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$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
$999,900
5 Beds ⋅ 4 Baths ⋅ 24196402 MLS
Tucked away at the end of a circular driveway and bordered by protected conservation land, this exceptional West Simsbury estate offers a rare combination of privacy, natural beauty, and timeless New England charm. Set on 3.28 acres, the property is surrounded by mature trees, perennial gardens, historic stone walls, rolling lawns, and a private stocked pond, creating a peaceful retreat unlike any other. Offering over 3,600 square feet of finished living space, this thoughtfully designed home features five bedrooms, three full baths, one half bath, and a dedicated second-floor home office. The updated kitchen opens to a spacious family room anchored by a wood-burning fireplace, while a private entertaining lounge with a wet bar, ice maker, and kegerator provides the perfect space for holidays, celebrations, and gatherings. Two additional wood stoves add warmth and character throughout the home. The finished lower level offers exceptional flexibility with a large recreation room, half bath, and bonus space ideal for a home gym, media room, playroom, or guest retreat. Outdoor living is equally impressive. An expansive 840-square-foot two-tier deck overlooks the beautifully landscaped grounds, while two covered porches invite you to relax and enjoy the surrounding scenery.

13 Woodchuck Hill Rd, Simsbury
$725,000
5 Beds ⋅ 4 Baths ⋅ 24193618 MLS
MAKE YOUR OFFER TODAY! BEST AND FINAL BY 8/2/26 BY 6PM! Perched atop the coveted Westledge ridgeline in West Simsbury, this custom-built ranch commands breathtaking panoramic "million-dollar" views across the Farmington Valley, with a peek-a-boo glimpse of the Hartford skyline. Set on more than 7.5 private acres this extraordinary property offers a front-row seat to spectacular sunrises, ever-changing weather patterns, and seasonal bird migrations from its elevated setting. A circular driveway welcomes you to over 4,600 square feet of thoughtfully designed living space on two expansive levels. The updated kitchen features granite countertops, a center island, pantry, skylight, and a distinctive octagonal dining area. The formal dining room is ideal for entertaining & flows into the inviting living room, with a fireplace, custom built-ins, & sliders to an airy sunroom overlooking the rolling landscape. The main level's generous primary suite has a sitting & dressing area, walk-in closet, & full bath. 2 additional bedrms share a full bath, while a mudrm, laundry & powder rm complete the 1st floor. The impressive walkout lower level is filled w/natural light from oversized daylight windows and expands the home's living space with 2 additional bedrms, a family room w/ fireplace & built-ins, a private study, and large recreation area. Beneath the rec room floor lies a former indoor pool, presenting intriguing possibilites for restoration. A rare opportunity awaits! SOLD AS IS

184 Westledge Rd, Simsbury
$799,900
5 Beds ⋅ 4 Baths ⋅ 24192241 MLS
***HIGHEST AND BEST DUE FRIDAY 8/14 BY 9:00 AM. Offers are being reviewed. No escalation clauses. GHAR contracts preferred. Submit with proof of funds or lender pre-approval including lender contact, inspection scope, and proposed closing date*** Seller reserves the right to accept an offer at any time. Here's what an acre-plus rarely gives you: the septic is in the FRONT yard, leaving the entire rear of the property open, level and unobstructed. Pool, pickleball, padel court - the room is there. An underground gas line already runs to the brick patio, ready for a grill or firepit. Custom built in 1996, 3,757 sq ft on 1.36 acres. Five true bedrooms above grade, septic verified for five. Three full and one half bath. Cherry country kitchen 13x26 with large island. A 29x15 family room anchored by a stone fireplace built with stones taken from this property. All-season sunroom. Primary suite with private sitting room and second fireplace. Custom built-in cabinetry and extensive millwork throughout, freshly painted in historic colors over oak hardwood. NEW 2025 GAF architectural roof. Exterior painted 2024. Central air, central vac, wired for generator, oversized 2-car garage. Full unfinished basement spans the footprint - a blank canvas.

276 Stratton Brook Rd, Simsbury

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