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Recently Sold Homes in 12029

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  • /31

    $715,000 Sold Aug 25, 2025

    • 1,890 Sq Ft
    • $378/SF
    • 44 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    70 Reardon York Estates, Canaan, NY 12029

    Down the end of a long, private drive awaits the dream you've been searching for. Welcome to 70 Reardon York Estates—a contemporary build that marries modern amenities with enchanting grounds. Nestled on 29 acres with extensive Stony Kill stream frontage, this thoughtfully designed home offers an unparalleled sense of peace and serenity, creating an ideal private refuge. The residence features

    Shaina Marron Houlihan Lawrence Inc.

    70 Reardon York Estates, Canaan, NY 12029
  • /46

    $750,000 Sold Aug 22, 2025

    • 2,910 Sq Ft
    • $258/SF
    • 47 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1790

    344 Peaceful Valley Rd, Canaan, NY 12029

    Welcome to the Capt. Silvanus Brown house, a historic country home located at the crossroads of Columbia and Berkshire Counties. This remarkable 1790 Colonial home retains many of the original 18th century details including high ceilings, spacious rooms, five fireplaces, original hardware, and beautifully burnished wood floors. The residence offers an easy flow with plenty of room for friends and

    Nancy Cuddihy STONE HOUSE PROPERTIES, LLC

    344 Peaceful Valley Rd, Canaan, NY 12029
  • /32

    $880,000 Sold Aug 21, 2025

    • 2,400 Sq Ft
    • $367/SF
    • 99 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1990

    72 Old Queechy Rd, Canaan, NY 12029

    Nestled in the foothills of the Berkshires sits this charming country cabin on seven lush acres with walking trails, a swimming pond, and rights to Queechy Lake. The home is light-filled and abundantly peaceful - each window looks out onto the surrounding greenery, with only the sounds of birds chirping flowing in. The first floor consists of a formal living room, office, guest bedroom and

    Raj Kumar Four Seasons Sotheby's International Realty

    72 Old Queechy Rd, Canaan, NY 12029
  • /32

    $375,000 Sold Aug 20, 2025

    • 1,000 Sq Ft
    • $375/SF
    • 14 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1947

    70 Miller Rd, Canaan, NY 12029

    Down a quiet country road where blacktop meets gravel and lush forest surrounds you, find the Canaan Cape peeking through the leaves. Perfectly situated equidistant from Boston and New York City this property offers a tranquil retreat from city life. For those who have already made the Hudson Valley or Berkshires your home you will enjoy the serene quiet of life in the woods while being within

    Thomas Pawlowski Four Seasons Sotheby's Int.

    70 Miller Rd, Canaan, NY 12029
  • /50

    $1,265,000 Sold Aug 04, 2025

    • 2,142 Sq Ft
    • $591/SF
    • 44 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    169 Cunningham Hill Rd, Canaan, NY 12029

    Experience the enchantment of this idyllic retreat! Nestled on a sprawling 36.95 acres, this stunning three-bedroom, two-bath contemporary farmhouse offers a serene escape from the hustle and bustle of everyday life. Accessed via a picturesque stone wall-lined driveway, off a quiet country dirt road, this property is a nature lover's paradise.Immerse yourself in the beauty of spectacular gardens,

    Anne Harrison Country Life Real Estate, LLC

    169 Cunningham Hill Rd, Canaan, NY 12029
  • /7

    $290,000 Sold Aug 01, 2025

    • Land
    • 32 Acres
    • $8,987 per Acre
    • 364 Days On Market

    0 New York 295, Canaan, NY 12029

    Over 32 surveyed acres of pure nature including open plateau, gently undulating countryside and soft far-reaching views ---- Located behind the Buddhist retreat and only 4 miles to Queechy Lake, 13 to Tanglewood/Lenox Mass and 7 to Chatham Village NY ---- 439' road frontage on Rte 295 ---- 580' on Barnegat Road ---- FIRST TIME ON MARKET

    Natalia de Amorim PREFERRED COUNTRY PROPERTIES

    0 New York 295, Canaan, NY 12029
  • /7

    $290,000 Sold Aug 01, 2025

    • Land
    • 32 Acres
    • $8,987 per Acre
    • 293 Days On Market

    L50.1 New York 295, Canaan, NY 12029

    Over 32 surveyed acres of pure nature including open plateau, gently undulating countryside and soft far-reaching views ---- Located behind the Buddhist retreat and only 4 miles to Queechy Lake, 13 to Tanglewood/Lenox Mass and 7 to Chatham Village NY ---- 439' road frontage on Rte 295 ---- 580' on Barnegat Road ---- FIRST TIME ON MARKET

    Natalia de Amorim Preferred Country Properties

    L50.1 New York 295, Canaan, NY 12029
  • /49

    $650,000 Sold Jul 22, 2025

    • 3,200 Sq Ft
    • $203/SF
    • 47 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1960

    116 Cunningham Hill Rd, Canaan, NY 12029

    Welcome to Constellation Farm, nestled in the peaceful countryside of Canaan, NY, where modern living meets the natural charm of rural life. This expansive property spans 10 acres and features a spacious home with 3 bedrooms and 3 bathrooms. The residence includes a luxurious primary suite addition, completed in 2019, designed as a private retreat with ample space and high-quality details.

    Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

    116 Cunningham Hill Rd, Canaan, NY 12029
  • /43

    $890,000 Sold Jul 15, 2025

    • 2,245 Sq Ft
    • $396/SF
    • 239 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    192 Old Queechy Rd, Canaan, NY 12029

    Nestled on 8.6 private acres, surrounded by nature conservancy and historic preservation land, this architect-designed compound offers the perfect blend of understated elegance and contemporary comfort. Located just minutes from Tanglewood, Jacob's Pillow, Kripalu, and world-class skiing in NY, MA, and Vermont, this serene escape is also within walking distance of one of the cleanest lakes in New

    Jean Howard RE/MAX Solutions - Troy

    192 Old Queechy Rd, Canaan, NY 12029
  • /23

    $539,900 Sold Jul 09, 2025

    • 950 Sq Ft
    • $568/SF
    • 52 Days On Market
    • 4 Beds
    • 1 Bath
    • Built 1910

    22 Paige Rd, Canaan, NY 12029

    Charming Lakefront Cottage with Stunning Berkshire ViewsDon't miss this rare opportunity to own a delightful four-bedroom, one-bath cottage nestled at the end of a quiet dirt road, overlooking the pristine waters of Queechy Lake, one of the cleanest lakes in New York. Thoughtfully designed and built with Scandinavian craftsmanship, this cozy 3 season retreat offers sunrise views over the

    Elisha Poirier STONE HOUSE PROPERTIES, LLC

    22 Paige Rd, Canaan, NY 12029
  • /40

    $987,000 Sold Jun 16, 2025

    • 3,270 Sq Ft
    • $302/SF
    • 41 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 2003

    44 Old Queechy Rd, Canaan, NY 12029

    This stunning five-bedroom, four-bath country cape is situated on 7.6 acres, surrounded by natural beauty, with breathtaking views overlooking a beaver pond and the Canaan Valley. This lovely home features a spacious open living room and dining room highlighted by a cozy wood-burning fireplace. There is also a generous sunroom equipped with a gas stove, and an oversized two-car garage with an

    Anne Harrison Country Life Real Estate, LLC

    44 Old Queechy Rd, Canaan, NY 12029
  • /4

    $60,000 Sold May 09, 2025

    • Land
    • 3.12 Acres
    • $19,231 per Acre
    • 90 Days On Market

    0 Old Queechy Rd, Canaan, NY 12029

    Three usable acres off a quiet dirt road in Canaan with Queechy Lake rights. Level parcel with a gentle rise that opens up for southern exposure. Lightly wooded. Great value.

    Tracy Tassinari Gabel Real Estate

    0 Old Queechy Rd, Canaan, NY 12029
  • /20

    $449,900 Sold May 02, 2025

    • 2,000 Sq Ft
    • $225/SF
    • 42 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1998

    27 N Valley Rd, Canaan, NY 12029

    OPEN HOUSE SUNDAY 3/9 11am-1pmMotivated owners are ready for your offer!Charming 3-Bed, 3-Bath Home on 2 Acres in Canaan, NY - A Perfect Retreat Near Chatham and the BerkshiresNestled on 2 serene acres in Canaan, NY, this inviting 3-bedroom, 3-bathroom home offers both tranquility and convenience. Just a short drive to the vibrant town of Chatham, NY, and the scenic Berkshires, this property is

    Carrie Dandridge Mahar Real Estate, LLC

    27 N Valley Rd, Canaan, NY 12029
  • /27

    $530,000 Sold Apr 22, 2025

    • 1,308 Sq Ft
    • $405/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    116B Cunningham Hill Rd, Canaan, NY 12029

    Escape to your perfect mountain Chalet in Canaan, New York! This beautiful home offers a serene and stylish sanctuary with 3 bedrooms, 2 bathrooms, and 1,300 square feet of thoughtfully designed living space. Surrounded by the breathtaking beauty of the mountains, this property promises stunning views that will captivate you every day. a convenient first-floor bedroom and full bathroom, provide

    Jessie Bennett William Pitt Sothebys Intn'l

    116B Cunningham Hill Rd, Canaan, NY 12029
  • /36

    $960,000 Sold Apr 22, 2025

    • 3,415 Sq Ft
    • $281/SF
    • 314 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1814

    41 Warner Crossing Rd, Canaan, NY 12029

    This c.1814 Federal protected by 27 acres retains much of the elegance and charm of 250 years ago.. set in a protected valley with other historic buildings, you experience the past while enjoying the present .. enter the maple lined driveway until the classic buildings begin to greet you .. 3,415 sqft home plus 4-stall 2-story horse barn with paddocks, a corn crib, separate garden house, a

    Natalia de Amorim Preferred Country Properties

    41 Warner Crossing Rd, Canaan, NY 12029
  • /13

    Sold Apr 21, 2025

    • Land
    • 10 Acres
    • 108 Days On Market

    0 Madison Ave Unit 155470, Canaan, NY 12029

    Catskill Mountain Views!! Nestled in at the end of a private road surrounded by moss covered rock outcrops, this 10 acres of land is ready for your dream home.Expansive western views that stretch across the horizon, offering a front-row seat to some of the most breathtaking sunsets. Whether you're savoring the warm hues of dusk or enjoying the crisp mountain air, this land invites you to relax

    Nikki Carchedi Stone House Properties, LLC

    0 Madison Ave Unit 155470, Canaan, NY 12029
  • /29

    $263,000 Sold Apr 21, 2025

    • Land
    • 10 Acres
    • $25,534 per Acre
    • 109 Days On Market

    Unlisted Address

    Catskill Mountain Views!! Nestled in at the end of a private road surrounded by moss covered rock outcrops, this 10 acres of land is ready for your dream home. Expansive western views that stretch across the horizon, offering a front-row seat to some of the most breathtaking sunsets. Whether you're savoring the warm hues of dusk or enjoying the crisp mountain air, this land invites you to relax

    Nikki Carchedi STONE HOUSE PROPERTIES, LLC

    Unlisted Address
  • /34

    $429,000 Sold Mar 28, 2025

    • 1,440 Sq Ft
    • $298/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2020

    14 Cunningham Hill Rd, Canaan, NY 12029

    Welcome to this beautiful, move-in-ready home, built less than 5 years ago and perfectly set back from the road for maximum privacy and tranquility. This spacious property offers a serene pond on-site, adding to the peaceful ambiance. Inside, you'll find an open floor plan that flows seamlessly, ideal for entertaining or relaxed everyday living. The kitchen is a chef's dream, featuring brand-new

    Cole Cioffi Weichert Realtors-Reliable Properties

    14 Cunningham Hill Rd, Canaan, NY 12029
  • /19

    Sold Feb 07, 2025

    • 1,510 Sq Ft
    • 151 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1900

    156 Upper Queechy Rd, Canaan, NY 12029

    Aladdin homes Pomona. Shaded by the picturesque maple planted when the house was built this 1900s gem located on a rural byway for a location as quiet as can be. Greeted by the extra deep rocking porch. Enter into the living room with a local fieldstone fireplace and wood floors. Bright office and laundry on first floor. Wonderful working kitchen with many windows and doors to bring the light in.

    Tracy Tassinari Gabel Real Estate

    156 Upper Queechy Rd, Canaan, NY 12029
  • /37

    $645,000 Sold Jan 22, 2025

    • 1,100 Sq Ft
    • $586/SF
    • 241 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1950

    84 Old Hudson Turnpike, Canaan, NY 12029

    On a road less traveled, and the first time on the market in a century, is this 93 ACRE property with an updated 2 bedroom 1950's cottage. Lots to explore from lightly wooded land to hilltop views The well constructed and updated cottage has central AC, a living room with WB fireplace, a large kitchen with a dining area, 2 bedrooms, a screened porch and updated bath. The lower level is newly

    Peter Newman Beach & Bartolo Realtors

    84 Old Hudson Turnpike, Canaan, NY 12029
  • /38

    $935,000 Sold Dec 20, 2024

    • 3,116 Sq Ft
    • $300/SF
    • 15 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1989

    43 Shaker Ridge Dr, Canaan, NY 12029

    As you enter this peaceful paradise, you are struck by the stunning landscaped gardens, the glorious pool and patio area, and the serenity that the 7+ acre property offers. The outdoor amenities include wrap around decks and a screened porch, beckoning you to come enjoy Mother Nature at her finest. Upon entering this contemporary gem, you will immediately be struck with the abundance of

    Philip Feiner COUNTRY LIFE REAL ESTATE LLC

    43 Shaker Ridge Dr, Canaan, NY 12029
  • /35

    $658,000 Sold Dec 12, 2024

    • 2,134 Sq Ft
    • $308/SF
    • 32 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2018

    319 Shaker Ridge Dr, Canaan, NY 12029

    Built in 2018, this pristine, light filled contemporary ranch home is now available for the first time. Experience the ease of single-level living with a seamless open-concept kitchen and living area, highlighted by a charming gas fireplace. Sip your morning coffee in the cozy breakfast nook or take in the serene backyard views from your private deck. The primary bedroom features an ensuite bath,

    Nikki Carchedi Stone House Properties, LLC

    319 Shaker Ridge Dr, Canaan, NY 12029
  • /36

    $315,000 Sold Nov 26, 2024

    • 1,100 Sq Ft
    • $286/SF
    • 128 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1945

    13249 State Route 22, Canaan, NY 12029

    A VERY MOTIVATED SELLER would like you to see this perfectly renovated and adorable COUNTRY COTTAGE with the FRONT PORCH you have dreamed about, on 2.6 acres and is move-in ready. Beautiful landscaping and a private setting ensure that this home will provide lots of enjoyment for you, friends and family. The sun filled home and property await your gardening inspirations. A large 2 story barn is

    Peter Newman Beach & Bartolo Realtors

    13249 State Route 22, Canaan, NY 12029
  • /42

    $400,000 Sold Nov 13, 2024

    • 1,320 Sq Ft
    • $303/SF
    • 18 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    13149 New York 22, Canaan, NY 12029

    A Rare Find and Opportunity on Route 22 in Canaan is this 43 acre property with a HUGE Dutch Barn and small home (in need of rehab) The property awaits your visions; a.home site, a destination venue, farming or? This property is residential/commercial and can be subdivided. There is extensive road frontage and the 43 acres consists of meadows, fields, open land, forest, a stream, and beautiful

    Peter Newman Beach & Bartolo Realtors

    13149 New York 22, Canaan, NY 12029
  • /29

    $720,000 Sold Oct 09, 2024

    • 2,336 Sq Ft
    • $308/SF
    • 109 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    2142 County Route 5, Canaan, NY 12029

    This one of a kind meticulously maintained home is perfectly sited down a long driveway off the main road on 6+ total private acres. The main house while circular offers a gourmet kitchen (Bosch Dishwasher,Smeg Italian fridge,Wine fridge & Jenn-Air Over/Range) living room with wood burning fireplace (trimmed with imported Spanish tile), dining area, two bedrooms, full bath (could easily be

    Martin Salerno The Kinderhook Group, Inc.

    2142 County Route 5, Canaan, NY 12029
  • /10

    $265,000 Sold Sep 20, 2024

    • 1,050 Sq Ft
    • $252/SF
    • 97 Days On Market
    • 1 Bed
    • 0.5 Baths
    • Built 1950

    215 County 24, Canaan, NY 12029

    Located in the quaint Hamlet of Red Rock. Former office space ready for a new owner's spin. Studio, office space, or convert into a home. Original fir floors aged to a great patina. Front to back rooms on both sides of the cape. Open floor upstairs. Back enclosed porch area and half bath. Three tax parcels. Queechy Lake rights. A rare opportunity to find a place that is rich in history, and in

    Tracy Tassinari Gabel Real Estate

    215 County 24, Canaan, NY 12029
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