Hebron Real Estate

**Discover the Charm of Hebron, Connecticut**

Nestled in the picturesque Tolland County, Hebron, Connecticut, is a hidden gem that beautifully marries rural charm with modern convenience. Known for its rich history and vibrant community spirit, this lovely town offers a serene escape from the hustle and bustle of city life while keeping you well-connected to nearby urban centers.

Hebron boasts an array of stunning landscapes, featuring rolling hills, lush forests, and tranquil lakes that invite outdoor enthusiasts to explore. Whether you're hiking the scenic trails of the nearby Gay City State Park or enjoying a leisurely afternoon at Lake Williams, there’s no shortage of natural beauty to appreciate. The town is also home to several charming farms, where residents can enjoy fresh produce and seasonal events, fostering a strong sense of community.

The heart of Hebron is its welcoming downtown area, filled with quaint shops, delightful eateries, and local businesses that reflect the town’s unique character. The annual Hebron Harvest Fair is a highlight of the calendar, celebrating the town's agricultural roots and bringing residents together for a weekend of fun, food, and festivities.

Families will appreciate the excellent school system, which is dedicated to providing quality education and fostering a supportive environment for students. With its friendly neighborhoods and strong community values, Hebron is an ideal place to raise a family or enjoy a peaceful retirement.

Experience the best of small-town living in Hebron, where every day feels like a breath of fresh air. Come and discover why so many are proud to call this charming town home!

Newest Listings in Hebron

$2,375,000

24195914 MLS

THIS LISTING IS AN OFFERING OF THE REAL PROPERTY AND SITE IMPROVEMENTS KNOWN AS 14-16 Main Street, Hebron CT ONLY. NO PART OF THE FLOUR GIRL BAKERY, LLC, OPERATIONS BUSINESS, OR THEIR LEASHOLD FIXTURES IN MADE A PART OF THIS OFFERING. This is a mixed use commercial and residential use complex consisting of 3 Free Standing Buildings with 3 Commercially lease space occupied by of the Flour Girl Bakery, Floor Girl Restaurant, and an Event/Function Space. The balance of the leased spaces consists of 4 Residential Apartment 1 and 2 BR Units. This incredible complex situated in the Hebron Green District has become the heart of "Hebron Center"! The location in the heart of HG district with its "billboard" visibility and high traffic count has a constant vibrant flow of daily visitors to amazingly planned combination of restored antique and new build post and beam structures! Renovations and New Construction undertaken in the Period of 2021 to Late 2025 offers genuinely well planned modern space with newer mechanicals serviced by public water, public sewer, and natural gas! Great site access by pedestrians from a grid work of public sidewalks with plenty of parking from both on-site and shared proximal public parking areas.

14-16 Main St, Hebron

$399,900

4 Beds ⋅ 2 Baths ⋅ 24195802 MLS

Ready to move in 4 bed/2 full bath colonial in a quiet neighborhood in Hebron! This home has been well maintained and has several new updates, including a newer roof, new flooring in several parts of the home, and a newer boiler. The first floor layout includes 2 bedrooms, a full bath, a living room and additional space that can be used as an additional seating area or office space, and the kitchen. On the 2nd level you have two more bedrooms, a full bath, and a extra space that can be used as a laundry room, office area, or a playroom! Home also features an enclosed porch that leads to a back deck, a spacious flat yard, a 1 car garage, and a workspace in the basement. Come and see this one today!

53 Jan Dr, Hebron

$549,000

3 Beds ⋅ 3 Baths ⋅ 24193742 MLS

Nestled on a quiet cul-de-sac in one of Hebron's most desirable neighborhoods, this beautifully maintained Cape offers timeless New England charm, exceptional versatility, and an abundance of natural light that fills every room. Thoughtfully designed for today's lifestyle, the home combines classic character with comfortable, flexible living spaces that adapt beautifully to the way you live. The gracious living room welcomes you with gleaming hardwood floors and a handsome fireplace, creating an inviting space for quiet evenings, holiday gatherings, or simply relaxing with family and friends. At the heart of the home is a beautifully appointed kitchen featuring stainless steel appliances, granite countertops, an expansive center island with seating, and generous workspace. Whether you're enjoying a quiet breakfast, preparing everyday meals, or hosting family celebrations, this warm and inviting space naturally brings everyone together. The adjoining formal dining room, accented by wood flooring and a generous pass-through from the kitchen, is perfectly suited for everything from intimate dinners to festive holiday celebrations. A first-floor office provides exceptional flexibility and can easily serve as a library, den, guest room, or formal dining room as your needs evolve.

87 Windrush Ln, Hebron

$549,900

4 Beds ⋅ 3 Baths ⋅ 24192721 MLS

Joshua Farms Subdivison-2330 SF, 9 Room,4 BR, 2.5 Bath Colonial with 3 bay garage offering 1.24 acre site abutting a Town owned Open Space Conservation area providing for a peaceful blend of a private yet neighborly location. This home's first floor plan has a remodeled kitchen with maple cabinetworks, granite counter w/tile back splash, butcher block food prep island, tile floor, and with a full complement of appliances with an adjoining formal dining room with wide pine flooring! A spacious front to back living room is appointed with a brick masonry fireplace with a pellet stove insert, carpeted flooring, crown molding, French doors leading to a private rear 30'x14' open sun deck. Additionally, there is a first floor family room with fieldstone fireplace, hardwood floors, and 9' ceilings-PLUS beautiful four season sunroom with property views and a second access to the 30'x14' private rear sun deck. Also, the first floor plan offers a remodeled half bath. The second floor is arranged with four bedrooms including a primary bedroom with walk in closet, remodeled full bath with walk in shower. The additoinal bedrooms all have center hallway access to a second remodeled full bath with tub/shower! The unfinished lower level offers potential to finish into living space. A new heat pump system was added in 11/2025, Bathroom-kitchen-window replacements in 2011! Close to local service and amenities! EZ Commuter location to Hartford, Manchester, Norwich, Willimantic, ECSU, and UCONN!

109 Cannon Dr, Hebron

$649,900

3 Beds ⋅ 2 Baths ⋅ 24193385 MLS

A rare opportunity to own 84 acres of privacy, natural beauty, and endless possibilities in Hebron! This unique property offers an incredible setting complete with a charming Christmas tree farm, private pond, barn, shed, and woodshed. With expansive acreage to explore, there is plenty of room for riding quads, outdoor recreation, hobbies, or simply enjoying the peace and privacy of your own surroundings. The 3-bedroom, 2-full-bath home features an updated kitchen with granite countertops and a versatile multi-purpose room just off the kitchen, that could serve as a first floor bedroom. The oversized primary bedroom offers additional flex space ideal for a sitting area, office, exercise space, or whatever best fits your needs. Enjoy the outdoors from the screened-in porch or relax and entertain on the patio while taking in the peaceful setting. An oil and wood-burning furnace provides heating options, while the multiple outbuildings offer valuable space for equipment, storage, and hobbies. More than a home, this is a truly special opportunity to own 84 acres in Hebron with exceptional privacy, versatility, and room to enjoy the outdoors.

559 East St, Hebron

$599,900

3 Beds ⋅ 2 Baths ⋅ 24193967 MLS

Built in 1750, this beautifully updated & meticulously maintained historic antique Colonial blends timeless character with modern comfort. Rich wide-board floors and classic 12-over-12 windows highlight its heritage, complemented by four fireplaces throughout the home. The inviting kitchen features granite countertops, custom cabinetry, a wood stove, and abundant natural light from multiple windows and a sliding door leading to the patio-perfect for everyday living & entertaining. A charming library with custom built-ins sits just off the kitchen, offering a cozy and functional retreat. Features a first floor bedroom.Both the living and dining rooms showcase impressive fireplaces with updated liners, enhancing both style and efficiency. Two staircases provide convenient access to the second floor, where you'll find two spacious bedrooms, a beautifully remodeled full bath, and an additional room ideal for a nursery. An open landing area between the bedrooms offers flexible space for a home office or playroom. New asphalt roof installed May 2026. New well pipe from well house to house installed Summer 2026. Set on 3.8 acres of rolling, usable land, the property also features a new driveway, an expansive three-car garage with a loft workshop-perfect for hobbies, storage, or creative pursuits, a barn and a well house. A rare opportunity to own a thoughtfully preserved historic home with modern updates in a serene setting. Please do not drive up the driveway without an appointmen

355 Wall St, Hebron

$609,900

4 Beds ⋅ 3 Baths ⋅ 24193809 MLS

This dynamic oversized New England Cape at 23 Pepperbush Drive in Hebron, Connecticut, is beautifully situated on 1.42 acres of level land on a quiet cul-de-sac in a highly sought-after neighborhood. This exceptional property offers outstanding curb appeal, including a very appealing front porch, and a private, expansive backyard ideal for recreation and entertaining. Inside, hardwood floors and abundant natural light enhance a thoughtfully designed layout. The updated kitchen is both stylish and functional, featuring a propane cooktop, double wall ovens, wine refrigerator, and ample prep space. A partially finished basement adds versatility for a home office, gym, or recreation area. The upper level includes a spacious primary suite with a large en suite bath, walk-in closet, and the convenience of second-floor laundry. Recent upgrades include a newer furnace, central AC, roof, and a septic system serviced in May 2026. Additional features include central vacuum, generator hookup, a two-car attached garage with endless possibilities, and a storage shed.

23 Pepperbush Dr, Hebron

$569,000

3 Beds ⋅ 4 Baths ⋅ 24189092 MLS

Welcome to this beautifully maintained and extensively updated 3-bedroom, 3.5-bath home offering timeless charm, modern upgrades, and exceptional comfort. The inviting exterior features gorgeous new vinyl siding and a covered front porch, perfect for relaxing outdoors. Inside, this expanded Cape offers a spacious layout with an open kitchen featuring newer stainless-steel appliances and a convenient eat-in area. The adjoining formal dining room, perfect for entertaining, flows into a stunning cathedral-ceiling living area with floor-to-ceiling windows, providing beautiful views of every season. A cozy front den with a fireplace provides additional living space and the first-floor additional living area with exterior access and a private full bath offers excellent potential as an in-law suite or flexible guest space. Upstairs you'll find three spacious bedrooms, a loft, and abundant storage/closet space. Major updates provide exceptional peace of mind, including a new roof (2025), siding/gutters/gutter guards (2025), new oil tank (2022), boiler (2023), hot water system (2023), professionally rebuilt chimneys (2024), updated lighting, fresh interior paint, generator hook-up, a custom pest prevention system (2022), and radon filtration system (2022). With generous living spaces, thoughtful improvements, and major systems already updated, this move-in-ready home offers the perfect blend of character and contemporary living. Don't miss this exceptional opportunity

75 Millstream Rd, Hebron

$439,900

2 Beds ⋅ 2 Baths ⋅ 24186944 MLS

TUCKED AWAY ON NEARLY 4 PRIVATE ACRES, THIS LOG CABIN OFFERS THE PERFECT BLEND OF PEACEFUL COUNTRY LIVING AND CONVENIENCE. RELAX ON THE SPACIOUS DECK OVERLOOKING THE BEAUTIFUL PROPERTY AND ENJOY THE PRIVACY OF YOUR OWN RETREAT. INSIDE, YOU'LL WILL FIND STUNNING STONE FIREPLACE THAT SERVES AS THE CENTERPIECE OF THE LIVING AREA. THE MAIN LEVEL FEATURES TWO BEDROOMS AND A FULL BATH, WHILE THE UPPER LEVEL OFFERS A THIRD BEDROOM PLUS AN ADDITIONAL ROOM THAT CAN BE USED A HOME OFFICE, OR LOFT. THE LOWER LEVEL INCLUDES ADDITIONAL HEATED SPACE PROVIDING FOR A FAMILY ROOM OR RECREATION AREA. ENJOY THE SERENITY OF A PRIVATE SETTING WHILE REMAINING CLOSE TO SHOPPING, DINING AND EVERYDAY AMENITIES. HOME IS IN GOOD CONDITION, SELLER PREFER TO SELL AS IS. WELL HAS BRAND NEW PUMP, WATER LINES AND ELECTRICAL. HOME HAS ALL NEW HIGH PRESSURE TOILETS.

446 W Main St, Hebron

$765,000

4 Beds ⋅ 3 Baths ⋅ 24185882 MLS

Introducing a beautiful new construction Colonial to be built on a fully approved, shovel-ready homesite in one of Hebron's most desirable locations. This thoughtfully designed home will feature 9-foot ceilings, an open-concept layout, a stunning kitchen with quartz/granite countertops, stainless steel appliances, tile backsplash, solid oak hardwood flooring, a sunroom, rear patio, full basement, and a spacious 2-car garage. With 4 bedrooms, 2.5 baths, a dedicated home office, and quality craftsmanship throughout, this home offers the perfect blend of style, comfort, and functionality. Best of all, there may be opportunities to customize finishes and upgrades before construction begins, allowing you to create a home that truly reflects your vision. Situated on a fully approved homesite with picturesque sunset views, a historic stone wall, and a private building envelope set back from the road, you'll enjoy the peace and charm of country living while remaining conveniently located just minutes from downtown Hebron, Blackledge Country Club, Tallwood Country Club, hiking trails, and only 25 minutes from Hartford. Build the home you've been waiting for and enjoy the best of New England living with modern amenities, energy efficiency, and low-maintenance construction.

3 Hall Rd, Hebron

$130,000

24185844 MLS

FULLY APPROVED and READY for your FOREVER home!! This location is shovel ready and waiting for YOU to build. Historic stone wall along the east side of the parcel, and the sunset views from this home site will be incredible!!! Proximity is ideal for commuters just 25 minutes from Hartford. Seconds away from the coveted Blackledge Country Club and Tall Woods golf courses and driving range, and within a 15 minute ride to downtown Glastonbury or 5 minutes from downtown Hebron. There are numerous hiking trails nearby. Just a few minutes of the Hebron Harvest Fair grounds, Hebron's largest annual event. The town of Hebron with its expanding historic downtown offers quiet New England charm with modern amenities. This site is suitable for a 4 bedroom home, 2.5 bath, 2 car garage and will be built on the interior portion of the lot, limiting any road noise, or neighbors. Enjoy privacy, nature, and build the home you've been waiting for.

3 Hall Rd, Hebron

$624,900

3 Beds ⋅ 4 Baths ⋅ 24186125 MLS

Fantastic Home that has space for everyone. With three bedrooms and a bonus room above the garage, a Den, eat in kitchen and Dining Room, there is no shortage of space.

389 Old Colchester Rd, Hebron

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