TOP 30 Best Countryside estates in Massachusetts

The Eustis Estate Museum and Study Center is a historic landmark located at 1424 Canton Avenue in Milton, Massachusetts. This beautifully preserved estate offers visitors a glimpse into the lives of the Eustis family, who once called this grand mansion home. The museum features a collection of period furnishings, artwork, and artifacts that provide insight into the history and culture of the region. Visitors can explore the meticulously restored rooms of the estate, including the elegant parlors, dining room, and bedrooms. The surrounding grounds offer a picturesque setting for leisurely strolls and picnics, with lush gardens and scenic views of the surrounding countryside.

s most beautiful estates, Castle Hill on the Crane Estate in Ipswich, Massachusetts. Explore the grandeur of this historic seaside estate, with its beautifully landscaped grounds, restored Grand Allée, gardens, and Casino complex. Originally stewarded by indigenous peoples, Castle Hill has a deep and storied past dating back to the 1600s. The estate was transformed into one of America's great Country Place Era estates by Chicago industrialist Richard Teller Crane Jr. and his wife Florence Higinbotham Crane in the early 1900s.

Kinlin Grover Real Estate is a leading real estate agency located in Wellfleet, Massachusetts. With a prime location on U.S. 6, this reputable institution offers a wide range of services to help clients buy, sell, or rent properties in the area. Their team of experienced agents is dedicated to providing top-notch customer service and expert guidance throughout the real estate process. Whether you are looking for a beachfront vacation home or a cozy cottage in the countryside, Kinlin Grover Real Estate has the expertise to help you find your dream property. Contact them today to learn more about their listings and services.

Welcome to Sarah Lewis, Engel & Völkers Real Estate Advisor NH | MA, your premier real estate agency located at 1310 Main Street, Tewksbury, Massachusetts. Specializing in both New Hampshire and Massachusetts markets, Sarah Lewis provides unparalleled expertise and personalized service to help you navigate the complex world of real estate. Whether you're buying, selling, or investing, our commitment to excellence ensures a seamless and satisfying experience. As part of the esteemed Engel & Völkers network, we offer a global reach with a local touch, providing you with access to exclusive listings and cutting-edge market insights. Discover your dream home or maximize your property's potential with Sarah Lewis, where your real estate goals become our mission. Contact us today to begin your journey with a trusted partner dedicated to turning your real estate aspirations into reality.

Oakholm Farm Estate is a picturesque and historic institution nestled on 500 acres of pristine land in Brookfield, Massachusetts. Located at 80 Lake Road, this stunning estate offers a tranquil escape from the hustle and bustle of everyday life. With its charming farmhouse, rolling fields, and serene lake, Oakholm Farm Estate is the perfect venue for weddings, corporate events, and other special occasions. Guests can enjoy horseback riding, fishing, hiking, and other outdoor activities while taking in the breathtaking views of the surrounding countryside. Come experience the beauty and tranquility of Oakholm Farm Estate for yourself.

The Stevens Estate At Osgood Hill is a historic and picturesque tourist attraction located at 723 Osgood Street in North Andover, Massachusetts. This beautiful estate offers visitors a glimpse into the past with its stunning architecture, lush gardens, and scenic views of the surrounding countryside. Whether you're interested in taking a guided tour of the estate, hosting a special event or wedding, or simply enjoying a leisurely stroll through the grounds, The Stevens Estate At Osgood Hill is a must-visit destination for history buffs and nature lovers alike. Come experience the charm and elegance of this hidden gem in the heart of New England.

Coastal Countryside Properties is a premier real estate agency located at 17 South Main Street in the picturesque town of Cohasset, Massachusetts. Specializing in properties along the stunning coastal countryside, our experienced team of agents is dedicated to helping clients find their dream home or investment property. Whether you are looking for a waterfront estate, a charming cottage by the sea, or a sprawling countryside retreat, Coastal Countryside Properties has a wide range of listings to suit every taste and budget. Trust us to guide you through the buying or selling process with expertise and personalized service. Contact us today to start your journey towards finding your perfect coastal countryside property.

The Brooks Estate is a historic estate located at 275 Grove Street in Medford, Massachusetts, United States. This beautiful tourist attraction offers visitors a glimpse into the past with its well-preserved architecture and lush gardens. Explore the grounds and learn about the fascinating history of the estate, which dates back to the early 19th century. With its picturesque setting and serene atmosphere, The Brooks Estate is the perfect destination for a relaxing day trip or a leisurely stroll through a piece of New England's history.

Welcome to Ellis Estate, a charming and historic tourist attraction nestled in the picturesque town of Scituate, Massachusetts. Located at 709 Country Way, our estate invites you to step back in time and experience the rich history and natural beauty that this region has to offer. Ellis Estate is more than just a destination; it's a journey into the past. Our beautifully preserved grounds and buildings offer a glimpse into the area's storied heritage, making it a perfect spot for history enthusiasts and curious travelers alike. Whether you're exploring our meticulously maintained gardens or wandering through the historic structures, there's a story waiting to be discovered around every corner.

Welcome to Norton Estates Co-Op Corporation, your premier destination for a relaxing and memorable stay in Norton, Massachusetts. Nestled at 250 Mansfield Avenue, our unique lodging and RV park offers a serene escape in the heart of the New England countryside. Whether you're seeking a peaceful retreat or an adventurous getaway, Norton Estates Co-Op is the perfect place to unwind and explore. Our well-maintained facilities cater to both short-term and long-term guests, providing a friendly and welcoming atmosphere. Enjoy the convenience of our modern amenities, including spacious RV sites with full hook-ups, clean and comfortable lodging options, and a range of recreational activities. Our dedicated staff is committed to ensuring your stay is enjoyable and stress-free.

Staffordshire Country Estates is a prestigious institution located at 500 Stafford Street in Leicester, Massachusetts, United States. Nestled in a picturesque setting, this estate offers luxurious and elegant living spaces for those seeking a refined lifestyle. With beautifully landscaped grounds, top-notch amenities, and unparalleled service, Staffordshire Country Estates provides residents with a truly exceptional living experience. Whether you're looking for a peaceful retreat or a vibrant community, this institution has something for everyone. Experience the epitome of luxury living at Staffordshire Country Estates.

Pine Ridge Estates is a premier residential community located at 52 Fitchburg Road in Townsend, Massachusetts, United States. Nestled in a serene and picturesque setting, Pine Ridge Estates offers a tranquil retreat for residents looking to escape the hustle and bustle of city life. The community features spacious homes with modern amenities, lush green spaces, and a variety of recreational facilities including a clubhouse, swimming pool, and walking trails. With its convenient location and peaceful surroundings, Pine Ridge Estates is the perfect place to call home.

Hill Estates is a prestigious residential institution located at 4 Hill Road in Belmont, Massachusetts, United States. Nestled in a picturesque setting, Hill Estates offers luxurious living spaces and a tranquil environment for its residents. With top-notch amenities, beautiful landscaping, and a convenient location near shops and restaurants, Hill Estates is the perfect place to call home. Experience the epitome of elegance and comfort at Hill Estates.

Hennigan Stables & Countryside is a premier equestrian facility located at 323 Oldham Street in Pembroke, Massachusetts, United States. Surrounded by picturesque countryside, our stables offer top-notch boarding services for horses of all breeds. Our experienced staff provides expert care and attention to ensure the well-being and happiness of every horse in our care. With spacious pastures, well-maintained riding arenas, and access to scenic trails, Hennigan Stables & Countryside is the perfect place for horse enthusiasts to enjoy their passion in a beautiful and peaceful setting. Come visit us and experience the beauty and tranquility of our facility firsthand.

Blue Heron Farm in Charlemont, Massachusetts is a charming lodging destination nestled on 250 acres of pristine countryside. This unique institution offers a tranquil retreat for visitors looking to escape the hustle and bustle of city life. The farm also serves as a real estate agency, helping clients find their dream homes in the picturesque New England landscape. Additionally, Blue Heron Farm operates as a travel agency, providing personalized itineraries for those looking to explore the beauty of western Massachusetts. Whether you're seeking a peaceful getaway or looking to invest in a piece of paradise, Blue Heron Farm is the perfect destination for all your lodging, real estate, and travel needs.

The William Cullen Bryant Homestead, located at 207 Bryant Road in Cummington, Massachusetts, is a museum and tourist attraction that offers a glimpse into the life of the celebrated poet. The iconic red barn and serene vista of the Westfield River Valley served as inspiration for Bryant, whose poetry influenced the land conservation movement in the 19th century. The Homestead, where Bryant spent his summers from 1865 until his death in 1878, is filled with Colonial and Victorian pieces from his family, as well as memorabilia from his travels. While the house is not currently open for tours, the grounds and trails are open to the public. Visitors can explore the Rivulet Trail, Pine Loop, and other features of the pastoral landscape. The Homestead is a National Historic Landmark and a must-visit for those interested in Bryant's life and work. Additionally, The Trustees, who oversee the property, offer a Hiking Challenge and other opportunities to explore their many historic homes and cultural landscapes. Plan your visit to the William Cullen Bryant Homestead for a peaceful and informative experience in the beautiful Massachusetts countryside.

Willow Spring Vineyards is a charming and picturesque destination located at 840 West Lowell Avenue in Haverhill, Massachusetts. This vineyard offers a unique experience for both food and wine enthusiasts, as well as tourists looking to explore the beauty of the Massachusetts countryside. With a variety of locally produced wines to sample, visitors can enjoy tastings and tours of the vineyard, learning about the winemaking process and the history of the estate. The stunning surroundings and serene atmosphere make Willow Spring Vineyards a must-visit attraction for anyone looking to experience the best of what Massachusetts has to offer.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

New England Vacation Rentals and Property Management is a premier institution located in Harwich, Massachusetts, United States. As a lodging, real estate, and travel agency all rolled into one, we offer a wide range of services to cater to all your vacation rental and property management needs. Our dedicated team is committed to providing top-notch customer service and ensuring that your stay in New England is nothing short of unforgettable. Whether you're looking for a cozy cottage by the beach or a luxurious vacation home in the countryside, we have the perfect property for you. Contact us today to start planning your dream vacation!

The Pinehills, located at 33 Summerhouse Drive in Plymouth, Massachusetts, is a unique institution that combines the charm of a New England village with modern amenities. As a general contractor and real estate agency, The Pinehills offers inspired new homes and daily adventures just 45 miles from Boston and near Cape Cod. Whether you are an outdoor enthusiast, a food lover, a history buff, or a golf aficionado, The Pinehills has something for everyone. With artfully crafted new homes nestled among towering pines and some with ocean views, the institution offers a range of housing options including custom homes, cottages, townhomes, condominiums, and luxury apartments for rent.

Wheel In Cottages is a charming lodging establishment located in Eastham, Massachusetts, United States. As a real estate agency and travel agency, we offer cozy and comfortable cottages for your vacation getaway. Our cottages are equipped with all the amenities you need for a relaxing stay, including fully equipped kitchens, private bathrooms, and outdoor seating areas. Whether you're looking for a romantic retreat or a family vacation, Wheel In Cottages has the perfect accommodation for you. Book your stay with us today and experience the beauty of Cape Cod in style and comfort.

Cliffside Apartment Homes offers modern and comfortable living in the picturesque town of Sunderland, Massachusetts. Conveniently located at 248 Amherst Road, our apartment community provides residents with stunning views of the surrounding countryside and easy access to local amenities. With spacious floor plans, top-notch amenities, and a friendly community atmosphere, Cliffside Apartment Homes is the perfect place to call home in Western Massachusetts. Come experience the beauty and tranquility of Cliffside Apartment Homes today!

Dunroamin Cottages is a charming real estate and travel agency located at 10 John Ewer Road in Sandwich, Massachusetts. Offering a selection of cozy cottages for rent, Dunroamin Cottages provides the perfect getaway for those looking to escape the hustle and bustle of city life. Situated in a picturesque location, guests can enjoy the tranquility of the surrounding nature while still being close to local attractions and amenities. Whether you're looking for a romantic retreat or a family vacation, Dunroamin Cottages has something for everyone. Book your stay today and experience the beauty of Cape Cod at Dunroamin Cottages.

Located at 60 Ocean Drive in Dennis, Massachusetts, Uppvall Cottages is a real estate and travel agency that offers the perfect homeport for your Cape Cod vacation. Whether you're looking to relax on the beach, go windsurfing, or explore the many points of interest on the Cape, we have something for everyone. With 115 sandy beaches to choose from, including the Cape Cod National Seashore, there's no shortage of fun in the sun. Choose to vacation with us in the bustling months of July and August, or opt for a more peaceful experience at the beginning or end of the summer season. Create wonderful vacation memories with us at Uppvall Cottages.

Fort Hill Rural Historic District is a charming institution located at 70 Fort Hill Road in Eastham, Massachusetts. This historic district is a picturesque reminder of Eastham's rural past, featuring well-preserved buildings and landscapes that showcase the area's rich history. Visitors can explore the district and learn about the early settlers who once called this area home. With its stunning views and peaceful atmosphere, Fort Hill Rural Historic District is a must-visit destination for anyone interested in experiencing the beauty of rural New England.

Welcome to the Rose Garden at Castle Hill, a serene oasis nestled in the picturesque town of Ipswich, Massachusetts. Located at 01938, this enchanting park offers visitors a tranquil escape into nature's beauty. Immerse yourself in the vibrant colors and intoxicating fragrances of our meticulously curated rose collection, featuring a stunning variety of blooms that captivate the senses. Wander along our scenic pathways, where each turn reveals a new vista of lush greenery and artfully designed landscapes. Whether you're seeking a peaceful retreat, a romantic setting, or a family-friendly outing, the Rose Garden at Castle Hill promises a memorable experience for all.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 1 Main Street, Andover, Massachusetts. As a premier real estate agency, we offer a comprehensive range of services tailored to meet the needs of both buyers and sellers. With a legacy of excellence dating back to 1967, Verani Realty brings decades of experience and a commitment to integrity, professionalism, and innovation to every transaction. Our team of seasoned professionals is dedicated to guiding you through your real estate journey, whether you're in search of your dream home or planning to make a strategic sale. Locally known, nationally recognized, and globally respected, Verani Realty is proud to be an affiliate of Berkshire Hathaway HomeServices, a global network of over 50,000 real estate professionals.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 297 South Main Street, Haverhill, Massachusetts. Since 1967, we have been dedicated to providing exceptional real estate services to both buyers and sellers, ensuring a successful and satisfying experience for all our clients. Our team of seasoned professionals is committed to guiding you every step of the way, whether you're in search of your dream home or looking to make a strategic sale. We pride ourselves on our integrity, professionalism, and innovative approach, which is evident in every transaction we handle.

Welcome to Berkshire Hathaway HomeServices Verani Realty, your trusted partner in real estate located at 61 State Street, Newburyport, Massachusetts. With a rich legacy of excellence dating back to 1967, Verani Realty is dedicated to providing a comprehensive range of services for both buyers and sellers. Our seasoned professionals are committed to ensuring your real estate journey is successful and satisfying, whether you're searching for your dream home or making a strategic move. As a proud affiliate of the globally respected Berkshire Hathaway HomeServices network, Verani Realty benefits from a vast network of over 50,000 real estate professionals across 1,500 offices worldwide. Our sterling reputation, built locally, is recognized nationally and respected globally. We believe in fostering meaningful relationships in every transaction, prioritizing collaboration over competition, and supporting the growth of successful real estate businesses.

Hidden Village is a premier real estate and travel agency located at 1700 Bridge Road in the picturesque town of Eastham, Massachusetts. Our agency specializes in providing unique and secluded properties for sale or rent, perfect for those looking for a peaceful getaway or a private retreat. Whether you are searching for a charming cottage nestled in the woods or a luxurious beachfront villa, Hidden Village has the perfect option for you. Our experienced team of agents are dedicated to helping you find your dream property or plan your next unforgettable vacation. Contact Hidden Village today and let us help you discover your own hidden paradise.