Head of Meadow Real Estate

Welcome to the enchanting neighborhood of Head of Meadow, nestled in the picturesque town of Newtown, Connecticut. This charming enclave is part of Fairfield County, where the serene beauty of nature meets the warmth of community living. Head of Meadow is known for its idyllic surroundings, featuring lush green spaces, scenic trails, and tranquil ponds that invite residents to embrace the great outdoors.

One of the standout features of Head of Meadow is its family-friendly atmosphere, making it an ideal place for families to grow and thrive. The neighborhood boasts a close-knit community spirit, where neighbors know each other by name and often gather for seasonal events and celebrations. Children can be seen playing in the yards, riding bikes along the quiet streets, and forming lifelong friendships.

Convenience is key in Head of Meadow, with easy access to Newtown's vibrant downtown area, where charming shops, delightful eateries, and essential services are just a short drive away. For those who appreciate a touch of history, Newtown offers a rich tapestry of cultural heritage, with historical landmarks and museums that tell the story of this quaint town.

Education is a priority in Head of Meadow, as it is served by Newtown's highly regarded school district, ensuring that children receive a top-notch education. With its combination of natural beauty, strong community ties, and excellent amenities, Head of Meadow is more than just a neighborhood; it's a place to call home. Come explore the magic of Head of Meadow and discover why so many have chosen to make this charming community their own.

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

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.