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22-24 Woodland St, Simsbury
$585,000
5 Beds ⋅ 3 Baths ⋅ 24198047 MLS
A rare opportunity to own a distinctive two-family home combining Simsbury history, comfortable living, income potential, and an exceptional natural setting along Stratton Brook. Tucked away at the end of a quiet residential street yet remarkably convenient to the heart of Simsbury, 22-24 Woodland Street offers the privacy of a neighborhood setting with easy access to the shops, restaurants, library, recreation, trails, and the amenities of Simsbury Center. An original Ensign-Bickford home, the property is part of an important chapter in Simsbury's history. Ensign-Bickford constructed housing in this area for its employees as the company and surrounding community grew, and Woodland Street remains a tangible connection to the town's industrial heritage. Today, the property offers something equally compelling: two comfortable and distinct residences under one roof. Unit 22 features 3 bedrooms and 2 full baths, while Unit 24 offers 2 bedrooms and 1 full bath, providing a total of 5 bedrooms and 3 full baths. The units offer comfortable living spaces and kitchens with appliances, allowing each residence to function as a complete and independent home. Basement space provides additional utility and storage, including laundry facilities for each unit, while tankless hot-water systems enhance the property's functionality, and gas heat and hot water keep the utilities affordable. The versatility is outstanding.

22-24 Woodland St, Simsbury

4 Carriage Dr Unit 4, Simsbury
$249,900
2 Beds ⋅ 2 Baths ⋅ 24200132 MLS ⋅ Heritage Glen BLDG.
Welcome home to 4 Carriage Drive, ranch living in one of the most desirable community of Simsbury! One of the largest living spaces that The Heritage Glen has to offer. This beautifully updated end unit condo has been thoughtfully renovated from top to bottom, allowing you to simply unpack and enjoy. Featuring a stunning renovated kitchen, new flooring throughout, updated electrical, and new plumbing, every detail has been designed with modern living in mind. Whether you're enjoying your morning coffee in the bright and inviting living space or entertaining friends and family in the updated kitchen, you'll appreciate the comfort and quality found throughout. Located in the heart of Simsbury, you'll love being just minutes from local shops, restaurants, parks, hiking and biking trails, golf courses, and all the conveniences the Farmington Valley has to offer. A truly move-in-ready home in an exceptional location! Minutes away from Talcott mountain state park. Enjoy the beautiful views Connecticut has to offer at your convenience.

4 Carriage Dr Unit 4, Simsbury

2 Green Valley Dr, Simsbury
$419,000
4 Beds ⋅ 3 Baths ⋅ 24188446 MLS
Incredible opportunity at 2 Green Valley Drive in Simsbury! Set on a spectacular, large and level corner lot within a quiet cul-de-sac neighborhood, this classic Dutch Colonial offers the setting, space, and potential to create something truly special. Perfectly positioned on the property, the home enjoys impressive curb appeal from the approach, while the expansive yard provides tremendous room for outdoor living, recreation, entertaining, or play. The home features four bedrooms and 2.5 baths, including a primary suite, along with a previously finished basement offering additional potential living space. Currently a naked pallet and in need of TLC, the property presents an ideal opportunity for a contractor, investor, or buyer looking to restore and customize a home to their own vision. With its timeless Dutch Colonial architecture, desirable neighborhood setting, exceptional lot, and generous footprint, the fundamentals are already here. Bring your ideas and transform this property into the beautiful Simsbury home it has the potential to become. A true fixer-upper opportunity where location, land, and upside come together.

2 Green Valley Dr, Simsbury

101 Cambridge Ct, Simsbury
$759,900
4 Beds ⋅ 4 Baths ⋅ 24198489 MLS
To be completed in approximately three months, this stunning 4-bedroom, 3.5-bath Colonial by Silvin Homes in Copper Hill Estates offers the opportunity to select your custom finishes while construction is underway. Featuring 2,161 sq ft above grade plus an additional 896 sq ft in the full finished walkout lower level, this home offers over 3,000 sq ft of beautifully designed living space. The open-concept main level features white oak hardwood flooring throughout and a beautifully appointed kitchen with a large center island, hidden walk-in pantry, and generous builder allowances for cabinetry, countertops, lighting, appliances, tile, and more. Tile showers have already been roughed in and are ready for your selections. Upstairs are four spacious bedrooms, including a private primary suite, along with a separate laundry room. The finished walkout lower level features a full bath and flexible additional living space, while a waterproof deck creates effortless indoor-outdoor living. Set within Copper Hill Estates, enjoy natural gas, city water and sewer, underground utilities, sidewalks, quiet cul-de-sacs, and Simsbury's award-winning schools. Experience exceptional craftsmanship and thoughtfully designed living in one of Simsbury's most desirable premier planned communities.

101 Cambridge Ct, Simsbury

Lot 20 Cambridge, Simsbury
$614,999
3 Beds ⋅ 3 Baths ⋅ 24195533 MLS
To Be Built- Welcome to Copper Hill Estates, one of Simsbury's most sought-after new construction communities. Built by Silvin Homes, the Hartland is a custom-built Cape in one of Connecticut's most desirable towns, known for its award-winning schools and timeless New England charm. Offering 1,781 square feet of thoughtfully designed living space with a spacious open-concept layout, the Hartland blends comfort and elegance for today's lifestyle. The kitchen features granite countertops, an optional island upgrade, and soft-close oak cabinetry, flowing seamlessly into the dining area and expansive great room, creating the perfect setting for entertaining or everyday living. The spacious first-floor primary suite features a walk-in closet and private full bath, offering the convenience of single-level living. Upstairs, you'll find two generously sized bedrooms, a full bath, and a versatile loft, providing comfortable space for family, guests, or a home office. Additional features include convenient first-floor laundry, Hardie Board siding, Harvey True Series windows, natural gas, city water, city sewer, underground utilities, and energy-efficient systems. Buyers may personalize their home with builder allowances for cabinetry, granite, tile, flooring, lighting, and appliances. The HOA includes lawn care, seasonal mulching, snow removal, and walkway salting. Experience exceptional craftsmanship and thoughtfully designed living in one of Simsbury's premier planned community.

Lot 20 Cambridge, Simsbury

537 Bushy Hill Rd, Simsbury
$579,900
3 Beds ⋅ 3 Baths ⋅ 24197868 MLS
Exceptional, fully renovated 3-bedroom, 3-bathroom home offering approximately 2,200 sq. ft. of total living space on a private, woodsy lot in the heart of the Farmington Valley. Rebuilt from the inside out, key upgrades include a new roof, windows, vinyl siding with striking stone accent facade, closed-cell spray foam insulation, new sheetrock, and fully updated mechanicals (electrical, plumbing, HVAC, and furnace). The main level features crisp hardwood floors, an open-concept floor plan designed for effortless entertaining, and a cozy working fireplace in the living room. The gourmet kitchen boasts custom granite countertops, a tiled backsplash, and a large central island. Escape upstairs to a private 800 sq. ft. primary suite highlighting a expansive walk-in closet and a spa-like ensuite bath featuring a freestanding soaking tub, dual-head custom shower, and a 72" double vanity. The fully finished 550 sq. ft. basement studio suite offers complete versatility with 100% waterproof luxury vinyl flooring. Outside, relax on the charming front porch or entertain on the paver patio directly off the kitchen/dining space. Newly paved driveway coming soon! Tesla charger installed in the home for convenient at-home EV charging. Agent/Owner

537 Bushy Hill Rd, Simsbury

Lot 18 Cambridge, Simsbury
$599,999
3 Beds ⋅ 3 Baths ⋅ 24195532 MLS
To Be Built - Welcome to Copper Hill Estates, one of Simsbury's most sought-after new construction communities. Built by Silvin Homes, the Brookfield is a custom-built Colonial in one of Connecticut's most desirable towns, known for its award-winning schools and timeless New England charm. Offering 1,759 square feet with a spacious open-concept layout, the Brookfield blends classic Colonial architecture with modern living. A stately facade, covered front porch, and oversized two-car garage create a striking first impression. Inside, the kitchen features granite countertops, a peninsula island, and soft-close oak cabinetry, flowing seamlessly into the dining area and expansive family room. A private first-floor office, convenient half bath, and dedicated laundry room add everyday functionality. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite with a walk-in closet and private full bath. Additional features include Hardie Board siding, Harvey True Series windows, luxury vinyl plank flooring throughout the main level, natural gas, city water, city sewer, underground utilities, and energy-efficient systems. Buyers may personalize their home with builder allowances for cabinetry, granite, tile, flooring, lighting, and appliances. The HOA includes lawn care, seasonal mulching, snow removal, and walkway salting.

Lot 18 Cambridge, Simsbury

80 Wolcott Rd, Simsbury
$3,599,000
2 Baths ⋅ 24191552 MLS
9.79 Total Acres. Zoned -Industrial 2. All around fence, city water and city sewer. Multiple existing improvements & approved plan for additional improvements. Existing 7500 SF maintenance facility building (4 large bays, 16 x 14 garage doors w/openers, natural gas, radiant floor heat, LED lighting, 16 camera security system. 1,200 Gallon contained used oil tanks, waste oil heater, 30,000 lbs. vehicle lift. 10 HP 3 Phase HD air compressor w/air dryer. Building also features a large office and parts room with heavy duty metal shelving, fuel island with above ground 5000 Gallon double wall tank and 10,000 Gallon dike tank, and includes Fuel Master keyed fuel management system). Also existing 2400 sq ft storage building with 14' garage doors & electric openers, 2 natural gas heaters and city water & concrete floor. 26 x 50 open end hoop house with paved floor. Additional already approved by Town of Simsbury (April 2026) subdivision including 7 Small Warehouse/Contractor Buildings w/Outdoor Storage and 1 Office Building would use approx. 2.25 Acres. 8 miles to Bradley International Airport, 9 miles to I-91, .2 miles to Simsbury Airport.

80 Wolcott Rd, Simsbury

14 Billingsgate Dr Unit 14, Simsbury
$750,000
2 Beds ⋅ 3 Baths ⋅ 24184380 MLS ⋅ Billingsgate BLDG.
Welcome to Billingsgate, Simsbury's distinguished 55+ community where tranquility and turnkey luxury converge. This elegant townhome enchants with a sunny front porch overlooking the fountain and gazebo. Inside, the residence has been elevated with extensive premium upgrades. The front formal living room is now a captivating, sophisticated library. A cozy sanctuary designed to unwind and lose yourself in another world. The main level is tailored for effortless living, featuring a dramatic family room with soaring windows and Kitchen equipped with a gas cooktop, panel-ready appliances, and butler's pantry with a Subzero wine fridge. A sliding glass door opens to a private patio where afternoon sun beautifully illuminates the thoughtfully curated plantings. Meticulous enhancements shine throughout, including designer lighting fixtures, fresh interior paint, a new staircase runner, plush new carpeting, a chic powder room with designer wallpaper and new mirror, and a brand-new AC compressor for absolute peace of mind. Main-level laundry adds ultimate convenience, and the upper level unfolds a private guest wing, full bath, and office with custom built-ins. The remodeled primary suite is a luxurious retreat with plush carpet, curated lighting, custom walk-in closet, and bath with a dual marble vanity, shower, and soaking tub. Complete with a lower level for immense storage, and situated moments from golf, fine dining, and trails, this home offers a lifestyle of unparalleled ease.

14 Billingsgate Dr Unit 14, Simsbury

30 Dorset Xing, Simsbury
$1,650,000
24171174 MLS
This is a premier medical office building in Simsbury. Located at Dorset Crossing on Route 202, the building features 12,679 square feet of usable space. Built in 2012, the building has clinical space with office suites and a community room; an urgent care suite with radiology room; and lab space with several blood drawing stations. The seller will entertain a lease with option to buy, or lease rate of $17.50 sf / yr plus $11.38 sf / yr CAM charge. Additional land approved for various uses is also available at Dorset Crossing, which features The Pointe apartment complex. The site has direct frontage on Route 202, where there is a signalized entrance into the complex. The land is level, with very well drained soils. Daily traffic count is about 12,000, and all utilities are available. The site is just 15 minutes from Bradley International Airport, and 25 minutes from downtown Hartford.

30 Dorset Xing, Simsbury

136 Hopmeadow St, Simsbury
$699,000
1 Baths ⋅ 24071591 MLS
Commercial opportunity in Simsbury! Currently occupied by a long standing, thriving barber shop, Avon Barber Shop, a true turnkey opportunity. Owner operated for many years by the owner who is willing to pass on a successful barber shop and clientele. The space is also suitable for a variety of businesses located on route 10 with a traffic count of over 11,000 vehicles daily approximately. Offering 1,584 square feet of space on one level that is ideal for hair salon / barbershop / spa service or other businesses. This asset is in an ideal location for a business on Hopmeadow Street. Immediate neighbors include Dunkin Doughnuts, Cumberland Farms and more. Built in 1976, with an open, flowing adaptable floor plan adaptable to many business options. Central air, natural gas heating, full kitchen, granite countertops, full bath, public water and sewer connected. Property sits on a level lot, with parking spaces as well as a covered carport, radiant exterior heating built in under the walkway to keep things snow and ice free, two compressors power the central air more than sufficiently and a quality roof in place with lots of life left on it in this very well maintained building. Owner willing to leave equipment and fixtures for the next barber to start up in a smooth transition with his assistance on a transfer. Don't miss out on this great opportunity to own a building and barber shop or other business here versus the high cost of franchising that does not include property ow

136 Hopmeadow St, Simsbury

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