Homes for Sale near Chatham Middle School

• 

  

  

  /19

  $325,000

  • Land
  • 29.39 Acres
  • $11,058 per Acre

  358 W Hill Rd, Austerlitz, NY 12017

  Nearly 30 wonderful private parcel of land with wooded glens, open fields and Green River frontage. Views of Harvey Mountain. Usable land with a great mix of open fields stream frontage, and pristine woodland. Nice hardwoods. Frontage on two roads. Subdividable. Level land with mature trees. Great location close to the Berkshires, Hawthorne Valley School, Hudson and Chatham.

  Tracy Tassinari Gabel Real Estate

  358 W Hill Rd, Austerlitz, NY 12017
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• 

  

  

  /33

  $2,450,000

  • 3 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  53 May Ln, Chatham, NY 12037

  Situated at the top of a private lane just outside the hamlet of Spencertown, sits a 14-acre sanctuary offering breathtaking views of the surrounding landscape with the majestic Catskill peaks in the distance. Wildflower meadows and lush gardens provide three seasons of color while an ecologically designed swimming pond, frame the home, complete with stone patios and porches - all to take in the

  Jeb Hart Licensed as Henry Hart Corcoran Country Living

  53 May Ln, Chatham, NY 12037
• 

  

  

  /15

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  424 Macedonia Rd, Austerlitz, NY 12165

  Manufactured home at the end of a quiet lane. Nearly 5 acres of tranquility. Close to State Forest and Beebe Hill for hiking. Two bedrooms with two full baths. Open floor plan. Easy maintenance. Enclosed porch and nice deck.Two hundred square foot enclosed. Doesn't get any more private than this. Shed for storage. Woodstove for the fall and winter nights. Cleared spot perfect for gardening or

  Tracy Tassinari Gabel Real Estate

  424 Macedonia Rd, Austerlitz, NY 12165
• 

  

  

  /28

  $349,000

  • 4 Beds
  • 1.5 Baths
  • 1,214 Sq Ft

  1976 State Route 203, Chatham, NY 12037

  Set along scenic Route 203, this four-bedroom home enjoys easy access to the vibrant Village of Chatham, where beloved restaurants, local shops, farmers markets, and cultural attractions create one of Columbia County's most sought-after communities. Inside, the home offers a practical floor plan with comfortable living spaces and abundant potential for updates and personalization. Whether you're

  Nikki Carchedi Stone House Properties, LLC

  1976 State Route 203, Chatham, NY 12037
• 

  

  

  /36

  $395,000

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  127 Queechy Shore Beach Rd, Canaan, NY 12029

  Welcome to Queechy Lake Cottage, a vintage Hudson Valley retreat on Queechy Lake in Northern Columbia County's Canaan. Built in the 1930s on land that once served as a boys' camp, this charming 1,008-square-foot cottage offers indoor-outdoor living with three bedrooms, a full bathroom, and the kind of peaceful lake living that feels increasingly rare. Outside, the compact cottage includes a level

  Anthony D'Argenzio Houlihan Lawrence Inc.

  127 Queechy Shore Beach Rd, Canaan, NY 12029
• 

  

  /20

  $550,000

  $45K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,872 Sq Ft

  52 Church St, Chatham, NY 12037

  Welcome to 52 Church Street, a c.1900 home set on a generously-sized quarter acre lot in the Village of Philmont. Enter through a large mudroom flanked with windows. A stylish living room flows seamlessly to a large kitchen overlooking the yard. Numerous windows and a door leading to the backyard flood the kitchen space with light. A hall leads to a second kitchen, bedroom and full bath, perfect

  MATTHEW CAREY Rouse + Co Real Estate

  52 Church St, Chatham, NY 12037
• 

  

  /21

  $299,000

  • 4 Beds
  • 2 Baths
  • 2,064 Sq Ft

  2261 New York 66, Ghent, NY 12075

  Fully Rented. Tenants require 48-hour notice to show and only after 10a.m. Sunday showings not preferred. All photos pre-occupancy. Easy living in this low-maintenance, fully renovated income home. Two two-bedroom apartments, each with refrigerator, range/oven, washer/dryer. Covered front porch with a second-floor veranda above. Bright, happy home. Cable/High-speed internet available. 3 miles to

  Natalia de Amorim Preferred Country Properties

  2261 New York 66, Ghent, NY 12075
• 

  

  /50

  $949,000

  • 5 Beds
  • 3.5 Baths
  • 3,390 Sq Ft

  23 Petty Dr, Ghent, NY 12075

  A large, turnkey home on 5.13 open acres in Ghent, with Hudson just ten minutes away and a floor plan that makes life easy. Three bedrooms on the main level, an expansive primary suite upstairs, a finished basement with a fifth bedroom alongside a sizable gym and rec room, plus an attached, insulated three-car garage. Furnishings are available, should you want to skip the moving-in part entirely.

  Arlena Armstrong Anatole House LLC

  23 Petty Dr, Ghent, NY 12075
• 

  

  /61

  $375,000

  • 5 Beds
  • 3 Baths
  • 3,146 Sq Ft

  22 Spring St, Chatham, NY 12037

  Fully Rented Income Property in the heart of Chatham Village NY. 3 non-owner-occupied units. All photos taken pre-occupancy. 5BRS total, 3 full baths. Municipal water/sewer. Private off-street parking. Total acreage for 2 parcels (66.6-1-45 is 0.23 acre and 66.6-1-48 is 0.24 acre). Total tax figures below include both parcels. A minute drive to Main St and all shops, theater, pubs, restaurants,

  Natalia de Amorim Preferred Country Properties

  22 Spring St, Chatham, NY 12037
• 

  

  /31

  $529,000

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft

  34 Queechy Shore Beach Rd, Canaan, NY 12029

  Welcome to Peggy's Cottage. The owner, a cellist, originally chose this Queechy Lake home for its proximity to Tanglewood and the cathedral ceilings in the family room, which served as her music room. She quickly grew to love the lake community's friendly neighbors, walking trails, and private beach. This cozy log cabin sits on a level .36 acre lot, offering rare privacy with lovely gardens, a

  Nancy Cuddihy Stone House Properties, LLC

  34 Queechy Shore Beach Rd, Canaan, NY 12029
• 

  

  /38

  $2,300,000

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

  79 Cemetery Rd, Chatham, NY 12037

  Brick House FarmTucked away in the highly sought-after Red Rock community, Brick House Farm is a rare 80-acre compound offering a distinctive blend of 19th-century character and expansive functional space. At the heart of the estate stands a classic 1810 brick home, featuring a versatile 4-bedroom, 2-bathroom layout highlighted by an extensive primary suite, rich custom woodwork, and a chef's

  Rachel Haley Compass Greater NY, LLC

  79 Cemetery Rd, Chatham, NY 12037
• 

  

  /14

  $190,000

  • 1 Bed
  • 1.5 Baths
  • 572 Sq Ft

  42 Pine Tree Ln, Canaan, NY 12029

  It's all about the location! Perched high on a hilltop, this charming cabin offers seasonal peekaboo views of Queechy Lake. The property includes three parcels complete right of way and mooring spot on the lake. Featuring one bedroom and one-and-a-half baths, this cozy retreat is ideal as a weekend getaway or a year-round residence. Enjoy the privacy of a hilltop setting while being just moments

  Elisha Poirier Stone House Properties, LLC

  42 Pine Tree Ln, Canaan, NY 12029
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  /7

  $495,000

  $55K PRICE DROP

  • Land
  • 39.1 Acres
  • $12,660 per Acre

  Tbd W Hill Rd, Austerlitz, NY 12017

  If you've been dreaming of a private compound—or the flexibility of building your own home alongside an investment property—this rare 39-acre offering in Austerlitz opens the door to endless possibilities. The land is thoughtfully divided into two separate parcels of 19.55 acres each, set within a neighborhood known for its sweeping landscapes, privacy, and architecturally impressive

  Diana Polack Compass Greater NY, LLC

  Tbd W Hill Rd, Austerlitz, NY 12017
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  /53

  $599,000

  $150K PRICE DROP

  • 9 Beds
  • 9 Baths
  • 6,935 Sq Ft

  1121 New York 295, East Chatham, NY 12060

  2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for

  Natalia de Amorim Preferred Country Properties

  1121 New York 295, East Chatham, NY 12060
• 

  

  /30

  $615,000

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  2318 County Route 9, East Chatham, NY 12060

  Tucked down a quiet country road, 2318 County Route 9 is the kind of place that feels like it's been waiting for you. Set on over five acres, this three bedroom, one bath cottage is thoughtfully designed from the inside out, every corner telling a story, every detail chosen with care.Sunlight pours through every window, framing the beauty of lush gardens and the natural world just beyond the

  Shaina Marron Houlihan Lawrence Inc.

  2318 County Route 9, East Chatham, NY 12060
• 

  

  /24

  $325,000

  • 3 Beds
  • 2 Baths
  • 3,000 Sq Ft

  1135 New York 295, East Chatham, NY 12060

  1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High

  Natalia de Amorim Preferred Country Properties

  1135 New York 295, East Chatham, NY 12060
• 

  

  /50

  $1,995,000

  • 3 Beds
  • 3 Baths
  • 4,409 Sq Ft

  3243 County Route 9, East Chatham, NY 12060

  Welcome to Bear Paw Creek. Explore this captivating 24.68-acre retreat in East Chatham, New York, where a private drive leads to an idyllic blend of historic charm and contemporary elegance in an 1825 farmhouse. Featured in Domino Magazine this designer home is nestled amid rolling pastoral valleys, dense woods, and a gently flowing stream, the property unfolds with sublime gardens, a unique

  Rachel Haley Compass Greater NY, LLC

  3243 County Route 9, East Chatham, NY 12060
• 

  

  /59

  $1,200,000

  • 16 Beds
  • 8 Baths
  • 8,208 Sq Ft

  85-87 Nelson Ave, Ghent, NY 12075

  BEST INVESTMENT PRESENTLY LISTED - EXCELLENT NOI - FULLY OCCUPIED 2 buildings, total 8 identical units on 1.4 acres. 2 bedrooms each unit and full bath, spacious L shaped LR/ DA and kitchen w/stove/fridge/range hood. Common laundry area in hallway w/washer/dryer. Private, off-street, asphalt parking lot. Total 16 bedrooms, 8 full baths. Walk to Dairy Queen, free tennis courts, sport field w/

  Natalia de Amorim Preferred Country Properties

  85-87 Nelson Ave, Ghent, NY 12075
• 

  

  /15

  $169,000

  • Land
  • 26.5 Acres
  • $6,377 per Acre

  0 County Route 9 Unit 20255066, New Lebanon, NY 12060

  26.5 acres of land to farm or build on . Fabulous views over surrounding farmland, valley and mountains.Great mix of open land & woods . Pond for fishing or irrigation for crops. Beautiful stream & rock walls. Perfect land to put in an agricultural program for lower taxes.Just 2.5 hours from NYC, 35 minutes to Hudson, 30 minutes to Albany, 15 minutes to Pittsfield & Jiminy Peak.

  Philip Feiner Country Life Real Estate, LLC

  0 County Route 9 Unit 20255066, New Lebanon, NY 12060
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  /33

  $509,900

  Open Mon 5:30PM - 7:30PM $15K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,768 Sq Ft

  524 Angel Hill Rd, Chatham, NY 12037

  Don't overlook this peaceful escape, tucked away on nearly five wooded acres with sweeping hilltop views--yet just minutes from Ghent and Chatham. This spacious contemporary home offers both privacy and a strong connection to the surrounding natural beauty. Set at the end of a long driveway on 4.8 wooded acres, coming home feels like a retreat into peace and stillness. The well-maintained home

  Darcey Volans The Kinderhook Group, Inc.

  524 Angel Hill Rd, Chatham, NY 12037
• 

  

  /20

  $59,000

  $16K PRICE DROP

  • Land
  • 4.74 Acres
  • $12,447 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 Millay

  Jennifer Sesma Beach & Bartolo Realtors

  0 New York 22, Austerlitz, NY 12017
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  /30

  $489,000

  • 3 Beds
  • 1.5 Baths
  • 1,910 Sq Ft

  15 Jones Ave, Chatham, NY 12037

  Home Sweet HomeLocated on a quiet side street, this wonderful village property has so much to offer. The bright and welcoming interior includes a living room, dining room, spacious kitchen, and a sunroom that leads to the backyard patio and garden. The first floor also features a convenient mudroom and a half bath. Upstairs you will find three bedrooms and a nicely appointed full bath.

  Lenore Packet Stone House Properties, LLC

  15 Jones Ave, Chatham, NY 12037
• 

  

  /25

  $625,000

  • 5 Beds
  • 3.5 Baths
  • 2,982 Sq Ft

  158 Hudson Ave, Chatham, NY 12037

  Experience the perfect blend of 1900s farmhouse charm and contemporary comfort in the heart of Chatham. This thoughtfully updated farmhouse features an expansive open-concept kitchen and great room designed for seamless entertaining. Filled with natural light, the great room includes a wood burning stove and cozy window seat. Relax in the light-drenched enclosed front porch or enjoy dining on the

  Beth Cozzolino Gabel Real Estate

  158 Hudson Ave, Chatham, NY 12037
• 

  

  /21

  $599,000

  $51K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  896 County Route 13, Old Chatham, NY 12136

  Nestled within the serene hamlet of Old Chatham, this exceptional country home offers 43 private acres with stream frontage and abundant wildlife. Thoughtfully renovated and impeccably maintained, the residence seamlessly blends timeless rural character with modern comfort. Recent enhancements include a beautifully redesigned kitchen and bath, upgraded sound attenuation for enhanced privacy, a

  Mary Turoci Keyology

  896 County Route 13, Old Chatham, NY 12136
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  /36

  $395,000

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  127 Queechy Shores, Canaan, NY 12029

  Welcome to Queechy Lake Cottage, a vintage Hudson Valley retreat in a private community in Northern Columbia County. Built in the 1930s and renovated in 2017/18, this charming three bedroom cottage offers indoor-outdoor living perfect for a family with a large deck, screened-in porch, fire pit, and rare beach lake access. The open living area has vaulted ceilings and the large, lovely screened

  Anthony D'Argenzio Houlihan Lawrence

  127 Queechy Shores, Canaan, NY 12029
• 

  

  /50

  $7,995,000

  $4M PRICE DROP

  • 8 Beds
  • 10 Baths
  • 8,000 Sq Ft

  47 White Bridge Rd, Old Chatham, NY 12136

  Where History Breathes and Beauty Dwells: WHITE BRIDGE FARM c1775 Welcome to White Bridge Farm, an exquisite historic18th century estate restored and designed honoring and preserving the history with imagination and perfection. White Bridge Farm will take your breath away at every turn from the original restored iron main gate to magical stonewalls, pathways and gardens landscaped to intrigue all

  Nancy Felcetto Brown Harris Stevens HV LLC

  47 White Bridge Rd, Old Chatham, NY 12136
• 

  

  /51

  $2,895,000

  • 7 Beds
  • 4 Baths
  • 5,188 Sq Ft

  311 County Route 13, Old Chatham, NY 12136

  Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

  Nikki Carchedi Stone House Properties, LLC

  311 County Route 13, Old Chatham, NY 12136
• 

  

  /14

  $795,000

  • Land
  • 95.24 Acres
  • $8,347 per Acre

  0 Scannell Rd, Ghent, NY 12075

  Estate parcel. One parcel with no restrictions that has the potential for many uses. Keep it as one parcel to build the end all estate on, develop the parcel into a compound of multiple parcels, farming, hunting, recreation. The potential in this parcel is beyond belief. End of the road parcel for complete privacy and tranquility. Potential for western views of the Catskills and local Punsit and

  Tracy Tassinari Gabel Real Estate

  0 Scannell Rd, Ghent, NY 12075
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  /42

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft

  682 New York 203, Spencertown, NY 12165

  Looking for a country home without large acreage to maintain and manage? Or looking to downsize but still have space for guests? This 3 bed, 2 bath, 1496 Sq ft ranch in Spencertown checks all those boxes. Built in 1965, the home sits back from the road in a park like setting on just 0.77 acres. With a beautiful view out back overlooking the neighbor's pasture it feels like you have much more

  Jennifer Sesma Beach & Bartolo Realtors

  682 New York 203, Spencertown, NY 12165
• 

  

  /9

  $125,000

  • 3 Beds
  • 1.5 Baths

  1903 Route 203 Unit 76, Chatham, NY 12037

  NEW 3 bedroom, 1.5 bath manufactured home available for sale. $125,000 + tax. Edgewood Acres is a quiet neighborhood with an authentic country vibe. You can walk to Chatham Village and find one-of-a-kind retail stores, restaurants and galleries. This rural upstate New York community is open, friendly, and welcoming. Crellin Community Park is walking distance from downtown Chatham with

  Darice Joerman Garden Homes Management

  1903 Route 203 Unit 76, Chatham, NY 12037
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  /72

  $1,535,000

  • 5 Beds
  • 4 Baths
  • 3,349 Sq Ft

  13 Conster Rd, East Chatham, NY 12060

  Tucked into five acres of private hillside with sweeping mountain views, this sophisticated five-bedroom, four-bathroom retreat offers a rare blend of seclusion and convenience -- close to charming Berkshires towns and the cultural riches of Tanglewood and Jacob's Pillow, four ski slopes, hiking trails and the delights of the Hudson Valley. From the moment you step into the welcoming foyer, the

  Gary Lazarus Compass Greater NY LLC

  13 Conster Rd, East Chatham, NY 12060
• 

  

  /64

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 3,190 Sq Ft

  76 Bowman Rd, Chatham, NY 12037

  A truly magical property tucked away at the end of a quiet country road, yet just minutes from the Village of Chatham. Set amid 10 lush and exceptionally private acres, the centerpiece of this enchanting retreat is a light-filled barn conversion featuring a soaring stone fireplace, wide-plank floors, a lofted primary suite, and a separate guest level with living room, two bedrooms, a full bath,

  Lisa Bouchard Hoe The Kinderhook Group, Inc.

  76 Bowman Rd, Chatham, NY 12037
• 

  

  /47

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,005 Sq Ft

  2228 State Route 203, Chatham, NY 12037

  This 9.5-acre property in Chatham, NY offers exceptional potential, with multiple structures including a huge 2 story barn in excellent condition with a private pond. for swimming. A true diamond in the rough, the 2,005-square-foot main home features 3 bedrooms and 3 full bathrooms and has solid bones, though it does need some TLC. Dual brick fireplaces in the living room and reading nook, a

  Claudia Zucker

  2228 State Route 203, Chatham, NY 12037
• 

  

  /14

  $190,000

  • 1 Bed
  • 2 Baths
  • 572 Sq Ft

  0 Pine Tree Ln, Canaan, NY 12029

  It's all about the location! Perched high on a hilltop, this charming cabin offers seasonal peekaboo views of Queechy Lake. The property includes three parcels complete right of way and mooring spot on the lake. Featuring one bedroom and one-and-a-half baths, this cozy retreat is ideal as a weekend getaway or a year-round residence. Enjoy the privacy of a hilltop setting while being just moments

  Elisha Poirier STONE HOUSE PROPERTIES, LLC

  0 Pine Tree Ln, Canaan, NY 12029
• 

  

  /28

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  3620 County Route 9, East Chatham, NY 12060

  Acreage | Fun Architecture | Absolute Privacy. A refined 3BR/2BA residence on over 2 acres, anchored by a soaring cathedral-ceiling great room opening to wraparound deck .. add'l family room, updated kitchen, den, plus CENTRAL AIR and numerous other amenities. Family Rm fireplace is propane; laundry/utility woodstove is wood-burning. Central propane, hot air heating system and propane hot water.

  Natalia de Amorim PREFERRED COUNTRY PROPERTIES

  3620 County Route 9, East Chatham, NY 12060
• 

  

  /58

  $649,900

  • 4 Beds
  • 3 Baths
  • 2,515 Sq Ft

  1209 County Route 22, Ghent, NY 12075

  Peaceful country living awaits on this unique 7-acre property featuring 2 parcels on one deed. The home sits on 1.8 acres surrounded by wildlife, fruit trees, and outdoor spaces designed for relaxation and entertaining. Enjoy your morning coffee on the screened-in porch, host gatherings on the wrap around deck with built in seating or spend evenings around the fire pit. Outdoor amenities include

  Wendy Kenney Davala Real Estate, LLC

  1209 County Route 22, Ghent, NY 12075
• 

  

  /21

  $299,000

  • 4 Beds
  • 2 Baths
  • 2,064 Sq Ft

  2261 State Route 66, Ghent, NY 12075

  Tenants require 48hour notice to show and only after 10a.m. No Sunday showings preferred. All photos pre-occupancy. Easy living in this low-maintenance, fully renovated income home. Two two-bedroom apartments, each with refrigerator, range/oven, washer/dryer. Covered front porch with a second-floor veranda above. Bright, happy home. Cable/High-speed internet available. 3 miles to Chatham

  Natalia de Amorim Preferred Country Properties

  2261 State Route 66, Ghent, NY 12075
• 

  

  /23

  $499,000

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  1129 New York 295, East Chatham, NY 12060

  Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/ I90/ Berkshire Spur, 15 minutes to Lenox/ Tanglewood, 30 minutes Albany/ Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and

  Natalia de Amorim Preferred Country Properties

  1129 New York 295, East Chatham, NY 12060

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