Head of Meadow Homes for Sale

Welcome to Head Of Meadow, a hidden gem nestled in the picturesque town of Newtown, Connecticut. This charming neighborhood is renowned for its serene ambiance, lush landscapes, and a strong sense of community, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Head Of Meadow boasts a variety of beautiful homes for sale, each exuding character and charm. From cozy ranch-style houses to spacious contemporary designs, there’s something to suit every taste and lifestyle. Many of these homes are set on generous lots, providing ample outdoor space for gardening, play, or simply enjoying the tranquility of nature. With well-maintained streets and friendly neighbors, this neighborhood fosters a welcoming environment where everyone feels at home.

The area is not only beautiful but also conveniently located. Residents enjoy easy access to local amenities, including shops, restaurants, and parks. Newtown’s vibrant downtown area is just a short drive away, offering a delightful mix of dining options and boutique shopping. Families will appreciate the highly-rated schools in the district, ensuring that children receive a quality education close to home.

Outdoor enthusiasts will find plenty to love in Head Of Meadow, with nearby hiking trails, serene lakes, and recreational facilities that encourage an active lifestyle. Whether you're looking for a peaceful place to raise a family or a quiet retreat to enjoy your golden years, Head Of Meadow in Newtown, CT, offers a perfect blend of comfort, community, and convenience. Explore the homes for sale today and discover the enchanting lifestyle that awaits you!

Newest Head of Meadow Homes for Sale

$875,000

5 Beds ⋅ 3 Baths ⋅ 24193317 MLS

Down a quiet stretch of Boggs Hill, framed by open land and historic stone walls, this 5-bedroom, 3,200+ sq ft country retreat is a rare blend of privacy, space, and view. A grand two-story foyer opens into a light-filled living and dining room, flowing easily into an eat-in kitchen overlooking the yard and a cozy family room with access to the stone patio. A sun porch wrapped in windows on nearly every side makes for the perfect morning-coffee or golden-hour spot. The main level offers a peaceful primary suite plus a second bedroom or office with oversized windows, ideal for one-level living, guests, or remote work. Upstairs, three generously sized bedrooms share a full bath, joined by a secret bonus space (playroom, studio, storage - your call) and an unfinished attic with soaring ceilings, ready to become whatever you need next. Hardwood floors in most of the house, central air, and stone walls throughout give this home timeless country character. And the setting doesn't stop at the property line. Newtown offers charming Main Street shops and restaurants, scenic hiking and lake access, top-rated schools, and an easy commute to NYC or Boston for those craving small-town calm without giving up convenience. Privacy. Space. A view worth coming home to.

60 Shepard Hill Rd, Newtown

$499,900

3 Beds ⋅ 3 Baths ⋅ 24186337 MLS

opportunity knocks!! attention builders-tradesmen-handyman. clean move in condition lovingly cared for home in need of updates. Spacious living rm w/fpl, formal dining rm, sunroom and a 24x20 family rm. Possible in-law-au-pair apartment. 3 full bedrooms 3 full baths 4 car garage!!! lots of charm & character easy to bring back to its original glory. 1.75 acres park like property. convenient to schools, shopping & commuting. Subject to probate

175 Sugar St, Newtown

$739,000

4 Beds ⋅ 4 Baths ⋅ 24174060 MLS

Set on a picturesque 2.23 acre lot at the end of a quiet cul-de-sac, this 4 bedroom Colonial offers a flexible layout for entertaining and everyday living. Main level features Living Room, formal Dining Room, a spacious light filled Kitchen with newer appliances opens to an adjoining sitting area ideal for a reading nook, home office or casual gathering space. The large light filled Family Room boosts a vaulted ceiling, huge brick Fireplace and access to a charming 4-Season Room. From here step out to a 50-foot mahogany deck that hugs the entire rear of the house and looks out on preserved park land with stone walls. This exceptional setting provides long term privacy. Fully finished walkout Adirondack style basement with full bath, workshop, gas log fireplace has many possibilities (In-law setup, man cave). 2nd floor you will find 4 spacious bedrooms, 2 full baths & the convenience of a dedicated laundry area. Abundant parking provides ample space for multiple vehicles and recreational equipment. Enjoy the space and privacy at this premium location. O' yes we forgot to mention walk to Ferris Creamery!!

17 Sweet Meadow Rd, Newtown

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