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Homes for Sale near Pawling Middle School

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  • /50

    $785,000

    • 3 Beds
    • 3 Baths
    • 3,729 Sq Ft

    103 S Harmony Hill Rd, Pawling, NY 12564

    Properties like this don't come along often! As you turn off the road, the world quiets. The driveway pulls you back through a canopy of mature trees, and by the time the house appears, you already feel the privacy with over five acres, buffered on all sides, thoughtfully expanded and upgraded far beyond its 1975 origins. Step inside to a living room anchored by a stone fireplace, original

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 720-4119

    103 S Harmony Hill Rd, Pawling, NY 12564
  • /25

    $469,000

    • 4 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    120 South Rd, Holmes, NY 12531

    Welcome to 120 South Rd/40 Great Bear Rd, a charming home at the end of a quiet cul-de-sac, offering peace, privacy, and a stunning lake view from the deck. Set on just under 3 acres, this property features a spacious front yard shaded by mature trees, perfect for outdoor gatherings, gardening, or simply relaxing in your own private oasis. Enjoy the comfort and efficiency of new windows

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    Omar Harper

    Epique Realty

    (845) 552-1998

    120 South Rd, Holmes, NY 12531
  • /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) 412-9125

    Lot 21 Cox Rd, Pawling, NY 12564
  • /24

    $590,000

    • Land
    • 63.9 Acres
    • $9,233 per Acre

    489 Grape Hollow Rd, East Fishkill, NY 12531

    Calling out for BUILDERS, HUNTERS, MULTI FAMILY HOMES OR LUXURY home owner desiring total privacy!! 63.9 acres of woodland in the Hudson Valley, undeveloped parcel. Prior approval ( needs to be updated by the buyer and engineer ) by the town for a 4 parcel to a 10 plot subdivision and has 3 wells drilled on parcels already, build less homes as desired with larger land parcels. OR Build a dream

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    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 683-5349

    489 Grape Hollow Rd, East Fishkill, NY 12531
  • /6

    $87,500

    • Land
    • 20,037 Sq Ft
    • $190,217 per Acre

    0 Lakeview Dr Unit KEY962482, Pawling, NY 12531

    Build your ideal home on this prime .46-acre lot perfectly situated within the sought-after Pawling Lake Estates community. Offering a rare blend of beauty and value, this property boasts picturesque views of Jones Pond and benefits from the lower property taxes of the Dover Union Free School District. Nature enthusiasts will love being surrounded by the sprawling West Mountain State Forest,

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    Colleen McGrath

    McGrath Realty Inc

    (845) 385-2808

    0 Lakeview Dr Unit KEY962482, Pawling, 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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 684-9806

    Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
  • /6

    $220,000

    • Land
    • 33,105 Sq Ft
    • $289,474 per Acre

    15 Dykeman St, Pawling, NY 12564

    Rare opportunity to build in the heart of the Village of Pawling! Cleared and ready for development, this residential lot at 15 Dykeman Street offers municipal water and sewer available at the street — a major advantage for new construction. The property features a defined driveway lined with item four stone, providing immediate access and a head start on site work. Level and open, the lot offers

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    Joanne Debellis

    Debellis Real Estate LLC

    (845) 660-6758

    15 Dykeman St, Pawling, NY 12564
  • /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
  • /15

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,920 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 Hillside Realty & Development

    120 Harmony Rd, Pawling, NY 12564
  • /31

    $859,000

    • 2 Beds
    • 2 Baths
    • 2,278 Sq Ft

    117 S Quaker Hill Rd, Pawling, NY 12564

    Tucked away on historic Quaker Hill - known for its picturesque horse farms and country estates - you will find this charming lodge-style home, offering a comfortable blend of character and rustic warmth. The 10.23 acre property is approached by a winding, level driveway that gently opens to a nature lovers dream.At the heart of the home lies an impressive great room, where a soaring stone

    Lisa Liffland McGrath Realty Inc

    117 S Quaker Hill Rd, Pawling, NY 12564
  • /48

    $1,799,000

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

    41 and 43 Meeting House Rd, Pawling, NY 12564

    Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious

    Richard Esman Douglas Elliman Real Estate

    41 and 43 Meeting House Rd, Pawling, NY 12564
  • /17

    $990,000

    • 4 Beds
    • 3.5 Baths
    • 3,768 Sq Ft

    194 South Rd, Holmes, NY 12531

    Currently being crafted by skilled local builders, this distinguished rocking chair porch Colonial sits gracefully on more than nine private acres, offering an exceptional blend of elegance, comfort, and modern design. Once complete, the home will be bathed in natural light, showcasing gleaming hardwood floors, 9 foot ceilings, and a sophisticated chef’s kitchen appointed with recessed lighting,

    Stacey Cronin Houlihan Lawrence Inc.

    194 South Rd, Holmes, NY 12531
  • /43

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,768 Sq Ft

    57 Buhleir Rd, Pawling, NY 12564

    Private

    Carolyn Ridenour Berkshire Hathaway HS NE Prop.

    57 Buhleir Rd, Pawling, NY 12564
  • /29

    $2,500,000

    • 6 Beds
    • 6.5 Baths
    • 6,625 Sq Ft

    3302 Route 55, Pawling, NY 12564

    Welcome to your forever home, serene retreat and mini estate. Enjoy the 88 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 expansive living space, luxury and customize finishes throughout. A true

    STACI MACKIN Dixon Smith Realty

    3302 Route 55, Pawling, NY 12564
  • /21

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    188 N Quaker Hill Rd, Pawling, NY 12564

    Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level,

    Gillian Stewart Gillian Stewart Real Estate

    188 N Quaker Hill Rd, Pawling, NY 12564
  • /16

    $499,999

    • 2 Beds
    • 1 Bath
    • 1,347 Sq Ft

    1141 Old Quaker Hill Rd, Pawling, NY 12564

    Welcome Home! Tucked away along storied Old Quaker Hill, this antique charmer invites you to experience a slower, richer pace of living—where history lingers in every beam and modern comfort quietly supports it. Offered fully furnished (or unfurnished) and available for immediate occupancy, this cozy retreat blends timeless character with everyday ease, making it an ideal escape for your weekend

    Chinenye Aguoji Real Broker NY LLC

    1141 Old Quaker Hill Rd, Pawling, NY 12564
  • /26

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,130 Sq Ft

    4 Beachway Dr, Holmes, NY 12531

    Welcome to 4 Beachway Drive! This charming ranch-style home offers 2 bedrooms and lives like a 3-bedroom, with year-round views of beautiful Whaley Lake and lake access through the HOA. A welcoming front deck invites you inside, where natural light fills the home through abundant windows and skylights. The kitchen features ample cabinets and counter space, and a door leading to the back

    Regan Andrews Coldwell Banker Realty

    4 Beachway Dr, Holmes, NY 12531
  • /50

    $725,000

    • 2 Beds
    • 2 Baths
    • 1,722 Sq Ft

    1080 Route 292, Holmes, NY 12531

    Step into this charming lakefront cottage and immediately feel at home. The foyer leads to the primary bedroom, featuring a full bath and breathtaking views of Whaley Lake. A second bedroom and a full hallway bath complete the main level. Upstairs, a loft offers another perspective of the serene lake, perfect for reading, relaxing, or watching the sunset. The open-concept kitchen flows into the

    Peggy MacLeay-Generoso McGrath Realty Inc

    1080 Route 292, Holmes, NY 12531
  • /23

    $388,500

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    11 Park Ln, Holmes, NY 12531

    Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay

    Ernie Acampora River Realty Services, Inc.

    11 Park Ln, Holmes, NY 12531
  • /16

    $387,000

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

    10 Timberline Trail, Pawling, NY 12564

    ~ Welcome to your spacious and cozy tri-level townhome in the desirable Cedar Valley Community. ~This rare end unit provides you with an abundance of light and additional outdoor space. Featuring 2 spacious bedrooms and 2.5 bathrooms, this home boasts an open and versatile layout ideal for everyday living and entertaining. The dining area and bright living room with its cozy fireplace opens

    Giorgio Palmisano Howard Hanna Rand Realty

    10 Timberline Trail, Pawling, NY 12564
  • /38

    $385,000

    • 2 Beds
    • 2 Baths
    • 1,639 Sq Ft

    16 Juniper Ln, Pawling, NY 12564

    Welcome to Cedar Valley! This bright corner unit offers the perfect blend of comfort and convenience, with potential for easy one-floor living. The main level features both bedrooms, while a spacious loft upstairs provides flexible bonus space—ideal for a home office, gym, guest area, or additional living space.Enjoy the ease of just two steps from the parking lot to your front door, with two

    Vanessa Longo Briante Realty Group, LLC

    16 Juniper Ln, Pawling, NY 12564
  • /22

    $599,900

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

    85 Harmony Hill Rd, Pawling, NY 12564

    **Highest & Best 7pm Monday 4/27.** Set on nearly three private acres just minutes from Metro-North, this fully renovated country retreat delivers the space, privacy, and lifestyle buyers are searching for right now. Bright, open, and thoughtfully updated, the home is designed for both everyday living and easy entertaining. The kitchen features custom cabinetry, quartz countertops, and stainless

    Anna Proctor Compass Greater NY, LLC

    85 Harmony Hill Rd, Pawling, NY 12564
  • /33

    $495,000

    • 2 Beds
    • 2 Baths
    • 1,088 Sq Ft

    17 Townsend Blvd, Pawling, NY 12564

    Fall in Love with this Charming Mediterranean Style Garden Home. A Private Oasis Hidden Away and Nestled among a Grove of Mature Trees. Follow meandering paths that lead to Splashes of Color from the Cultivated Perennial Gardens of a Lifetime and a Gentle Woodland Stream. This Home is Sparkling Clean, Freshly Polished, Newly Painted, Move-In Ready and awaits your Arrival. Tucked in at the end of

    Martha Woodhouse Howard Hanna Rand Realty

    17 Townsend Blvd, Pawling, NY 12564
  • /10

    $999,000

    • Land
    • 68.39 Acres
    • $14,607 per Acre

    0 Old Quaker Hill Rd Unit KEY986977, Pawling, NY 12564

    You can stop looking now because this is the piece of land you've been dreaming of. Over 68 acres atop Pawling's prestigious Quaker Hill. Approximately 20 acres clear and level with the remainder old woods crisscrossed by multiple streams and revolutionary era or older trails. In the heart of Quaker Hill's equestrian enclave, your views are the neighboring mountains and large estates. The short

    Brian McGrath McGrath Realty Inc

    0 Old Quaker Hill Rd Unit KEY986977, Pawling, NY 12564
  • /8

    $135,000

    • Land
    • 31,798 Sq Ft
    • $184,932 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
  • /41

    $2,500,000

    • 3 Beds
    • 3.5 Baths
    • 2,292 Sq Ft

    34 Meeting House Rd, Pawling, NY 12564

    Nestled in the heart of historic Quaker Hill, this bucolic property offers timeless charm just a stone’s throw from the iconic Meeting House. Originally built in 1983, the home underwent a meticulous, top-to-bottom renovation in 2016, thoughtfully upgrading all major systems, finishes, and living spaces to modern standards while preserving its serene setting. The residence is exceptionally

    Mark Friedman McGrath Realty Inc

    34 Meeting House Rd, Pawling, NY 12564
  • /13

    $345,000

    • 2 Beds
    • 2.5 Baths
    • 1,567 Sq Ft

    1 Cushing Green N, Pawling, NY 12564

    This great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attached garage, formal dining room, fireplace, rear deck and more. This is a Fannie Mae HomePath property.

    Matthew Cave Hudson Property Services, LLC

    1 Cushing Green N, Pawling, NY 12564
  • /46

    $39,000,000

    • 9 Beds
    • 15 Baths
    • 55,000 Sq Ft

    104 N Garden Dr, Pawling, NY 12564

    Welcome to Woodland Waters. Offered for the first time, this private estate is a secluded sanctuary where luxury and nature exist in perfect harmony. Over the course of five decades, the same owner has shaped and nurtured the property with remarkable care and attention, creating a setting that embodies both artistry and authenticity. With its vast landholdings, exceptional lifestyle offerings, it

    Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

    104 N Garden Dr, Pawling, NY 12564
  • /37

    $14,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,942 Sq Ft

    15 Kirby Hill Rd, Pawling, NY 12564

    Kirby Hill Farm, an exceptional equestrian estate set on 247 acres of Quaker Hill's finest countryside. The turnkey, multi-discipline, equestrian facility offers 4 barns with 81 stalls, 2 indoor riding arenas, 3 outdoor riding rings, 37 paddocks, 7 additional paddocks with winterized waterers, 21 fields, polo field, over 100 acres of fenced property, and 150 acres of riding trails with direct

    Brian McGrath McGrath Realty Inc

    15 Kirby Hill Rd, Pawling, NY 12564
  • /12

    $325,000

    • Land
    • 4.36 Acres
    • $74,524 per Acre

    576 Holmes Rd, Holmes, NY 12531

    Positioned at the intersection of Route 52 and Holmes Road, directly across from Milltown Road, this exceptional offering presents two commercial parcels totaling 4.361 acres, comprised of 3.19 acres and 1.171 acres. With a NYS DOT annual average daily traffic count of 5,415 on Route 52, the property benefits from steady visibility and strong exposure, making it an ideal setting for a wide range

    Claudia Jiskra McGrath Realty Inc

    576 Holmes Rd, Holmes, NY 12531
  • /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.

    225 Route 22, Pawling, NY 12564
  • /10

    $135,000

    • Land
    • 18,730 Sq Ft
    • $313,953 per Acre

    0 Prospect St Unit KEY985758, Pawling, NY 12564

    First time on market! BOHA not required - Town Water and Sewer must be hooked-up. Nice level lot, the majority of which is mostly cleared. Great location! Short drive to Metro-North, great restaurants and shops, Pawling schools, Lakeside Park with beach, playground area, trails, and pickleball courts. Dutcher Golf Course is a 9-hole gem, the oldest public course in America. Also close to grocery

    Lisa Liffland McGrath Realty Inc

    0 Prospect St Unit KEY985758, Pawling, NY 12564
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