57

Homes for Sale near Trinity-Pawling School

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  • /23

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    26 Rodina Dr, Pawling, NY 12564

    Welcome to your brand new dream home! Nestled on a beautiful and peaceful two and half acres. Be the first to live in this stunning four bedroom, two and a half bath home. Step onto the full length front porch and inside to a light, bright and airy interior boasting a modern open floor plan. Spacious entrance foyer with double coat closets and sleek iron railing with motion sensor lighting on

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    Douglas Servello

    Home Sweet Home Properties

    (845) 415-1257

    26 Rodina Dr, Pawling, NY 12564
  • /42

    $598,500

    • 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 TOWARDS

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    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 Old Route 55, Pawling, NY 12564
  • /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

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    Colleen McGrath

    McGrath Realty Inc

    (845) 584-8385

    7 Glen Ct, Pawling, NY 12564
  • /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

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    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 299-9362

    101 Bundy Hill Rd, Holmes, NY 12531
  • /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

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    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 478-8605

    49 Lakeview Dr, Holmes, NY 12531
  • /22

    $1,350,000

    • Land
    • 3.9 Acres
    • $346,154 per Acre

    178 Charles Colman Blvd, Pawling, NY 12564

    Exclusive Mixed-Use Property in Pawling N.Y.! Incredible Investment or Business Opportunity offering a rare blend of Residence, Greenhouse, Floral Shop, & Nursery.This beautiful Sprawling estate boasts a Commercial c & Residential component? with a 2,500 sqft greenhouse fully-equipped floral shop with retail space There is Ample parking & easy accessibility for Commercial

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    Vince Buccieri

    Today Realty Corp.

    (845) 280-5951

    178 Charles Colman Blvd, Pawling, NY 12564
  • /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

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    Shaylene Neumann

    Houlihan Lawrence Inc.

    (845) 377-2512

    225 Route 22, Pawling, NY 12564
  • /46

    $1,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,390 Sq Ft

    43 Meeting House Rd, Pawling, NY 12564

    A Bucolic Retreat in Prestigious Quaker Hill, nestled among grand equestrian estates in the coveted Quaker Hill community of Pawling, this magnificent country retreat artfully blends modern luxury with rustic charm. Set on five serene acres surrounded by rolling meadows, scenic horse farms, and distinguished country homes, 43 Meeting House Lane offers an inspiring escape that celebrates the best

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    Alicia Goldman

    Christie's Int. Real Estate

    (845) 373-3547

    43 Meeting House Rd, Pawling, NY 12564
  • /45

    $505,000

    • 4 Beds
    • 2 Baths
    • 1,210 Sq Ft

    23 Lakeview Dr, Holmes, NY 12531

    You get to enjoy the Lakehouse lifestyle all year round at this newly updated raised ranch. Convenient to the restaurants and shops of downtown Pawling and your pick of the Pawling, Patterson, or Southeast Metro North stations as well as I-84 and the Taconic State Parkway. The current owner has made extensive improvements to the property, including all new baths and a master bedroom with

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    Lisbeth Furke

    World Homes Realty

    (845) 851-0605

    23 Lakeview Dr, Holmes, NY 12531
  • /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

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    Shannon Tully

    McGrath Realty Inc

    (845) 378-9417

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

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    Shannon Tully

    McGrath Realty Inc

    (845) 328-6866

    Lot 21 Cox Rd, Pawling, NY 12564
  • /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

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    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 957-9518

    750 Route 292, Holmes, NY 12531
  • /42

    $710,000

    • 3 Beds
    • 3 Baths
    • 1,680 Sq Ft

    1098 New York 292, Holmes, NY 12531

    Here's a fantastic opportunity to own a piece of waterfront paradise, perfect for those seeking a tranquil escape without sacrificing convenience! This charming ranch-style home boasts three comfortable bedrooms and three full baths, ensuring ample space and privacy for everyone. You'll love the dedicated office, ideal for remote work, and a cozy den for a quiet reading nook while enjoying the

    John Derevjanik BHHS Hudson Valley Properties

    1098 New York 292, Holmes, NY 12531
  • /45

    $849,000

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    70 Lakeview Dr, Holmes, NY 12531

    Nature lover's lakefront paradise! Exceptional views of beautiful Whaley Lake. Peaceful, breathtaking, panoramic vista from living room, dining area, decks & patios. Beach, boathouse & manicured frontage for endless summer fun. Fish, swim, boat, canoe or kayak at your leisure. Home features attractive open floor plan with center island kitchen, granite counters & stainless appliances. Living room

    Dan Axtmann BHHS Hudson Valley Properties

    70 Lakeview Dr, Holmes, NY 12531
  • /39

    $699,900

    • 4 Beds
    • 4 Baths
    • 4,196 Sq Ft

    561 Route 292, Holmes, NY 12531

    Welcome to 561 Route 292 in Holmes, New York — a stunningly renovated luxury residence showcasing exceptional craftsmanship and modern design. This beautifully reimagined home offers four spacious bedrooms and four full bathrooms, including a primary bedroom with an ensuite bath. The main level features gleaming new hardwood floors, cathedral ceilings, an inviting fireplace, and a seamless open

    Justin Phillips United RE Hudson Valley Edge

    561 Route 292, Holmes, NY 12531
  • /37

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 3,611 Sq Ft

    4 Mane Way, Pawling, NY 12564

    Elegant and Updated Center Hall Colonial, ideally situated in The Highlands—a beautiful and highly sought-after neighborhood in the charming Town of Pawling. This spacious four-bedroom, two-and-a-half-bath home seamlessly blends timeless architectural character with modern luxury, offering comfort, style, and functionality for today’s lifestyle. Gleaming hardwood floors flow throughout the main

    Sharon Sheil Coldwell Banker Realty

    4 Mane Way, Pawling, NY 12564
  • /36

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 3,152 Sq Ft

    48 W Main St, Pawling, NY 12564

    The PERFECT location for a Weekend/Vacation home or Extended/Large Family. 19th Century Colonial/Farmhouse completely remodeled in 2025. Located in the highly desirable Hudson Valley village of Pawling, NY. The photos tell the story of the updates, but it is the LOCATION that is unbeatable! Imagine a brisk autumn morning, waking up in your oversized Primary Bedroom to the warm glow of the morning

    Christopher Filangeri BHHS Hudson Valley Properties

    48 W Main St, Pawling, NY 12564
  • /36

    $725,000

    • 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
  • /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
  • /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
  • /39

    $699,000

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

    108 Beyer Dr, Poughquag, NY 12570

    Sun-filled and spacious 4 bedroom, 4 bath home on a quiet country road with breathtaking mountain views. Designed for comfortable living and entertaining this home features a chefs kitchen, formal dining room, formal den and large family room with vaulted ceilings and a fireplace. The bonus sunroom allows you to enjoy the sweeping views in any weather. Upstairs the 4 bedrooms are filled with

    Greta Ferrari Keller Williams Hudson Valley

    108 Beyer Dr, Poughquag, NY 12570
  • /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
  • /47

    $1,175,000

    • 4 Beds
    • 6 Baths
    • 3,012 Sq Ft

    16 Anderson Rd, Pawling, NY 12564

    Welcome to 16 Anderson Road — a beautifully crafted modern home perched atop the prestigious Quaker Hill in Pawling. Built in 2023, construction completed in 2024, this thoughtfully designed residence blends contemporary elegance with exceptional functionality, offering over 3,000 square feet of refined living space. From the moment you arrive, the home's charm is undeniable — lush landscaping

    Ryan Arket Compass Greater NY, LLC

    16 Anderson Rd, Pawling, NY 12564
  • /25

    $1,199,000

    • 4 Beds
    • 3.5 Baths
    • 4,854 Sq Ft

    21 Holiday Point Rd, Sherman, CT 06784

    [ONE OF A KIND] This house has it all. Located in the desired Atchison Cove private lake community the house sits atop a hill (privacy & sun exposure) safely tucked away from the road and features everything a family may desire: large inground gunite pool with a slide, kids' playground, volleyball, supersized deck, magnificent library, 2 floor game room, 3 fireplaces, giant kitchen, separate

    Jorge Zea Blue Lighthouse Realty, Inc

    21 Holiday Point Rd, Sherman, CT 06784
  • /5

    $590,000

    • Land
    • 55 Acres
    • $10,727 per Acre

    0 Pleasant Ridge Rd, Poughquag, NY 12570

    Nature at its Best. Eye pleasing 55 Acres of meadows and wooded terrain. Beautiful cleared bucolic parcel. Road frontage on Pleasant Ridge Road and Stowe Drive. Would make a great subdivision of homes or a very private and convenient place to build a home. Open land ready for your ideas and planning. This aesthetically pleasing parcel is located in Beekman. The driveway is on Stowe Drive. The

    CONSTANCE FREDRICKSON BHHS Hudson Valley Properties

    0 Pleasant Ridge Rd, Poughquag, NY 12570
  • /50

    $399,999

    • 2 Beds
    • 2.5 Baths
    • 1,838 Sq Ft

    2 Spruce St, Pawling, NY 12564

    Welcome home to 2 Spruce St.! 2 full floors plus a completely finished walk out basement. Home has central air and heat. Completely updated and freshly painted, all you need to do is move in. Living room features a built in flue that can be opened up for adding a wood burning fireplace. 2 full primary bedrooms, each with it's own full bathroom, plus a powder room on the first floor. One of the

    Robin Butler-Koschei Hanson Real Estate Partners

    2 Spruce St, Pawling, NY 12564
  • /40

    $670,000

    • 3 Beds
    • 4 Baths
    • 2,450 Sq Ft

    7 Ridge Rd, Sherman, CT 06784

    Don't be fooled by first glances, When you pull into the driveway you will see a sweet log home in a peaceful and private landscape, what you don't see is the large newer thoughtful Architect designed addition on the north side of the house. This is the heart of Sherman, a short walk to the store, school, park and library. Charm and character through out ! There is a country kitchen with lots of

    Beth Simon William Raveis Real Estate

    7 Ridge Rd, Sherman, CT 06784
  • /40

    $1,849,000

    • 6 Beds
    • 5 Baths
    • 5,500 Sq Ft

    6 Brinsmade Ln, Sherman, CT 06784

    Escape the city and discover this wonderful estate, formerly Brinsmade Farm, in Sherman, Connecticut, offered for the first time in 60 years. Set on approximately 10 scenic acres in the heart of charming Sherman, this exceptional country home combines timeless New England charm with modern living. Originally a working dairy farm, the property was transformed in 1945 when the barn became a private

    Ginny Gordon-O’Neill William Raveis Real Estate

    6 Brinsmade Ln, Sherman, CT 06784
  • /50

    $619,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    322 Old Route 22, Pawling, NY 12564

    Welcome to 322 Old Route 22! Spacious, newly remodeled 2-family home is a great opportunity for owner-occupants, investors, or extended families. Great location just a few minutes from the heart of the Village of Pawling! Each unit features 2 bedrooms, a full bath, living room, dining area, kitchen and bright, enclosed sunporches, providing plenty of space and natural light throughout. Inside,

    Susan Stevens BHHS Hudson Valley Properties

    322 Old Route 22, Pawling, NY 12564
  • /12

    $150,000

    • 3 Beds
    • 2 Baths
    • 980 Sq Ft

    63 Sasso Ln, Wingdale, NY 12594

    Walking Distance to Metro North Railroad, here is your chance to own a charming 3-bedroom, 2-full bathroom mobile home in tight-knit Wingdale Village. The screened in front porch leads to an open concept living room/kitchen combo - perfect for entertaining! This move-in ready home is waiting for you!!

    Michael Herman McGrath Realty Inc

    63 Sasso Ln, Wingdale, NY 12594
  • /40

    $550,000

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

    36 Byrds Hill Rd, Pawling, NY 12564

    Welcome to 36 Byrds Hill Rd, Pawling, NY—a serene 3.95-acre country retreat that feels like home from the moment you arrive. This charming property features a well-designed country house that offers all the comforts of modern living, with the warmth and character of a classic country setting. Step inside and you’re immediately welcomed by a spacious mudroom—perfect for keeping shoes, boots,

    Regan Andrews Houlihan Lawrence Inc.

    36 Byrds Hill Rd, Pawling, NY 12564
  • /9

    $1,250,000

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

    2 Coburn Road W, She Coburn Rd W, Sherman, NY 06784

    Discover the rare opportunity to build your custom modern ranch in the tranquil countryside of Sherman, Connecticut, just minutes from the New York line. Nestled on a private, wooded 1.02-acre lot in the exclusive Timber Trails area, this to-be-built contemporary home blends sleek design with serene living. Built by renowned SHERMAN BUILDING DESIGNS, every element will reflect the latest in

    Chelsea Stinson Coldwell Banker Realty

    2 Coburn Road W, She Coburn Rd W, Sherman, NY 06784
  • /16

    $250,000

    • Land
    • 1.02 Acres
    • $245,098 per Acre

    2 Coburn Rd W, Sherman, CT 06784

    Absolute Privacy Tucked Away on 1+ Acre in true nature setting- abuts open space. POTENTIAL FOR VIEWS EAST TOWARD TIMBER LAKE. This approved building lot offers an acceptional opportunity awaits a savvy buyer to create their own personal retreat in the small Town of Sherman. Test work completed with approved 4 BDRM Septic Plan. Driveway is 1600 ft long, passiing through a majestic pond at the

    Kathleen Harrison Coldwell Banker Realty

    2 Coburn Rd W, Sherman, CT 06784
  • /46

    $580,000

    • 3 Beds
    • 2.5 Baths
    • 1,893 Sq Ft

    10 Rebecca Dr, Pawling, NY 12564

    Nestled in the charming village of Pawling, this delightful house offers new owners the opportunity to create their dream home with a touch of personal flair. Situated on just over 2 acres, the property boasts 3 spacious bedrooms, 2 full bathrooms, and a convenient powder room.The large eat-in kitchen, illuminated by a skylight, provides abundant natural light and features sliders that open

    Maria Justo Howard Hanna Rand Realty

    10 Rebecca Dr, Pawling, NY 12564
  • /33

    $549,999

    • 4 Beds
    • 3 Baths
    • 2,792 Sq Ft

    105 Sheldon Rd, Wingdale, NY 12594

    This beautifully maintained raised ranch has the perfect potential for a mother/daughter arrangement and sits on nearly two acres of peaceful, park-like grounds. With 2,792 square feet of living space, there’s plenty of room for extended family or guests. The main level features a bright living room, a formal dining room with sliders to the deck, and a well-appointed kitchen with granite

    Barbara Negro Century 21 Alliance Realty Grp

    105 Sheldon Rd, Wingdale, NY 12594
  • /45

    $605,000

    • 3 Beds
    • 2.5 Baths
    • 2,233 Sq Ft

    3 Lisa Ct, Patterson, NY 12563

    Price Improvement! You will love this beautiful contemporary home on a quiet cul-de-sac in the small community of Patterson. As you enter the front door, you are greeted by the openness of the floor plan, the warmth of the vaulted wood ceiling, and the welcoming natural light. Downstairs boasts a living room, dining room, large kitchen with eating area, family room with fireplace, and a half

    Dana Duncan Houlihan Lawrence Inc.

    3 Lisa Ct, Patterson, NY 12563
  • /29

    $699,000

    • 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
  • /10

    $159,000

    • Land
    • 0.73 Acre
    • $217,808 per Acre

    0 Walnut St, Pawling, NY 12564

    Great lot in the Village of Pawling! *Board of Health Approval is NOT required because the house will be hooked up to municipal water and sewer! This .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its quaint shops, bakeries, restaurants, library, post office, health care, so much more! Metro-North Train Station (Harlem Line) is located in the Village as

    Lisa Liffland McGrath Realty Inc

    0 Walnut St, Pawling, NY 12564
  • /28

    $419,900

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

    23 Union St, Pawling, NY 12564

    3 Bed | 2 Bath | Fully Electric | Walkable Village LocationTurnkey, updated, freshly painted, 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

    Brett David Miller K Fortuna Lighthouse Realty

    23 Union St, Pawling, NY 12564
  • /47

    $574,900

    • 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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