TL;DR

• 3 bedrooms, 4.5 bathrooms
• 3,180 total sq ft
• 2.61-acre secluded lot
• Brazilian teak deck installed in 2021
• Finished lower level with wet bar and full bath
• Hardwood floors throughout main living areas and bedrooms
• Two-story foyer and flexible layout
• Listed at $599,900
• Ideal for buyers looking for space, privacy, and updated entertaining areas

Overview of the Home

Located at 29 Chestnut Hill Rd in Hebron, CT, this beautifully maintained Colonial offers a combination of spacious living, thoughtful updates, and exceptional functionality. Set on a secluded 2.61-acre lot, the property provides privacy while still being conveniently located near local amenities, parks, and commuter routes.

Inside, the home features over 3,100 square feet of living space with hardwood floors throughout the main living areas and bedrooms. A stunning two-story foyer creates an impressive first impression, while the flexible floor plan is designed to accommodate both everyday living and entertaining.

The kitchen is equipped with granite countertops, double wall ovens, a wine chiller, pantry storage, and a slider leading directly to the Brazilian teak deck installed in 2021. Just off the kitchen, the mudroom includes a convenient laundry area for added functionality.

Upstairs, all bedrooms feature walk-in closets, with two bedrooms offering private ensuite full baths. The spacious primary suite includes a soaking tub, custom tile, and a remodeled bathroom designed for comfort and relaxation.

The finished lower level expands the home’s living space even further with a large wet bar, full bath, storage area, and flexible recreation space ideal for entertaining, a home theater, gym, or guest area.

Outside, the backyard has been designed for enjoying all seasons with a pergola featuring built-in swings, a fire pit area, and plenty of open space surrounded by lightly wooded privacy.

Key Features of This Property

• 3 bedrooms, 4 full baths, 1 half bath
• 3,180 total square feet
• 2.61-acre secluded lot
• Hardwood floors throughout main living areas and bedrooms
• Two-story foyer
• Spacious primary suite with soaking tub and custom tile
• Walk-in closets in all bedrooms
• Two ensuite bedrooms
• Private office with built-ins, French doors, and barn door
• Granite countertops
• Double wall ovens
• Wine chiller
• Pantry storage
• Brazilian teak deck installed in 2021
• Finished lower level with wet bar and full bath
• Pergola with built-in swings
• Fire pit area
• Attached 2-car garage
• Central air conditioning
• Floored attic storage
• Shed for additional outdoor storage

What Makes This Home Stand Out

What separates this home from others in Hebron is its balance of size, flexibility, and entertaining space.

Many buyers today are searching for homes that offer both practical daily living and room to host family and friends. This property delivers that with multiple gathering spaces, a finished lower level, and a backyard designed for entertaining.

The private office setup is another standout feature, especially for buyers working remotely. With built-ins, French doors, and additional privacy from the barn door, it creates a true dedicated workspace rather than simply using a spare bedroom.

Additionally, the Brazilian teak deck, pergola with swings, and fire pit area create outdoor living spaces that feel intentional and inviting—perfect for relaxing evenings or hosting guests.

For buyers searching for homes for sale in Hebron, CT that combine modern updates, storage, and flexible living space, 29 Chestnut Hill Rd offers a rare opportunity.

Location: Living in Hebron, CT

Hebron is known for its rural New England charm, scenic roads, and strong sense of community. Residents enjoy access to local parks, golf courses, walking trails, and nearby recreational opportunities while still being within commuting distance to Hartford and other surrounding towns.

The home is located within the RHAM school district and is serviced by Gilead Hill School, Hebron Elementary, and RHAM Middle and High School.

For buyers looking for more privacy, larger lots, and a quieter lifestyle while remaining connected to everyday conveniences, Hebron continues to be one of eastern Connecticut’s most desirable towns.

Who This Home Is Perfect For

This home is ideal for:

• Buyers looking for more living space and privacy
• Families needing multiple ensuite bedrooms
• Remote professionals seeking a dedicated home office
• Buyers who love entertaining indoors and outdoors
• Homeowners wanting a finished lower level for recreation or guests
• Buyers searching for updated homes on acreage in Hebron, CT
• Anyone looking for a move-in ready Colonial with flexible living space

Schedule a Showing

Call or text 860-452-3153 to schedule a private showing or get more information.

FAQ Section

What is the listing price for 29 Chestnut Hill Rd in Hebron, CT?
The home is listed at $599,900.

How much land does the property include?
The property sits on a secluded 2.61-acre lot.

Does the home have a finished basement?
Yes. The finished lower level includes a wet bar, full bathroom, storage area, and flexible recreation space.

What updates have been completed on the home?
The home includes a Brazilian teak deck installed in 2021, updated bathrooms, hardwood floors, and numerous thoughtful improvements throughout.

Does the home have space for working remotely?
Yes. The home features a dedicated office with built-ins, French doors, and additional privacy features ideal for remote work.

About the Author

Jason Boice is a REALTOR® with eXp Realty serving Hebron, Andover, Marlborough, Colchester, East Hampton, Tolland, and surrounding Connecticut towns. He helps homeowners sell with clear strategies, strong negotiation, and a process designed to reduce stress while maximizing results.

If you’re thinking about selling your home in Hebron or the surrounding area, Jason offers a no-pressure home value and strategy consultation so you can understand your options before making a decision. Call or text 860-452-3153 to get started.