3,417

Dutchess, NY Homes

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  • 16 Anderson Rd, Pawling, NY 12564
    16 Anderson Rd, Pawling, NY 12564
    16 Anderson Rd, Pawling, NY 12564
    /47

    $1,250,000

    • 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
  • 18 Evergreen Way, Pawling, NY 12564

    $376,500 Sold Jun 18, 2025

    • 1,427 Sq Ft
    • $264/SF
    • 13 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1997

    18 Evergreen Way, Pawling, NY 12564

    Welcome to this well maintained end unit in the desirable Cedar Valley. This home features two spacious bedrooms including a large first floor primary with en suite bath and walk in closet. The second bedroom is located upstairs and also includes a full bath along with plenty of closet space and storage. The main living area boasts a cozy fireplace with large windows that flood the space with

    Vicki Reinach BHHS Hudson Valley Properties

    18 Evergreen Way, Pawling, NY 12564
  • 134 Old Pawling Rd, Pawling, NY 12564
    134 Old Pawling Rd, Pawling, NY 12564
    134 Old Pawling Rd, Pawling, NY 12564
    /48

    $799,900

    • 4 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    134 Old Pawling Rd, Pawling, NY 12564

    Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • 32 Elm St, Pawling, NY 12564

    $645,000 Sold Jun 13, 2025

    • 1,900 Sq Ft
    • $339/SF
    • 20 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1880

    32 Elm St, Pawling, NY 12564

    Welcome to 32 Elm Street – a stunning blend of historic charm and modern convenience! This beautifully renovated 1880s home, reimagined in 2025, offers 3 spacious bedrooms, 2.5 bathrooms, and 1,900 sq ft of stylish living space. Nestled on a .27-acre lot with easy access from both Elm and Walnut Streets, this home is perfectly located just a 4-minute walk to the Metro North train station and a

    Patrycja Warda

    32 Elm St, Pawling, NY 12564
  • 5 Red Tail Ct, Pawling, NY 12564
    5 Red Tail Ct, Pawling, NY 12564
    5 Red Tail Ct, Pawling, NY 12564
    /38

    $699,000

    • 5 Beds
    • 2.5 Baths
    • 2,924 Sq Ft

    5 Red Tail Ct, Pawling, NY 12564

    Tucked away on a quiet cul-de-sac in the sought-after Deerfield Ponds community, 5 Red Tail Court is a beautifully maintained 5-bedroom, 2.5-bathroom Colonial offering space, style, and convenience. With 2,924 sq ft of living space, this home features an inviting floor plan, perfect for both everyday living and entertaining.Step inside to find a sun-filled living room with a cozy

    Julius Cooper eXp Realty

    5 Red Tail Ct, Pawling, NY 12564
  • 103 Mohawk Trail, Pawling, NY 12564

    $435,000 Sold Jun 06, 2025

    • 1,917 Sq Ft
    • $227/SF
    • 13 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2001

    103 Mohawk Trail, Pawling, NY 12564

    Welcome to your dream home nestled in the heart of Pawling's coveted Deerfield Ponds community! This rarely available and most sought-after 3-bedroom, 2 1/2-bathroom townhome features the primary bedroom conveniently located on the first floor. Spanning 1,917 square feet across two floors, with an additional 1,104 square foot unfinished basement, this home offers unlimited potential, complete

    Claudia Jiskra McGrath Realty Inc

    103 Mohawk Trail, Pawling, NY 12564
  • 120 Harmony Rd, Pawling, NY 12564
    120 Harmony Rd, Pawling, NY 12564
    120 Harmony Rd, Pawling, NY 12564
    /15

    $1,250,000

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

    120 Harmony Rd, Pawling, NY 12564

    New construction 4 bedroom, 4.5 bathroom home on 5 acres. Don't miss this opportunity to customize your dream home. This home features a open floor plan with large kitchen, perfect for entertaining. The main living area has exposed beams and high ceilings. The primary bedroom has large walk in closet and ensuite. There is also a junior suite with ensuite. See attached floor plans for full detail.

    Bliss Voutsinas

    120 Harmony Rd, Pawling, NY 12564
  • 10 John Kane Ct, Pawling, NY 12564

    $412,500 Sold May 27, 2025

    • 1,564 Sq Ft
    • $264/SF
    • 43 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2000

    10 John Kane Ct, Pawling, NY 12564

    Welcome to your dream home in the heart of Pawling's Deerfield Ponds community! This beautiful 2-bedroom, 2-bathroom townhouse features an open floor plan that flows between the dining room and the spacious living room, which has a wood-burning fireplace. It also includes a bonus room and a full unfinished basement. The basement could become a playroom, multimedia room, or a storage area. This

    Jessica Diaz Coldwell Banker Realty

    10 John Kane Ct, Pawling, NY 12564
  • 51 Estate Dr, Pawling, NY 12564
    51 Estate Dr, Pawling, NY 12564
    51 Estate Dr, Pawling, NY 12564
    /9

    $1,100,000

    • 5 Beds
    • 3.5 Baths
    • 3,500 Sq Ft

    51 Estate Dr, Pawling, NY 12564

    Don't miss this opportunity to have your dream home built and custom designed to your finishes. As you step inside, you're greeted by a grand foyer entrance with high ceilings open to the second floor. Discover a beautifully designed eat-in kitchen, complete with custom cabinetry, stainless steel appliances, quartz countertops, and center island. The oversized open floor plan seamlessly

    Tony Zaccardo Coldwell Banker Realty

    51 Estate Dr, Pawling, NY 12564
  • 85 W Deer Trail, Pawling, NY 12564

    $540,000 Sold May 23, 2025

    • 2,341 Sq Ft
    • $231/SF
    • 23 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    85 W Deer Trail, Pawling, NY 12564

    Nestled just minutes from the charming Village of Pawling, this stunning 4-bedroom, 2.5-bath home offers the perfect blend of comfort, elegance, and breathtaking views of a neighboring horse farm. Step onto the inviting front porch and enter through a formal entryway that sets the tone for the warmth and beauty found throughout. Hardwood floors guide you past the traditional living room and into

    Shannon Tully McGrath Realty Inc

    85 W Deer Trail, Pawling, NY 12564
  • 27 Millstream Ct, Pawling, NY 12564
    27 Millstream Ct, Pawling, NY 12564
    27 Millstream Ct, Pawling, NY 12564
    /43

    $734,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,283 Sq Ft

    27 Millstream Ct, Pawling, NY 12564

    Welcome to your new home in the neighborhood you want and with all the amenities you want. Imagine waking in your Oversized Primary bedroom to the sounds of birds chirping and the sun warming your face. Get the day going in your Primary Bath Suite with Double Vanity, Heated Floors, Heated Towel Rack and Jacuzzi Tub. Smell the coffee brewing in your Chef's kitchen where you can prepare meals that

    CHRISTOPHER FILANGERI BHHS Hudson Valley Properties

    27 Millstream Ct, Pawling, NY 12564
  • 24 Sheridan Dr, Pawling, NY 12564

    $674,900 Sold May 21, 2025

    • 2,876 Sq Ft
    • $235/SF
    • 134 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1930

    24 Sheridan Dr, Pawling, NY 12564

    Check out this Charming Country Cottage in the Village of Pawling! Nestled on almost 7 acres of serene land, this delightful country cottage offers the perfect blend of comfort and tranquility. Hardwood floors flow throughout the home, enhancing the warm, rustic charm. The sun-soaked living room, complete with a wood-burning fireplace, invites relaxation, while the eat-in kitchen is perfect for

    John Gabriel Jr KW MidHudson

    24 Sheridan Dr, Pawling, NY 12564
  • 14 Old Route 55, Pawling, NY 12564
    14 Old Route 55, Pawling, NY 12564
    14 Old Route 55, Pawling, NY 12564
    /31

    $299,950 Open Sat 11AM - 1PM

    • 3 Beds
    • 1 Bath
    • 1,653 Sq Ft

    14 Old Route 55, Pawling, NY 12564

    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 open up to the

    Ronald Green KW MidHudson

    14 Old Route 55, Pawling, NY 12564
  • 130 Old Route 55, Pawling, NY 12564

    $560,000 Sold May 20, 2025

    • 2,552 Sq Ft
    • $219/SF
    • 132 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1975

    130 Old Route 55, Pawling, NY 12564

    Single family 5 bedroom, 3 bath country home. Secluded in the woods, but close to town. 10.39 acres with pool and 2 paddock barn offering a unique experience for those desiring privacy and a connection to nature. Small bungalow in back perfect for an office or recreational area.

    Derek Eisenberg Continental Real Estate Group

    130 Old Route 55, Pawling, NY 12564
  • 0 Walnut St, Pawling, NY 12564
    0 Walnut St, Pawling, NY 12564
    0 Walnut St, Pawling, NY 12564
    /4

    $175,000

    • Land
    • 0.73 Acre
    • $239,726 per Acre

    0 Walnut St, Pawling, NY 12564

    Great opportunity to build a home in the beautiful Village of Pawling! This property is on municipal water and sewer! Thousands will be saved - no expense incurred on a drilled well or septic system! .73-acre lot offers a lovely western view. Walk to the picturesque Village center with its shops, bakeries, restaurants, library, so much more! Metro-North Train Station, Harlem Line, is located in

    Lisa Liffland McGrath Realty Inc

    0 Walnut St, Pawling, NY 12564
  • 17 Fenwood Dr, Pawling, NY 12564

    $490,000 Sold May 16, 2025

    • 1,716 Sq Ft
    • $286/SF
    • 85 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    17 Fenwood Dr, Pawling, NY 12564

    This charming, tucked-away Raised Ranch offers 3 bedrooms and 2 bathrooms, providing a cozy and modern living space. As you step through the front door and ascend the stairs, you're greeted by a bright and airy living room featuring a bay window and hardwood floors, which seamlessly flow into the dining area and open kitchen. The updated kitchen is equipped with stainless steel appliances,

    Shannon Tully McGrath Realty Inc

    17 Fenwood Dr, Pawling, NY 12564
  • 7 Elm St, Pawling, NY 12564
    7 Elm St, Pawling, NY 12564
    7 Elm St, Pawling, NY 12564
    /11

    $319,000

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

    7 Elm St, Pawling, NY 12564

    Historical 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

    Teddie Leonaggeo McGrath Realty Inc

    7 Elm St, Pawling, NY 12564
  • 32 Gristmill Ln, Pawling, NY 12564

    $607,000 Sold May 16, 2025

    • 3,732 Sq Ft
    • $163/SF
    • 235 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1967

    32 Gristmill Ln, Pawling, NY 12564

    Enjoy the village lifestyle in historic Pawling. This private, 1.4-acre, treelined property is less than a mile to the Village with shops, restaurants, library, Metro North station, Dutcher Golf Course, and the Village Green with Farmer's Market (June-October). Close proximity to Lakeside & Morrow parks and the Appalachian & Oblong Trails. This sprawling, mother/ daughter style home includes an

    Carol Aprile

    32 Gristmill Ln, Pawling, NY 12564
  • 23 Union St, Pawling, NY 12564
    23 Union St, Pawling, NY 12564
    23 Union St, Pawling, NY 12564
    /28

    $480,000

    • 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
  • 54 Burgess Rd, Pawling, NY 12564

    $1,375,000 Sold May 13, 2025

    • 2,910 Sq Ft
    • $473/SF
    • 60 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1926

    54 Burgess Rd, Pawling, NY 12564

    Nestled in the prestigious Quaker Hill Hamlet of Pawling, NY, Burgess House is a distinguished estate where historic charm meets modern refinement. Perched atop a scenic hillside, this exceptional residence offers breathtaking panoramic views of the protected landscapes of Connecticut Audubon’s Deer Pond Farm, ensuring a serene and private retreat. Steeped in history, the 3-bedroom, 3.1-bathroom

    Jake Garay Serhant LLC

    54 Burgess Rd, Pawling, NY 12564
  • 51 Kirby Hill Rd, Pawling, NY 12564
    51 Kirby Hill Rd, Pawling, NY 12564
    51 Kirby Hill Rd, Pawling, NY 12564
    /12

    $250,000

    • Land
    • 5 Acres
    • $46,642 per Acre

    51 Kirby Hill Rd, Pawling, NY 12564

    Down a winding country road, across the street from 350 acres of hiking trails and just 10 minutes from the heart of Pawling, this 5.36-acre parcel offers a rare blend of readiness and wildness. This is the kind of place where ideas can take shape beneath a canopy of oaks and mountain laurel. The elevated, partially cleared build site holds promise for views, with a roughed-in driveway already

    Donna Kennedy Keller Williams Prestige Prop

    51 Kirby Hill Rd, Pawling, NY 12564
  • 139 Old Quaker Hill Rd, Pawling, NY 12564

    $900,000 Sold May 09, 2025

    • 2,538 Sq Ft
    • $355/SF
    • 197 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    139 Old Quaker Hill Rd, Pawling, NY 12564

    First time on market in 44 years, this 4.08 acre magical property on Quaker Hill has been fully renovated. One won't believe the charm, character, interest & detail that has been added. Wall to wall bookshelves in the primary suite, w/a large wic, a bathroom w/shower & pocket doors, floor to ceiling windows to absorb the outdoors & guest cottage w/deck & patio nestled in a Birch grove. The LR has

    Gillian Stewart Gillian Stewart Real Estate

    139 Old Quaker Hill Rd, Pawling, NY 12564
  • 36 Spruce St, Pawling, NY 12564
    36 Spruce St, Pawling, NY 12564
    36 Spruce St, Pawling, NY 12564
    /28

    $335,000 Open Sun 12PM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 1,414 Sq Ft

    36 Spruce St, Pawling, NY 12564

    Comfortable Townhouse Living at Cedar Valley36 Spruce Street, Pawling, NY located in cedar valley development. This 2 bedroom, 2 1/2 bath home is just waiting for you to give it a little TLC. The first floor has a dining/living room, door to an open patio, perfect for your morning coffee or your afternoon tea. The kitchen and half bath finish off the 1st floor. The second floor has two

    Peggy MacLeay-Generoso McGrath Realty Inc

    36 Spruce St, Pawling, NY 12564
  • 14 Little Pond Rd, Pawling, NY 12564

    $949,900 Sold May 02, 2025

    • 3,798 Sq Ft
    • $250/SF
    • 6 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2000

    14 Little Pond Rd, Pawling, NY 12564

    This Colonial home is absolutely lovely and is situated in a serene and beautiful setting. With 7.88 acres of land on a quiet country road, it offers both privacy and convenience. The design and features are perfect for comfortable living, whether you're looking for a year-round residence or a weekend retreat. The home welcomes you through a charming rocking chair front porch, leading into a

    Teddie Leonaggeo McGrath Realty Inc

    14 Little Pond Rd, Pawling, NY 12564
  • 37 Baxter Rd, Pawling, NY 12564
    37 Baxter Rd, Pawling, NY 12564
    37 Baxter Rd, Pawling, NY 12564
    /29

    $579,900

    • 3 Beds
    • 3.5 Baths
    • 2,616 Sq Ft

    37 Baxter Rd, Pawling, NY 12564

    Welcome to this charming Colonial-style residence, offering 3 bedrooms, 3.5 bathrooms, and a versatile bonus room—ideal for a potential in-law suite. With over 2,600 square feet of comfortable living space, this home is located in the desirable Baxter Green community, nestled in the scenic Village of Pawling.The interior showcases beautiful hardwood floors throughout, while the spacious

    Matt Rose Keller Williams Prestige Prop

    37 Baxter Rd, Pawling, NY 12564
  • 0 S Quaker Hill Rd Unit KEY822354, Pawling, NY 12564

    $200,000 Sold Apr 30, 2025

    • Land
    • 11 Acres
    • $17,953 per Acre
    • 47 Days On Market

    0 S Quaker Hill Rd Unit KEY822354, Pawling, NY 12564

    Very nice size building lot 11.14 Acres. Builders take a look. 869 feet road frontage on S Quaker Hill Road Zoned CD-R5 residential. directions look for mail box # 40 property located right across the street. long road frontage. four real estate signs along the frontage. new listing. you know some one once said .drive up for the week end stay a life time. this is a keeper will not last long

    John Melchior Howard Hanna Rand Realty

    0 S Quaker Hill Rd Unit KEY822354, Pawling, NY 12564
  • 33 Grandview Ave, Pawling, NY 12564
    33 Grandview Ave, Pawling, NY 12564
    33 Grandview Ave, Pawling, NY 12564
    /38

    $395,000

    • 4 Beds
    • 1 Bath
    • 1,157 Sq Ft

    33 Grandview Ave, Pawling, NY 12564

    Charming Cape Cod in the village of Pawling, one owner since it was built in 1953. The home has been well maintained throughout the years. The interior was painted 2 years ago and there are recently installed windows throughout. There are 2 BR's on the first floor, a living room with wood fireplace & hardwood floors. The eat in kitchen has Corian & butcher block counters, a gas range &

    Gillian Stewart Gillian Stewart Real Estate

    33 Grandview Ave, Pawling, NY 12564

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