Homes for Sale near Trinity-Pawling School

• 

  

  

  /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

  

  Philip Bisesto

  HomeSmart Homes & Estates

  (845) 576-1665

  126 Old Route 55, Pawling, NY 12564
• 

  Explore Trinity-Pawling School

• 

  

  

  /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

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 957-9518

  750 Route 292, Holmes, NY 12531
• 

  

  

  /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

  

  Douglas Servello

  Home Sweet Home Properties

  (845) 599-8285

  26 Rodina Dr, Pawling, NY 12564
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  /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

  

  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

  

  Omar Harper

  Epique Realty

  (845) 552-1998

  120 South Rd, Holmes, NY 12531
• 

  

  /50

  $599,000

  • 2 Beds
  • 2 Baths
  • 1,428 Sq Ft

  168 Old Route 55, Pawling, NY 12564

  Step into the very year our nation was born and own a piece of American history! Originally constructed in 1776, this iconic stone residence later became the "Pawling Toll Gate and Toll House," serving as a vital gateway for travelers, a general store, a post office, and a legendary tavern. It is even whispered that George Washington himself once proved his strength within these walls, winning a

  

  Colleen McGrath

  McGrath Realty Inc

  (845) 932-0435

  168 Old Route 55, Pawling, NY 12564
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  /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

  

  Vince Buccieri

  Today Realty Corp.

  (845) 280-5951

  178 Charles Colman Blvd, Pawling, NY 12564
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  /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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 415-7723

  64 S Quaker Hill Rd, Pawling, NY 12564
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  /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.

  (845) 377-2512

  225 Route 22, 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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6866

  Lot 21 Cox Rd, Pawling, NY 12564
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  /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

  

  Lisbeth Furke

  World Homes Realty

  (845) 851-0605

  23 Lakeview Dr, Holmes, NY 12531
• 

  

  /23

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,788 Sq Ft

  106 Johnson Rd, Wingdale, NY 12594

  Raised Ranch with 3 bedrooms, 1 full bath - Open floor plan with kitchen, dining room and living room. Sliding glass doors to deck and back yard. Basement has finished family room with exterior door to driveway. Laundry room. Lots of potential. Does need work. Owner is selling it as is. Septic 2021, Roof is 15 years old, new breaker box 2025. Located minutes to Route 22 and the Wingdale train

  

  Teddie Leonaggeo

  McGrath Realty Inc

  (845) 252-8278

  106 Johnson Rd, Wingdale, NY 12594
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  /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

  

  Shannon Tully

  McGrath Realty Inc

  (845) 378-9417

  Lot 25 Brady Brook Farm Rd, Pawling, NY 12564
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  /46

  $420,000

  • 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
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  /36

  $335,850

  • 1 Bed
  • 1 Bath
  • 536 Sq Ft

  3 Gelston Rd, Sherman, CT 06784

  Steeped in history and dripping with cottage charm, the "Maltby Gelston" house is more than just a home-it's a piece of Sherman's history! This residence has worn many hats over its 200 (or so) years: from the homestead of a prominent 19th-century family, to "Brush House", to an early 20th-century harness shop. Today, this iconic "little yellow house" is celebrated as one of the cutest properties

  Larry Corrow Coldwell Banker Realty

  3 Gelston Rd, Sherman, CT 06784
• 

  

  /18

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  39 Brothers Rd, Poughquag, NY 12570

  Discover the potential of this rare gem at 39 Brothers Rd, a prime opportunity nestled in the scenic Poughquag, NY. This property promises not only unbeatable unobstructed views but also a canvas ready for your creative vision. Set on a picturesque lot, the home offers 3 bedrooms and one full bath, and a layout brimming with possibilities. This property is a golden opportunity to transform a

  Ari Lee Sunbelt Sales & Development

  39 Brothers Rd, Poughquag, NY 12570
• 

  

  /18

  $1,250,000 New Construction

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

  2 Coburn Rd W, Sherman, CT 06784

  TO BE BUILT MODERN RANCH - 1 Mile to New York Line - An exceptional opportunity awaits the savvy buyer to create their own personal retreat in the small Town of Sherman CT. SHERMAN BUILDING DESIGNS will incorporate the latest architectural styles, energy efficient features, and cutting edge technology. Open concept design and incomparable craftsmanship to be built by hands on Architect/Builder.

  Kathleen Harrison Coldwell Banker Realty

  2 Coburn Rd W, Sherman, CT 06784
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  /50

  $619,000

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

  322 Old Route 22, Pawling, NY 12564

  Multi-family in Pawling! This spacious, newly remodeled 2-family home is located just a few minutes from the Village of Pawling - a great opportunity for owner-occupants, investors, or extended families! 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, both units are

  Susan Stevens BHHS Hudson Valley Properties

  322 Old Route 22, Pawling, NY 12564
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  /4

  $100,000

  • Land
  • 1 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 Hillside Realty & Development

  149 Johnson Rd, Wingdale, NY 12594
• 

  

  /30

  $1,499,999

  • 2 Beds
  • 1 Bath
  • 1,600 Sq Ft

  165 Duell Hollow Rd, Wingdale, NY 12594

  Exceptional opportunity to acquire this contemporary masterpiece designed by renowned architect Allan Shope. Tucked away in the serene woods of Wingdale, this property spans 29.7 acres and boasts a substantial pond, once part of the historic Camp Sacajawea. The residence is positioned on a secluded, wooded parcel, offering breathtaking views of mountains and the tranquil pond—making it an ideal

  Bianca D'Alesandro Serhant LLC

  165 Duell Hollow Rd, Wingdale, NY 12594
• 

  

  /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
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  /47

  $785,000

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  475 Mooney Hill Rd, Patterson, NY 12563

  Calling all gardeners! The landscaping that has been done on this property is not to be believed! The original owners have been here since 1978 & have made this home a unique & special place, constantly updating & improving it. The house itself had a major renovation 10 years ago & has been so lovingly maintained throughout the years. The home is on almost an acre, with an in ground pool, a pool

  Gillian Stewart Gillian Stewart Real Estate

  475 Mooney Hill Rd, Patterson, NY 12563
• 

  

  /47

  $799,000

  • 4 Beds
  • 5 Baths
  • 2,968 Sq Ft

  387 Cornwall Hill Rd, Patterson, NY 12563

  The search is OVER! Welcome Home to your Income Producing 4 Bedroom Turnkey Dream Home with Legal Handi Cap Accessible Accessory 1 Bed/ 1 Full & one 1/2 Bath apartment-Owner Occupied required per town to rent. This is truly the house that keeps on giving. Upstairs your sunny living room with mountain views awaits. Doors to dual back decks. Top newly painted and lower newly constructed with

  Monica Marsich Progeny Realty Inc

  387 Cornwall Hill Rd, Patterson, NY 12563
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  /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
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  /8

  $150,000

  • Land
  • 0.46 Acre
  • $326,087 per Acre

  20 Hickory Ln, Pawling, NY 12564

  Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

  Tela Cook McGrath Realty Inc

  20 Hickory Ln, Pawling, NY 12564
• 

  

  /24

  $950,000

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  Welcome to 128 Old Pawling Road, a beautifully situated property in Pawling, NY. Set back from the road, the home is approached by a long private driveway and gated entrance, offering a sense of privacy while still being part of a neighborhood setting. Resting on over 5 acres, the property showcases stunning mountain views that create an impressive backdrop to everyday living year-round. Whether

  Juliska Martino Compass Greater NY, LLC

  128 Old Pawling Rd, Pawling, NY 12564
• 

  

  /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
• 

  

  /24

  $485,000

  • 3 Beds
  • 3.5 Baths
  • 2,503 Sq Ft

  20 Saratoga St, Pawling, NY 12564

  Welcome to this stunning 3-bedroom, 3.5-bath end-unit townhome in the highly desirable Deerfield Ponds community. Bright, warm, and beautifully maintained, this home offers an ideal blend of comfort, convenience, and modern living. Step inside to an inviting living room that seamlessly flows into the dining area and a charming kitchen with a cozy breakfast nook, all appliances updated within the

  Julia Lear Coldwell Banker Realty

  20 Saratoga 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
• 

  

  /6

  $225,000

  • Land
  • 0.76 Acre
  • $296,053 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

  Joanne Debellis Debellis Real Estate LLC

  15 Dykeman St, Pawling, NY 12564
• 

  

  /23

  $425,000

  • 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
• 

  

  /28

  $355,000

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  490 Depot Hill Rd, Poughquag, NY 12570

  Opportunity Awaits! - Your Own Private Retreat on 4+ Acres in Beekman! - Needs work, sold as is...Set back on 4 private acres, this 4-bedroom, 2 bath home offers 2,300 sq. ft. living space, surrounded by nature, tucked away from road is a true diamond in the rough just waiting for you to bring your vision to life! Upper-level features spacious living room w/cathedral ceilings,

  Susan Stevens BHHS Hudson Valley Properties

  490 Depot Hill Rd, Poughquag, NY 12570
• 

  

  /10

  $1,900,000

  • Land
  • 53 Acres
  • $35,849 per Acre

  245 Birch Hill Rd, Patterson, NY 12563

  Welcome to 53 acres of stunning land in Patterson, NY. This remarkable property offers a unique opportunity to own a piece of history. Originally part of a border dispute between New York and Connecticut, this land became part of New York in 1731 and shortly thereafter was acquired by one of Quaker Hill's oldest families who farmed it for generations. The parcel is beautifully ringed with mature

  Brian McGrath McGrath Realty Inc

  245 Birch Hill Rd, Patterson, NY 12563
• 

  

  /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
• 

  

  /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
• 

  

  /6

  $400,000

  • Land
  • 55.89 Acres
  • $7,157 per Acre

  326 Cornwall Hill Rd, Patterson, NY 12563

  Gorgeous, mostly level meadow, waiting for your dream Home / Farm. With lots of road frontage and two small picturesque man made ponds. There are two signs marking the main parcel starting points. Residential (R4), 4 acre zoning.

  Lawrence Zacks Keller Williams Realty Partner

  326 Cornwall Hill Rd, Patterson, NY 12563
• 

  

  /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
• 

  

  /7

  $385,000

  • Land
  • 3.83 Acres
  • $100,522 per Acre

  515 Depot Hill Rd, Poughquag, NY 12570

  Discover the perfect canvas for your dream home at 515 Depot Hill Rd, Poughquag, NY 12570. This expansive 3.83-acre vacant parcel of land is perched high on a hill, offering unobstructed views in all directions and is approved by the town for a 3-bedroom, 2-bathroom house. The stunning scenic vistas promise to captivate and inspire, providing a breathtaking backdrop for a home that complements

  Ari Lee Sunbelt Sales & Development

  515 Depot Hill Rd, Poughquag, NY 12570
• 

  

  /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

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