“Your journey, Your home. My priority.”
Finding the right home shouldn’t feel stressful.
Buying or selling real estate is a big decision, but it doesn’t have to feel overwhelming. My role is to walk alongside you through the process, making things clear, simple, and stress-free.
With years of experience helping people across Connecticut, I’ve learned that success in real estate isn’t just about transactions — it’s about people. Your goals, your timeline, and your peace of mind come first.
When you understand your options, you can move forward with confidence — whether you’re buying your first home, upgrading, investing, or selling a property.
My mission is simple: to guide you with honesty and care, and to make the journey not only smooth and rewarding, but enjoyable too.
Let’s find a place you’ll be proud to call home.
Cheshire
Cheshire, Connecticut, is a classic New England town located in New Haven County, known for its strong sense of community, beautiful neighborhoods, and excellent quality of life. Settled in the late 1600s and incorporated in 1780, Cheshire was originally a farming community before growing into one of Connecticut’s most sought-after suburbs. Its historic center, tree-lined streets, and well-preserved colonial homes give it timeless charm, while its parks, schools, and amenities make it ideal for modern living. Today, Cheshire perfectly blends small-town warmth with a convenient central location — a true gem in the heart of Connecticut.
Cheshire Real Estate
Cheshire’s real estate market continues to be one of the strongest in the area, offering consistent value and steady growth. The town is known for its beautiful single-family homes, spacious lots, and well-kept neighborhoods. Buyers are drawn to Cheshire for its award-winning school system, safe environment, and convenient access to I-84, I-691, and Route 10. Home values have appreciated steadily, and properties tend to sell quickly — especially those that are move-in ready. For anyone looking for a peaceful, family-friendly town with lasting appeal, Cheshire is always a top choice.
Things to Do in Cheshire
Cheshire offers a wonderful mix of outdoor recreation, community events, and family-friendly activities that make it an enjoyable place to live year-round. Whether you’re hiking, shopping local, or attending a town festival, there’s always something to do close to home.
Cheshire Fall Festival & Marketplace – Community Celebration
Held each September, this popular event features food trucks, local vendors, music, and family activities. It’s one of the biggest annual celebrations and a great example of Cheshire’s small-town pride.
Bartlem Park – Heart of Town Recreation
Located near the center of town, Bartlem Park offers sports fields, walking paths, and playgrounds. It’s also home to summer concerts and town events, making it a favorite gathering spot for residents.
Roaring Brook Falls – Natural Beauty & Hiking
This hidden gem is one of Connecticut’s tallest waterfalls. The short hike to the falls offers peaceful forest scenery and a great outdoor escape without leaving town.
Where to Eat in Cheshire
Cheshire’s dining scene reflects its community vibe — local, friendly, and full of variety. From casual pizza spots to cozy cafés and fine dining, you’ll find plenty of options to suit any mood or occasion.
Viron Rondo Osteria – Italian Cuisine & Patio Dining
A popular Cheshire destination known for its wood-fired pizza, house-made pasta, and modern Italian dishes. The large patio and warm atmosphere make it perfect for date nights or dinners with friends.
Cheshire Pizza & Ale – Local Favorite with Craft Beers
A staple in town serving up great pizza, sandwiches, and a relaxed bar atmosphere. It’s the go-to for casual meals and local hangouts.
Sweet Claude’s Ice Cream – Family Treat Spot
A beloved stop for homemade ice cream and frozen yogurt. Whether it’s after a ballgame or on a summer evening, it’s a Cheshire classic.
At Tyler Mach Real Estate, my focus is simple: to make your real estate journey as smooth and supportive as possible, while building lasting relationships in the communities I serve.
With years of experience helping buyers, sellers, and investors across Connecticut, I know that no two situations are the same. That’s why I take the time to understand your unique goals and guide you with care, clarity, and honesty.
Whether you’re buying your first home, selling a property, or making an investment, my mission is to help you move forward with confidence — and even enjoy the process along the way.
📞 Ready to talk about your next move? Let’s connect — I’d love to help.