Chester MA Real Estate & Homes for Sale

Be sure to check out this one-of-a-kind opportunity for to-be-built new construction in the peaceful town of Hartland. Set on a beautiful lot, this proposed build offers the chance to create your dream home from the ground up-with flexibility to choose finishes and customize the layout to fit your lifestyle. This plan reflects the builder's current vision, but the design can be modified to your liking. Want to bring your own builder? No problem-land can be purchased separately. For buyers using the builder's preferred lender, take advantage of a 5% down new construction program-a rare and exciting option in today's market. Book an appointment today to discuss finishes, layout options, and how to make this future home truly yours. See supplements for additional information.

For Sale: Timeless Circa 1783 Colonial Home on Corner Lot This 1783 Colonial, offers 2,316 square feet of living space, is a hidden gem ready for your personal touch. With 4 bedrooms, wide board wood flooring, and a charming spiral front stairway, this home is filled with historic character but in need of updating to reach its full potential. Set on a level 1.1-acre corner lot along a scenic road that encircles the reservoir, you'll enjoy tranquil surroundings and access to nearby walking trails. Plus, benefit from a short commute to Bradley International Airport. Bring your vision and make this historic Colonial your own!

This is a beautiful, newly renovated property in the quiet town of East Hartland. The location is very convenient, 13 mins. to Granby Town Center, 22 mins. to Bradley Int'l Airport and just 25 mins. away from I-91. This 2200 square-foot home sits on just over an acre of land with a large lawn, bordered by trees. The original home was built in 1950, and a new addition with a first-floor master bedroom suite, mudroom, and deck has been added. There are four bedrooms, two full baths, and one 1/2 bath. Laundry on the first floor, and a first-floor master bedroom suite with a large master bathroom and walk-in closet. Almost everything is new, inside and out, and many upgrades have been made. These include a new septic system, all appliances, new windows and doors, a new roof, upgraded insulation, and a new driveway. Please see the attached list of improvements. There is also a large three-car garage with a storage loft or studio space above, a refinished floor, and new painted drywall. There's also a full basement, ready to be finished or used as a workshop or for storage.

A Rare Gem! The historic John Gates House is a beautifully preserved center-chimney Colonial in the heart of East Hartland, just over the Granby line. Seamlessly blending timeless charm with modern efficiency, this stunning home showcases original details alongside thoughtful updates. The first floor boasts a huge great room with a wood stove, wide board floors, & custom built-ins. The chef's eat-in kitchen is a dream, featuring granite countertops, stainless steel appliances, a center island, tile flooring, exposed beams, a double oven, & a fireplace. The dining room offers warmth & character with its fireplace & wide board floors. A living room, currently used as a first-floor bedroom, also features wide board floors. The sunroom is a showstopper with its cathedral ceiling and natural light. A full bath completes the main level. Upstairs, you'll find three spacious bedrooms and another full bath, plus a walk-up attic for extra storage. The home, currently configured as a 3-bedroom, could easily be converted back to 4 bedrooms. Adding to its versatility, a legal 860+ sq. ft. 4-room apartment provides rental income, in-law potential, or a home office. Notable updates include a painted exterior with chic liquid vinyl, solar panels (transferable lease), energy-efficient triple-pane windows, leaf guard gutters, a whole-house Generac generator, two high-efficiency furnaces, & a newer hot water heater. Set on a gorgeous, level property, the home also features a 34x16 barn.

Nestled in the heart of the completely private 1700 acres of the Doolittle Lake Company woods on 2 parcels, this 100 acre 5,670 sq ft beautifully maintained 1780 center hall colonial boasts colonial & art deco architectural details. Moved to its current location in the 1930s NY architect Robert Carrere renovations include generous reception rooms, wide red pine floors, high ceilings, 2 wet bars, 9 wood burning fireplaces. Rotary dial phones, butler bells, & other period details capture the charm of the 1930s. Gourmet kitchen with fireplace custom cabinetry, a fish sink on the back porch for cleaning trout! Elegant sunny dining room & breakfast terrace with herb garden. Sun porch glass doors open to stone walled perennial gardens & pool. Dramatic arches & vaulted ceiling adorn the poolhouse with kitchenette, 1/2 bath, dressing rooms & outdoor shower. Custom oval gunite heated pool. Main bedroom with private sitting area, fireplace & steam shower, 3 large ensuite bedrooms with fireplaces, playroom and laundry on upper floor. Ensuite studio above heated garage. Ownership includes all benefits of hunting, fishing, boating, hiking in this private community on pristine lake & pond. Available caretaking service make maintaining this beautiful home stress free. Enjoy year round peaceful lake area living on unique private estate in gorgeous Doolittle Lake Woods located 2 1/2 hours from Boston or NY. Agent Owned.

Tower Hill house sits on 7 acres with 800 feet of frontage along the western shore of Doolittle Lake in Norfolk, CT. Designed by a local architect and built by local craftspeople, the house is privately sited down a long driveway and sits on a little bluff so there are lovely views over the lake. The Doolittle community takes great care to protect the health of the lake and its surrounding woodlands. Hiking, swimming, kayaking, canoeing and sailing (no motor boats allowed) are among the fun and healthy things to do and town is only a few minute car ride away.

LOVELY RAISED RANCH nestled on a lush and private lot boasts 3 bedrooms, 2 FULL baths, and new flooring throughout the main level of the home! Light and bright living room easily flows into the dining area and updated kitchen that features new appliances and lighting fixtures! Freshly painted, updated bathrooms and an oversized 2-car garage! The finished lower level with full bath is roomy enough to be a rec room, office/workout area, or anything else your heart desires! Warmer weather is upon us, and you can enjoy lounging in a comfy chair on your spacious deck while you enjoy the sunset or entertain guests and wow them with your BBQ skills. Tucked away from the hustle and bustle of daily life yet conveniently close to local shopping, restaurants, parks, hiking trails and local highways!

Nestled in one of the most desirable areas of Western Massachusetts, this spacious 4-bedroom, 3-bathroom post-and-beam home offers the perfect blend of rustic charm and modern efficiency. Thoughtfully designed with exposed wood beams, cathedral ceilings, and skylights that flood the interior with natural light, this property exudes warmth and character throughout. Set on a serene lot that abuts the Federally Protected Appalachian Trail Corridor, nature lovers will find peace and privacy just steps from their door. Enjoy the benefits of green living with the home's electricity powered by a nearby solar farm at Weston Abbey-a rare and sustainable perk. The home features a partially finished basement ideal for a home office, gym, or creative studio, offering flexible space for work or play. With a Great Barrington mailing address, but home is located in Sheffield giving residents lower Sheffield taxes -plus the ability to vote in Sheffield. Conveniently located just minutes from Guido's Fresh Marketplace, shops, restaurants, and outdoor recreation, this exceptional property is a true gem that combines tranquility, community, and eco-conscious living.

Welcome to your own peaceful retreat! This stunning 4-5 bedroom, 2.5-bath ranch is set on 8.73 private, picturesque acres-ideal for horse enthusiasts or anyone seeking a tranquil lifestyle surrounded by nature. The 36x30 barn includes 4 stalls, wash rack, tack/feed room, and new 85'x103' riding ring. Fenced pasture ideal for horses. The home features an updated granite eat-in kitchen with breakfast bar with cozy living area and French doors leading to back deck. The expansive great room impresses with its vaulted ceiling, exposed beams, and striking stone fireplace, seamlessly flowing into a sunken sunroom that offers year-round relaxation with beautiful views. The primary suite is located in its own wing with walk-in closet and updated full bath with double vanity. Three additional bedrooms, and a spacious laundry room on main floor. Room for office, great for working at home! The usable lower level could easily be a in-law has hot and cold hookup for additional laundry or potential bath, has abundant storage and flexible space for a home gym, workshop, or hobbies. Recent updates include new oil tanks, well pump, pasture fencing, and furnace. Solar powered, owned not leased! Convenient to town center, shopping, commuter routes, and Bradley International Airport. Suitable for one-level living, entertaining, or a private retreat.

Welcome to a once-in-a-lifetime lakefront retreat, where the beauty of Lake Congamond meets everyday tranquility. Situated on 2.1 acres with 170 feet of private, sandy shoreline, this 5 bed 2 bath home is your gateway to the ultimate lake lifestyle. Spend your days swimming, boating, or relaxing on your own beach, and your evenings watching sunsets reflected over the water. Designed for multi-generational living or a forever family home, the spacious and flexible layout is filled with charm, character, and room to grow. Whether it's morning coffee by the water, hosting unforgettable gatherings, or simply enjoying the peace of nature, this home offers the perfect backdrop. Surrounded by scenic parks and hiking trails, outdoor adventures await just beyond your door. Conveniently located only 30 minutes from Bradley International Airport, 1.5 hours from Boston, and just over 2 hours from New York City, this lakeside escape offers privacy without sacrificing accessibility. Don't miss this rare opportunity to make lakefront living your reality, schedule your private tour today!

Why wait for new construction when you can move right into this stunning, fully renovated home offering over 2,500 sq ft of beautifully updated living space? No detail was overlooked-enjoy peace of mind with a newer roof, new windows, new flooring throughout main floor, and three fully renovated bathrooms. The chef's kitchen is equipped with all new appliances, modern lighting, and premium finishes. Step outside onto the brand-new deck, perfect for entertaining, and admire the freshly paved driveway leading to a spacious 3-car garage. This home features efficient propane tankless heating and hot water, and the septic system has been professionally cleaned and inspected. Truly turnkey, this property feels like new construction inside and out. Everything is done-just unpack and enjoy! Don't miss your chance to own this exceptional home-schedule your private showing today before it's gone!

New construction ! Permits in process to use existing foundation with complete new home. Home design is currently for a 3 bedroom home with an up stair office or possible 4th bedroom. Pick out many of the finishes on the home and possible design changes are now possible.

Discover your ideal country retreat on nearly 9 acres of mostly cleared land-perfect for creating your own small animal farm! This quality-built 3-bedroom ranch on scenic Silkey Road offers peaceful living. The main level features hardwood floors, a spacious foyer, and a bright granite kitchen with ample cabinets and a breakfast bar. There's a mudroom with laundry, a front-to-back living room with a fireplace, and a dining area with built-ins. The primary suite includes a remodeled full bath. The walk-out lower level has been beautifully updated, with a full bath, family room with woodstove, and a slider to the backyard-great for outdoor entertaining. Two additional bedrooms and plenty of storage complete this level. There is a workshop off the garage. Located in North Granby, a charming area offering peaceful rural life with easy access to highways, cities, and airports. Enjoy nearby outdoor recreation like hiking, biking, McLains Game Refuge, and Enders State Forest. This move-in-ready home combines comfort, quality, and space-your perfect retreat awaits!

Discover the perfect blend of luxury, charm, and opportunity with this exceptional property package at 261 and 269 Halladay Drive! Whether you're dreaming of a serene lakeside retreat or a high-return investment, this offering checks every box. Step into the iconic "Red Roof Inn" at 269 Halladay, where breathtaking water views, direct lake access, and over 100 feet of private shoreline set the stage for an unparalleled lifestyle. Inside, enjoy expansive living spaces bathed in natural light, hardwood floors, a stunning 3-floor spiral staircase, a private movie theater, and modern amenities that make every day feel like a getaway. Take in the serene vistas from the gorgeous balconies or unwind by the water's edge. Adding to the appeal is a detached, three-story garage, part of which is finished as a cozy apartment-perfect for guests or rental income. Together, these two properties, complete with separate deeds and a shared driveway, provide at least four potential income-generating opportunities, making this a rare and lucrative find. Don't miss your chance to own this one-of-a-kind lakeside compound-schedule your private tour today!

Nestled in the heart of the Berkshires, this historic Richmond compound presents a rare blend of colonial charm and modern equestrian excellence. Spanning 11+ bucolic acres with sweeping pastoral views, the legendary c1776 estate boasts a meticulously maintained main residence, three enchanting cottages, and the potential to include the region's premier full-service equestrian facility (see related listing for $2.25m and ask for pictures). The main residence, a testament to time-honored craftsmanship, features 7 bedrooms and 7.5 baths, each room telling a story of centuries past. The inn's dignified presence is complemented by a dining room, entrance parlor, library, den, period greenhouse, and a well-appointed kitchen that cater to both intimate family gatherings and grand celebrations.

Welcome to the Chestnut Heights Congamond Lake community. House located across street from private beach where you can launch your canoe/kayak at this private area. Just down street is private swimming beach. In 2019 - Second floor addition of a bedroom, a full bath and large sitting room/great room with windows looking out at the lake. The second floor has mitsubishi mini splits for you air-conditioning comfort in the summer, heat in winter. First floor you need window units to cool. Kitchen has granite counters, breakfast bar and newer cabinets. Kitchen is open to family room. Bay window in family room gives you a view of the lake. The house solar panels were added 2020. There is an oversized 24x30 (720sf) detached garage which was built 1989. House being sold "as is". Please use "as is" rider.

Nestled in the foothills of the Berkshires on a quiet country road, this circa 1790 colonial, "The Tobey House," awaits its new stewards! This special property features authentic period details & is sited on a majestic 3.88 acre lot with direct access to the waterfalls at Campbells Falls. The sprawling, versatile floorplan is the perfect canvas to bring your antique Pinterest board to life! With windows in all the right places, the home is awash in natural light that perfectly showcases the rich patina of the wide plank flooring and rustic detailing throughout. Entering the architect-designed kitchen, you'll take a deep breath: this is truly a HOME. Cabinet packed with a large granite island overlooking one of 7 (4 functional) original fireplaces, it creates the perfect command center. Built-in enthusiasts will marvel at the absolutely stunning carpentry in every room. An XL dining room flows seamlessly into a charming den. The lovely center hall provides access to the ultimate work from home wing, guest room with ensuite 1/2 bath, & a fantastic covered porch overlooking the pastoral grounds, former pool area w hookups still intact, & massive barn. Upstairs, the capacious primary BR is adorned with hand-stenciled walls. 2 addl well sized BRs share a massive full bath w laundry. Ideal location on MA line - the perfect launch point to enjoy the best of the Berkshires & NW corner. This home's rich heritage is ready to converge with your next chapter: a dream homestead beckons!

Lake life at its best! Welcome to this charming home filled with character throughout, surrounded by extensive gardens and showcasing stunning sunset views of South Pond at Lake Congamond! Entertain at your best with a seamless floor plan offering open living and dining spaces leading to an updated kitchen with pantry and lav, right through glass sliders to the deck where you can sip coffee in the mornings and perhaps cocktails in the evenings. Upstairs you will find a soaring ceiling, large full bath with new dual vanity and jetted tub; two bedrooms each with double closets, including the primary overlooking South Pond with sliders to a private balcony. The lower level offers a bonus room (previously used as a teen bedroom), workshop and laundry. Several updates include new walkway/landscaping/shed 2024, dryer 2023, washer 2021, oil boiler 2020, septic 2017, exterior painting 2017, well pump 2012, kitchen appliances all 2-7 years old and roof approximately 17 years (all approximate, per owner). With so many updates you can spend your time enjoying a leisure lake life! A $70 annual fee allows access to the private beach, boat launch and playground. An additional fee will offer dock space (when space available) for your boat providing direct access to waterfront restaurants and entertainment. Bike/walking trails, stables and golf courses are all nearby. Now is the time to secure your summer or year-round retreat!

Attention investors! Nestled on a peaceful 1-acre lot, this 2 bedroom, 2 bath Cape provides warmth, character, and opportunity! A spacious kitchen, with adjoining pantry, and dining area provides plenty of room for gathering. The inviting living room features exposed beams and a brick hearth, perfect for a wood or pellet stove. The first floor includes a bedroom, laundry and full bath, while upstairs boasts a large bedroom, another full bath and a versatile landing area. Outside you will find an oversized shed with ample storage, perfect for tools, equipment or hobby space. With major updates already done by the owners of 23 years, this home is ready for your personal touch. A little vision and TLC can transform it into the perfect starter home, cozy getaway or AirBnB! A short drive to Great Barrington. Don't miss out! Newly adjusted price.

This beautifully renovated lakeview home on Lake Congamond's South Pond offers the perfect blend of modern upgrades and lakeside charm. Expertly redesigned by renowned local builder Briarwood Homes, no detail was overlooked in this stunning transformation. Inside, you'll find brand-new natural wood flooring throughout and a completely updated kitchen featuring custom cabinetry, a spacious island, quartz countertops, and GE stainless steel appliances. The home also includes a new roof, updated plumbing-siding-windows, brand new washer and dryer, offering worry-free living for years to come. Energy efficiency is enhanced with spray foam insulation in the basement. Step outside to an oversized front deck-ideal for entertaining or relaxing as you take in breathtaking sunset views over the lake. Just a few steps from your front door, enjoy your community, private beach access and dock, making this a true lakefront retreat ready for summer fun or year-round living.

Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at your fingertips. The property's outdoor allure is undeniable. Multiple walking or riding trails invite adventure, and the gardens, barn, carriage house and stone outbuilding offer endless possibilities for outdoor enjoyment. Step inside and be greeted by the warm embrace of rich hardwood floors, two fireplaces, French doors, and meticulously crafted woodwork that tell tales of yesteryear. The updated kitchen, equipped with a premium Wolf gas stove and a convenient butler's pantry, offers a perfect stage for culinary exploration. The living room, anchored by a cozy fireplace, formal dining room, and library, are infused with great natural light that dances across the spaces. The primary bedroom suite, a sanctuary of comfort, boasts its own fireplace, ensuring a restful retreat at day's end. Accommodate guests in style with four additional bedrooms, including a secluded guest room with a private stairway. Located in the heart of nature's playground in Litchfield county. Close to skiing, hiking, restaurants, and parks in Norfolk and Barkhamsted, and near the Farmington River.

This lot is one of 7 lots (4 on Day Street and 3 on North Granby Road) being offered subject to final subdivision approval from the Town of Granby. This lot can be reserved by entering into a Reservation Arrangement with the Contract Owner. These lots are all in an open rolling meadow, so no clearing and a lot of design flexibility. There is plenty of room for a swimming pool on all 7 lots. Some lots feature walk-out basements. These are really beautiful lots. We will be happy to meet with you to walk this lot and to discusss the building process. We have suggested several home designs, however, we will work with you to build the custom home that you want. Our mission is to have you "Live Happily Ever After". These homes will be built by Kirk and Reed MacNaughton of Blue Sky Builders. They have been building custom homes in Northern Connecticut for over 30 years and specialize in upscale energy efficient new homes. Their Blue Sky Energy Saver Branded New Homes represent the "State of the Art" in intelligent, energy efficient new construction. These homes are built tight to minimize outside air flow and are meticulously insulated. These homes feature high performance air sealing and insulation, Energy Star windows, mechanical systems and appliances. Geothermal heating and cooling is an available option. Builder and Broker are affiliated. Sale dependant upon the Contract Owner's ability to take title. IF YOU PREFER, YOU CAN BRING YOUR OWN BUILDER.

This lot is one of 7 lots (4 on Day Street and 3 on North Granby Road) being offered subject to final subdivision approval from the Town of Granby. This lot can be reserved by entering into a Reservation Arrangement with the Contract Owner. These lots are all in an open rolling meadow, so no clearing and a lot of design flexibility. There is plenty of room for a swimming pool on all 7 lots. Some lots feature walk-out basements. These are really beautiful lots. We will be happy to meet with you to walk this lot and to discusss the building process. We have suggested several home designs, however, we will work with you to build the custom home that you want. Our mission is to have you "Live Happily Ever After". These homes will be built by Kirk and Reed MacNaughton of Blue Sky Builders. They have been building custom homes in Northern Connecticut for over 30 years and specialize in upscale energy efficient new homes. Their Blue Sky Energy Saver Branded New Homes represent the "State of the Art" in intelligent, energy efficient new construction. These homes are built tight to minimize outside air flow and are meticulously insulated. These homes feature high performance air sealing and insulation, Energy Star windows, mechanical systems and appliances. Geothermal heating and cooling is an available option. Builder and Broker are affiliated. Sale dependant upon the Contract Owner's ability to take title. IF YOU PREFER, YOU CAN BRING YOUR OWN BUILDER.

This lot is one of 7 lots (5 on Day Street and 2 on North Granby Road) being offered subject to final subdivision approval from the Town of Granby. This lot can be reserved by entering into a Reservation Arrangement with the Contract Owner. These lots are all in an open rolling meadow, so no clearing and a lot of design flexibility. There is plenty of room for a swimming pool on all 7 lots. Some lots feature walk-out basements. These are really beautiful lots. We will be happy to meet with you to walk this lot and to discusss the building process. We have suggested several home designs, however, we will work with you to build the custom home that you want. Our mission is to have you "Live Happily Ever After". These homes will be built by Kirk and Reed MacNaughton of Blue Sky Builders. They have been building custom homes in Northern Connecticut for over 30 years and specialize in upscale energy efficient new homes. Their Blue Sky Energy Saver Branded New Homes represent the "State of the Art" in intelligent, energy efficient new construction. These homes are built tight to minimize outside air flow and are meticulously insulated. These homes feature high performance air sealing and insulation, Energy Star windows, mechanical systems and appliances. Geothermal heating and cooling is an available option. Builder and Broker are affiliated. Sale dependant upon the Contract Owner's ability to take title. IF YOU PREFER, YOU CAN BRING YOUR OWN BUILDER.

This lot is one of 7 lots (4 on Day Street and 3 on North Granby Road) being offered subject to final subdivision approval from the Town of Granby. This lot can be reserved by entering into a Reservation Arrangement with the Contract Owner. These lots are all in an open rolling meadow, so no clearing and a lot of design flexibility. There is plenty of room for a swimming pool on all 7 lots. Some lots feature walk-out basements. These are really beautiful lots. We will be happy to meet with you to walk this lot and to discusss the building process. We have suggested several home designs, however, we will work with you to build the custom home that you want. Our mission is to have you "Live Happily Ever After". These homes will be built by Kirk and Reed MacNaughton of Blue Sky Builders. They have been building custom homes in Northern Connecticut for over 30 years and specialize in upscale energy efficient new homes. Their Blue Sky Energy Saver Branded New Homes represent the "State of the Art" in intelligent, energy efficient new construction. These homes are built tight to minimize outside air flow and are meticulously insulated. These homes feature high performance air sealing and insulation, Energy Star windows, mechanical systems and appliances. Geothermal heating and cooling is an available option. Builder and Broker are affiliated. Sale dependant upon the Contract Owner's ability to take title. IF YOU PREFER, YOU CAN BRING YOUR OWN BUILDER.