Pawling Homes under $400,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Pawling and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Pawling Homes under $400,000

$369,000

2 Beds ⋅ 1 Baths ⋅ 1056846 MLS

Charming ranch nestled on a generous .57-acre property in Pawling. Offering approximately 832 square feet of above-grade living space, this 2-bedroom, 1-bath home features a comfortable and functional layout with the primary living areas conveniently located on one level. Access to the main living area includes approximately 10 exterior steps. Inside, hardwood flooring and abundant natural light create a warm and inviting atmosphere. A deck extends the living space outdoors and provides a peaceful setting to enjoy the surrounding wooded landscape. The partial unfinished basement/garage offers additional storage, utility space, and flexibility. Set on a spacious lot with a tranquil natural backdrop, this inviting home offers a manageable footprint, valuable storage, and outdoor space with the opportunity to make it your own. Located in the scenic Hudson Valley, Pawling is known for its charming village atmosphere and access to an abundance of outdoor recreation, including the Appalachian Trail, Great Swamp, nature preserves, lakes, and parkland. Metro-North service from the Village of Pawling provides convenient access for those traveling throughout the region and into New York City.

401 W Dover Road, Pawling

$395,000

2 Beds ⋅ 2 Baths ⋅ 1052304 MLS

Welcome to 136 Bundy Hill Road, a private 1.7-acre retreat surrounded by mature landscaping and peaceful natural beauty. Thoughtfully designed for both relaxation and entertaining, this property offers a wonderful blend of privacy, charm, and inviting outdoor living spaces. Step inside through the charming enclosed front porch, a bright and welcoming space surrounded by windows and offer peaceful views of the surrounding greenery. The porch provides a seamless transition into the home’s inviting living room, offering warm hardwood floors, and an open connection to the kitchen create a comfortable setting for both relaxing and entertaining. The bright, inviting kitchen features crisp white cabinetry, dark hardware, light-toned countertops, stainless steel appliances, and a farmhouse sink overlooking the backyard. A subway tile backsplash, beverage/wine station, built-in dining area and open breakfast bar add both style and functionality, while warm wood accents create a welcoming feel. The spacious bedroom offers an inviting retreat with beautiful natural light and a cozy, rustic character, and serene views through oversized windows and a glass door to the backyard. A striking stone fireplace adds warmth and rustic charm. The home is completed by a full hall bathroom and a second bedroom featuring its own ensuite full bathroom and stairs that lead to an unfinished attic, offering excellent additional storage. Enjoy the best of outdoor living with an enclosed garden perfect for growing your own vegetables, a custom deck/patio ideal for entertaining, and a cozy outdoor fire where you can relax and unwind. Additional highlights include: 2-year-old roof, new oil tank, 1-year-old hot water tank, 6-year-old kitchen appliances, and a 1-car detached garage. Enjoy the perfect balance of privacy and convenience—nearby bike trail and in under 10 minutes you can enjoy the charming Village of Pawling, known for boutique shopping and dining, plus access to the Pawling Metro North Train Station for an easy commute to NYC.

136 Bundy Hill Road, Holmes

$249,000

1 Beds ⋅ 1 Baths ⋅ 1031078 MLS

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. While the home will need some renovation, the roof was replaced 2 years ago. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

1555 Route 292, Holmes

$339,000

3 Beds ⋅ 2 Baths ⋅ 926453 MLS

Town of Pawling! Looking for a great starter home with privacy? This 3 Bedroom, 1 Bath Raised Ranch located on .58 acres at end of a private road is for you! Commuter's Dream! Close to I-84! Open floor plan with hardwood flooring in living room & dining room, large kitchen with plenty of counter & cabinet space. Large family room on lower level with sliding door to yard. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

11 Park Lane, Holmes

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.