Head of Meadow Homes for Sale

Welcome to Head of Meadow, an enchanting neighborhood nestled in the picturesque town of Newtown, Connecticut. This charming enclave, located in Fairfield County, offers a perfect blend of suburban tranquility and vibrant community spirit. Known for its lush landscapes and friendly atmosphere, Head of Meadow is an ideal place for families, professionals, and anyone seeking a serene lifestyle without sacrificing convenience.

The neighborhood boasts a variety of homes for sale, each exuding unique character and charm. From spacious single-family residences to cozy townhouses, there’s something to suit every taste and budget. Many of these homes feature modern amenities and expansive yards, perfect for outdoor gatherings or simply enjoying the natural beauty that surrounds you. With an emphasis on community and family-oriented living, Head of Meadow is home to several parks, walking trails, and recreational facilities, encouraging an active lifestyle for residents of all ages.

Education is a cornerstone of this community, with highly-rated schools in close proximity, ensuring that your children receive the best possible education. Additionally, the neighborhood’s convenient location allows for easy access to shopping, dining, and entertainment options in downtown Newtown and beyond.

If you’re searching for a welcoming community with an array of homes for sale, Head of Meadow is the perfect place to call home. Discover the charm and warmth of this delightful neighborhood and envision your future in this idyllic setting. Explore the available listings today and take the first step toward your new life in Head of Meadow!

Newest Head of Meadow Homes for Sale

$875,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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