MLS Listings for Sale in Pawling, NY

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OPEN NOV 20, 11AM TO 1PM

ABOUT THIS HOME
MLS Listings for Sale in Pawling, NY
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 of Hudson Valley living. The property features a fully renovated three-bedroom main residence and a charming two-bedroom guest cottage, each with its own utilities—ideal for hosting guests, accommodating extended family, or providing a caretaker’s residence. Originally conceived as a cla

$1,995,000

5 beds4.5 baths5,390 sq ft

43 Meeting House Rd, Pawling, NY 12564

Five serene acres • Vaulted ceilings • 5 acre lot

Listing by Christie's Int. Real Estate

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Pawling, NY
Welcome to 561 Route 292 in Holmes, New York — a stunningly renovated luxury residence showcasing exceptional craftsmanship and modern design. This beautifully reimagined home offers four spacious bedrooms and four full bathrooms, including a primary bedroom with an ensuite bath. The main level features gleaming new hardwood floors, cathedral ceilings, an inviting fireplace, and a seamless open layout that combines elegance with comfort. No detail has been overlooked in this complete top-to-bottom renovation, which includes a new roof and windows, new HVAC system with AC and heat pump, all-new electric and plumbing, a new water heater—ensuring years of worry-free living, and a n

$699,900

4 beds4 baths4,196 sq ft

561 Route 292, Holmes, NY 12531

1.04 acre lot • 2 garage spots • Built 1988

Listing by United RE Hudson Valley Edge

ABOUT THIS HOME
MLS Listings for Sale in Pawling, NY
Welcome home to 2 Spruce St. ! 2 full floors plus a completely finished walk out basement. Home has central air and heat. Completely updated and freshly painted, all you need to do is move in. Living room features a built in flue that can be opened up for adding a wood burning fireplace. 2 full primary bedrooms, each with it's own full bathroom, plus a powder room on the first floor. One of the bedrooms features a huge walk in closet. Home features include an office plus large flex space for a playroom/home theater, etc. Newer mechanicals. There is a walk out patio, plus a deck featuring a hard wired, lighted Sunsetter awning. Community features a large in-ground pool and clubhouse. Never

$399,999

2 beds2.5 baths1,838 sq ft

2 Spruce St, Pawling, NY 12564

Walk out patio • Huge walk in closet • Large in-ground pool

Listing by Hanson Real Estate Partners

ABOUT THIS HOME
MLS Listings for Sale in Pawling, NY
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.

$325,000

2 beds1 bath672 sq ft

5 Birch Dr, Holmes, NY 12531

Summer views • Dock • Winter views

Listing by RE/MAX Classic Realty

ABOUT THIS HOME
MLS Listings for Sale in Pawling, NY
Nature lover's lakefront paradise! Exceptional views of beautiful Whaley Lake. Peaceful, breathtaking, panoramic vista from living room, dining area, decks & patios. Beach, boathouse & manicured frontage for endless summer fun. Fish, swim, boat, canoe or kayak at your leisure. Home features attractive open floor plan with center island kitchen, granite counters & stainless appliances. Living room w/ fireplace & dining area with wall of expansive windows welcomes in bright sun and endless views. Two bedrooms & renovated bathroom on main level. Lower level features family room/summer kitchen ideal for guest quarters, fitness area or media room, renovated bathroom

$849,000

2 beds2 baths1,600 sq ft

70 Lakeview Dr, Holmes, NY 12531

Open floor plan • Boathouse • Lakefront paradise

Listing by BHHS Hudson Valley Properties

Property at 379 S White Rock Rd, Holmes, NY 12531, 3 beds, 2 baths

$720,000

3 beds2 baths1,822 sq ft

379 S White Rock Rd, Holmes, NY 12531

Listing by Coldwell Banker Realty

Property at 120 South Rd, Holmes, NY 12531, 4 beds, 2.5 baths

$500,000

4 beds2.5 baths1,608 sq ft

120 South Rd, Holmes, NY 12531

Listing by Epique Realty

Property at 4 Mane Way, Pawling, NY 12564, 4 beds, 2.5 baths

$775,000

4 beds2.5 baths3,611 sq ft

4 Mane Way, Pawling, NY 12564

Listing by Coldwell Banker Realty

Property at 1565 Route 292, Holmes, NY 12531, 3 beds, 2 baths

$250,000

3 beds2 baths1,488 sq ft

1565 Route 292, Holmes, NY 12531

Listing by Coldwell Banker Realty

Property at 11 Park Ln, Holmes, NY 12531, 3 beds, 2 baths

$419,000

3 beds2 baths1,232 sq ft

11 Park Ln, Holmes, NY 12531

Listing by River Realty Services, Inc.

Property at 10 Rebecca Dr, Pawling, NY 12564, 3 beds, 2.5 baths

$580,000

3 beds2.5 baths1,893 sq ft

10 Rebecca Dr, Pawling, NY 12564

Listing by Howard Hanna Rand Realty

Property at 48 W Main St, Pawling, NY 12564, 5 beds, 3.5 baths

$699,900

5 beds3.5 baths3,152 sq ft

48 W Main St, Pawling, NY 12564

Listing by BHHS Hudson Valley Properties

Property at 23 Lakeview Dr, Holmes, NY 12531, 4 beds, 2 baths

$505,000

4 beds2 baths1,210 sq ft

23 Lakeview Dr, Holmes, NY 12531

Listing by World Homes Realty

Property at 322 Old Route 22, Pawling, NY 12564, 4 beds, 2 baths

$619,000

4 beds2 baths1,950 sq ft

322 Old Route 22, Pawling, NY 12564

Listing by BHHS Hudson Valley Properties

Property at 5 Perri Ln, Pawling, NY 12564, 3 beds, 2.5 baths

$725,000

3 beds2.5 baths3,564 sq ft

5 Perri Ln, Pawling, NY 12564

Listing by Jefferson Valley Realty

Property at 604 N Quaker Hill Rd, Pawling, NY 12564, 5 beds, 7.5 baths

$1,450,000

5 beds7.5 baths5,470 sq ft

604 N Quaker Hill Rd, Pawling, NY 12564

Listing by Ellis Sotheby's Intl Realty

Property at 23 Union St, Pawling, NY 12564, 3 beds, 2 baths

$419,900

3 beds2 baths1,480 sq ft

23 Union St, Pawling, NY 12564

Listing by K Fortuna Lighthouse Realty

Property at 12 Rebecca Dr, Pawling, NY 12564, 4 beds, 3 baths

$699,000

4 beds3 baths3,888 sq ft

12 Rebecca Dr, Pawling, NY 12564

Listing by eRealty Advisors, Inc

Property at 28 Gobblers Knob Rd, Pawling, NY 12564, 3 beds, 2 baths

$574,900

3 beds2 baths2,107 sq ft

28 Gobblers Knob Rd, Pawling, NY 12564

Listing by eXp Realty

Property at 2 Bridle Way, Pawling, NY 12564, 3 beds, 3.5 baths

$504,900

3 beds3.5 baths3,467 sq ft

2 Bridle Way, Pawling, NY 12564

Listing by Jonathan D. Gineo

Property at 60 Lakeview Dr, Holmes, NY 12531, 2 beds, 2.5 baths

$735,000

2 beds2.5 baths1,424 sq ft

60 Lakeview Dr, Holmes, NY 12531

Listing by Keller Williams Realty Partner

Property at 49 Lakeview Dr, Holmes, NY 12531, 2 beds, 3 baths

$425,000

2 beds3 baths2,140 sq ft

49 Lakeview Dr, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 29 Cunningham Ln, Pawling, NY 12564, 4 beds, 4 baths

$699,000

4 beds4 baths4,199 sq ft

29 Cunningham Ln, Pawling, NY 12564

Listing by Gillian Stewart Real Estate

Property at 7 Glen Ct, Pawling, NY 12564, 3 beds, 2.5 baths

$575,000

3 beds2.5 baths2,318 sq ft

7 Glen Ct, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at 215 Little Pond Rd, Pawling, NY 12564, 5 beds

$399,000

5 beds— baths1,062 sq ft

215 Little Pond Rd, Pawling, NY 12564

Listing by Douglas Elliman Real Estate

Property at 750 Route 292, Holmes, NY 12531, 11 beds, 8 baths

$1,400,000

11 beds8 baths— sq ft

750 Route 292, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 14 Akindale Rd, Pawling, NY 12564, 4 beds, 2.5 baths

$975,000

4 beds2.5 baths3,000 sq ft

14 Akindale Rd, Pawling, NY 12564

Listing by Houlihan Lawrence Inc.

Property at 101 Bundy Hill Rd, Holmes, NY 12531, 3 beds, 3.5 baths

$537,500

3 beds3.5 baths2,106 sq ft

101 Bundy Hill Rd, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 618 Quaker Hill Rd, Pawling, NY 12564, 17 beds, 11 baths

$5,500,000

17 beds11 baths15,000 sq ft

618 Quaker Hill Rd, Pawling, NY 12564

Listing by Douglas Elliman Real Estate

Property at 6 Byrds Hill Rd, Pawling, NY 12564, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths3,035 sq ft

6 Byrds Hill Rd, Pawling, NY 12564

Listing by William Pitt Sothebys Int Rlty

Property at 126 Old Route 55, Pawling, NY 12564, 4 beds, 4.5 baths

$599,000

4 beds4.5 baths2,361 sq ft

126 Old Route 55, Pawling, NY 12564

Listing by HomeSmart Homes & Estates

Property at 120 Harmony Rd, Pawling, NY 12564, 4 beds, 4.5 baths

$1,250,000

4 beds4.5 baths3,200 sq ft

120 Harmony Rd, Pawling, NY 12564

Listing by Hillside Realty & Development

Property at 13 Rebecca Dr, Pawling, NY 12564, 6 beds, 2 baths

$650,000

6 beds2 baths2,856 sq ft

13 Rebecca Dr, Pawling, NY 12564

Listing by Briante Realty Group, LLC

Property at Walnut St, Pawling, NY 12564

$159,000

— beds— baths— sq ft

Walnut St, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at Lot 18 Cox Rd, Pawling, NY 12564

$229,000

— beds— baths— sq ft

Lot 18 Cox Rd, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

$229,000

— beds— baths— sq ft

Lot 25 Brady Brook Farm Rd, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at Lot 21 Cox Rd, Pawling, NY 12564

$229,000

— beds— baths— sq ft

Lot 21 Cox Rd, Pawling, NY 12564

Listing by McGrath Realty Inc

$149,900

— beds— baths— sq ft

South Rd, Holmes, NY 12531

Listing by Howard Hanna Rand Realty

Property at Kirby Hill Rd, Pawling, NY 12564

$189,000

— beds— baths— sq ft

Kirby Hill Rd, Pawling, NY 12564

Listing by Howard Hanna Rand Realty

Property at 178 Charles Colman Blvd, Pawling, NY 12564

$1,350,000

— beds— baths— sq ft

178 Charles Colman Blvd, Pawling, NY 12564

Listing by Today Realty Corp.

Property at Lot "d" Oblong Ln, Pawling, NY 12564

$190,000

— beds— baths— sq ft

Lot "d" Oblong Ln, Pawling, NY 12564

Listing by Howard Hanna Rand Realty

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Based on information submitted to the MLS GRID as of Wed Nov 12 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

MLS Listings for Sale in Pawling

There are currently 44 mls listings for sale in Pawling at a median listing price of $449K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Pawling stay on the market for 82 days. This map is refreshed with the newest listings in Pawling every 15 minutes.

In the past month, 1 home has been sold in Pawling. In addition to houses in Pawling, there were also 0 condos, 1 townhouse, and 1 multi-family unit for sale in Pawling last month. Find your dream home in Pawling using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Pawling are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Pawling. Our Pawling real estate stats and trends will give you more information about home buying and selling trends in Pawling. If you're looking to sell your home in the Pawling area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Pawling with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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