Homes for Sale near Trinity-Pawling School

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  /30

  $575,000

  • 2 Beds
  • 2.5 Baths
  • 1,820 Sq Ft

  36 Byrds Hill Rd, Pawling, NY 12564

  Set on a quiet, scenic road in the prestigious Quaker Hill area, this home offers the perfect blend of seclusion and accessibility. You're only 3 miles from the serene waters of Quaker Lake, 2 miles from the Connecticut border, and just 20 minutes from charming CT towns like Sherman, New Milford, and Kent. From the outside, it’s a barn-like farmhouse surrounded by rolling green acreage and space

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 630-1049

  36 Byrds Hill Rd, Pawling, NY 12564
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  Explore Trinity-Pawling School

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  /49

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,318 Sq Ft

  7 Glen Ct, Pawling, NY 12564

  Welcome to this exquisitely renovated 3-bedroom, 2.5-bath Colonial home, showcasing over 2,300 square feet of elegant and comfortable living space. Perfectly situated in a serene cul-de-sac within the picturesque town of Pawling, this move-in-ready residence masterfully blends timeless charm with modern enhancements.As you step through the front door, you are greeted by a gracious

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 584-8385

  7 Glen Ct, Pawling, NY 12564
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  /11

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  7 Elm St, Pawling, NY 12564

  Home in the Village of Pawling - Come make this your special home - 3 Bedrooms, 2 Full Baths. Located right in the Village, walk to EVERYTHING! Metro North, Shops, Restaurants, Ice Cream, Boutiques. Upstairs has 3 Bedrooms with a full bath. Main floor has Living Room, Dining Room, nice size kitchen with full Bath. Deck off back to fenced in yard. Bring your vision and make your village

  

  Teddie Leonaggeo

  McGrath Realty Inc

  (845) 660-8512

  7 Elm St, Pawling, NY 12564
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  /42

  $599,000

  • 4 Beds
  • 4.5 Baths
  • 2,361 Sq Ft

  126 Old Route 55, Pawling, NY 12564

  Back on the market, the deal fell through from the buyer side. 9/17/2025 This house is owned by a church and in New York a sale has to be approved by the Attorney Generals office which can take up to six months. This can work to your benefit depending on your own timeline. This can also be set up a s a short term rental as well while waiting for the approvals WITH PORTION OF RENT GOING

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
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  /33

  $9,750,000

  • Land
  • 558.35 Acres
  • $17,462 per Acre

  225 Route 22, Pawling, NY 12564

  Unparalleled Opportunity Awaits! Discover this breathtaking 558+ acre parcel, just 90 minutes from Manhattan, offering a canvas of endless possibilities for personal and commercial endeavors. Whether you envision a sprawling family compound or a premier commercial facility, this land is primed for your dreams. Featuring level terrain, extensive trails, and vibrant pastures, this property is

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (845) 377-2512

  225 Route 22, Pawling, NY 12564
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  /8

  $229,000

  • Land
  • 7.02 Acres
  • $32,621 per Acre

  Lot 18 Cox Rd, Pawling, NY 12564

  Come build your dream home on this 7.02-acre Board of Health Approved lot in the highly desirable Brady Brook Falls community. Approved for a 5-bedroom residence, this property offers the perfect setting to create your ideal retreat while being just minutes from all the conveniences of Pawling. Enjoy easy access to Route 22, Route 55, shopping, the Village of Pawling, Metro-North, and even the

  

  Shannon Tully

  McGrath Realty Inc

  (845) 516-8037

  Lot 18 Cox Rd, Pawling, NY 12564
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  /11

  $229,000

  • Land
  • 6.63 Acres
  • $34,540 per Acre

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

  Come build your dream home on this 6.63-acre Board of Health–approved lot in the desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom home, this property offers the perfect setting for those seeking privacy while remaining just minutes from all the conveniences the Town of Pawling has to offer. Enjoy easy access to Route 22, Route 55, Metro-North, shopping, the charming

  

  Shannon Tully

  McGrath Realty Inc

  (845) 378-9417

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
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  /8

  $229,000

  • Land
  • 5.57 Acres
  • $41,113 per Acre

  Lot 21 Cox Rd, Pawling, NY 12564

  Come build your dream home on this 5.6-acre Board of Health–approved lot in the highly desirable Brady Brook Falls community of Pawling. Approved for a 5-bedroom residence, this property offers both privacy and convenience—just minutes from Route 22, the Village of Pawling, shopping, Metro-North, Route 55, and even the Appalachian Trail. Nestled within the Oblong Trails, residents of Brady Brook

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6866

  Lot 21 Cox Rd, Pawling, NY 12564
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  /41

  $450,000

  • 2 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  27 Washington Ct, Pawling, NY 12564

  Welcome to 27 Washington Court, located in the sought-after Deerfield Ponds community!This end-unit 2-bedroom, 2.5-bath townhome offers spacious living with beautiful pond views. Step inside from the inviting front porch and you’ll be greeted by a bright, airy entryway featuring a mudroom area, half bath, and a window opening into the pass-through kitchen. The eat-in kitchen boasts stainless

  

  Shannon Tully

  McGrath Realty Inc

  (845) 444-3725

  27 Washington Ct, Pawling, NY 12564
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  /48

  $749,000

  • 4 Beds
  • 3 Baths
  • 3,360 Sq Ft

  94 S Quaker Hill Rd, Pawling, NY 12564

  Set on 3.62 acres of picturesque and private land, this expansive 4-bedroom split-level home offers the perfect balance of spacious living and resort-style outdoor amenities, highlighted by a 20’ x 50’ saltwater in-ground pool. As you arrive along the freshly paved driveway, you’ll feel instantly at home in your own private oasis. Inside, a bright foyer with gleaming hardwood floors leads to the

  

  Shannon Tully

  McGrath Realty Inc

  (845) 253-5932

  94 S Quaker Hill Rd, Pawling, NY 12564
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  /48

  $949,999

  • 3 Beds
  • 4 Baths
  • 5,206 Sq Ft

  50 Carol Ln, Poughquag, NY 12570

  Welcome to 50 Carol Lane – A Tudor-Colonial Masterpiece on 3.67 Acres of Private Paradise! Experience timeless elegance and modern luxury at this extraordinary retreat nestled on beautifully landscaped grounds. This one-of-a-kind residence offers the perfect balance of historic charm and contemporary comfort, providing a private sanctuary inside and out. Boasting 3 bedrooms and 4 bathrooms, this

  Melvin Ramos Coldwell Banker Realty

  50 Carol Ln, Poughquag, NY 12570
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  /36

  $739,900 Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 3,564 Sq Ft

  5 Perri Ln, Pawling, NY 12564

  Nestled in the foothills of the Berkshires, this exquisite front Porch Center Hall Colonial sits perfectly on a beautiful rolling 1.4 acres of private property in the heart of Pawling. With it's amazing Bonus Room above the 2 car garage, it lives like a huge 4 Bedroom, 2 1/2 bath, offering all the amenities anyone could ask for. There is an Open Floor Plan with an Updated Kitchen, Granite

  Kristine Hansmann Jefferson Valley Realty

  5 Perri Ln, Pawling, NY 12564
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  /38

  $1,250,000

  • 4 Beds
  • 4 Baths
  • 3,994 Sq Ft

  Unlisted Address

  Modern country elegance is displayed at this residential retreat in Sherman CT. Sited amid 10 acres of preserve-like land, a distinctive blend of timeless character and architectural prescience unites the original construction with a striking 2014 addition. There are generous spaces, refined details, and seamless indoor-outdoor living. German designed Leitch cabinetry and white quartz countertops

  Chris Garrity Bain Real Estate

  Unlisted Address
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  /40

  $819,900

  • 4 Beds
  • 2.5 Baths
  • 3,214 Sq Ft

  12 Sunny Ln, Sherman, CT 06784

  Welcome to this charming 4 Bedroom, 2.5 Bath Colonial tucked away in the desirable pastoral town of Sherman, offering both comfort and versatility. Inside, you'll find a bright and inviting layout with spacious living areas, a well-appointed kitchen, and a cozy family room perfect for gatherings. The primary suite includes a private bath, while three additional bedrooms provide space for family,

  Heidi Mitchell Luks Realty

  12 Sunny Ln, Sherman, CT 06784
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  /34

  $699,000

  • 4 Beds
  • 5 Baths
  • 4,199 Sq Ft

  29 Cunningham Ln, Pawling, NY 12564

  Harmony Woods, an enclave of beautiful homes on the outskirts of the Village. This contemporary home has so much living space. Meticulously & continuously maintained by the current owners, there is nothing to be done! The 2 story foyer w/tile floors leads to the sunken LR which has high ceilings, a 2 sided fireplace, large windows & w/w carpet. There is formal DR, 2 powder rooms, then on to the

  Gillian Stewart Gillian Stewart Real Estate

  29 Cunningham Ln, Pawling, NY 12564
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  /40

  $869,900

  • 4 Beds
  • 2.5 Baths
  • 2,613 Sq Ft

  5 Bridgeworth Ln, Sherman, CT 06784

  Welcome to this striking Cape/Colonial nestled on a picture-perfect, dead-level parcel in one of Sherman's most desirable locations. With timeless curb appeal featuring classic wood clapboard siding and a charming cedar shingle roof, this home effortlessly blends character, comfort, and functionality. Step inside to discover a warm and inviting interior. The spacious family room is a true

  Cory Neumann Houlihan Lawrence

  5 Bridgeworth Ln, Sherman, CT 06784
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  /41

  $739,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 1,424 Sq Ft

  60 Lakeview Dr, Holmes, NY 12531

  *LAKEFRONT retreat on Serene Whaley Lake*Welcome to your dream escape on the tranquil waters of Whaley Lake—a breathtaking lakefront property offering panoramic water views from every room. Whether you're seeking a peaceful year-round home or the ultimate vacation getaway, this exquisite home delivers the perfect blend of comfort, style, and natural beauty.Wake up to golden sunrises from

  Amy Gold Keller Williams Realty Partner

  60 Lakeview Dr, Holmes, NY 12531
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  /36

  $1,225,000

  • 4 Beds
  • 3 Baths
  • 4,509 Sq Ft

  2 Autumn Dr, Sherman, CT 06784

  Tucked away on a private enclave of homes in desirable Southern Sherman, just minutes from the NY line, this stunning residence offers the perfect blend of seclusion, luxury and convenience for year-round living, weekend and summer escapes from the city. A very special property interior designed and decorated by AlvinYorkDesign of NYC, this is nothing short of exceptional, blending comfort with

  Angelina Valentini Coldwell Banker Realty

  2 Autumn Dr, Sherman, CT 06784
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  /40

  $829,999

  • 3 Beds
  • 2.5 Baths
  • 2,895 Sq Ft

  1034 Route 311, Patterson, NY 12563

  Experience the perfect blend of timeless charm and modern amenities in this stunning, fully refurbished and expanded 1867 farmhouse-style Victorian. Every inch of this 3-bedroom, 2.5-bathroom home has been thoughtfully redesigned for modern living while preserving its original character. The home's first floor layout centers around a beautifully designed kitchen with vaulted ceilings, original

  Jennifer Bumgarner

  1034 Route 311, Patterson, NY 12563
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  /39

  $699,000

  • 4 Beds
  • 4 Baths
  • 2,712 Sq Ft

  108 Beyer Dr, Poughquag, NY 12570

  Beautifully updated, 4 bedroom, 4bath home set back on a quiet country road with breathtaking views of the surrounding mountains. Sun-filled, spacious and thoughtfully designed for comfortable living and entertaining. The classic foyer leads to a chefs kitchen with granite countertops, center island, eat in area and plenty of storage. The formal dining room opens to a large family room with

  Greta Ferrari Keller Williams Hudson Valley

  108 Beyer Dr, Poughquag, NY 12570
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  /15

  $975,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  14 Akindale Rd, Pawling, NY 12564

  TO BE BUILT Welcome to Brady Brook falls, part of historic Quaker Hills one of Pawling's most distinguished country side. Enter onto freshly paved road and stone wall entrance. This beautiful lot is on 8.44 pastoral acres with amazing views of open sky and grassy meadows. When the days grow longer and temperatures rise or when the days grow shorter and temperatures drop , there is no better

  Kathryn McCoach Houlihan Lawrence Inc.

  14 Akindale Rd, Pawling, NY 12564
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  /37

  $699,000

  • 4 Beds
  • 5 Baths
  • 4,018 Sq Ft

  175 Old Quaker Hill Rd, Pawling, NY 12564

  A Stately Cape Cod Estate with exceptional Potential awaits. Set on an expansive, flat parcel of land surrounded by farms, rolling hills, and mountain views, this once grand and elegant residence offers a rare opportunity to restore and reimagine a home of timeless distinction. A property of this caliber, featuring grand proportions, architectural charm, and breathtaking grounds, is a true gem

  Tom Consaga RE/MAX Ace Realty

  175 Old Quaker Hill Rd, Pawling, NY 12564
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  /26

  $299,999

  • 2 Beds
  • 2.5 Baths
  • 1,170 Sq Ft

  308 Covington Green Ln, Patterson, NY 12563

  Beautiful Three-Level End Unit in Move-In ConditionThis lovely, quiet end unit offers peaceful surroundings and scenic views. Featuring three spacious levels, the home is in move-in ready condition. Conveniently located just minutes from Metro North and shopping destinations, this property combines comfort, privacy, and accessibility—perfect for commuters or anyone seeking a low-maintenance

  Robert Dutra My Seasons Realty LLC

  308 Covington Green Ln, Patterson, NY 12563
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  /33

  $335,000

  • 2 Beds
  • 2.5 Baths
  • 1,755 Sq Ft

  608 Covington Green Ln, Patterson, NY 12563

  Experience the Comfort and Convenience of 608 Covington Green Lane. A Charming Townhouse in Patterson’s Desirable Covington Green Community. This 2 Bedroom, 2.5 Bath Home Offers a Practical Layout Designed for Everyday Living and Entertaining. Enjoy Cozy Evenings in the Living Room with a Fireplace, or Gather with Friends and Family in the Dining Area Adjacent to a Lovely Kitchen. Step Outside to

  Stephen Mancini Mancini Realty Inc.

  608 Covington Green Ln, Patterson, NY 12563
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  /32

  $1,400,000

  • 11 Beds
  • 8 Baths

  750 Route 292, Holmes, NY 12531

  Multi-generational housing opportunity with 3 individual homes on one property. 3 distinct home styles with plenty of options. The perfect balance of togetherness and privacy. And investors - you may want to give this property some serious consideration as well.Unit A: Colonial style renovated home. Hardwood floors, crown molding and recessed lighting throughout. Spacious Living Room with

  Judy Albert BHHS Hudson Valley Properties

  750 Route 292, Holmes, NY 12531
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  /40

  $489,900

  • 4 Beds
  • 2 Baths
  • 1,613 Sq Ft

  49 Quaker Ridge Rd, Sherman, CT 06784

  Cape on Quaker Ridge! Looking for an affordable entry into Sherman? This 4-bedroom, 2-bath Cape, set at the end of a quiet cul-de-sac on sought-after Quaker Ridge Road, offers just that-plus a premium 2.28-acre lot. Owned by the same owner for over 40 years, this home is ready for its next chapter and new owners to enjoy for decades to come. Opportunities for expansion are plentiful, with an

  Todd Sargent Coldwell Banker Realty

  49 Quaker Ridge Rd, Sherman, CT 06784
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  /39

  $425,000

  • 3 Beds
  • 1 Bath
  • 1,620 Sq Ft

  96 Lakeview Dr, Pawling, NY 12564

  Welcome to this renovated 1,620 SF raised ranch in Pawling Lake Estates, a charming lake community nestled atop West Mountain and adjacent to West Mountain State Park. Steps in reveal freshly painted walls and refinished hardwood flooring throughout the 1,120 SF first floor. The living room has a massive stone fireplace and wood-burning stove insert, which opens to the dining area. A renovated

  Claudia Jiskra McGrath Realty Inc

  96 Lakeview Dr, Pawling, NY 12564
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  /30

  $390,000

  • 2 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  23 Juniper Ln, Pawling, NY 12564

  A quiet cul-de-sac welcomes you to a well-maintained town home in the desirable Cedar Valley Community. Easy accessibility to all the Pawling Village amenities: restaurants, shops, Farmer’s Market, professional services and commuting with Metro North. This home has so much to offer – open Living and Dining areas with hardwood floors, working fireplace and pass through to Kitchen. Also glass doors

  Judy Albert BHHS Hudson Valley Properties

  23 Juniper Ln, Pawling, NY 12564
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  /49

  $1,550,000

  • 3 Beds
  • 2.5 Baths
  • 2,363 Sq Ft

  71 Carol Ln, Poughquag, NY 12570

  coming soon

  Spyros Spyrou RE/MAX Town & Country

  71 Carol Ln, Poughquag, NY 12570
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  /29

  $749,000

  • 4 Beds
  • 3 Baths
  • 3,888 Sq Ft

  12 Rebecca Dr, Pawling, NY 12564

  Surrounded by the natural beauty of the Hudson Valley region, this Multi-Family home benefits from a private environment that outdoor enthusiasts will find irresistible. This property's location offers convenient access to the Lakeside Park Disc Golf Course, the nearby Appalachian Trail which provides endless hiking opportunities for nature lovers and the Metro-North Railroad being about a 5

  Kevin Sanabria eRealty Advisors, Inc

  12 Rebecca Dr, Pawling, NY 12564
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  /36

  $425,000

  • 2 Beds
  • 3 Baths
  • 2,140 Sq Ft

  49 Lakeview Dr, Holmes, NY 12531

  The next best thing to Lakefront! This sprawling ranch home is a stone’s throw from access to Whaley Lake, with lake rights to all the great amenities: private beach, motorboats allowed, kayaking, fishing, swimming, sunbathing, picnicking, fall leaf watching and winter ice fishing too! With 2 bedrooms plus an Office, Den, Living Room and Family Room – there’s so much potential including one floor

  Judy Albert BHHS Hudson Valley Properties

  49 Lakeview Dr, Holmes, NY 12531
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  /29

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft

  12 Anderson Way, Pawling, NY 12564

  This charming cottage is within walking distance of the picturesque village of Pawling and on the market for the first time in over 35 years. Lovingly maintained and enhanced by its owner, this home boasts the ease and convenience of one level living. The renovated front porch welcomes you to the house while the beautiful sundrenched addition features heating, hardwood floor, oversized windows,

  Stacey Cronin Houlihan Lawrence Inc.

  12 Anderson Way, Pawling, NY 12564
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  /36

  $359,999

  • 2 Beds
  • 2.5 Baths
  • 1,413 Sq Ft

  33 Spruce St, Pawling, NY 12564

  Welcome to 33 Spruce Lane, a charming 2-bedroom, 2.5-bath home located in the sought-after Cedar Valley community in Pawling. This inviting townhome lives like a single-family home and offers the perfect balance of comfort, convenience, and amenities.Step inside to find a bright and open living space designed for easy living. The home features a spacious living room, a functional kitchen with

  Edmond Albano Keller Williams NY Realty

  33 Spruce St, Pawling, NY 12564
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  /33

  $2,500,000

  • 6 Beds
  • 6.5 Baths
  • 6,094 Sq Ft

  3302 Route 55, Pawling, NY 12564

  Welcome to your forever home, serene retreat and mini estate. Enjoy the 72 private acres with breath taking views. Mother Nature is at her best. Exceptional beauty for all four seasons. The unique and exquisite architectural design of this home lends to expansive living space, tucked behind gated entry. This home offers unique living space, luxury and customize finishes throughout. A true

  STACI MACKIN Dixon Smith Realty

  3302 Route 55, Pawling, NY 12564
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  /31

  $275,000

  • 3 Beds
  • 1 Bath
  • 1,653 Sq Ft

  14 Old Route 55, Pawling, NY 12564

  FULLY Available! Welcome home to this historic and charming 3 bedroom, 1 bathroom beauty located above a stunning stream in the heart of Pawling. This beautifully antique home offers a rare blend of historic character and contemporary updates. Walk into the welcoming sunroom with plenty of natural light that opens up to a cozy living room featuring a wood burning fireplace and French doors that

  Ronald Green KW MidHudson

  14 Old Route 55, Pawling, NY 12564
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  /46

  $650,000

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

  85 Harmony Hill Rd, Pawling, NY 12564

  This charming fully remodeled, bright, and sunny ranch—featuring 3 bedrooms, 3 full bathrooms, and 2.90 acres of land. Prepare meals in the beautiful new kitchen, complete with custom cabinets, LG appliances, and quartz countertops. Relax in the family room beside the gorgeous stone fireplace. From there, step out onto the lovely wood deck and savor your morning coffee surrounded by

  Mary Craig Coldwell Banker Realty

  85 Harmony Hill Rd, Pawling, NY 12564
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  /9

  $169,000

  • Land
  • 0.73 Acre
  • $231,507 per Acre

  0 Walnut St, Pawling, NY 12564

  Village of Pawling building lot is on municipal water and sewer! Thousands will be saved - No expensive well or septic system! .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants, library, so much more! Metro-North Train Station, Harlem Line, is located in the Village as well. You will love Lakeside Park! 36-acre Green

  Lisa Liffland McGrath Realty Inc

  0 Walnut St, Pawling, NY 12564
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  /28

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  23 Union St, Pawling, NY 12564

  3 Bed | 2 Bath | Fully Electric | Walkable Village LocationTurnkey, updated, and full of charm—this 3-bedroom, 2-bath home is perfectly situated in the heart of Pawling Village. Whether you're a first-time buyer using FHA or VA financing, a downsizer, or simply seeking a low-maintenance, energy-efficient home, this property offers a flexible layout, thoughtful upgrades, and access to

  Brett David Miller K Fortuna Lighthouse Realty

  23 Union St, Pawling, NY 12564
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  /28

  $537,500

  • 3 Beds
  • 3.5 Baths
  • 2,106 Sq Ft

  101 Bundy Hill Rd, Holmes, NY 12531

  Nestled in between trees and rocks, privacy abounds in this Contemporary Colonial style dwelling with numerous upgrades. A down to the studs remodel in 2016, the home boasts generous open concept living, dining and kitchen areas all with recessed lighting. Kitchen includes butcherblock counter tops and stainless-steel appliances. Entry nook convenient for coats, purses, backpacks and shoes. First

  Judy Albert BHHS Hudson Valley Properties

  101 Bundy Hill Rd, Holmes, NY 12531
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  /47

  $599,900

  • 3 Beds
  • 2 Baths
  • 2,107 Sq Ft

  28 Gobblers Knob Rd, Pawling, NY 12564

  Welcome to 28 Gobblers Knob Road – A Hudson Valley Retreat! Nestled in the heart of the rolling hills of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on over 20 acres, offering peace, privacy, and natural beauty in every direction. Just over 3 miles from the Metro-North line to Manhattan, you can enjoy the quiet of a country escape without sacrificing

  Mark Snyder eXp Realty

  28 Gobblers Knob Rd, Pawling, NY 12564

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