Set back on nearly two acres, this architecturally inspired ranch captures the best of mid-century design with a dramatic wall of windows, soaring beamed ceilings, a floor-to-ceiling stone fireplace, and seamless indoor-outdoor living centered around a large in-ground pool. Natural light pours through the expansive windows, giving the main living space an open, airy feel while framing peaceful views of the surrounding property. The stone fireplace elegantly separates the great room from the dining area, creating distinct spaces while maintaining an easy flow for everyday living and entertaining. Just beyond, a spacious three-season room lives like a second family room, opening directly to the patio and pool for the kind of summer living Hudson Valley buyers dream about. The kitchen is thoughtfully designed with stainless steel appliances, generous cabinetry, and a functional layout with everything within easy reach. A dedicated laundry room connects the kitchen to the attached two-car garage, adding convenience and thoughtful flow, while central air conditioning keeps the home comfortable all summer long. Down the hall, the king-sized primary suite features an en suite bath, while two additional well-proportioned bedrooms share a second full bathroom, creating a practical layout for family, guests, or a home office. Located on Highland's scenic south side, where orchards, vineyards, and farmland begin to define the landscape, the setting feels distinctly Hudson Valley while remaining just 5 minutes from the center of town. Spend weekends exploring local farm stands, wineries, cafés, restaurants, galleries, and the Hudson Valley Rail Trail with direct access to the Walkway Over the Hudson. Metro-North service in Poughkeepsie is just nine minutes away, New Paltz proper is just 15 minutes away and the GWB is under 90 minutes from your doorstep.
Single-familyProperty Type
1979Year Built
1.77 acresLot Size
$381Price/Sq.Ft.
1 car garageParking
Listing by Craig Smith• Compass Greater NY, LLC
Bought with Non MLS HVCR MLS• HV Catskill Region MLS
Est. $2,944 per month, based on comparable rentals
Sale and tax history for 321 Orchard Rd
Sale History
Tax History
Date
Event
Price
HVCRMLS #20263807
Nov 2, 2026
Sold
$612,500
$381/sq ft
Sep 9, 2026
Pending
—
Aug 18, 2026
Contingent
—
Jul 29, 2026
Price Changed
$625,000
$388/sq ft
Jul 7, 2026
Listed
$650,000
$404/sq ft
HVCRMLS #20201262
Jul 16, 2020
Sold
$335,000
$208/sq ft
May 8, 2020
Listed
$329,900
$205/sq ft
+18
Sprawling three bedroom contemporary ranch home located in a private setting. New carpeting throughout, new gas fireplace insert, updated bathroom, freshly painted. Living room has beamed cathedral ceiling, beautiful stone fireplace. Enjoy this summer in the 16'x32' in ground pool and large paved patio for entertaining. This house is a must see! Minutes to shopping, Walkway over Hudson, quaint Highland village area, Metro North train station, etc. Owner will arrange showings to prequalified buyers by adhering to the strict, precautionary guidelines for Covid-19; provided by the state department.
OneKey® MLS as Distributed by MLS Grid #M390214
Jul 16, 2020
Sold
$335,000
$208/sq ft
May 7, 2020
Listed
$329,900
$205/sq ft
Sprawling three bedroom contemporary ranch home located in a private setting. New carpeting throughout, new gas fireplace insert, updated bathroom, freshly painted. Living room has beamed cathedral ceiling, beautiful stone fireplace. Enjoy this summer in the 16'x32' in ground pool and large paved patio for entertaining. This house is a must see! Minutes to shopping, Walkway over Hudson, quaint Highland village area, Metro North train station, etc. Owner will arrange showings to prequalified buyers by adhering to the strict, precautionary guidelines for Covid-19; provided by the state department.,Unfinished Square Feet:1609,ExteriorFeatures:Outside Lighting,ROOF:Asphalt Shingles,AboveGrade:1609,FLOORING:Ceramic Tile,Wood,InteriorFeatures:Beamed Ceilings,Sliding Glass Doors