LISA CAMPBELL Exit Realty Connections
• 

  

  /47

  $1,195,000

  $180K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,820 Sq Ft

  101 Drake Rd, Pleasant Valley, NY 12569

  Historic Barn Conversion Meets Modern Luxury in the Hudson Valley Tucked away along a quiet country road in Pleasant Valley, this extraordinary estate offers a rare opportunity to own a meticulously restored 19th-century barn conversion that seamlessly blends historic character with modern luxury. Originally two separate barns, the property has been thoughtfully reimagined into a one-of-a-kind

  Jake Garay Serhant LLC

  101 Drake Rd, Pleasant Valley, NY 12569
• 

  $598,800

  Sold Sep 17, 2025

  65 Cooper Dr, Verbank, NY 12585

  • 3 Beds
  • 2.5 Baths
  • 2,537 Sq Ft
  • Built 1985

  Last Sold Summary

  • $236/SF
  • 24 Days On Market

  Current Estimated Value $620,002

  Last Listing Agent Julie Goldberg HomeSmart Homes & Estates

  65 Cooper Dr, Verbank, NY 12585
• 

  Est $375,196

  Not Listed For Sale

  2322 Route 44, Pleasant Valley, NY 12569

  • 2 Beds
  • 1 Bath
  • 1,196 Sq Ft
  • Built 1970

  2322 Route 44, Pleasant Valley, NY 12569

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Don Maher BHHS Hudson Valley Properties
• 

  

  /28

  $450,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  88 Rymph Rd, Pleasant Valley, NY 12569

  A peaceful ranch across from a working orchard, with all the big-ticket updates done. Few homes in this price range offer the same combination of comfort, convenience, and long-term value. Set on a level acre directly across from a working apple orchard, 88 Rymph Road brings open skies, seasonal orchard views, and genuine quiet to your everyday backdrop, all while staying just minutes from

  Anthony Flores Upstate Down

  88 Rymph Rd, Pleasant Valley, NY 12569
• 

  $475,000

  Sold Oct 07, 2025

  36 Heritage Rd, Clinton Corners, NY 12514

  • 3 Beds
  • 1.5 Baths
  • 1,610 Sq Ft
  • Built 1976

  Last Sold Summary

  • 17% Below List Price
  • $295/SF
  • 110 Days On Market

  Current Estimated Value $488,444

  Last Listing Agent Kaye Saglibene Houlihan Lawrence Inc.

  36 Heritage Rd, Clinton Corners, NY 12514
• 

  Est $635,535

  Not Listed For Sale

  21 Trillium Rd, Pleasant Valley, NY 12569

  • 3 Beds
  • 2.5 Baths
  • 2,930 Sq Ft
  • Built 1993

  21 Trillium Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 117 Days On Market

  Last Listing Agent Peggy Santamorena Houlihan Lawrence Inc.
• 

  

  /37

  $1,250,000

  $250K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,068 Sq Ft

  3311 Franklin Ave, Millbrook, NY 12545

  Don't miss this exceptional value in the heart of the Village of Millbrook: a beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home (2,132 sq ft) complemented by a detached 1,750 sq ft two-car garage with an approximately 1,000 sq ft, 1-bedroom, 1-bath guest apartment above, currently generating rental income that pays for the taxes and maintenance for the entire

  Ann Stettner Neil Charles Real Estate, LLC

  3311 Franklin Ave, Millbrook, NY 12545
• 

  $390,000

  Sold Aug 29, 2025

  32 Halcyon Rd, Millbrook, NY 12545

  • 3 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 1910

  Last Sold Summary

  • 15% Below List Price
  • $174/SF
  • 205 Days On Market

  Current Estimated Value $399,817

  Last Listing Agent Jo-Ann Campagiorni Houlihan Lawrence Inc.

  32 Halcyon Rd, Millbrook, NY 12545
• 

  Est $449,187

  Not Listed For Sale

  234 Rossway Rd, Pleasant Valley, NY 12569

  • 4 Beds
  • 2 Baths
  • 1,694 Sq Ft
  • Built 1968

  234 Rossway Rd, Pleasant Valley, NY 12569

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc
• 

  /2

  $325,000

  • Land
  • 12.8 Acres
  • $25,391 per Acre

  0 Deer Pond Rd Unit KEY958812, Union Vale, NY 12585

  Ideal 12+ acre home site, near the iconic Millbrook Village. This level fertile land features an existing pond and privacy being at the end of a cul-de-sac. This property is Board of Health approved for a four bedroom home (no filled required). Create your own country farm estate. Make an inspection visit today!

  Robert D Ferris R. Ferris Real Estate, LLC

  0 Deer Pond Rd Unit KEY958812, Union Vale, NY 12585
• 

  $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 $538,224

  Not Listed For Sale

  31 Birch Dr, Pleasant Valley, NY 12569

  • 3 Beds
  • 1.5 Baths
  • 2,028 Sq Ft
  • Built 1970

  31 Birch Dr, Pleasant Valley, NY 12569

  Last Sold Summary

  • 177 Days On Market

  Last Listing Agent Susan Stevens BHHS Hudson Valley Properties
• 

  

  /46

  $699,900

  $29K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 1,196 Sq Ft

  676-678 Oak Summit Rd, Millbrook, NY 12545

  Escape to this private retreat sited on 1.5 acres, on a country road, minutes to the Village of Millbrook. Imagine what you could do with this property. The two separate structures offer endless possibilities. The huge barn, with a garage below, which can accommodate 8+ cars, is perfect for a car enthusiast or other hobbyist, also includes a 1900 square foot, three bedroom, two-bath finished

  Lori Rheingold Houlihan Lawrence Inc.

  676-678 Oak Summit Rd, Millbrook, NY 12545
• 

  $687,000

  Sold May 29, 2026

  4 Theresa Ct, Lagrangeville, NY 12540

  • 3 Beds
  • 2.5 Baths
  • 2,594 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Above List Price
  • $265/SF
  • 31 Days On Market

  Current Estimated Value $685,311

  Last Listing Agent Lisa Jeanneret Corcoran Country Living

  4 Theresa Ct, Lagrangeville, NY 12540
• 

  Est $484,454

  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
• 

  

  /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
• 

  $550,000

  Sold May 29, 2026

  279 Milewood Rd, Millbrook, NY 12545

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 2005

  Last Sold Summary

  • 11% Above List Price
  • $364/SF
  • 27 Days On Market

  Current Estimated Value $545,844

  Last Listing Agent Michele Rios BHHS Hudson Valley Properties

  279 Milewood Rd, Millbrook, NY 12545
• 

  Est $498,156

  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
• 

  

  /36

  $374,900

  Pending

  • 3 Beds
  • 2 Baths
  • 4,072 Sq Ft

  646 Oak Summit Rd, Millbrook, NY 12545

  Discover a unique and rare opportunity in this sprawling ranch-style 2-family home with generous space, flexible layout, and charming character— ready for your renovations and visions. Set on a picturesque 1.7-acre corner lot with an expansive yard, gazebo, shed, mature landscaping, the potential of this home welcomes a serene Hudson Valley lifestyle.The upper unit features over 2,000 sq. ft.

  LISA WOHLMUTH KW MidHudson

  646 Oak Summit Rd, Millbrook, NY 12545
• 

  

  /25

  $850,000

  Sold Jun 18, 2026

  1 Johnson Ln, Millbrook, NY 12545

  • 2 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 1895

  Last Sold Summary

  • 13% Above List Price
  • $552/SF
  • 27 Days On Market

  Current Estimated Value $815,948

  Last Listing Agent Annabel Taylor Four Seasons Sotheby's Int.

  1 Johnson Ln, Millbrook, NY 12545
• 

  Est $475,421

  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
• 

  

  /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
• 

  $1,200,000

  Sold Sep 15, 2025

  108 N Smith Rd, Lagrangeville, NY 12540

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1938

  Last Sold Summary

  • 4% Below List Price
  • $429/SF
  • 83 Days On Market

  Current Estimated Value $1,546,761

  Last Listing Agent Nancy Felcetto Brown Harris Stevens HV LLC

  108 N Smith Rd, Lagrangeville, NY 12540
• 

  Est $487,615

  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
• 

  

  /16

  $899,000

  • Land
  • 49.36 Acres
  • $18,213 per Acre

  0 Mallory Rd Unit KEY1016545, Union Vale, NY 12585

  Nearly 50 acres of enchanted woodland in the heart of Clove Valley, just minutes from the Village of Millbrook and within the Millbrook Central School District. Meandering trails wind through mature forest, past centuries-old stone walls and a picturesque pond, opening to sweeping countryside and distant Catskill views. A place of extraordinary beauty and complete privacy, where every season

  DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

  0 Mallory Rd Unit KEY1016545, Union Vale, NY 12585
• 

  $580,000

  Sold May 22, 2026

  3985 Route 82, Millbrook, NY 12545

  • 4 Beds
  • 2 Baths
  • 1,961 Sq Ft
  • Built 1938

  Last Sold Summary

  • 10% Above List Price
  • $296/SF
  • 33 Days On Market

  Current Estimated Value $564,657

  Last Listing Agent Susan Whalen George T Whalen Real Estate

  3985 Route 82, Millbrook, NY 12545
• 

  Est $727,242

  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
• 

  

  /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
• 

  $750,000

  Sold Aug 04, 2026

  477 Canoe Hill Rd, Millbrook, NY 12545

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft
  • Built 1900

  Last Sold Summary

  • 32% Below List Price
  • $309/SF
  • 679 Days On Market

  Current Estimated Value $987,816

  Last Listing Agent HEATHER CRONER William Pitt Sothebys Int Rlty

  477 Canoe Hill Rd, Millbrook, NY 12545
• 

  Est $470,560

  Not Listed For Sale

  26 Bobolink Ln, Salt Point, NY 12578

  • 3 Beds
  • 1.5 Baths
  • 1,850 Sq Ft
  • Built 1979

  26 Bobolink Ln, Salt Point, NY 12578

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Debra Allan BHHS Hudson Valley Properties
• 

  

  /20

  $665,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  12 Ciferri Dr, Millbrook, NY 12545

  Welcome to this charmer located right in the Village of Millbrook and set on one acre of beautifully landscaped land with magnificent specimen trees and a covered patio that invites one to cook, eat or just sit and admire the lush property. Abundant light streams through this cape style home which features a handsome eat-in kitchen with all modern appliances and gleaming granite counters, a

  SHARON MAHAR Compass Greater NY, LLC

  12 Ciferri Dr, Millbrook, NY 12545
• 

  $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 $666,038

  Not Listed For Sale

  26 Goldfinch Dr, Salt Point, NY 12578

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft
  • Built 1979

  26 Goldfinch Dr, Salt Point, NY 12578

  Last Sold Summary

  • 105 Days On Market

  Last Listing Agent Lynne Riccoboni BHHS Hudson Valley Properties
• 

  

  /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
• 

  $2,377,500

  Sold Jul 17, 2026

  188 Nine Partners Ln, Millbrook, NY 12545

  • 3 Beds
  • 6 Baths
  • 2,614 Sq Ft
  • Built 1872

  Last Sold Summary

  • 9% Below List Price
  • $910/SF
  • 127 Days On Market

  Last Listing Agent ANN WILKINSON Compass Greater NY, LLC

  188 Nine Partners Ln, Millbrook, NY 12545

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