Luxury properties for sale Richmond, United States

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare colonial charm. The legendary c. 1776 estate boasts a well maintained main residence/Inn, three cottages and a great barn for entertaining. The residence/Inn features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. Its dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that caters to both intimate family gatherings and grand celebrations. For the serious equestrian, the estate offers multiple barns and paddocks. Training is a year-round luxury thanks to the 6,000 square foot heated indoor arena, which includes an owner's apartment and viewing area--and a professional-grade outdoor ring.

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

Crosby House, a property with a storied Lenox history and a location second to none, presents a rare opportunity to own a residence of remarkable character, scale, and flexibility in the heart of the village. Currently configured as two spacious residences, this distinctive multifamily property offers an exceptional array of possibilities. Subject to applicable zoning, permitting, and approvals, the existing configuration may offer the potential to be thoughtfully combined into one extraordinary single-family residence or could provide the foundation for two highly distinctive condominium residences. Each residence offers two plus bedrooms and two full baths, along with generous kitchens featuring high-end Bosch appliances, hardwood floors, tiled baths, in-unit laundry, central air, natural gas heat, and an abundance of windows. All major systems have been updated, providing modern comfort and efficiency while complementing the property's historic character. Both primary bedrooms feature adjoining flexible spaces ideally suited to an office, nursery, sitting room, dressing room, or private retreat. The first-floor residence features a magnificent screened porch opening to the front porch, as well as a separate rear deck; wonderful spaces for outdoor dining, entertaining, and enjoying the seasons. The upper residence offers its own private deck, while cathedral ceilings and both front and rear landings add architectural interest and a wonderful sense of space. The property is further enhanced by an oversized two-car garage with an attached greenhouse, ample parking, owned solar, and separate utilities. These thoughtful amenities, together with the updated systems and generous living spaces, create an exceptional blend of historic character and contemporary convenience. With its storied past, substantial proportions, versatile configuration, and enviable in-town setting, Crosby House represents a truly rare Lenox offering. Just minutes from the heart of the village, the property combines the best of location and lifestyle with the opportunity to shape a residence, or residences, of exceptional distinction. Subject to zoning and required approvals, its possibilities are extraordinary; its location is simply second to none.

In the heart of historic downtown Lenox, 85 Church Street presents an exciting opportunity to own a versatile two-family property in one of the Berkshires' most desirable villages. Zoned commercial and delivered vacant, the property offers an unusual degree of flexibility for an owner-occupant, investor, or buyer seeking income-producing potential in the center of Lenox. The property features two two-bedroom, one-bath units, each with natural wood details and its own separate natural gas heating system. Both units are equipped with a refrigerator, dishwasher, and range. Refreshed bathrooms, some replacement windows, and a second-floor rear landing/mudroom add to the comfort and functionality. The first floor also enjoys an enclosed rear porch, while open porches provide additional outdoor space. Town water and sewer add to the convenience. Delivered vacant, 85 Church Street allows a new owner to immediately determine how best to utilize the property--live in one unit and rent the other, lease both units, or explore the possibilities afforded by its commercial zoning. Just steps from Lenox's renowned restaurants, shops, galleries, and cultural attractions, the location is truly exceptional. For an even more compelling opportunity, 85 Church Street may also be purchased as part of a package with 22 and 24 Franklin Street, creating the potential to acquire multiple properties in the heart of downtown Lenox. A rare combination of location, flexibility, and opportunity, 85 Church Street offers an exciting chance to own in the center of it all.

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

This serene 5-acre property boasts open meadows and mature trees, offering a tranquil retreat that feels a world away, yet remains highly accessible to the best of the Hudson Valley and Berkshires. Its proximity to the Taconic State Parkway and Interstate 90 ensures an easy retreat from both New York City and Boston. Locally, you'll delight in the charming town of Chatham's cafes, restaurants, bars, and a burgeoning art museum scene, with Queechy Lake just a 10-minute drive away. Popular destinations like Hudson and Great Barrington are also easily reached in just 35 minutes. Inside, discover the ease of single-floor living, featuring a spacious living room with a high vaulted ceiling and a warming wood-burning fireplace. The perfectly updated kitchen is both tasteful and functional, complemented by three generously sized bedrooms and two full bathrooms. The full-footprint basement, partially finished, presents an excellent opportunity to create additional bedrooms, home theater or even a self contained inlaw suite. True to its agricultural surroundings, this perfect home is perched above grounds that are mostly flat and highly versatile for a variety of activities. A charming chicken coop is discreetly tucked behind a 1.5-car garage, inviting you to embrace the farm-to-table lifestyle of the area. A barn sits across the field behind the home providing a bucolic view and awaits your vision for an art studio, guest house or stable. Truly a fantastic value for those looking to find peace of mind in their own private Hudson Valley oasis.

This well-maintained multi-unit property presents an exceptional opportunity in the heart of Pittsfield's thriving Downtown Cultural District. Offering spacious units with strong rental appeal, the property combines classic character with important updates including newer siding, a high-efficiency natural gas heating system and a new roof in 2021. A unique feature of the property is the versatile third unit, formerly utilized as a commercial storefront, which may offer future mixed-use potential with the appropriate permitting--ideal for investors, entrepreneurs, or those seeking added income flexibility. Rare for downtown living, the property also includes generous off-street parking. Located just moments from restaurants, shopping, entertainment, public transportation, and the city's cultural attractions this property offers convenience, visibility, and long-term potential in one of downtown's most desirable locations. Whether you're looking to expand your investment portfolio or explore owner-occupancy possibilities, this is an opportunity not to be missed.

Welcome to this immaculately maintained two-family home--a turnkey property that meets today's timeless standards! This choice 2-family home beautifully balances sophisticated living with incredible versatility, making it an ideal match for owner-occupants, multigenerational families, or savvy investors alike. Including features you are sure to love: Modern Living: Bright, open floor plan living areas featuring fresh paint and updated appliances. Comfort and Convenience: Both units boast primary bedrooms with ensuite baths, large dedicated laundry areas, updated windows, and pristine ceramic-tile bathrooms. Flex Space: A partially finished basement offers the perfect canvas for storage, workshop, craft area, home gym, etc. Outdoor Oasis: Enjoy your morning coffee or warm evenings from the screened-in porch or private second-floor deck, all overlooking a backyard ideal for gardening and relaxing by the charming water fountain. Whether you are looking for rental income or a spacious multifamily retreat, this property offers an extraordinary lifestyle opportunity!

Set in a desirable southeast Pittsfield neighborhood, this charming 3 bedroom, 1 bath Colonial offers a compelling blend of timeless character, natural light, and thoughtfully addressed updates. Original hardwood floors lend warmth and authenticity throughout the living spaces, while updated windows bring added brightness to the home. The updated kitchen, with granite countertops, provides a comfortable foundation for everyday living and entertaining, while a fully heated sunroom adds an especially appealing dimension to the home; an inviting year-round retreat for morning coffee, reading, or simply enjoying the changing seasons. Important improvements, including updated electrical, have already been completed, offering peace of mind while leaving room for the next owner to bring their own vision and personal style. Ideally located in southeast Pittsfield, this welcoming Colonial presents an opportunity to enjoy the character of a classic New England home with many of the essential updates already in place. A must see!

Welcome to this wonderful Colonial in a quiet, sought after neighborhood in Lee, MA. 3 bedrooms, 2.5 baths, and a finished lower level. Enjoy an expansive deck overlooking the rear yard; providing plenty of outdoor living space. Amenities include vinyl siding, gas heat, hardwood floors, eat-in kitchen, dog fence, and a two car attached garage.

Rare, renovated Berkshire investment compound on 0.59 acres in pedestrian-friendly Housatonic. This turnkey property features two separate legal duplexes (4 units total) offering stellar cash flow. The front home (392 Park St) features a 5BR/2BA unit, a sleek 2BR flat, and a prominent street-front walk-out lower level with incredible commercial/addition potential. The rear Swiss-Gothic home (394 Park St) hosts two updated 2BR units. Enjoy a sprawling backyard with mountain views, a community garden, and fruit-bearing trees. Fully insulated and optimized for easy management with 4 separate heating/electric systems, town sewer/water, and off-street parking for 10+ cars. Moments from Berkshire Mountain Bakery; minutes to downtown Great Barrington and Tanglewood. A rare, turnkey find!

Escape the hustle of city life and discover Bellavista Country Estate, a grand 12,000-square-foot Georgian brick residence set on over 25 private acres in the foothills of the Berkshires, ideally situated between the Hudson River Valley and the Berkshires. Offering 6 to 9 beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, and both a fully stocked eat-in kitchen and a formal dining room, the estate blends elegance and comfort with ease. Recreation and relaxation abound, with a spacious in-ground pool, a serene pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, guests enjoy a full gym, a game and entertainment room with arcade favorites, a home theater, a library of hundreds of books, and a finished attic, while a 4,500-square-foot barn with foosball, ping pong, and bar space provides additional room for gatherings and events. Perfect for weddings, anniversaries, family celebrations, and private retreats, Bellavista also offers access to private chefs, caterers, and event planning support, with every detail—from fiber-optic internet and full-house generators to weekly pool and grounds maintenance—thoughtfully attended to. Since 2011, the estate has been a successful luxury rental for vacations and retreats, equally suited to private full- or part-time residence, a hybrid work-from-home escape, or an unforgettable destination getaway. Just minutes from Chatham, Hudson, and Kinderhook, and a short drive to Lenox, Stockbridge, and Great Barrington, the estate is surrounded by farm-to-table dining, art galleries, organic markets, and the renowned Crandell Theater, with easy access via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, or Albany International Airport.

Built in 2004, this exquisitely-crafted historic reproduction home seamlessly blends old-world charm with contemporary comfort. Set on 1.82 acres with sweeping mountain views, this 3-bedroom, 2.5-bathroom home features meticulous hand-crafted details throughout, honoring traditional design while offering the conveniences of modern construction. The welcoming gourmet eat-in kitchen is perfect for everyday living and entertaining. Step out to the inviting covered porch--an ideal spot to savor morning coffee and evening sunsets with mountain vistas. The primary suite captures stunning views, while the expansive yard provides additional room to roam. 2-car oversized garage. Secluded setting just minutes to downtown Great Barrington and other Berkshire attractions.

Rare opportunity to own an enchanting horse farm in the heart of Columbia County. A historic Hudson Valley 1840s center hall Colonial farmhouse sits on over 20 stunning acres of rolling fields, fenced paddocks with water troughs and run-in sheds, a horse barn with a large hay loft and 8 stalls + an additional 3-stall pony shed that could be used as a chicken coop, garden beds, mature trees, a supplementary living space above the garage with a full bathroom, and a charming wooden bridge over a clean spring-fed creek where wild watercress grows. Prime farmland with 3 fields on the property currently leased to neighboring Hawthorne Valley Farm. Step from the L-shaped porch into the bright house filled with character, featuring exposed wood beams, vaulted ceilings, original moldings and wood floors, 2 wood-burning fireplaces, 6 bedrooms including a spacious, first-floor primary bedroom with an en suite bath and a private entrance, 4.5 bathrooms, wet bar, 10' ceilings, plaster walls, window seats, flagstone patio, mudroom. Recent improvements include a brand-new generator, fresh paint, new laundry with a new LG clothes dryer, and recessed LED lighting. This equestrian property is in an idyllic countryside setting and mere minutes from everything one might need in terms of culture, social life, sports and schools for children. N earby Hudson and Rhinebeck offer fine shopping and dining. There's certainly no lack of things to do and places to eat! Take your pick of farm-to-table restaurants, farm stores, farmer's markets, bookstores, bars, cideries, distilleries, hikes, art galleries, antique stores, and more.

Newly completed and set on 11.7 private acres in the heart of Hillsdale, this architect-designed 4-bedroom, 4-bath modernist residence combines striking contemporary architecture with sweeping pastoral and mountain views in every direction. Arriving via a long private driveway, rolling lawns and open fields unfold toward a home defined by bold geometric forms, expansive walls of glass, and a seamless connection to the surrounding landscape. Just minutes from the Hamlet of Hillsdale, Catamount Mountain Resort, Great Barrington, and Hudson, the property offers a rare balance of architectural refinement, privacy, and access to the region’s most desirable destinations. The residence is centered around a dramatic great room with a soaring 20-foot vaulted ceiling and a wood-burning fireplace clad in richly toned chestnut marble. Floor-to-ceiling glass and oversized Arcadia sliding doors dissolve the boundary between interior and exterior, opening onto more than 540 square feet of covered outdoor living space designed for year-round entertaining and relaxed outdoor living. Throughout the home, natural light shifts across clean architectural lines and warm materiality, reinforcing a strong connection between structure and landscape. The kitchen serves as both a design centerpiece and functional workspace, featuring custom walnut cabinetry crafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A fully equipped butler’s pantry and bar area provides additional prep space, storage, second dishwasher, and additional refrigeration, allowing the main kitchen to remain clean and open for entertaining. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble, featuring a soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second ensuite bedroom offers its own walk-in closet and marble-appointed bath, complemented by an additional guest bedroom suite. A versatile fourth bedroom on the main level provides flexible use as a guest suite, office, media room, or wellness space with direct access to the outdoor terrace. Designed for high-performance modern living, the home includes spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a detached heated 26' x 26' two-car garage. Located just minutes from Catamount Mountain Resort and within easy reach of Great Barrington and Hudson, the home places owners at the center of the Hudson Valley and Berkshires lifestyle. Days might begin with coffee overlooking the fields, followed by a visit to the Saturday farmers market, skiing at Catamount, or hiking nearby trails. Afternoons can be spent browsing Hudson’s celebrated design and antique shops or exploring the galleries, bookstores, and restaurants of Great Barrington. Evenings bring performances at local theaters and live music venues, or a quiet return home as the light settles across the landscape. The setting balances architectural refinement, outdoor recreation, and cultural depth in equal measure. A rare expression of contemporary Hudson Valley living, where architecture, light, and landscape are held in perfect balance. An adjoining 6.73-acre parcel is also available for purchase, offering the opportunity to expand the estate or create a private family compound. (listing agent has a financial interest in the property)

A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you’ll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You’ll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.

The Philmont Collection presents a rare opportunity to acquire a 36-unit multifamily portfolio encompassing nine buildings across seven tax lots in the heart of Philmont's National Register Historic District. Spanning approximately 26,606 square feet, the collection combines immediate scale, strong in-place cash flow, historic character, and meaningful redevelopment potential within one of the Hudson Valley's most closely watched village investment markets. Strategically clustered within a few walkable blocks of one another, the portfolio includes seven stabilized income-producing assets together with two historic value-add buildings, creating a level of operational efficiency and market presence rarely available in a single acquisition. The collection comprises 36 residential units with 48 bedrooms and 28 bathrooms, offering a diverse mix of apartments and duplex residences that support broad tenant appeal and stable occupancy. The stabilized core portfolio is projected to generate approximately $350,000-$360,000 in annual NOI, providing attractive current returns while preserving opportunities for future value enhancement. Ownership has invested substantially throughout the portfolio in capital improvements, infrastructure upgrades, and operational efficiencies designed to improve long-term performance and reduce operating costs. A cornerstone asset within the collection, 62 Main Street has undergone extensive renovation, including updated residential units, restored facade improvements, enhanced insulation, conversion from central oil heat to individual electric systems, and renovated bathrooms. These improvements, together with portfolio-wide upgrades, position the collection as a well-maintained and professionally operated investment. Current operations utilize the DoorLoop management platform for leasing, maintenance coordination, rent collection, tenant communication, applications, and screening, facilitating a seamless transition for future ownership. The portfolio also includes the historic front and rear buildings at 7 Church Street, presenting a compelling redevelopment opportunity within Philmont's historic core. Subject to purchaser verification and approvals, these buildings may be eligible for substantial federal and New York State historic rehabilitation tax incentives, creating a potentially powerful avenue for future value creation and income growth. Long appreciated for its architectural character and strategic location, Philmont continues to attract investors, entrepreneurs, artists, and designers drawn to its affordability relative to neighboring Hudson, its historic building stock, and its ongoing revitalization. Significant public and private investment, adaptive reuse projects, and preservation initiatives continue to strengthen the village's long-term trajectory. Ideally situated just minutes from the Taconic State Parkway and approximately fifteen minutes from Hudson and Amtrak service to New York City, the portfolio enjoys convenient access to the Berkshires, Hawthorne Valley Farm, Art Omi, hiking trails, skiing, boating, waterfalls, acclaimed dining destinations, and the cultural amenities that define the Hudson Valley lifestyle. Combining immediate income, operational scale, historic character, redevelopment potential, and an extraordinary village-wide footprint, The Philmont Collection represents a truly uncommon opportunity to establish a meaningful position within a growing and increasingly recognized Hudson Valley market. MLS information reflects the primary parcel only. Seller reserves the right to sell individual assets or subsets of assets separately from the portfolio offering. Complete financial statements, rent rolls, parcel information, and supporting materials are available upon request. Annual tax amount reflects the entire portfolio.