Grassy Hill Homes for Sale

Grassy Hill Homes for Sale

Welcome to Grassy Hill, a hidden gem nestled in the picturesque town of Woodbury, Connecticut. This charming neighborhood is part of Litchfield County and offers a delightful blend of serene landscapes and vibrant community life. Known for its rolling hills, lush greenery, and stunning views, Grassy Hill is the perfect place for those seeking a tranquil retreat while still enjoying easy access to urban amenities.

Grassy Hill boasts a rich history and a strong sense of community, making it an ideal location for families and individuals alike. The area is characterized by its beautiful homes, many of which feature classic New England architecture, spacious yards, and modern amenities. Whether you’re looking for a cozy cottage or a sprawling estate, there’s something for everyone in this inviting neighborhood.

Residents of Grassy Hill enjoy a plethora of outdoor activities, from hiking and biking along scenic trails to relaxing in local parks. The community is also known for its excellent schools, making it a great choice for families. With a charming downtown area filled with boutique shops, cafes, and restaurants, you’ll find plenty of opportunities to connect with neighbors and enjoy the local culture.

If you’re considering a move to this enchanting neighborhood, now is the perfect time to explore the homes for sale in Grassy Hill. With a variety of options available, you can find the perfect place to call home in this idyllic setting. Experience the warmth and charm of Grassy Hill, where community spirit meets natural beauty. Discover your dream home today!

Newest Grassy Hill Homes for Sale

323 Upper Grassy Hill, Woodbury
$574,900
3 Beds ⋅ 3 Baths ⋅ 24200605 MLS
A Fresh Look at a Home with So Much Flexibility! Come take a look at this versatile and beautifully maintained home, where generous living spaces and unexpected possibilities give you room to make it your own. The first floor offers a wonderful layout with a comfortable living room, spacious great room, and separate dining room, creating plenty of flexibility for everyday living and entertaining. The kitchen has been thoughtfully updated, from the main living spaces, step outside onto the deck - a natural extension of the home for relaxing, dining, or enjoying the outdoors. Upstairs, you'll find generously sized bedrooms with the space and comfort today's buyers are looking for. But the real surprise is downstairs. The walk-out lower level offers even more usable space, including a large room currently used as a workout area and another area that can serve as storage, recreation space, or additional living space. Step outside to the screened-in deck, adding another terrific spot to enjoy the property. And for those looking for flexibility, the large lower-level room has its own separate entrance and offers intriguing potential to create a private studio or guest suite with the addition of a kitchen and bathroom. Whether you envision a home office, gym, creative studio, guest quarters, or future additional living space, the possibilities are here. Turn-key, versatile, and full of potential - this is a home that can adapt to the way you live. Come see!

323 Upper Grassy Hill, Woodbury

261-1 Grassy Hill Rd, Lyme
$1,595,000
6 Beds ⋅ 6 Baths ⋅ 24185580 MLS
Privately sited on more than 10 picturesque acres, this special country retreat offers a rare blend of architectural distinction, refined comfort, and effortless indoor-outdoor living. Surrounded by pastoral vistas, the property provides a remarkable sense of privacy. The home is filled with light and character. High ceilings, expansive walls of glass, and beautifully proportioned living spaces create an atmosphere that is both sophisticated and welcoming. The stunning great room serves as the heart of the home, where French doors open to sweeping views and seamlessly connect the interior to the patio for alfresco dining & long lazy days outside. A main-level primary suite offers convenience, allowing for easy single-level living. The well-appointed kitchen flows effortlessly into gathering and dining spaces, making everyday living and entertaining equally enjoyable. A charming, screened porch provides the perfect setting for morning coffee, summer dinners, or quiet evenings overlooking the grounds. Multiple doors and windows frame beautiful views in every direction, bringing the landscape into the home year-round. Complementing the residence is a barn offering endless possibilities. Whether utilized for equestrian pursuits, livestock, hobbies, vehicle storage, or a workshop, the barn enhances the property. A truly special country retreat where timeless design, natural beauty, and the lifestyle of a gentleman's farm come together in perfect harmony.

261-1 Grassy Hill Rd, Lyme

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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.

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