Vintage homes for sale & real estate in Dutchess County, NY

Vintage Home for sale in Dutchess County, NY:

* * * Note that the list price is NOT indicative of the seller's final reserve amount; it is just the starting auction bid amount * * * This 2345 SF ranch home sits on an 1.32 acre lot. This property is eligible under the Freddie Mac First Look Initiative through 10/27/2026. It is sold only to owner-occupants, non-profit organizations, and government entities during the First Look period. This property is part of an online bidding event; please visit the Auction company's website to place a bid and contact your real estate agent for auction bidding instructions. Inspections of this property and contact with occupants are strictly prohibited. Property is sold "as is" with NO i

Vintage Home for sale in Dutchess County, NY:

This beautifully restored c. 1850 country home blends historic character with thoughtful updates in a picturesque setting. Located in the charming hamlet of Shekomeko, the property is framed by exceptional perennial gardens, with layers of native plantings creating a lush and beautifully established landscape. A stone patio with a pergola sits amid the gardens, offering an intimate setting for outdoor dining and entertaining, while protected Dutchess Land Conservancy land borders the property. The two bedroom, two bath residence offers privacy, timeless charm, and an inviting connection to the outdoors. A gracious entry leads to a formal dining room, comfortable living room with fireplace,

Vintage Home for sale in Dutchess County, NY:

Welcome to 26 Oakwood Boulevard, a classic 4 square 3-bedroom, 2-bath home set in the heart of Poughkeepsie. Built in 1925, this residence offers the enduring appeal of a well-established home with the space and flexibility to make it your own. Start your morning on the rocking chair front porch, then step inside to a bright and inviting interior where an abundance of windows fills the home with natural light. Original details like the wood banister and living room windows with cornices add timeless character, complemented by hardwood floors in select rooms. The kitchen is well appointed with solid surface countertops, a tiled backsplash, and pendant lighting hanging over the breakfast bar,

Vintage Home for sale in Dutchess County, NY:

This is the home you pause to admire as you drive through the Hudson Valley on a golden afternoon. A Victorian inspired home set back from the road captivates your attention. Walking into the home from the sweeping wrap around porch you can’t help but feel as if it was pulled from the pages of a novel. The house welcomes you inside with custom millwork, French doors, diamond-pane windows, and hardwood floors. Beyond the front door, gracious living spaces unfold from a light-filled living room with custom built-ins and a marble wood-burning fireplace, to a charming parlor with coffered ceilings, perfect for a piano, library, or your Christmas Tree. The home opens naturally into a dinin