Homes for Sale near Trinity-Pawling School

/25
$500,000
- 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
Explore 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
/23
$799,000
- 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

(845) 415-1257

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

Judith 'Judy' Albert

BHHS Hudson Valley Properties

(845) 299-9362

101 Bundy Hill Rd, Holmes, 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

Shannon Tully

McGrath Realty Inc

(845) 378-9417

Lot 25 Brady Brook Farm Rd, 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

Judith 'Judy' Albert

BHHS Hudson Valley Properties

(845) 957-9518

750 Route 292, Holmes, NY 12531
/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
/46
$1,995,000
- 5 Beds
- 4.5 Baths
- 5,390 Sq Ft
43 Meeting House Rd, Pawling, NY 12564

A Bucolic Retreat in Prestigious Quaker Hill, nestled among grand equestrian estates in the coveted Quaker Hill community of Pawling, this magnificent country retreat artfully blends modern luxury with rustic charm. Set on five serene acres surrounded by rolling meadows, scenic horse farms, and distinguished country homes, 43 Meeting House Lane offers an inspiring escape that celebrates the best

Alicia Goldman

Christie's Int. Real Estate

(845) 373-3547

43 Meeting House Rd, 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

Shannon Tully

McGrath Realty Inc

(845) 415-7723

64 S Quaker Hill Rd, Pawling, NY 12564
/36
$425,000
- 2 Beds
- 3 Baths
- 2,140 Sq Ft
49 Lakeview Dr, Holmes, NY 12531

The next best thing to Lakefront! This sprawling ranch home is a stone’s throw from access to Whaley Lake, with lake rights to all the great amenities: private beach, motorboats allowed, kayaking, fishing, swimming, sunbathing, picnicking, fall leaf watching and winter ice fishing too! With 2 bedrooms plus an Office, Den, Living Room and Family Room – there’s so much potential including one floor

Judith 'Judy' Albert

BHHS Hudson Valley Properties

(845) 478-8605

49 Lakeview Dr, 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.

(845) 377-2512

225 Route 22, Pawling, NY 12564
/4
$199,000
- Land
- 16.67 Acres
- $11,938 per Acre
1D Margherita Ln, Pawling, NY 12564

Discover an incredible opportunity to build on a rare 16+ acre parcel in the town of Pawling! Located just five minutes from the charming village, which is filled with lively shops and restaurants, this property offers a peaceful retreat in the woods. The parcel is approved by the board of health and is ready for you to construct a home with up to four bedrooms. New York City is conveniently

Colleen McGrath

McGrath Realty Inc

(845) 470-5610

1D Margherita Ln, 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
/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

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

Lisbeth Furke

World Homes Realty

(845) 851-0605

23 Lakeview Dr, Holmes, NY 12531
/3
$199,000
- Land
- 17.63 Acres
- $11,288 per Acre
1C Margherita Ln, Pawling, NY 12564

Over 17.6 acres to build your hillside oasis! This private lot is approved by the Board of Health for a four-bedroom home, and is located less than two miles from the charming village of Pawling, which offers shops, restaurants, a train station, and parks! Commute to NYC in under two hours (by car OR train), or explore nearby hiking trails, including the infamous Appalachian Trail.

Colleen McGrath

McGrath Realty Inc

(845) 552-2709

1C Margherita Ln, Pawling, NY 12564
/15
$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 place

Kathryn McCoach Houlihan Lawrence Inc.

14 Akindale Rd, 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
/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
/50
$619,000
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
322 Old Route 22, Pawling, NY 12564

Welcome to 322 Old Route 22! Spacious, newly remodeled 2-family home is a great opportunity for owner-occupants, investors, or extended families. Great location 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
/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
/2
$650,000
- 6 Beds
- 2 Baths
- 2,856 Sq Ft
13 Rebecca Dr, Pawling, NY 12564

THIS HOME WILL NOT BE AVAILABLE FOR OCCUPANCY UNTIL DECEMBER 2026. THERE IS A RESIDENTIAL FACILTY IN PLACE AT THIS SITE UNTIL THEN. This Ranch home offers 6 bedrooms and 2 full baths. There is 2,856 sqft of living space above the walk-out basement. Home is currently being used as a Residential Facility and will be held as a Rental with existing Residents in the home until DECEMBER 2026. This is a

Angela Briante Briante Realty Group, LLC

13 Rebecca Dr, Pawling, NY 12564
/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
/43
$849,999
- 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
/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
/35
$849,000
- 5 Beds
- 3 Baths
- 2,708 Sq Ft
14 Fox Wood Terrace, Patterson, NY 12563

New Construction – Recently completed November 2025. Welcome to your future dream home—where contemporary design meets peaceful country living. Situated on 5.58 private acres, this brand-new split-level residence offers living 2,708 sq. ft of beautifully designed living space and an ideal blend of comfort, functionality, and style. Thoughtfully designed for modern living, the home will feature 5

Maria Miller William Raveis Real Estate

14 Fox Wood Terrace, Patterson, NY 12563
/17
$308,750
- 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
/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
/40
$869,900
- 4 Beds
- 2.5 Baths
- 2,613 Sq Ft
5 Bridgeworth Ln, Sherman, CT 06784

Welcome to this striking Cape/Colonial nestled on a picture-perfect, dead-level parcel in one of Sherman's most desirable locations. With timeless curb appeal featuring classic wood clapboard siding and a charming cedar shingle roof, this home effortlessly blends character, comfort, and functionality. Step inside to discover a warm and inviting interior. The spacious family room is a true

Cory Neumann Houlihan Lawrence

5 Bridgeworth Ln, Sherman, CT 06784
/13
$408,888
- 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
/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
/47
$415,999
- 2 Beds
- 2.5 Baths
- 2,066 Sq Ft
107 Cornwall Meadows Ln, Patterson, NY 12563

Welcome to this light-filled end unit in Cornwall Meadows. This townhome boasts over 2,000sf and lives like a single-family home. Kitchen with stainless steel appliances and granite countertops on the first floor with updated half bathroom, eating area, and living room which flows out to your deck and yard. The second floor includes the Primary Suite with en-suite bathroom, 2nd bedroom, and a

Edmond Albano Keller Williams NY Realty

107 Cornwall Meadows Ln, Patterson, NY 12563
/2
$100,000
- Land
- 2.55 Acres
- $39,216 per Acre
115 S Quaker Hill Rd, Patterson, NY 12563

Build the home of your dreams On this 2.55 wooded acre lot surrounded by lovely homes in the area. Owner will sell subject to buyer getting approvals. Close proximity to The Great Swamp for kayaking and Thunder Ridge for skiing and snowboarding, night and day! The location is ideal with minutes to everything, schools, shops, restaurants and for ease of commute, Route 22, major highways and

Carmela Tassone Coldwell Banker Realty

115 S Quaker Hill Rd, Patterson, NY 12563
/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
/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
/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
/3
$649,000
- 3 Beds
- 3 Baths
- 2,000 Sq Ft
149 Johnson Rd, Wingdale, NY 12594

New construction home to be built ! This raised ranch home features 3 bedrooms and 3 full bathrooms and 2 car garage. The open floor plan connects the kitchen, dining room and living room. The primary bedroom with ensuite bathroom features a spa like walk in shower. The plans are approved and ready to build, don't miss the opportunity to customize this home

Bliss Voutsinas Hillside Realty & Development

149 Johnson Rd, Wingdale, NY 12594
/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

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