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Homes for Sale near Trinity-Pawling School

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  • /29

    $575,000

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

    36 Byrds Hill Rd, Pawling, NY 12564

    The Perfect Weekend Escape or Full-Time Country Home, just 90 minutes from NYC. Set on a quiet, scenic road in the prestigious Quaker Hill area, you’re a short drive to the Village of Pawling with shopping, restaurants, highways, and Metro-North access. From the outside, it’s a classic farmhouse with rolling green acreage and space to breathe. Step inside, and you’re met with modern, yet cozy

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 630-1049

    36 Byrds Hill Rd, Pawling, NY 12564
  • /49

    $595,000

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

    7 Glen Ct, Pawling, NY 12564

    Welcome to this beautifully renovated 3-bedroom, 2.5-bath Colonial home offering over 2,300 sq ft of stylish and comfortable living space. Nestled in a quiet cul-de-sac and private setting in Pawling, this move-in-ready residence blends classic charm with modern upgrades. Step into the heart entryway where you can hang your coat, kick your shoes off, and feel right where you need to be. Make your

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 584-8385

    7 Glen Ct, Pawling, NY 12564
  • /42

    $599,000

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

    126 Old Route 55, Pawling, NY 12564

    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. This charming, expansive ranch home is thoughtfully designed to suit a variety of living

    Agent Photo

    Philip Bisesto

    HomeSmart Homes & Estates

    (845) 576-1665

    126 Old Route 55, Pawling, NY 12564
  • /33

    $9,750,000

    • Land
    • 558 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
  • /43

    $749,000

    • 3 Beds
    • 2 Baths
    • 1,284 Sq Ft

    81 Lakeview Dr, Holmes, NY 12531

    Welcome to 81 Lakeview Drive — a quintessential log cabin estate offering deeded lake rights and endless opportunities to embrace the coveted Whaley Lake lifestyle. Nestled on a generous and private double lot, this charming retreat isn’t just a home — it’s your front-row seat to summer on the water.From the moment you arrive, the inviting front porch draws you in with panoramic,

    Agent Photo

    Colleen McGrath

    McGrath Realty Inc

    (845) 447-9689

    81 Lakeview Dr, Holmes, NY 12531
  • /48

    $785,000

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

    94 S Quaker Hill Rd, Pawling, NY 12564

    Welcome to Sunset View! Nestled on 3.24 acres of picturesque private land, this sprawling 4-bedroom split-level home offers a perfect blend of spacious living and expansive outdoor amenities including a 20 x 50 salt water inground pool. As you approach along the freshly paved driveway, you'll be welcomed into your very own private oasis. Upon entering through the front door, you’ll step into a

    Agent Photo

    Shannon Tully

    McGrath Realty Inc

    (845) 622-7595

    94 S Quaker Hill Rd, Pawling, NY 12564
  • /40

    $879,999

    • 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
  • /46

    $675,000

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

    85 Harmony Hill Rd, Pawling, NY 12564

    Escape to charming Pawling, New York, and enjoy your own 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

    Mary Craig Coldwell Banker Realty

    85 Harmony Hill Rd, Pawling, NY 12564
  • /30

    $875,000

    • 2 Beds
    • 1 Bath
    • 1,784 Sq Ft

    202 Bundy Hill Rd, Holmes, NY 12531

    This spectacular property is available for the first time in 2 decades. Currently owned and loved by a cook, artist and true Renaissance Man this home is sure to appeal to those with a sharp eye for design as well as a love for the outdoors. The house sits about a half mile from the road at the end of a gravel driveway. It is situated so as to afford seasonal 360 degree mountain views. The

    Daniel Balassone VYLLA Home

    202 Bundy Hill Rd, Holmes, NY 12531
  • /38

    $780,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 3.5 Baths
    • 3,608 Sq Ft

    2 Bridgeworth Ln, Sherman, CT 06784

    Elegant, well appointed colonial with endless possibilites nestled in the heart of Sherman. An exceptionaly thought out floorplan with high ceilings throughout. Features include a kitchen with sliding doors and dining room with French doors both leading to the back porch perfect for outdoor dinning. A large living room with fireplace, spacious bedrooms including a primary suite with full bath and

    Rebecca Ward William Pitt Sotheby's Int'l

    2 Bridgeworth Ln, Sherman, CT 06784
  • /39

    $719,000 Open Sat 12PM - 3PM

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

    108 Beyer Dr, Poughquag, NY 12570

    Don't wait to see this beautifully updated, sun-filled and spacious colonial home. Set back on a quiet country road with breathtaking views of the surrounding mountains this 4 bedroom, 4 bath home is 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

    Greta Ferrari Keller Williams Hudson Valley

    108 Beyer Dr, Poughquag, NY 12570
  • /17

    $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
  • /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
  • /29

    $879,000

    • 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

    Douglas Servello Home Sweet Home Properties

    26 Rodina Dr, Pawling, NY 12564
  • /46

    $825,000

    • 3 Beds
    • 3.5 Baths
    • 4,211 Sq Ft

    66 Carol Ln, Poughquag, NY 12570

    Welcome to this deluxe twelve room contemporary colonial, located 75 miles north of NYC, offering a perfect blend of classic charm and modern sophistication. The first floor features a grand two-story foyer, hardwood flooring, an expansive chef's kitchen with a large island and stainless steel appliances and seamless access to a private,wrap around deck and pool. Unforgettable living spaces

    Helen Schweitzer Helen Schweitzer Realty, LLC

    66 Carol Ln, Poughquag, NY 12570
  • /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
  • /37

    $699,000

    • 2 Beds
    • 2 Baths
    • 2,008 Sq Ft

    1 Coburn Rd W, Sherman, CT 06784

    Enchanting 1700's Antique Home with Modern Artistry and Bucolic Charm! Step back in time, to this extraordinary residence brimming with character and nestled in a tranquil setting. As you enter, you are greeted by the timeless beauty of exposed wooden beams that evoke the home's rich history. The kitchen is a chef's delight, featuring a stunning copper farmhouse sink, which complements the

    Alan O'Doherty William Pitt Sotheby's Int'l

    1 Coburn Rd W, Sherman, CT 06784
  • /40

    $575,000

    • 3 Beds
    • 3 Baths
    • 2,058 Sq Ft

    283 Johnson Rd, Wingdale, NY 12594

    Fabulous opportunity to purchase a Beautiful Home on .65 level ac on park-like property! Sellers are INCLUDING an adjoining .48 lot with Two Huge Detached Garages built in 2015, 40 X 28 and 24 X 24! Taxes and acreage for both lots are combined. Let's begin with the house. Inviting home was completely renovated in 2002 and expanded with a huge second floor primary suite. On the main level is a

    Lisa Liffland McGrath Realty Inc

    283 Johnson Rd, Wingdale, NY 12594
  • /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
  • /46

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 3,308 Sq Ft

    135 Stowe Dr, Poughquag, NY 12570

    A/O, inspections to be done. This stunning Center Hall Colonial offers luxurious living on a picturesque knoll with breathtaking mountain views and a park-like backyard, perfect for family gatherings and outdoor activities. The expansive three-level home features a spacious interior with hardwood and tile flooring, multiple bedrooms including a primary suite with sunrise views and a spa-like

    Crystal De Raffele RE/MAX Town & Country

    135 Stowe Dr, Poughquag, NY 12570
  • /11

    $350,000

    • 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
  • /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
  • /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
  • /28

    $340,000

    • 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
  • /29

    $579,900

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

    37 Baxter Rd, Pawling, NY 12564

    Welcome to this beautiful 3-bedroom 3.5-bath Colonial-style home with bonus room that could be used a possible in-law suite. offering over 2,600 sq ft of comfortable living space. Nestled in the beautiful Village of Pawling in the Baxter Green community. Built in 2004 and set on a level parcel, this home features hardwood floors throughout , a cozy fireplace in the living room, and a welcoming

    Matt Rose Keller Williams Prestige Prop

    37 Baxter Rd, Pawling, NY 12564
  • /49

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,288 Sq Ft

    1467 Route 292, Holmes, NY 12531

    Welcome to 1467 Route 92 in Holmes, NY. Your Lakeside Retreat Awaits. This charming 3-bedroom, 1-bath Cape Cod-style home is tucked into a peaceful and picturesque setting just across the street from Whaley Lake, the largest lake in Dutchess County with full motorboat access. With deeded lake rights, you'll enjoy all-season activities including boating, swimming, kayaking, fishing, and relaxing

    Hamar Clarke Clarke Realty & Associates LLC

    1467 Route 292, Holmes, NY 12531
  • /39

    $529,000

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

    16 Mountain View Dr, Holmes, NY 12531

    Escape to your own Private OasisDiscover unparalleled tranquility and comfort in this immaculate 3-bedroom, 2-bath raised ranch with office, perfectly situated on a 2.85- private lot. Wake up to scenic views and enjoy the serenity of your own expansive outdoor haven.The home offers a bright kitchen with stainless steel appliances and Corian countertops. Enjoy year-round comfort with

    LUCIANA BENNETT McGrath Realty Inc

    16 Mountain View Dr, Holmes, NY 12531
  • /50

    $498,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    57 Panorama Dr, Patterson, NY 12563

    Swimming, skiing, snowboarding, kayaking in the Patterson Great Swamp, walking or biking the nearby rail trail or Wonder Lake State Park, just minutes to the quaint Village of Pawling, shopping, dining, highway and train...these are just a few of the perks that living at 57 Panorama Dr. has to offer. This desirable neighborhood with its incredible views and convenient location boasting Carmel

    Karyne Aabel Briante Realty Group, LLC

    57 Panorama Dr, Patterson, NY 12563
  • /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
  • /20

    $510,000

    • 3 Beds
    • 1.5 Baths
    • 1,415 Sq Ft

    1098 Route 311, Patterson, NY 12563

    Historically rich single-family home nestled on a 0.13 lot within a rural-residential enclave of Patterson. Property overview; 3 bedrooms, 1 full bathroom + 1.5 bathroom on the main level. Plenty of outdoor space with a concrete patio/deck with direct yard access- perfect for summer gatherings. Interior highlights: Renovated gourmet kitchen featuring stainless-steel appliances. Abundant of

    David Matos Premium Choice INC

    1098 Route 311, Patterson, NY 12563
  • /21

    $699,000

    • 6 Beds
    • 3 Baths
    • 4,108 Sq Ft

    16 New York 292 Unit 14, Patterson, NY 12563

    Don’t miss this rare chance to own a 2-family property featuring a spacious 4-bedroom, 2-bath front house with beautiful hardwood floors throughout. A 2 bedroom apartment above 2 car garage is ideal for owner-occupants or investors, this versatile property offers strong rental income potential. Whether you're looking to live in one unit and rent the other, or add to your portfolio, this property

    Vera Karaqi Coldwell Banker Realty

    16 New York 292 Unit 14, Patterson, NY 12563
  • /21

    $350,000

    • 3 Beds
    • 1 Bath
    • 1,488 Sq Ft

    1565 Route 292, Holmes, NY 12531

    Seize the chance to transform this quaint fixer-upper into your dream residence or a lucrative rental property. Enjoy picturesque Whaley Lake views from the second floor. This vintage-style home is brimming with potential and awaits your creative touch. The kitchen was updated in 2018. The roof and interior need TLC. Note: The second full bathroom is not included in the town tax records. A

    Denise Taylor Coldwell Banker Realty

    1565 Route 292, Holmes, NY 12531
  • /48

    $1,575,000

    • 4 Beds
    • 4 Baths
    • 3,311 Sq Ft

    1034 Route 292, Holmes, NY 12531

    Welcome to This Stunning Center Hall Colonial on Whaley Lake. Tucked back from the road for ultimate privacy, sits this exceptional lakefront home that offers the perfect blend of timeless charm, modern convenience, and breathtaking views of Whaley Lake. As you step into the foyer, you're immediately greeted by elegance and sweeping water views. Designed with both luxury and functionality in

    Regan Andrews Houlihan Lawrence Inc.

    1034 Route 292, Holmes, NY 12531
  • /34

    $625,000

    • 3 Beds
    • 3 Baths
    • 1,450 Sq Ft

    54 Nanny Hill Rd, Pawling, NY 12564

    This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

    Kaye Saglibene

    54 Nanny Hill Rd, Pawling, NY 12564
  • /28

    $550,000

    • 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
  • /37

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,912 Sq Ft

    294 New York 292, Holmes, NY 12531

    Nestled on a serene 1.35-acre lot, this charming raised ranch offers the perfect blend of privacy and convenience, with easy access to shopping, highways, the train station, and the beloved Thunder Ridge Ski Area. Step inside to discover a warm and inviting interior featuring three spacious bedrooms, two beautifully appointed full bathrooms, a finished basement, and a two-car garage, complemented

    Brittany Pisco, SRS William Raveis-New York, LLC

    294 New York 292, Holmes, NY 12531
  • /47

    $649,900

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

    28 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 28 Gobblers Knob Road – A Hudson Valley Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The

    Mark Snyder eXp Realty

    28 Gobblers Knob Rd, Pawling, NY 12564
  • /45

    $456,600

    • 3 Beds
    • 2.5 Baths
    • 1,835 Sq Ft

    19 Cushing Green S, Pawling, NY 12564

    Comfortable Townhouse Living at Squire GreenWelcome to this spacious and bright end-unit townhouse featuring 3 bedrooms, 2.5 bathrooms, and a one-car garage—all set within the highly sought-after Squire Green community. The main floor offers a welcoming layout ideal for daily living and entertaining. Enjoy an eat-in kitchen, a living room with cathedral ceilings, cozy fireplace, and a sliding

    Peggy MacLeay-Generoso McGrath Realty Inc

    19 Cushing Green S, 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

    Jillian Pajer Douglas Elliman Real Estate

    215 Little Pond Rd, Pawling, NY 12564
  • /4

    $100,000

    • Land
    • 1.00 Acre
    • $100,000 per Acre

    149 Johnson Rd, Wingdale, NY 12594

    Land for sale with board of health approval- Approved plans for a 3 bedroom, 3 bathroom raised ranch home. Well is drilled, land is ready to start building your dream home today

    Bliss Voutsinas

    149 Johnson Rd, Wingdale, NY 12594

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