Staatsburg Homes under $500,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Staatsburg 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 Staatsburg Homes under $500,000

$450,000

3 Beds ⋅ 3 Baths ⋅ 1050337 MLS

Welcome to 2 Enderkill, where the beauty of the Hudson Valley and the comfort of everyday living come together in a way that feels truly special. Tucked away on a private lot and framed by striking natural rock outcroppings, this 3 bedroom, 3 full bath retreat has a one of a kind character and a real connection to the land around it, with room to breathe, room to gather, and room to grow. Inside, the kitchen opens to the dining area for easy everyday meals and festive gatherings, while the generous living room centers around a cozy fireplace, perfect for quiet evenings and cold winter nights. A flexible bonus room on the main level adapts to the way you live, whether you need a home office, guest room, playroom, or a potential first floor bedroom. Upstairs, three spacious bedrooms and two full baths offer comfort and privacy for everyone, including a primary suite with its own private bath and a sliding glass door that opens to a secluded balcony overlooking the property, a peaceful spot for morning coffee or unwinding at the end of the day. Outdoor living shines with a large deck for entertaining, an above ground pool for summer fun, a detached garage, an attached carport, and an additional .32 acre parcel that adds even more space and opportunity, while a new roof brings welcome peace of mind for years to come. The location is just as appealing, with Rhinebeck, Hyde Park, and Poughkeepsie only minutes away and Metro North nearby for easy commuting or weekend getaways. Boutique shopping, acclaimed dining, parks, hiking trails, and storied historic sites are all close at hand, and being directly across from Norrie State Park means outdoor adventure is right at your doorstep, with Dinsmore Golf Course and the iconic Mills Mansion just a short drive away. If you have been searching for privacy, convenience, and the timeless charm the Hudson Valley is celebrated for, 2 Enderkill is ready to welcome you home.

2 Enderkill Drive, Staatsburg

$499,900

4 Beds ⋅ 3 Baths ⋅ 1052548 MLS

This beautiful 4 Bedroom, two story, Victorian style home is located in the sought after Hamlet of Staatsburg. It has been completely updated but it retains lots of its original charm along with many modern updates. The home features its original hardwood flooring throughout. The whole house has been freshly painted inside and out. Gorgeous updated kitchen with granite countertops and center island. All 3 bathrooms have been beautifully renovated. All new energy efficient windows in every room. Each and every bedroom is nicely sized. Fantastic 2 car detached garage behind the home. Full unfinished basement. Large deck off of the kitchen is great for entertaining your guests. You can walk to restaurants, the library, Dinsmore Golf Course, and the historic site at Mills Mansion. You will not find a true Victorian home for this price anywhere in Dutchess County and especially not in the Hamlet of Staatsburg.

46 Old Post Road, Staatsburg

$199,900

3 Beds ⋅ 2 Baths ⋅ 1049221 MLS

Nestled against NYS Taconic Park land, this older single-family home offers unlimited potential in an irreplaceable setting. Surrounded by 1.4 acres of lush, mature landscaping, the backyard borders a scenic trail linking the historic Ogden Mills Estate to the Norrie Point Environmental Center and Marina. Whether you are looking to create a lucrative short-term rental or craft a private retreat for buyers who appreciate nature and historic Hyde Park, the possibilities are endless. Enjoy year-round outdoor recreation right from your doorstep. Located in the quaint hamlet of Staatsburg—featuring a vibrant local library, basketball and pickleball courts, a renowned golf course, local dining, and a 10-minute drive to the train station. Unique location. Property is being sold as-is and awaits your vision!

10 Cedar Street, Staatsburg

$499,000

4 Beds ⋅ 3 Baths ⋅ 1045888 MLS

WOW!! Welcome to 6 Vanessa lane, this house is just like new construction. This raised ranch is in the Hyde Park School District and has been totally renovated from top to bottom. Located on .92 acres of land, New roof, new siding, new windows. Living room has a bay window, recess lighting, and a wood burning fireplace to enjoy on a cold winters night. Dining room has hard wood floors and a nice area for meals. Kitchen is brand new with electric stove, Quartz countertops, hardwood floors, tons of cabinets space and a wine cooler. Primary bedroom has hardwood floors, full bath with shower, 2 other bedrooms on this level offers hardwood floors, 4th bedroom is in the lower level adjacent to the family room which has a sliding glass door to the patio area, another full bath on this level. Also has a 2 car attached garage. This home is minutes to Historic Rhinebeck and Hyde Park. This home is waiting for a new owner, show this house today before it is gone tomorrow.

6 Vanessa Lane, Staatsburg

$369,000

4 Beds ⋅ 1 Baths ⋅ 1025200 MLS

This lovely home is situated on a peaceful road in a charming little neighborhood in Staatsburg. It’s in need of some TLC and a bit of a refresh, which is why it’s priced as it is. The property spans 1.1 acres, giving you plenty of space to unwind and enjoy the outdoors. Close to the villages of Hyde Park and Rhinebeck, shopping, restaurants, medical facilities, historic sites, and so much more!

26 W Cookingham Drive, Staatsburg

$389,000

2 Beds ⋅ 1 Baths ⋅ 1010205 MLS

Charming, well-maintained ranch conveniently located on a quiet one-way street. This ranch has been lovingly cared for over the past 20 years. Many updates have been made to the kitchen and bath. Windows have been replaced and the roof is new, reducing maintenance costs for the new owner. The basement is clean and dry – perfect for storage. The home opens into a cozy living room with fireplace and continues to an ample dining room, eat-in kitchen with a gas stove and stainless appliances offering a modern appeal. A comfortable family room, 2 bedrooms and a full bath. In addition, the large light-filled 3 season room is a standout feature, perfect for enjoying summer nights or hosting family gatherings in a bright, airy environment. Another bonus is a large laundry room with plenty of room for storage. The combination of updated features, ample storage and inviting spaces make it a great starter home or perfect for downsizing. Ready to just move in, relax and enjoy. Come take a look – priced to sell – make your appointment today!

8 S Creek Road, Staatsburg

$495,000

3 Beds ⋅ 2 Baths ⋅ 988726 MLS

Welcome to 7 Jonathan Drive, a beautifully renovated raised ranch offering modern comfort and move-in-ready living in Staatsburg. This 3-bedroom, 2-bath home has been thoughtfully updated throughout, including a brand-new roof, energy-efficient split systems, a stylish new kitchen, and completely renovated bathrooms. The bright and inviting main level features an open flow between the living room, dining area, and kitchen, creating the perfect space for everyday living and entertaining. The finished lower level provides additional flexible living space that can be used as a family room, home office, gym, or guest area. Additional highlights include an attached garage, ample driveway parking, and a spacious yard with plenty of room to relax, play, or entertain. With major improvements already completed, all that’s left to do is move in and enjoy!

7 Jonathan Drive, Staatsburg

$425,000

3 Beds ⋅ 2 Baths ⋅ 975827 MLS

Step into the lifestyle you’ve been waiting for in this beautifully upgraded 3-bedroom home, where modern style, everyday comfort, and exceptional indoor-outdoor living come together seamlessly. From the moment you enter, you’ll be welcomed by sun-filled living spaces, elegant finishes, and thoughtful updates throughout. Designed for both relaxing and entertaining, the home features a spacious living room bathed in natural light and a warm, inviting family room with a charming fireplace—perfect for cozy evenings at home. Fresh paint and upgraded wood flooring create a sophisticated, move-in-ready feel from top to bottom. At the heart of the home is a stunning, fully renovated kitchen that will impress any chef. Complete with brand-new Whirlpool appliances, sleek quartz countertops, a designer backsplash, and generous prep and storage space, this kitchen blends beauty with functionality. The adjoining dining area makes hosting family and friends effortless. The beautifully updated bathrooms showcase stylish tilework, modern vanities, and contemporary lighting, while the oversized primary bedroom offers a peaceful retreat with a spacious walk-in closet. A dedicated laundry room with a brand-new washer and dryer adds everyday convenience. One of the home’s standout features is the incredible indoor-outdoor living experience. Relax year-round in the bright sunroom or escape to your own private backyard oasis featuring a patio, sparkling in-ground swimming pool, separate pool house, and additional storage space—an ideal setting for entertaining, summer gatherings, or simply unwinding in privacy. Additional highlights include a 2-car garage, a roof approximately 4 years old, and a quiet, desirable neighborhood with convenient access to major highways and train transportation for an easy commute. Beautifully updated, thoughtfully designed, and perfectly located, this home offers the complete package. Opportunities like this don’t come around often—schedule your private showing today!

22 Prospect Street, Staatsburg

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.