Head of Meadow Real Estate

Welcome to Head of Meadow, a charming neighborhood nestled in the heart of Newtown, Connecticut. Known for its serene surroundings and family-friendly atmosphere, Head of Meadow offers a perfect blend of suburban tranquility and modern convenience. This picturesque community is characterized by its beautiful tree-lined streets, spacious lots, and a variety of architectural styles that create a welcoming ambiance.

Residents of Head of Meadow enjoy easy access to a wealth of outdoor activities, thanks to the nearby parks and nature reserves. The area boasts numerous hiking trails, playgrounds, and picnic spots, making it an ideal place for families and nature enthusiasts alike. The neighborhood’s close-knit community spirit is evident through various local events and gatherings that foster connections among neighbors.

In addition to its natural beauty, Head of Meadow is conveniently located near Newtown's vibrant town center, where you can explore a delightful mix of boutique shops, cafes, and restaurants. The local school district is highly regarded, providing excellent educational opportunities for children of all ages. With a strong commitment to community involvement and a focus on quality of life, residents take pride in their neighborhood.

For those commuting to nearby cities, Head of Meadow offers easy access to major highways, making it an attractive option for professionals seeking a peaceful retreat after a busy day. Whether you're looking for your first home or a place to settle down, Head of Meadow is a delightful neighborhood that truly feels like home. Discover the charm and warmth of this wonderful community today!

Newest Listings in Head of Meadow

$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

$639,000

4 Beds ⋅ 3 Baths ⋅ 24178529 MLS

New England Classic Center Hall Colonial offers mid century character on 1.67 pristine parklike acres in desirable walking neighborhood. Inviting center hall foyer flows into the Charming living room w/custom built in bookcases & wood burning fireplace. Spacious formal dining room for all to gather. French doors to family room/den. Cheerful Eat in kitchen has walk in pantry, double ovens, Bosch dishwasher with plenty of granite counter space overlooking stunning yard. Main level library has thoughtful craftmanship w/custom built in bookcases next to the full bath. Escape to upper level primary bedroom with 2 closets and half bath. 3 additional bedrooms and full bath. Many Updates to include Newer Anderson windows throughout, 200 amp electrical service, Reliable whole house generator, newer oil tank in basement 2023. Workshop in lower level. Beautiful original oak hardwood floors throughout. Escape to the parklike level yard w/ beautiful perennial gardens abound. Garden shed. Attached garage-entry from exterior. Ideal sought after Head o Meadow western location, minutes to downtown Newtown, shops, restaurants, park, library, schools. Great commute location.

39 Boggs Hill Rd, Newtown

$499,000

3 Beds ⋅ 2 Baths ⋅ 24190351 MLS

**Multiple offers - highest and best due Monday 8 PM**. Welcome home to this 3-bedroom, 2-bath ranch set on a desirable corner lot with a private in-ground pool-perfect for summer entertaining! Hardwood floors run throughout the home, except in the kitchen and bathrooms. The updated kitchen features granite countertops, stainless steel appliances, and a casual dining area and opens directly to a comfortable family room with sliding doors leading to the expansive rear deck overlooking the pool and backyard. The spacious formal living room is filled with natural light from a beautiful bow window and features a classic wood-burning fireplace, while the formal dining room offers the perfect setting for holidays and gatherings and conveniently connects to both the foyer and kitchen. The primary suite is privately situated at the end of the hallway and includes its own full bath. Two additional bedrooms and a beautifully updated hall bath complete the main level. The full unfinished basement provides abundant storage, a dedicated laundry area, and direct access to the attached two-car garage. Enjoy your morning coffee or unwind in the evening from the inviting covered front porch. Ideally located and move-in ready, this exceptional home offers comfort, space, and timeless appeal both inside and out.

22 Ridge 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

$824,900

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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