37

Homes for Sale near Pawling Elementary School

Section Image Section Image
  • /23

    $799,000

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

    26 Rodina Dr, Pawling, NY 12564

    Be the first to live in this stunning four bedroom, two and a half bath home nestled on a beautiful two and a half acre lot. This home is located on the border of Putnam and Duchess counties. 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 staircase with

    Agent Photo

    Douglas Servello

    Home Sweet Home Properties

    (845) 599-8285

    26 Rodina Dr, 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

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 299-9362

    101 Bundy Hill Rd, Holmes, NY 12531
  • /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

    Agent Photo

    Omar Harper

    Epique Realty

    (845) 552-1998

    120 South Rd, Holmes, NY 12531
  • /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

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 Old Route 55, 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

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 957-9518

    750 Route 292, 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

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 328-6866

    Lot 21 Cox Rd, Pawling, NY 12564
  • /4

    $169,000

    • Land
    • 4.87 Acres
    • $34,702 per Acre

    51 Estate Dr, Pawling, NY 12564

    Discover your dream sanctuary at lot #21, now cherished as 51 Estate Drive, nestled within the serene Cushman Farms subdivision in picturesque Pawling, NY. This enchanting property offers nearly 5 acres of secluded, buildable land, beckoning you to design the home you've always envisioned OR take advantage of the current plans in place. Picture waking up surrounded by nature's beauty, while still

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 622-7384

    51 Estate Dr, 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

    Agent Photo

    Lisbeth Furke

    World Homes Realty

    (845) 851-0605

    23 Lakeview Dr, Holmes, NY 12531
  • /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

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 683-5349

    489 Grape Hollow Rd, East Fishkill, 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) 378-9417

    Lot 25 Brady Brook Farm Rd, 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

    Agent Photo

    Vince Buccieri

    Today Realty Corp.

    (845) 280-5951

    178 Charles Colman Blvd, Pawling, NY 12564
  • /48

    $1,200,000

    • 5 Beds
    • 4 Baths
    • 4,248 Sq Ft

    64 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to Country Living at Its Finest!Nestled on 24.5 scenic acres, this classic 1910 farmhouse offers endless potential for those looking to restore a piece of history. A long, tree-lined driveway leads to this charming 4-bedroom, 4-bath home surrounded by open fields, mature trees, and peaceful country views. The property features a spacious 4-car garage with finished living space with

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 415-7723

    64 S Quaker Hill Rd, 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

    Agent Photo

    Shaylene Neumann

    Houlihan Lawrence Inc.

    (845) 377-2512

    225 Route 22, Pawling, NY 12564
  • /44

    $848,800

    • 3 Beds
    • 2.5 Baths
    • 3,026 Sq Ft

    57 S White Rock Rd, Holmes, NY 12531

    Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property and a must see. Privacy awaits in a pristine area with nearly 5 acres. Enchanting landscapes surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house

    Patrice Copeland-Ainsworth Epique Realty

    57 S White Rock Rd, Holmes, NY 12531
  • /17

    $420,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 2,596 Sq Ft

    7 Juniper Ln, Pawling, NY 12564

    Welcome home to your spacious and cozy tri-level end unit in the Cedar Valley complex! The eat-in kitchen opens to the dining area and bright living room with a cozy fireplace, perfect for everyday living and entertaining. The main level features a primary bedroom with private bath and walk-in closet, plus a second bedroom with a full hall bath. The loft overlooking the living area offers

    Elizabeth Poggiogalle Real Broker NY LLC

    7 Juniper Ln, 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
  • /50

    $619,000

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

    322 Old Route 22, Pawling, NY 12564

    Hard-to-find multi-family in Pawling! Spacious, newly remodeled 2-family home is a great opportunity for owner-occupants, investors, or extended families located 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
  • /5

    $399,000

    • Land
    • 61.82 Acres
    • $6,454 per Acre

    0 S White Rock Rd Unit 6015368, Pawling, NY 12531

    Approved 7 lot residential subdivision: Pristine, secluded, quiet area with DCBOH approved residential building lots 3.02-6.41 acres surroundinga 31 acre open space area. All lot sites selected for privacy. Partial physical improvements (over $350K) to include 2 (partially complete) roads and storm water works in place. Tax assessments in appeal. HOA established, shared fees for roads & storm

    John Ravetto Houlihan Lawrence Inc.

    0 S White Rock Rd Unit 6015368, Pawling, NY 12531
  • /17

    $228,000

    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    5 Birch Dr, Holmes, NY 12531

    2 bedroom home on Whaley Lake in Shore Haven Civic Association. Access to 3 beaches and dock. Winter (and a little summer) views of the lake.

    James Bergstraser RE/MAX Classic Realty

    5 Birch Dr, Holmes, NY 12531
  • /27

    $450,000

    • 4 Beds
    • 1.5 Baths
    • 1,776 Sq Ft

    40 Walnut St, Pawling, NY 12564

    Spacious 4 BR Home is located in the Village of Pawling. Nice property has a wonderful western view with amazing sunsets! Sunny Living Rm with picture window is open to the Dining Rm. The Kitchen has space for a breakfast table or island. The main floor has been freshly painted and has solid oak hardwood floors. Walking distance to Metro-North Train Station, Library, Medical Offices, Village

    Lisa Liffland McGrath Realty Inc

    40 Walnut St, 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 Hillside Realty & Development

    120 Harmony Rd, Pawling, NY 12564
  • /13

    $368,888

    • 3 Beds
    • 2.5 Baths
    • 1,960 Sq Ft

    21 Kings Way, Pawling, NY 12564

    Welcome to 21 Kings Way, a charming 3-bedroom, 2.5-bathroom townhome nestled in a wonderful community in Pawling, NY. This beautifully maintained home offers a perfect blend of comfort, style, and convenience. Step inside to discover an inviting open floor plan with spacious living areas, perfect for both entertaining and everyday living. The large windows flood the space with natural light,

    Bopaul Sookdeo YourHomeSold Guaranteed Realty

    21 Kings Way, Pawling, NY 12564
  • /24

    $399,000

    • 5 Beds
    • 1,062 Sq Ft

    215 Little Pond Rd, Pawling, NY 12564

    Private Lake House on a Private Lake! Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and peaceful environment.

    Jillian Pajer Douglas Elliman Real Estate

    215 Little Pond Rd, Pawling, NY 12564
  • /20

    $3,900,000

    • Land
    • 108 Acres
    • $36,111 per Acre

    57 S Quaker Hill Rd, Pawling, NY 12564

    Seldom does a property like this become available. Two parcels totaling 108 acres create the most idyllic setting on Quaker Hill. Imagine a pastoral retreat blanketed by farmed fields, well-maintained trails, and productive land. With approximately 56 cleared acres, the possibilities are endless. Build your dream country estate, an extended family compound, or an equestrian paradise with ample

    Brian McGrath McGrath Realty Inc

    57 S Quaker Hill Rd, Pawling, NY 12564
  • /23

    $399,900

    • 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
  • /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

    $154,900

    • Land
    • 0.73 Acre
    • $212,192 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
  • /11

    $125,000

    • Land
    • 0.31 Acre
    • $403,226 per Acre

    3 Pine Dr, Pawling, NY 12564

    This property offers endless possibilities, whether for development, investment, or creating a personalized mobile home environment. Key features include: Expansive Lot: 13,500 sq ft for development, investment, or personal use.Prime Location: Close to town with shops, dining, and community events.Transportation Access: Near major routes and public transit (Dover Plains Metro North

    Brandon Doswell-Stephens Silverside Realty LLC

    3 Pine Dr, Pawling, NY 12564
  • /3

    $149,900

    • Land
    • 4.21 Acres
    • $35,606 per Acre

    0 South Rd Unit KEY853088, Pawling, NY 12531

    Beautiful 4.21-acre lot in Pawling, NY presents a unique opportunity to build your dream home. This secluded property offers the ideal blend of privacy and convenience, situated just minutes from the charming Village of Pawling, Metro-North train station, restaurants, shopping, and all the amenities the historic Hudson Valley has to offer. Only three miles off I-84. Perfect for a year-round

    Michael Knecht Howard Hanna Rand Realty

    0 South Rd Unit KEY853088, Pawling, NY 12531
  • /3

    $189,000

    • Land
    • 11.4 Acres
    • $16,579 per Acre

    0 Kirby Hill Rd, Pawling, NY 12564

    Great 11 acre BOHA property in Quaker Hill area of Pawling. Great views. Located quiet area next to historic library (not active. Shown as museum in warmer weather). Fantastic getaway area or permanent dream house.

    Richard Castro Howard Hanna Rand Realty

    0 Kirby Hill Rd, Pawling, NY 12564
  • /33

    $889,900

    • 3 Beds
    • 2 Baths
    • 2,048 Sq Ft

    1125 Old Quaker Hill Rd, Pawling, NY 12564

    Tucked away in the prestigious Quaker Hill area of Pawling, this expansive ranch-style country home offers a private setting, on 6.8 wooded acres, where time slows and weekends linger. Thoughtfully renovated in 2018, the residence is rich in character, featuring 100-year-old reclaimed posts and beams from a barn in Western PA and 150-year-old wide-board floors reclaimed from a CT tobacco barn

    Diana Murphy HomeSmart Homes & Estates

    1125 Old Quaker Hill Rd, 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
  • /42

    $675,000

    • 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
  • /49

    $425,000

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

    13 Cushing Green S, Pawling, NY 12564

    A rare find and an incredible opportunity awaits in Squire Green with this two-story end-unit townhome featuring the highly sought-after attached garage. Townhomes are seldom available in the Squire Green section of the Deerfield Ponds community, and end units are even more uncommon, making this offering especially desirable. Steps inside reveal a spacious entry foyer leading to an updated

    Claudia Jiskra McGrath Realty Inc

    13 Cushing Green S, Pawling, NY 12564
  • /44

    $299,900

    • 5 Beds
    • 4 Baths
    • 2,790 Sq Ft

    6 Laurel Dr, Holmes, NY 12531

    Fantastic 3-Family Opportunity in Holmes, NY!Discover the potential in this unique multifamily property, featuring a single-family home plus an additional 2-family house on one parcel. Whether you're a homeowner looking for a fixer-upper with rental income potential or an investor seeking a high-demand rental property, this is the one you’ve been waiting for. Both homes need repairs and

    Arafat Ibrahim AI Realty Brokerage LLC

    6 Laurel Dr, Holmes, NY 12531
  • /26

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,822 Sq Ft

    379 S White Rock Rd, Holmes, NY 12531

    Welcome to 379 South White Rock Road — a completely renovated country home in the charming town of Pawling, NY, offering a truly distinctive blend of modern luxury and timeless rural character. Rebuilt from the foundation up in 2023, every inch of this home has been meticulously reimagined by a master builder using only premium, top-quality materials and finishes. The result is a living

    Laurence Wallace Coldwell Banker Realty

    379 S White Rock Rd, Holmes, NY 12531
  • /27

    $299,500

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

    14 Old Route 55, Pawling, NY 12564

    Welcome HOME to this charming and historic 3-bedroom, 1-bath residence located in the heart of Pawling in the Pawling School District. This beautifully updated antique home offers the perfect blend of timeless character and modern convenience. Recent updates include brand-new carpeting, refinished hardwood floors, fresh paint, updated fixtures, an updated bathroom, and a renovated kitchen with

    Ronald Green KW MidHudson

    14 Old Route 55, Pawling, NY 12564
How to Buy a Home How to Finance a Home How to Sell a Home