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9-11 Winthrop St, Simsbury
$495,000
6 Beds ⋅ 3 Baths ⋅ 24177617 MLS
A rare multi-home opportunity! Nestled on 1.26 acres in a highly desirable Simsbury location, this unique property features two single family homes on one lot --an exceptional opportunity for investors, multi-generational living, or owner-occupants seeking supplemental rental income. The 1400 sq ft owner-occupied Ranch style home features three bedrooms and is ideal for true one floor living, complete with fully paid solar panels, main floor laundry, an oversized primary bedroom suite with ensuite bath, & a slider leading to a private deck for relaxing or entertaining. The tenant-occupied Cape style home (1107 sq ft) offers 3 bedrooms, gleaming hardwood floors, a screened porch, and an attached 2-car garage - a comfortable and inviting rental property with excellent long-term appeal. Ideally situated just a short walk to the elementary school, popular restaurants, and local amenities, this special property combines convenience with the charm and lifestyle Simsbury is known for. Enjoy top-rated schools, scenic walking and biking trails, parks, and outstanding town amenities, all while being conveniently located for an easy commute to Hartford or Springfield and just 20 minutes to Bradley International Airport. A truly unique and exciting opportunity in one of Connecticut's most sought-after communities!

9-11 Winthrop St, Simsbury

138 Tariffville Rd, Simsbury
$487,500
4 Beds ⋅ 2 Baths ⋅ 24205272 MLS
**HIGHEST AND BEST TERMS requested by 5 pm Tuesday September 15.** WOW! Impeccably maintained and truly move-in ready, this charming 4-bedroom Cape reflects pride of ownership throughout. Blending classic character with thoughtful updates, the home offers a spacious, comfortable and flexible floor plan with 2 full baths, beautiful hardwood floors, and wonderful natural light. The inviting eat-in kitchen features granite countertops, updated appliances, terrific storage and a skylight, creating a bright and welcoming space for everyday meals and gatherings. A sun-filled living room offers timeless warmth and character, while the separate family room-with additional skylights-provides the perfect spot for movie nights, relaxing, or casual entertaining. Outside, the beautifully landscaped property is just as impressive. The patio and landscaping were recently updated, complemented by additional newer landscaping and a retaining wall, creating an attractive setting for outdoor dining, entertaining, or simply enjoying the yard. Conveniently located with easy access to highways, Bradley International Airport, shopping, restaurants, and everyday amenities. Meticulously cared for, thoughtfully updated, and exceptionally well presented, this delightful Cape is ready for its next owners to simply move in and enjoy.

138 Tariffville Rd, Simsbury

47 Hayes Rd, Simsbury
$365,000
3 Beds ⋅ 2 Baths ⋅ 24184216 MLS
Welcome home to this beautifully maintained ranch in one of Simsbury's most sought-after neighborhoods. Offering the ease of single-floor living, this home features a bright, open layout designed for both everyday comfort and entertaining. The inviting living room showcases a fireplace, built-ins, and sliders leading to the private backyard. A family room with private entry and door provides additional flexible living space, and the primary bedroom includes its own convenient half bath. Hardwood floors run throughout most of the home, complemented by thermopane windows and central air. The partially finished lower level offers extra space for a home gym, equipped with wall mirrors and a ballet bar. Situated on a level .35-acre corner lot with a privacy fence, this home is located on a popular neighborhood street known for its strong sense of community and annual gatherings. Recent updates include a new furnace, central air unit, and coil installed in winter 2025. Conveniently located near shopping, schools, restaurants, and major commuter routes. A complete list of upgrades is available. Property is being sold as-is.

47 Hayes Rd, Simsbury

5 Quail Dr Unit 5, Simsbury
$353,000
3 Beds ⋅ 3 Baths ⋅ 24183888 MLS ⋅ Governors Bridge BLDG.
Beautifully maintained and tastefully updated townhouse in Governors Bridge. From the moment you enter, the pride of ownership and attention to detail are clear. The foyer and kitchen feature gleaming hardwoods, while the living and dining rooms showcase parquet flooring. The main level offers an open, easy flow with sliders to a private deck-perfect for grilling, entertaining, or unwinding. The efficient kitchen includes stainless steel appliances and granite counters, and beadboard accents in the entry add classic charm. A convenient half bath completes this level. Upstairs, you'll find two generous bedrooms and a remodeled full bath with a sliding barn door. New carpeting (2023) and a refreshed stair entry lead to the top floor, currently used as a bedroom with its own full bath and shower stall. A mini-split system provides added heating and cooling, making this a great guest suite, teen retreat, or home office. The finished lower level adds even more flexible space, with a newer ceiling. System updates include a new furnace (2015), A/C approximately 2016, new windows and slider (2020), and community roof and road improvements (2020-2022). In total: four finished levels and 2.5 baths.

5 Quail Dr Unit 5, Simsbury

38 Main St, Simsbury
$299,000
2 Baths ⋅ 24192818 MLS
Steeped in history and overlooking the picturesque Tariffville Green for more than a century, this charming antique Colonial offers a rare combination of character and exceptional versatility. Due to the property's unique zoning, the possibilities are endless-create a charming single-family home, convert it to a two-family residence by adding a kitchen to the main level, enjoy multi-generational living with an in-law suite, or take advantage of the property's commercial potential. The upper level is currently configured as a comfortable apartment featuring a spacious eat-in kitchen, two bedrooms, a full bath with tub and shower, and a partially finished walk-up attic offering additional space or future expansion possibilities. The main level offers three large, sun-filled rooms and a full bath with a step-in shower, providing flexible space for living, working, or a business opportunity. The basement includes laundry and ample storage, while outside you'll appreciate off-street parking for 5-6 vehicles-a valuable amenity in this desirable village setting. Just steps from the heart of Tariffville, you'll enjoy easy access to local restaurants, shops, parks, and community events. Whether you're searching for a distinctive home, an income-producing property, or a live/work opportunity, this one-of-a-kind property is ready for its next chapter.

38 Main St, Simsbury

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