Pawling, NY homes for sale & real estate

35 homes

Sort:

Recommended

ABOUT THIS HOME
Pawling, NY Homes for Sale
Welcome to 2 Bridle Way, a rare opportunity to own a spacious 3-bedroom, 3.5-bath Colonial in one of Pawling’s most desirable and well-kept communities. Built in 1992, this young home offers an impressive layout with generous room sizes, abundant natural light, and endless potential for the next owner to bring their vision to life. Located in a sought-after HOA neighborhood, residents enjoy the convenience of included water, sewer, and professional landscaping services, creating a low-maintenance lifestyle with exceptional value. The main level features a traditional Colonial flow with ample living and dining space, while the upper level offers well-proportioned bedrooms, including a

$479,900

3 beds3.5 baths3,467 sq ft

2 Bridle Way, Pawling, NY 12564

Primary suite • 0.78 acre lot • 4 garage spots

Listing by AI Realty Brokerage LLC

ABOUT THIS HOME
Pawling, NY Homes for Sale
Begin the New Year in a charming home featuring 3 spacious bedrooms, 2 full baths nestled on a picturesque 1.19 acre wooded lot. Property is a short walk from Whaley Lake, which is adjacent to Empire State Trail and the MTA-owned Maybrook Rail Trail. Located at the end of a cul-de-sac with stunning seasonal lake views, this home offers a serene retreat. There is a Marina on the lake and you can purchase lake rights. Roof was replaced in 2017 with a 25yr transferable warranty, a heat pump was installed in 2022 but still have the oil based heat as an option, and a new water heater added in 2024. Radon System installed only as a precaution. Town Water via community well/ Septic Syst

$520,000

3 beds2 baths1,631 sq ft

145 Mountain View Dr, Holmes, NY 12531

Marina on the lake • Wooded lot • Seasonal lake views

Listing by Regency Real Estate

ABOUT THIS HOME
Pawling, NY Homes for Sale
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 is a once-in-a-lifetime opportunity. Nestled in the heart of nature, this extraordinary private estate spans nearly 1,338 acres, offering unparalleled seclusion, natural beauty, and world-class amenities. Designed as a one-of-a-kind sanctuary, the retreat spans 23 tax lots and showcases breathtakin

$39,000,000

9 beds12 baths55,000 sq ft

104 North Garden Dr, Pawling, NY 12564

Vast landholdings • Secluded sanctuary • Private estate

Listing by Julia B Fee Sothebys Int. Rlty

ABOUT THIS HOME
Pawling, NY Homes for Sale
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 updating, but the property is aggressively priced for a quick sale. Live in one unit and let the other two generate income, or renovate and rent all three for stronger cash flow. The possibilities are endless for the savvy buyer. Opportunities like this don’t last—priced to sell! Schedule

$299,900

5 beds4 baths2,790 sq ft

6 Laurel Dr, Holmes, NY 12531

2 family house • Multifamily property • Single family home

Listing by AI Realty Brokerage LLC

ABOUT THIS HOME
Pawling, NY Homes for Sale
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.

$240,000

2 beds1 bath672 sq ft

5 Birch Dr, Holmes, NY 12531

Summer views • Dock • Winter views

Listing by RE/MAX Classic Realty

Property at 64 S Quaker Hill Rd, Pawling, NY 12564, 5 beds, 4 baths

$1,200,000

5 beds4 baths4,248 sq ft

64 S Quaker Hill Rd, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at 1098 292 Rte, Holmes, NY 12531, 3 beds, 3 baths

$675,000

3 beds3 baths1,680 sq ft

1098 292 Rte, Holmes, NY 12531

Listing by BHHS Hudson Valley Properties

Property at 21 Kings Way, Pawling, NY 12564, 3 beds, 2.5 baths

$368,888

3 beds2.5 baths1,960 sq ft

21 Kings Way, Pawling, NY 12564

Listing by YourHomeSold Guaranteed Realty

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

$399,900

3 beds2 baths1,232 sq ft

11 Park Ln, Holmes, NY 12531

Listing by River Realty Services, Inc.

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 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 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 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 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 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 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 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 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 16 Anderson Rd, Pawling, NY 12564, 4 beds, 6 baths

$1,175,000

4 beds6 baths3,012 sq ft

16 Anderson Rd, Pawling, NY 12564

Listing by Compass Greater NY, LLC

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

$598,500

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

$240,000

— beds— baths— sq ft

194 Road, Holmes, NY 12531

Property at 1D Margherita Dr, Pawling, NY 12564

$199,000

— beds— baths— sq ft

1D Margherita Dr, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at 51 Estate Dr, Pawling, NY 12564

$169,000

— beds— baths— sq ft

51 Estate Dr, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at Walnut St, Pawling, NY 12564

$154,900

— beds— baths— sq ft

Walnut St, 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 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

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 57 Quaker Hill Rd, Pawling, NY 12564

$3,900,000

— beds— baths— sq ft

57 Quaker Hill Rd, Pawling, NY 12564

Listing by McGrath Realty Inc

Property at 225 Route 22, Pawling, NY 12564

$9,750,000

— beds— baths— sq ft

225 Route 22, Pawling, NY 12564

Listing by Houlihan Lawrence Inc.

Property at S White Rock Rd, Holmes, NY 12531

$399,000

— beds— baths— sq ft

S White Rock Rd, Holmes, NY 12531

Listing by Houlihan Lawrence Inc.

Viewing page 1 of 1

Based on information submitted to the MLS GRID as of Fri Jan 02 2026. 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.

Average home prices near Pawling, NY

Cities

Brewster homes for sale
$569,000
Hopewell Junction homes for sale
$575,000
Millbrook homes for sale
$65,000,000
Wappinger homes for sale
$584,925
Lewisboro homes for sale
$950,000
Yorktown homes for sale
$829,900
Carmel homes for sale
$670,000
Mahopac homes for sale
$744,450
Somers homes for sale
$839,450
Patterson homes for sale
$580,000
North Salem homes for sale
$1,037,400
Putnam Valley homes for sale
$600,000
Amenia homes for sale
$377,000

Zip Codes

12564 homes for sale
$619,000

Pawling, NY real estate trends

$560K

Sale price

+40.0%
since last year

$214

Sale $/sq ft

-39.5%
since last year

Over list price

3.6%

Days on market

32.5

Down payment

—

Total homes sold

See more Pawling, NY market insights

More to explore in Pawling, NY

How to buy a house in Pawling, NY

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in New York

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.