Nestled across some of the most picturesque corners of upstate New York, from the tranquil shores of Round Pond to the serene acres of Woodstock’s Wittenberg Hamlet, four extraordinary homes await. Priced between $2,299,900 and $2,800,000, these properties—each a masterpiece of modern architecture—blend seamlessly with their natural surroundings. Whether it’s the dramatic rock formations of Little York Road or the sleek lines echoing lakeside ripples at Lakeside Drive, these residences promise privacy, sophistication, and a deep connection to the landscape. Discover what makes each of these to-be-built or newly completed homes truly desirable.
A Modern Sanctuary Of Glass Light Landscape | $2,800,000


John Ruggieri

John Ruggieri
Set against a dramatic landscape of natural rock formations, this architecturally striking modern residence, completed in 2025, offers an unparalleled blend of privacy and refined living. Spanning 3,564 square feet, the home embodies serenity and sophistication with every detail thoughtfully curated. The great room, crowned by 10-foot ceilings, seamlessly connects to the outdoors through expansive floor-to-ceiling glass, while a Porcelanosa-tiled wood-burning fireplace serves as a captivating focal point. A chef’s kitchen elevates daily routines with custom cabinetry, a waterfall island, and premium appliances, including a GE Café 6-burner gas range. Four ensuite bedrooms provide sanctuary, each adorned with spa-inspired Porcelanosa finishes and radiant heated floors. A wellness wing, complete with a gym and panoramic sauna, offers a personal retreat. Outside, a 20’ x 42’ saltwater pool nestles among striking terrain, creating an idyllic setting for relaxation or entertaining.
- Price:
- $2,800,000
- Size:
- 3,564 sq ft
- Contact:
- John Ruggieri, BHHS Hudson Valley Properties, 917.608.2980
Modern Lakeside Architectural Retreat Private Wooded Setting With Round Pond Access | $2,495,000


Doug Maxwell

Doug Maxwell
Set against the serene backdrop of Round Pond, this modernist residence in Rhinebeck offers a harmonious blend of sleek design and natural beauty. Spanning approximately 4.5 acres of primarily wooded land, the property captivates with its rugged terrain, rock outcroppings, and mossy knolls. A short stroll leads to a shared dock on the tranquil, non-motor lake, ideal for morning swims or leisurely kayaking. The architecture unfolds across three wings on a single level, creating dynamic indoor-outdoor spaces that prioritize ease and flow. Inside, natural materials like oak hardwood floors and Danish cabinetry complement the inspired design, while a luxe kitchen with a large island and secondary scullery elevates functionality. The private primary suite boasts radiant floor heat and stunning views, while outdoor patios invite entertaining amidst the landscape. Just under 10 minutes from Rhinebeck village, this estate balances remote tranquility with accessibility to NYC.
- Price:
- $2,495,000
- Size:
- 2,790 sq ft
- Contact:
- Doug Maxwell, Upstate Modernist, 212.518.3130
Create Your Own Private Compound | $2,400,000


Peter Cantine

Peter Cantine
Tucked away on 2.44 tranquil acres in the Woodstock Hamlet of Wittenberg, this exceptional to-be-built estate offers a rare blend of architectural brilliance and rustic charm. Crafted by renowned builder James Nelson, the property features a three-bedroom, three-and-a-half-bath main residence, a one-bedroom guest house, and a spacious two-car garage with an integrated workshop and storage—totaling 3,440 square feet of meticulously designed space. Using indigenous Eastern White Pine, harvested and milled on-site, Nelson ensures unparalleled material quality and a deep connection to the land. This unique opportunity allows you to collaborate directly with the builder, shaping a bespoke compound ideal for multi-generational living, a permanent home, or a sophisticated retreat. Perfect for gathering and entertaining, this estate promises a lifestyle of serenity and craftsmanship amidst the natural beauty of the Hudson Valley.
- Price:
- $2,400,000
- Size:
- 3,420 sq ft
- Contact:
- Peter Cantine, Halter Associates Realty, 845.832.7119
Spectacular CustomBuilt Home Pond Near Ski Resort In Clymer | $2,299,900


Paul Vaicunas

Paul Vaicunas
Rising above the rolling hills near the renowned Peek N Peak ski and golf resort, this extraordinary 4,933-square-foot custom-built log home estate offers a rare blend of luxury and seclusion. Spanning 64.9 acres of pristine hardwoods, the property features a 3.9-acre park-like yard, a stocked pond with bass, and abundant wildlife, creating a serene retreat for nature lovers. Just minutes from Findley and Chautauqua Lakes, as well as the Chautauqua Institution and Western New York wine country, endless outdoor adventures await. The three-level residence includes four bedrooms, three and a half bathrooms, and a spacious finished basement for added living space. A six-car garage ensures ample storage, while a 2,200-square-foot multi-level deck with a built-in hot tub invites grand gatherings beneath shady trees. Nearby, a 7,000-square-foot heated barn offers versatility for vehicles or potential guest quarters.
- Price:
- $2,299,900
- Size:
- 4,933 sq ft
- Contact:
- Paul Vaicunas, Whitetail Properties Real Estate LLC, 330.301.2682

















