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Homes for Sale near Chatham Middle School

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  • /45

    $775,000

    • 4 Beds
    • 4 Baths
    • 3,036 Sq Ft

    340 Lower Cady Rd, Old Chatham, NY 12136

    Private Adirondack-inspired retreat set on 21 private acres in Old Chatham! This 3,200-square-foot home offers an exceptional opportunity to reimagine a rustic yet refined home in a premier Hudson Valley location. With four bedrooms, four bathrooms, and four wood-burning fireplaces, this home provides plenty of room for entertaining and gatherings, as well as cozy spaces for quiet

    Agent Photo

    Christine Hinz

    Coldwell Banker Village Green

    (518) 620-5873

    340 Lower Cady Rd, Old Chatham, NY 12136
  • /38

    $565,000

    • 2 Beds
    • 2 Baths
    • 897 Sq Ft

    214 Fog Hill Rd, Austerlitz, NY 12017

    Tucked away on a country mountain road and set into the bucolic landscape of the Beebe Hill State Forest is Fog Hill Cabin. A modern cottage with a cabin-like feel. Recently the current owners have made significant upgrades to the cabin. These upgrades include an additional living area on the lower level that features its own kitchenette and en suite bathroom. A Mini Spit (heat pump) system

    Agent Photo

    Rachel Levine

    Patricia A. Hinkein Realty

    (518) 759-5502

    214 Fog Hill Rd, Austerlitz, NY 12017
  • /35

    $189,900

    • Land
    • 23 Acres
    • $8,084 per Acre

    00WP Albany Turnpike Rd, Old Chatham, NY 12136

    Welcome to this versatile and picturesque 23.49-acre property located in the charming and historic town of Old Chatham, New York. Nestled in the heart of Columbia County, this buildable and subdividable parcel presents a rare opportunity for those looking to invest, build, or simply enjoy a private natural retreat. Whether you're envisioning a secluded country estate, a family compound, or a

    Mitch Serlin

    00WP Albany Turnpike Rd, Old Chatham, NY 12136
  • /33

    $650,000

    • 4 Beds
    • 1.5 Baths
    • 1,968 Sq Ft

    9 Jones Ave, Chatham, NY 12037

    Welcome home!This thoughtfully restored 1880's village residence maintains its original integrity. The home has been meticulously renovated, featuring spacious rooms with lofty ceilings, abundant natural sunlight, and beautiful hardwood floors throughout.A beautiful front entryway opens to an elegantly curved staircase and parlor. Just beyond the French doors an inviting dining

    Lenore Packet Stone House Properties, LLC

    9 Jones Ave, Chatham, NY 12037
  • /30

    $1,295,000

    • 4 Beds
    • 2 Baths
    • 2,505 Sq Ft

    54 Fowler Lake Rd, Ghent, NY 12075

    An easygoing country home on fifteen acres of lovely lawn & wildflower meadows, forest with trails for walking & cross-country skiing, old stone walls and two spring fed ponds. Perennial, native gardens tuck the house into the landscape on a quiet country road. The site is private and peaceful. Enter the house through a charming mudroom with built in cubbies and shaker wood pegs. The Great Room

    Annabel Taylor Four Seasons Sothebys Intl

    54 Fowler Lake Rd, Ghent, NY 12075
  • /18

    $695,000

    • 5 Beds
    • 4 Baths
    • 2,731 Sq Ft

    20 Depot Ln, Old Chatham, NY 12136

    Depot LaneNestled at the end of a quiet country lane, this charming historic home in the hamlet of Old Chatham offers the perfect blend of rural tranquility and warm community connections. Surrounded by sprawling gardens and quiet woods, the first floor of this peaceful retreat offers a spacious living room, complete with a wood-burning fireplace, an inviting eat-in kitchen perfect for family

    Andrea Gabel Gabel Real Estate

    20 Depot Ln, Old Chatham, NY 12136
  • /32

    $715,000

    • 3 Beds
    • 2 Baths
    • 1,890 Sq Ft

    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
  • /17

    $899,000

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    33 Wild Flower Rd, Valatie, NY 12184

    Located on a lovely country road, near the towns of Kinderhook and Chatham, lies this spacious and sunny well-maintained homeon over 5 acres. There is a 1st floor primary ensuite bedroom, large eat-in kitchen and wonderful sun room looking out on the salt water swimming pool.Den/office, laundry plus 3 bedrooms upstairs and a full finished basement provide excellent living space in a gorgeous

    Janet Kain The Kinderhook Group, Inc.

    33 Wild Flower Rd, Valatie, NY 12184
  • /44

    $865,000

    • 3 Beds
    • 2.5 Baths
    • 2,623 Sq Ft

    25 Ridge Rd, East Chatham, NY 12060

    Exceptional Views & Elevated ComfortPerched high above Mercer Road at the top of Ridge, this stunning 2,600+ sq ft contemporary home offers panoramic views that stretch across the valley to the Catskills—some of the best in the region. Set on 10 private acres, the home pairs modern ease with total tranquility.The vaulted great room, anchored by a floor-to-ceiling wood-burning fireplace, is

    Baris Demirel Serhant LLC

    25 Ridge Rd, East Chatham, NY 12060
  • /37

    $850,000

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    35 Jilroy Ln, Spencertown, NY 12165

    Spencertown Pond House: Your Private Sanctuary AwaitsTucked away on over 5 picturesque acres, the Spencertown Pond House offers an idyllic escape, where nature and comfort converge. With its own private, spring-fed pond visible from every room, this home is the epitome of serene, lakeside living. Imagine waking up each morning to breathtaking views of shimmering water, framed by lush greenery

    Dina Palin Houlihan Lawrence Inc.

    35 Jilroy Ln, Spencertown, NY 12165
  • /36

    $629,000

    • 4 Beds
    • 2 Baths
    • 2,402 Sq Ft

    662 Albany Turnpike, Old Chatham, NY 12136

    Step back in time with this enchanting 1820s village Colonial, a true jewel box filled with original details and timeless charm. This home exudes warmth and tranquility, featuring high ceilings, wide plank floors, and both front and back staircases leading to three generously sized bedrooms. A hidden ''secret'' nook offers the perfect space for hide-and-seek, quiet reflection, or a cozy

    Jonathan Hallam The Kinderhook Group, Inc.

    662 Albany Turnpike, Old Chatham, NY 12136
  • /39

    $674,900

    • 4 Beds
    • 2 Baths
    • 2,500 Sq Ft

    2640 New York 203 Unit Stop 21, Valatie, NY 12184

    Welcome to Sheriff's Pasture—a rare and storied property nestled in the heart of Kinderhook, offering some of the most fertile and picturesque land in Columbia County. This historic 14.71-acre parcel sits far off the road for ultimate privacy, framed by mature trees, wide-open pasture, and the peaceful sound of Kinderhook Creek flowing at the property's edge. Once a thriving dairy farm, this land

    Michael Castellano Gilcrest Properties

    2640 New York 203 Unit Stop 21, Valatie, NY 12184
  • /31

    $679,000

    • 3 Beds
    • 3.5 Baths
    • 2,050 Sq Ft

    1582 State Route 203, Chatham, NY 12037

    A Chatham farm property with endless possibilities. Anchoring this 7-acre parcel is a 3BR, 3-1/2 BA home surrounded by fields, paddocks and woodlands. Set off from the home is an amazing barn complex and spring-fed pond. All less than a minute to downtown Chatham and equally close to the Taconic Pkwy. The property abuts the 65-acre Borden Pond conservation land - a hiker's paradise. The barn

    Jason Karadus Corcoran Country Living

    1582 State Route 203, Chatham, NY 12037
  • /72

    $1,148,000

    • 4 Beds
    • 2 Baths
    • 2,520 Sq Ft

    54 Mercer Mountain Rd, East Chatham, NY 12060

    OPEN HOUSE, Sunday June 22nd 11AM-1PMOn a clear day, you can see forever and ever... VIEWS, VIEWS, VIEWS, for endless miles.to The.Catskills, and the Towers in Albany. From sunrise to sunset, you will be mesmerized by the gorgeous rolling hillside vistas to the mountains beyond. The sleekly styled contemporary home on 12 acres is your window to the world. Built in the late 1980's, and

    Peter Newman Beach & Bartolo Realtors

    54 Mercer Mountain Rd, East Chatham, NY 12060
  • /18

    $699,000

    • 3 Beds
    • 1.5 Baths
    • 1,700 Sq Ft

    477 Fog Hill Rd, Austerlitz, NY 12017

    Wonderful farmhouse with the best of all worlds. Renovated for modern use and function with old world charm. Pine floors. Great working kitchen with eating area. Large dining area for entertaining friends and family. Great room with high ceilings and Vermont Castings propane stove to warm the cooler spring nights, wrapped in windows to bring nature in. French doors off the eating area to large

    Tracy Tassinari Gabel Real Estate

    477 Fog Hill Rd, Austerlitz, NY 12017
  • /47

    $745,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    263 Old Hudson Turnpike, Canaan, NY 12029

    PRICE CUT! All new eyebrow colonial transformed in to a modern efficient home with 3 bedrooms and 2 full baths. New Anderson windows, doors, roof, Smart siding. All new lighting throughout the house, new floors. All brand new appliances. Literally Brand new everything. New hot water heater tank with heat pump, water purification system. New Radon system.New wrap around deck to enjoy your

    Sharon McArdle Berkshire Hathaway Home Services Blake

    263 Old Hudson Turnpike, Canaan, NY 12029
  • /31

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,958 Sq Ft

    326 Pratt Hill Rd, Chatham, NY 12037

    Nestled in a serene, wooded setting, 326 Pratt Hill Road is a thoughtfully designed Cape-style home that blends rustic charm with modern comforts. Originally a quaint cabin, it has been carefully expanded over the years and now offers three bedrooms, two full bathrooms, and 8.1 private acres – perfect for a weekend escape or year-round living. The oversized living area features hardwood floors, a

    Callan Bergmann Compass Greater NY, LLC

    326 Pratt Hill Rd, Chatham, NY 12037
  • /29

    $649,000 New Construction

    • 1 Bath
    • 600 Sq Ft

    208 E East Hill Rd, Austerlitz, NY 12017

    Your Private Waterfall Retreat: New Cabin Backing State ForestDiscover unparalleled tranquility at this newly built, top-quality cabin. Tucked away on a quiet dirt road, a private drive leads you past your own stream and picturesque waterfall, right to your door.This beautifully designed cabin features an open floor plan with a comfortable sleeping loft, and a huge deck perfect for

    Rachel Haley Houlihan Lawrence Inc.

    208 E East Hill Rd, Austerlitz, NY 12017
  • /23

    $429,000

    • 3 Beds
    • 1.5 Baths
    • 1,779 Sq Ft

    66 River St, Chatham, NY 12037

    Nestled on a knoll, River Song is a charming 1853 cottage that blends timeless character with the comforts of modern living. This enchanting home boasts rich period details creating a warm, nostalgic ambiance throughout. A separate 16 X 10 studio with electric and heat, provides a creative space for a multiple of uses for artists, writers, yoga enthusiasts and musicians alike. Tucked away amid

    Karen Volino Houlihan Lawrence, Inc.

    66 River St, Chatham, NY 12037
  • /20

    $75,000

    • Land
    • 4.74 Acres
    • $15,823 per Acre

    0 New York 22, Austerlitz, NY 12017

    Beautiful wooded lot on the Green River is a great spot to build your new home. The lot is 4.74 acres gently sloping upwards towards the east with the Green River running across the southwestern corner, so no bridge will be needed to access the land. Less than 5 mins to Beebe Hill State Forest, Harvey Mountain State Forest, Austerlitz Historical Society and Steepletop (the Edna St. Vincent

    Jennifer Sesma Beach & Bartolo Realtors

    0 New York 22, Austerlitz, NY 12017
  • /28

    $189,900

    • Land
    • 23 Acres
    • $8,084 per Acre

    00WP Albany Turnpike, Old Chatham, NY 12136

    Welcome to this versatile and picturesque 23.49-acre property located in the charming and historic town of Old Chatham, New York. Nestled in the heart of Columbia County, this buildable and subdividable parcel presents a rare opportunity for those looking to invest, build, or simply enjoy a private natural retreat. Whether you're envisioning a secluded country estate, a family compound, or a

    Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

    00WP Albany Turnpike, Old Chatham, NY 12136
  • /31

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft

    797 State Route 203, Spencertown, NY 12165

    Charming 1923 Sears Arts & Crafts Bungalow - Timeless Elegance Meets Modern Comfort a rare and beautifully preserved home that radiates character, craftsmanship, and warmth. Nestled in the peaceful Spencertown hamlet this Sears home holds historic charm with thoughtful updates for today's lifestyle. Step inside through the inviting front porch(enclosed for year-round enjoyment) and experience the

    Qizhan Yao Realmart Realty, LLC

    797 State Route 203, Spencertown, NY 12165
  • /78

    $1,500,000

    • 4 Beds
    • 4.5 Baths
    • 2,658 Sq Ft

    788 White Mills Rd, Valatie, NY 12184

    Step back in time without sacrificing modern amenities in this fully renovated 1850's farmhouse, nestled on an expansive 163+ acre estate set within serene woods. This exceptional property offers a rare combination of historic charm and contemporary convenience, featuring 4 bedrooms and 4.5 modern baths - each designed during a down to the studs renovation completed within the last 10 years. The

    Faith Adamec RE/MAX Capital

    788 White Mills Rd, Valatie, NY 12184
  • /12

    $160,000

    • Land
    • 8 Acres
    • $20,833 per Acre

    400 Mercer Mountain Rd, East Chatham, NY 12060

    Welcome to Mercer Mountain—an exclusive enclave of million-dollar-plus homes nestled in the rolling Taconic Mountains of Columbia County. Perfectly situated between the world-class cultural offerings of the Berkshires and the awe-inspiring Catskill Mountains, this remarkable 7.68-acre parcel offers a rare opportunity to build your dream estate in one of the Hudson Valley’s most sought-after

    Callan Bergmann Compass Greater NY, LLC

    400 Mercer Mountain Rd, East Chatham, NY 12060
  • /32

    $395,000

    • 4 Beds
    • 1 Bath
    • 2,052 Sq Ft

    12 Mill St Unit 14, Chatham, NY 12037

    Charming and walkable 4BR home in the heart of Chatham village! Set on a spacious half-acre lot, this sun-filled home blends original character with modern updates—featuring hardwood floors, a flexible layout with home office/music room, and plumbing in place for a second bath. Enjoy golden hour on the front porch or entertain in the deep, private backyard with a stone patio. Steps to yoga,

    Joseph Briggs William Pitt Sotheby's

    12 Mill St Unit 14, Chatham, NY 12037
  • /27

    $139,000

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    296 New York 295 Unit Lot 19, Chatham, NY 12037

    Charming 2-Bed, 2-Bath Single-Wide Mobile Home in Sought-After Chatham - No Age Restrictions!Don't miss this rare opportunity to own a beautifully maintained 2-bedroom, 2-full-bath single-wide mobile home in the highly desirable area of Chatham—and best of all, it's located in a non-55+ community!This home offers a bright, open-concept layout with a spacious living area, a functional kitchen with

    Margaret Guerra Gilcrest Properties

    296 New York 295 Unit Lot 19, Chatham, NY 12037
  • /17

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,594 Sq Ft

    1900 New York 203, Chatham, NY 12037

    Contractor Special: Office building ready for transformation to many possibilities. Common areas can accommodate open living/dining/kitchen concepts. Wideboard floors throughout. Attached shed serves as ample storage. A detached three bay garage is also on this 1.5 acre lot. Bring your vision for single-floor living to this blank slate just outside of Chatham Village.

    Jennifer Wall Anderson Agency

    1900 New York 203, Chatham, NY 12037
  • /30

    $535,000

    • 3 Beds
    • 2 Baths
    • 1,630 Sq Ft

    50 Payn Ave, Chatham, NY 12037

    Welcome to Dogwood Cottage! Tucked along one of the most darling streets in the Village of Chatham, Dogwood Cottage is a storybook gem framed by the blooms of its namesake tree. Set on a sweet quarter-acre lot, this 3 bedroom, 2 bath 1945 ''Victory Cottage'' offers the perfect blend of charm, privacy, and village convenience.Inside, natural light pours through every room, highlighting the warmth

    Brittany Craig Houlihan Lawrence Inc.

    50 Payn Ave, Chatham, NY 12037
  • /16

    $695,000

    • Land
    • 34 Acres
    • $20,245 per Acre

    10 Thomas Rd, Valatie, NY 12184

    Magnificent opportunity to own a large barn in great condition on 34+ acres with a two-bedroom apartment and a massive office space. Views of the Catskill mountains with two ponds and 20 acres of pasture. Direct access to the property from Thomas Rd, Boice Rd. and Route 66. The barn has 15 stalls, concrete floors, and water spigots. The smaller of the two horse stall wings would make a great

    Patrick Lilly Patrick Lilly Team, LLC

    10 Thomas Rd, Valatie, NY 12184
  • /11

    $390,000

    • Land
    • 45 Acres
    • $8,667 per Acre

    0 County Route 28-A Unit 20251992, Chatham Center, NY 12184

    Commanding panoramic views in the heart of Chatham Center span the Helderbergs, Jiminy Peak and the Berkshires, and into Village of Chatham — all visible from the top of this dramatic hilltop parcel. With 5-acre zoning, the property has potential for subdivision, or the perfect opportunity to build a striking home on the hill, surrounded by sweeping, bucolic landscapes. A rare and spectacular

    Scott Paladino Chatham Properties

    0 County Route 28-A Unit 20251992, Chatham Center, NY 12184
  • /23

    $799,000

    • 4 Beds
    • 3 Baths
    • 4,566 Sq Ft

    33 Hudson Ave, Chatham, NY 12037

    Unique Mixed-Use Opportunity in the Heart of Chatham VillageThis rare 4,566 sq. ft. mixed-use property on 0.17 acres offers prime visibility in the Village of Chatham, complete with free on-street parking and a rich blend of business, residential, and lifestyle potential. Thoughtfully renovated by the resident/owner, two storefronts have been combined into a vibrant boutique and pottery studio

    Joseph Briggs William Pitt Sothebys Int Rlty

    33 Hudson Ave, Chatham, NY 12037
  • /50

    $598,000

    • 4 Beds
    • 4 Baths
    • 3,050 Sq Ft

    635 Albany Turnpike, Old Chatham, NY 12136

    In the heart of Old Chatham, is this rare opportunity to purchase a historic, well maintained, 3 unit property with views of breathtaking, cascading waterfalls. The Old Chatham Post Office currently occupies one unit (3 years remain on the lease) and, there are 2 updated, currently vacant apartments to rent, live in or use as office space. The two level, 2 bedroom apartment and a 1 (could be 2)

    Peter Newman Beach & Bartolo Realtors

    635 Albany Turnpike, Old Chatham, NY 12136
  • /40

    $169,000

    • 3 Beds
    • 1 Bath
    • 2,048 Sq Ft

    2907 County Route 9, East Chatham, NY 12060

    Calling all Barn Lovers and Period Home Restorers! Come reimagine a legacy. Nestled on nearly 2 rolling acres of meadow and sky, This Old East Chatham Farmhouse invites you to revive a piece of Columbia County's earliest roots. Built in 1820 and rumored to be one of the area's oldest homes, this storied brick farmhouse still holds echoes of its past—wide-plank heart pine floors (milled from

    Brittany Craig Houlihan Lawrence Inc.

    2907 County Route 9, East Chatham, NY 12060
  • /19

    $485,000

    • Land
    • 60 Acres
    • $8,066 per Acre

    0 County Route 5 & I90 Unit 202517807, Canaan, NY 12060

    Nestled in the coveted Taconic Mountains, known for their rugged beauty, rich wildlife, clear streams, and hidden ponds, this double parcel boasts over 60 acres in Canaan, NY offering both accessibility and seclusion. The Taconics create a tranquil, less-traveled alternative to the busier Berkshires, offering privacy, natural beauty, and easy access to state forests and rural charm. The front 15+

    Jessica Coutsonikas KW Platform

    0 County Route 5 & I90 Unit 202517807, Canaan, NY 12060
  • /16

    $485,000

    • Land
    • 60 Acres
    • $8,066 per Acre

    0 County Rte 5 & I90 Unit 20251524, Canaan, NY 12029

    Nestled in the coveted Taconic Mountains, known for their rugged beauty, rich wildlife, clear streams, and hidden ponds, this double parcel boasts over 60-acres in Canaan, NY offering both accessibility and seclusion. The Taconics create a tranquil, less-traveled alternative to the busier Berkshires, offering privacy, natural beauty, and easy access to state forests and rural charm. The front 15+

    Jessica Coutsonikas KW Platform

    0 County Rte 5 & I90 Unit 20251524, Canaan, NY 12029
  • /30

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    11351 New York 22, Austerlitz, NY 12017

    Timeless Charm Meets Thoughtful Modernity on the Banks of the Green RiverNestled in the storybook hills of Austerlitz, NY—just 15 minutes from the heart of Chatham and 20 minutes to the cultural riches of Great Barrington—this fully renovated Cape Cod offers a rare blend of historic character and contemporary comfort. Set on 2.4 private acres with lush lawns, expansive planting beds, and

    John Barbato Compass, Hillsdale

    11351 New York 22, Austerlitz, NY 12017
  • /97

    $1,700,000

    • 9 Beds
    • 9.5 Baths
    • 5,195 Sq Ft

    632 Albany Turnpike, Old Chatham, NY 12136

    Own a piece of Old Chatham history with the distinguished Samuel Wilbor House. Built circa 1770 and listed on the National Register of Historic Places, the estate includes a beautifully updated main house, three stylishly renovated apartments, and a converted barn. The main house features white pine woodwork, four fireplaces, an original Palladian window, and a large kitchen with floor-to-ceiling

    Anthony D'Argenzio Houlihan Lawrence

    632 Albany Turnpike, Old Chatham, NY 12136
  • /34

    $545,000

    • 6 Beds
    • 6 Baths
    • 2,816 Sq Ft

    19 - 21 Moore, Chatham, NY 12037

    Chatham Village Income Gem! This tastefully updated Craftsman two-family offers substantial investment return and steady income. Situated on a quiet village street, this meticulously maintained property with two spacious, side-by-side units, each featuring 3 bedrooms, an office area, sunroom, and large enclosed entryway. Enjoy a large yard, four-car garage, and storage/workshop. Recent

    Rachel Haley Houlihan Lawrence Inc.

    19 - 21 Moore, Chatham, NY 12037
  • /28

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft

    1108 New York 295, East Chatham, NY 12060

    Was on the market before as just a shell. You have to see it now that it is redone and almost finished. Only room not yet finished is the kitchen for you to add your personal touch. New everything inside and out. New septic and well, new front landscaping, new siding, roof, furnace, hot water heater, insulation, wiring, plumbing, hardwood floors downstairs, windows and doors. Downstairs bedroom

    Karen Westman BERKSHIRE HATHAWAY HOME SERVICE BLAKE

    1108 New York 295, East Chatham, NY 12060
  • /49

    $3,995,000

    • 5 Beds
    • 3.5 Baths
    • 4,100 Sq Ft

    2705 County Route 9, East Chatham, NY 12060

    Welcome to The Anson Pratt House, a masterfully restored Federal Adams-style residence located in the historic hamlet of New Concord in East Chatham, NY. Built in 1793 atop a marble clad foundation, this architectural jewel is honored in the Library of Congress as part of the Historic American Buildings Survey. Featured in numerous architectural and design publications, The Anson Pratt House is

    Rachel Haley Houlihan Lawrence Inc.

    2705 County Route 9, East Chatham, NY 12060

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