Current Dutchess County real estate listings: Below are our current properties for sale in Dutchess County located in the Hudson Valley region of Upstate New York in the Tri-State area of Connecticut and Massachusetts. Whether you are looking for a home for sale, a land parcel or the perfect country rental you can find it here. Other properties located outside of Dutchess County can be found by navigating above. Also, check our Communities page to learn more about the unique appeal of each of each of the 40+ different communities we serve.
CHESTNUT RIDGE FARM EH# 3922
EH# 3922
Chestnut Ridge Farm is a 250-acre country estate which includes two Guesthouses and a privately situated equestrian training and show facility in the heart of the Millbrook Hunt Country dating back to 1797. The property, including the additional building lot, …
9 Bedrooms • 8 Baths
• 3832 Sq Ft • 250 Acres
Country Setting Gardens Historic Horse Property Pool With Views
On The Market
Hunt Country Spectacular Renovation EH# 3627
EH# 3627
Stunning 1780 Historic Center Hall Colonial has been beautifully restored throughout offering 5 Bedrooms, 5 Baths, 5 wood burning fireplaces, and gracious details in every room. Highly desirable Chestnut Ridge Road property for sale boasting 196 acres of open fields, …
5 Bedrooms • 5 Baths
• 5600 Sq Ft • 196.19 Acres
Country Setting Gardens Large Acreage Property Pool Private Location With Views
On The Market
Understated Country Estate with Pastoral Views EH# 3823
EH# 3823
Located within the Coleman Station Historic District, this 2005 custom designed and built 5200+/- sf Federal style home is thoughtful in scale and design, and nothing has been overlooked in creating a perfect venue for comfortable family living and sophisticated …
4 Bedrooms • 6 Baths
• 5200 Sq Ft • 51.17 Acres
Country Setting Large Acreage Property Pool With Views
On The Market
CHESTNUT RIDGE ELEGANCE EH# 3618
EH# 3618
Stunning 1780 Historic Center Hall Colonial has been beautifully restored throughout offering 5 Bedrooms, 5 Baths, 5 wood burning fireplaces, and gracious details in every room. Highly desirable Chestnut Ridge Road property for sale boasting 98 acres of open fields, …
5 Bedrooms • 5 Baths
• 5600 Sq Ft • 98.7 Acres
Country Setting Gardens Large Acreage Property Pool Private Location With Views
On The Market
STISSING RISING EH# 3899
EH# 3899
Stissing Rising, in the heart of Pine Plains’ Shekomeko Valley, sits high above a panoramic vista of neighboring farms and undulating landscapes. Integrated mixed-mediums throughout exude a calming balance of modern sophistication with the home’s classic timber-framing and stonework. This 5-Bedroom, …
5 Bedrooms • 5 Baths
• 5604 Sq Ft • 20.95 Acres
Country Setting Pool With Views
On The Market
Between the Brooks EH# 3773
EH# 3773
This modern home is imbued with the historical design aesthetic of architect, Richard Crowley, who specializes in the renovation and preservation of historic structures in the Hudson Valley. Located on 34 acres in the Scenic Tower Hill Road Protection area, this classic 4-Bedroom, …
4 Bedrooms • 4 Baths
• 4080 Sq Ft • 34.5 Acres
Country Setting Gardens Private Location With Views
On The Market
South Taconic Mountain Views EH# 3749
EH# 3749
This 147 private acres has sweeping views facing the South Taconic Range. Located near pristine Winchell Mountain this large undeveloped parcel looks across the Harlem Valley toward Taconic State Park and the summits of Mt. Riga, Brace Mountain, Mt. Alander …
147.28 Acres
Country Setting Large Acreage Property With Views
On The Market
Meadows, Views, Creek - Beautiful EH# 3710
EH# 3710
These gorgeous 75+ acres flow around exquisite contours. A high building site offers magnificent distant views and a lower building site is nestled in a protected meadow. The land includes the Webatuck Creek and permission has been granted for a …
75.84 Acres
Country Setting Large Acreage Property With Views
On The Market
Nature’s Bounty EH# 3858
EH# 3858
Light breeze blows thru the grassy fields and the cattle graze on this 47 + acre parcel in the town of Northeast located in Dutchess County, New York. Agricultural area of many diversified farms, this contemporary 3 bedroom 2.5 bath …
3 Bedrooms • 3 Baths
• 3162 Sq Ft • 47.47 Acres
Country Setting Gardens Horse Property Large Acreage Property Private Location Waterfront Property With Views
On The Market
Stunning Panoramic Views EH# 3868
EH# 3868
Top of the World 270-degree views of the Hudson Valley, Berkshires, & Litchfield Hills! This exquisite 27-acre property has the most outstanding views you will find anywhere in the Tri-State area! Build your dream home in this most spectacular location offering …
27.01 Acres
Country Setting Large Acreage Property Private Location With Views
On The Market
Spectacular Sunsets EH# 3901
EH# 3901
Unbelievable afternoon sunsets with unobstructed views. Architectural detail that brings in nature's bounty while enjoying the picturesque surroundings. Dawn to dusk sun light filled windows and stain glass adorn the many spacious rooms that will chaperon your guest from the …
2 Bedrooms • 3 Baths
• 3515 Sq Ft • 35.86 Acres
Country Setting Gardens Horse Property With Views
On The Market
97 Acres In Millbrook Country EH# 3626
EH# 3626
Fabulous opportunity to own large acreage in Millbrook Hunt Country at a great price with exceptionally low taxes due to Agricultural and Forestry Exemptions. This gorgeous property offers 3 separate parcels; 68.91 acres, 15.76 acres, and 12.82 acres, each with …
97.49 Acres
Large Acreage Property With Views
On The Market
84.67 Acres in Millbrook Country EH# 3925
EH# 3925
Fabulous opportunity to own large acreage in Millbrook Hunt Country at a great price with exceptionally low taxes due to Agricultural and Forestry Exemptions. This gorgeous property offers 2 separate parcels; 68.91 acres and 15.76 acres, each with unique offerings …
84.67 Acres
Country Setting Horse Property Large Acreage Property With Views
On The Market
Privacy Near Village of Millerton EH# 3720
EH# 3720
Clean and Natural Living! This unrestricted 90.96 acres offers wonderful privacy yet just minutes to the Village of Millerton. A secluded 7 acre meadow graced with majestic spreading oak trees, tranquil sounds of Sawmill Brook and distant views await you …
90.96 Acres
Country Setting Large Acreage Property With Views
On The Market
Boston Corners Golden Valley EH# 3748
EH# 3748
Large level plateau an exceptional building site for a new home on a stunning 86 acre historic Farm property located on Boston Corners Road in the Town of North East, NY. In an area of conserved land, state forest and …
86 Acres
Country Setting Horse Property Large Acreage Property With Views
On The Market
Eye Catching Views EH# 3843
EH# 3843
Meticulously designed home with wondrous attention to detail. Whether you are the gourmet who loves to entertain or the one who wants to work the land and be one with nature, look no further. Private home on 19+ acres sited with …
2 Bedrooms • 3 Baths
• 2433 Sq Ft • 19.28 Acres
Country Setting Gardens
On The Market
Secret Meadow EH# 3855
EH# 3855
Beautiful road with a fabulous piece of land for sale in Pine Plains, New York. Wonderful views of the surrounding agricultural area. Open field of 31.61 acres with an opportunity to build a home in the private meadow. Additional property …
31.61 Acres
Country Setting Horse Property Large Acreage Property With Views
On The Market
Pride of Ownership EH# 3884
EH# 3884
For sale, a meticulously cared for 3 bedroom, 2.5 bath home located in the beautiful area of Dutchess County, New York. A handsome brick walkway welcomes your guests as they approach the covered porch to your front door. Once inside, …
3 Bedrooms • 3 Baths
• 2328 Sq Ft • 1.2 Acres
Country Setting Gardens With Views
On The Market
Tranquility with Privacy EH# 3322
EH# 3322
All the best in country living, this modern home has many amenities and conveniences. Home is minutes from the Wassaic Train Station, shopping, restaurants, Silo Ridge, Catamount Skiing and many other points of interest. Home for sale offers 4 bedrooms …
4 Bedrooms • 3 Baths
• 3024 Sq Ft • 11.6 Acres
Country Setting Horse Property Waterfront Property With Views
On The Market
“Well Maintained Colonial” EH# 3786
EH# 3786
Located just on the outskirts of the Village of Millerton in the Town of Northeast, in Dutchess County New York. Light and bright home for sale has the charm and character of yesteryear, but with modern amenities. Large eat-in modern …
4 Bedrooms • 2 Baths
• 2977 Sq Ft • 7.36 Acres
Country Setting Gardens In Town
On The Market
Indian Lake Retreat EH# 3797
EH# 3797
Indian Lake Retreat, a 3 Bedroom and 2.5 bath home for sale in Millerton, NY. Set upon 2 private and park-like acres, this 4 season home boasts a large wrap-around deck, a great room with vaulted ceiling, central air, Brazilian …
3 Bedrooms • 3 Baths
• 1524 Sq Ft • 1.8 Acres
Country Setting Gardens With Views
On The Market
Three Millerton Lots EH# 3920
EH# 3920
Three building lots, totaling 19.26 acres, flat open land with frontage on the Webutuck Creek; private building location set well back from road. Views. Close to the Villages of Millerton, NY, and Lakeville and Sharon, CT, the property is ideal …
19.26 Acres
Large Acreage Property With Views
On The Market
A Ray of Sunshine EH# 3894
EH# 3894
Well maintained 2 bedroom, 1 bath stucco home located on 5.32 acres in the beautiful area of Pine Plains, NY. Welcoming vestibule thru perennial gardens lead to an office/bedroom. Living Room has wood floors, built-ins and a propane fireplace. Two …
2 Bedrooms • 1 Baths
• 1613 Sq Ft • 5.32 Acres
Country Setting Gardens With Views
On The Market
Village Living in Millerton, NY EH# 3788
EH# 3788
Voted one of the 10 coolest small towns in 2007 is the Town of Northeast in Dutchess County, NY. This well cared for, light and bright 3 bedroom, 1.5 bath home has a newer kitchen, tiled baths, furnace, hot water …
3 Bedrooms • 2 Baths
• 1200 Sq Ft • 0.44 Acres
Country Setting In Town
On The Market
Beautiful Perennial Gardens EH# 3813
EH# 3813
Charming farmhouse colonial for sale located just outside the Village of Millerton. Close to the restaurants, shops and the Harlem Valley Rail Trail. This spacious Circa 1900 home has original woodwork, hardwood floors throughout, radiant floor heat on entire first …
3 Bedrooms • 2 Baths
• 1792 Sq Ft • 1.56 Acres
Country Setting Gardens In Town
On The Market
12.82 acres in Millbrook Country EH# 3926
EH# 3926
Fabulous opportunity to own large acreage in Millbrook Hunt Country at a great price with exceptionally low taxes due to Agricultural and Forestry Exemptions. This gorgeous property offers 12.82 acres of open fields. Build your dream home on one of the most …
12.82 Acres
Country Setting Horse Property Large Acreage Property With Views
On The Market
Valley Views EH# 3869
EH# 3869
14.7 acres for sale in Columbia County, New York just over the Dutchess County New York line. Rearmost part of the property provides a great building site for some fantastic valley views and borders Columbia Land Conservancy. Owner currently has …
2 Bedrooms • 1 Baths
• 980 Sq Ft • 14.7 Acres
Country Setting Horse Property Private Location With Views
On The Market
“Deceiving At First Glance” EH# 3780
EH# 3780
Located in the Town of Pine Plains in Dutchess County, New York. Home is deceiving from the outside, but very spacious in the inside. Home for sale has 4 bedrooms with 3 baths. Main floor living area offers Master bedroom …
4 Bedrooms • 3 Baths
• 1544 Sq Ft • 0.26 Acres
Country Setting In Town
On The Market
Newly Renovated Two Family EH# 3687
EH# 3687
Located at walking distance to the Village of Millerton in the Greater Hudson Valley, this Two Family home is ready for occupancy. Unit One has a Kitchen and Living Room with open floor plan, vaulted ceilings and access to the …
4 Bedrooms • 3 Baths
• 1912 Sq Ft • 0.82 Acres
Country Setting In Town
On The Market
Versatile Village Home in Millerton EH# 3452
EH# 3452
Opportunity for Income Investment or creating one single family in this versatile home located in Dutchess County, New York. Two-family home is now for sale and now there is an opportunity to purchase the home, live in one half and …
4 Bedrooms • 3 Baths
• 1947 Sq Ft • 0.56 Acres
In Town
On The Market
Two Family in Village of Millerton EH# 3930
EH# 3930
Motivated Sellers. Tenants pay for all their own utilities and the rent currently covers the mortgage payment. Older style building has two units with two bedrooms each and the second floor apartment has den/office. Each unit has one bath and …
4 Bedrooms • 2 Baths
• 2034 Sq Ft • 0.09 Acres
Country Setting In Town
On The Market
Generational Home in Village of Millerton EH# 3902
EH# 3902
First time in many years that this home has been on the market for sale. Family owned for many years with charm of yesteryear still intact and ready for a 21st century update. Featuring wood floors, French doors between dining …
3 Bedrooms • 2 Baths
• 1473 Sq Ft • 0.53 Acres
Country Setting In Town
On The Market
Renovated Village Home EH# 3805
EH# 3805
Walk to the Village of Millerton from this completely renovated home for sale in Dutchess County’s North East Corner. Light and bright home offers two bedrooms and two full baths. Living room and dining room have hardwood floors. New Kitchen …
2 Bedrooms • 2 Baths
• 1232 Sq Ft • 0.21 Acres
Country Setting In Town
On The Market
11.5 Acres on Tower Hill Road EH# 3601
EH# 3601
Highly Desirable Location in Millbrook, NY! Fabulously located 11.5 acres of land for sale in the heart of Millbrook Hunt Country. Land features stunning views and has frontage on Tower Hill, Short Road and Route 44. Conveniently and privately situated, …
11.5 Acres
Country Setting
On The Market
Location! Location! Location! EH# 2621
EH# 2621
This Dutchess County Land for Sale is located on a quiet country road in the Shekomeko Valley, this 8-acre building lot is sited high on a knoll offering the discerning buyer privacy and seasonal views from a lovely meadow. Enjoy …
8 Acres
Country Setting
On The Market
“Level .92 Acres” EH# 3787
EH# 3787
Located in the Town of Northeast in Dutchess County New York. Level residential land for sale located on Route 22. A lovely site for a home. Building and shed on property with unknown conditions. Septic and well to be installed …
0.92 Acres
Country Setting In Town
On The Market
Private Indian Lake Location EH# 3370
EH# 3370
Wooded, private Indian Lake parcel with shared access to water and picnic/recreation area. Located on a quiet dead end road just off the water.
1.9 Acres
Lakefront Private Location
On The Market
Village Lot in Millerton EH# 3655
EH# 3655
A rare find for the village of Millerton. BOHA lot ready for a two bedroom home. Lot size is 74’x119’. Village Water. Cleared lot. Walk to the Village, ride your bike to the Harlem Valley Rail Trail. 15 Minutes to …
0.2 Acres
Country Setting
On The Market
.5 Acre Private Lot on Dead End Street EH# 3893
EH# 3893
Great opportunity to build a home in Millerton! This .5 acre lot is on a private dead-end street in the Town of North East. Walking distance to all Millerton has to offer: restaurants, shops, Eddie Collins Park, Millerton Moviehouse, Irving …
0.5 Acres
Country Setting In Town Private Location
On The Market
STISSING RISING
EH# 3943
This 5-Bedroom, 4.5 Bath family retreat with additional Guest Home offers meticulous attention to detail throughout. Floor-to-ceiling windows frame breathtaking sunsets from the Great Room with a dramatic stone Fireplace. An inviting Kitchen with Wet Bar and Dining Room open …
Available: Yearly
Total Rooms: 13
Bedrooms: 5
Bathrooms: 4
1/2 Baths: 1
Total Rooms: 13
Bedrooms: 5
Bathrooms: 4
1/2 Baths: 1
Sq. Ft.:
Heating: Propane
Air: Central Air
Fireplace: Yes
Furnished: Yes
Heating: Propane
Air: Central Air
Fireplace: Yes
Furnished: Yes
Pets: To Be Determined
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Bucolic View
EH# 3829
School Year rental on a beautiful estate. Bucolic setting with open fields, pastures, and corn fields. This well maintained 4 bedroom home with 3 baths is close to train, recreational, rail trail, private schools and many other points of interest. …
Available: School Year Summer
Total Rooms: 8
Bedrooms: 4
Bathrooms: 3
1/2 Baths: 0
Total Rooms: 8
Bedrooms: 4
Bathrooms: 3
1/2 Baths: 0
Sq. Ft.:
Heating: Oil
Air: Window Units
Fireplace: Yes
Furnished: Either/Or
Heating: Oil
Air: Window Units
Fireplace: Yes
Furnished: Either/Or
Pets: Yes
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Quintessential Home
EH# 3779
School year rental in this charming 2 bedroom in a beautiful, bucolic area of Northeast in Dutchess County, New York. This 1880 farmhouse has been totally renovated to meet all the 21st century needs. First floor living room, dining room …
Available: School Year
Total Rooms: 5
Bedrooms: 2
Bathrooms: 1
1/2 Baths: 0
Total Rooms: 5
Bedrooms: 2
Bathrooms: 1
1/2 Baths: 0
Sq. Ft.:
Heating: Propane
Air: None,
Fireplace: No
Furnished: Yes
Heating: Propane
Air: None,
Fireplace: No
Furnished: Yes
Pets: None Allowed
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Walk to Pine Plains
EH# 3528
Well maintained 2 Bedroom Duplex with wood floors. First floor offers 1/2 Bath ,Eat-in Kitchen, Dining Room, and Living Room. Upstairs has Full Shower Bath and 2 Bedrooms. Light and bright enclosed front porch. Walk to Pine Plains. Laundromat across …
Available: Yearly
Total Rooms: 5
Bedrooms: 2
Bathrooms: 1
1/2 Baths: 1
Total Rooms: 5
Bedrooms: 2
Bathrooms: 1
1/2 Baths: 1
Sq. Ft.:
Heating: Oil
Air:
Fireplace: No
Furnished: No
Heating: Oil
Air:
Fireplace: No
Furnished: No
Pets: None Allowed
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Charming Millerton Rental
EH# 3504
Ready for occupancy, this inviting, well maintained, furnished 3 Bedroom, 2 Bath home is located within minutes to the Village of Millerton. Open floor plan on first floor with Kitchen, Living Room and Dining Room. Bedroom and Full Bath with …
Available: School Year Yearly
Total Rooms: 6
Bedrooms: 3
Bathrooms: 2
1/2 Baths: 0
Total Rooms: 6
Bedrooms: 3
Bathrooms: 2
1/2 Baths: 0
Sq. Ft.:
Heating: Electric
Air:
Fireplace: No
Furnished: Yes
Heating: Electric
Air:
Fireplace: No
Furnished: Yes
Pets: To Be Determined
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Television: Cable
Internet: Cable
Pool:
Waterfront: No
Stissing Rising
EH# 3502
Stunning Westerly panoramic views of Stissing Mountain in the forefront and the Catskills in the background. This spacious Contemporary Post & Beam house is ideal for entertaining with its open floor plan in the Living Room, Dining Room and Kitchen, …
Available: Winter
Total Rooms: 13
Bedrooms: 4
Bathrooms: 4
1/2 Baths: 1
Total Rooms: 13
Bedrooms: 4
Bathrooms: 4
1/2 Baths: 1
Sq. Ft.:
Heating: Propane
Air:
Fireplace: Yes
Furnished: Yes
Heating: Propane
Air:
Fireplace: Yes
Furnished: Yes
Pets: To Be Determined
Television: Satellite
Internet: Cable
Pool:
Waterfront: No
Television: Satellite
Internet: Cable
Pool:
Waterfront: No
All Commercial Properties for Lease
4 properties
On The Market
On The Market
On The Market
On The Market
BEAUTIFULLY RENOVATED OFFICES AVAILABLE
EH# 3936
Available:
Yearly
Yearly
Pricing:
$Price depends on office size and quantity rented.
$Price depends on office size and quantity rented.
On The Market
Central Lakeville, CT Retail or Office Rental
EH# 3914
Available:
Yearly
Yearly
Pricing:
$875-1750 per month
$875-1750 per month
On The Market
Commercial Spaces on Main Street in Lakeville CT
EH# 3912
Available:
Yearly
Yearly
Pricing:
$550 per month
$300 per month/each
$550 per month
$300 per month/each
On The Market
Beautifully Renovated Offices for Rent
EH# 1101
Available:
Yearly
Yearly
Pricing:
$300 per month
$800 per month
$300 per month
$800 per month
On The Market
