Middlebury CT Real Estate & Homes for Sale

Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

Fantastic business opportunity awaits you to own and operate a highly successful recreational club. Presenting the Edgewood Bath and Tennis Club, complete with a state-of-the-art fitness center, newly installed paddle courts, a playground, basketball courts, 5 tennis courts, 6 pickleball courts, and a beach volleyball area. Situated in the heart of Middlebury, just minutes away from exit 16 on I84, this pristine club spans over 10 acres of commercially zoned land, offering ample room for expansion and the potential for year-round operation. This is a rare chance to acquire a Swim and Tennis Club that boasts an impressive $4 million in capital improvements and has been impeccably maintained throughout the years. Enhance the building's square footage to accommodate additional recreational activities, introduce a seasonal bubble over the tennis courts for winter play, or consider adding a golf simulator to diversify revenue streams. Recent upgrades include resurfaced tennis and pickleball courts, a town permit for winterizing the back three tennis courts, enabling year-round usage, and the acquisition of a liquor license, simplifying event catering. The possibilities are endless for this turn-key business. Explore the option of a 2 to 5-year Lease-to-Buy arrangement with a substantial nonrefundable upfront deposit. Contact us for more details and make your dream of owning a thriving recreational club a reality.

Discover your dream home in a sought-after area! This newly constructed gem boasts 4500 sqft of open floor plan living, offering 10 spacious rooms, including 4 bedrooms and 3.5 bathrooms. The heart of this home is a stunning great room featuring cathedral ceilings and a gas fireplace that stretches to the ceiling. The expansive kitchen is a chef's delight, complete with quartz countertops, a generous island, stainless steel range, double oven, microwave, dishwasher, and a convenient wine chiller. The first floor also offers a den and an office, providing flexible spaces to suit your lifestyle. Beautiful hardwood flooring flows seamlessly throughout the house, adding elegance and warmth. Upstairs, the primary bedroom is a luxurious retreat with a full bath featuring a soaking tub, large shower, and two walk-in closets. The second bedroom also boasts a walk-in closet and a full tub/shower. Two additional bedrooms and another full bath upstairs provide comfort and convenience. The laundry room is exceptionally spacious, simplifying daily chores. Need more living space? The upstairs family room, located above the 3-car garage, offers endless possibilities—a perfect game room or home theatre. The walk-out basement offers the potential for additional living space to accommodate your unique needs. This magnificent home will be ready for you just in time for the holidays—seize this opportunity to make your move and embrace the lifestyle you've always wanted. Your dream home awaits!

The most adorable home with many updates. Freshly painted inside and out, updated kitchen with granite counters, new flooring and stainless appliances, new propane line for the stove. There are also refinished hardwood floors up and down, plus updated electrical service and generator hook up. Great deck, relaxing side yard with firepit and lots of pretty landscaping. Conveniently located for commuting, shopping and a few restaurants within walking distance. On the upper level you will find three bedrooms with full bath and walk-in storage closet. Main level has a living room with fireplace, dining room, updated kitchen, 1/2 bath and office area which leads to the deck. Come see all this adorable home has to offer and also comes with a 1-year home warranty. Located in the beautiful town of Middlebury Connecticut, with Region 15 schools, great shops, restaurants, parks & walking trails. The bottom portion of the driveway belongs to the neighbor with a right away granted and a maintenance agreement to split the costs of expenses and plowing will be on file, the garage at the bottom of driveway belongs to the neighbor's.

Come enjoy a unique, elegant, old-world experience designed with artful accents and architectural accentuations throughout. The grand sweeping foyer with porcelain & marble tile flooring, the curved custom stairway, and the 20’ ceiling mirrors that of the grande European Manors. The authentic reproduction of the French porcelain flooring, coupled with multiple French & English influences elevates this estate home to a level of art and elegance. The splendid formal living room boasts a circa 1776 antique French chestnut mantel accenting a hand-built limestone fireplace. The 12’ ceilings with hand-sculptured beams magnify the exhilarating sense of space felt throughout this stunning manor. The striking conservatory encompassed by a dynamic amount of glass illuminates the blue stone floors and brick trim. A focus point of the elegant dining room is the double-tier octagonal tray ceiling along with the custom hand-painted stencils continued from the living room through to the kitchen. The flow of the living space extends out onto the blue stone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The captivating French country kitchen equipped with custom cabinets, high-end appliances, center island breakfast bar continues to provide a great space for entertaining and relaxing. Completing the first floor are the walnut-paneled Library, office, a huge cedar-clad porch, and the expansive Master Suite. Continued in public remarks.

Lake front home in Middlebury on gorgeous Lake Quassapaug! The very special home that you have been waiting for. An architectural beauty, this stone and shingle home has direct waterfrontage on pristine Lake Quassapaug! Improved with care so that the natural beauty of this home has not been compromised. You will love the bead board walls and ceilings along with hardwood floors and a gorgeous stone fireplace. The combination living/dining room faces the lake and features a corner fireplace (propane). Kitchen has been updated. Enjoy your morning coffee on the spacious front porch overlooking the sparkling water of the lake. This house has its own well and septic. This house is on leased land with approximately 70 years left on the pre paid lease.

Ridgewood Ranch - Bethal model. Surrounded on 2 sides by trees, unit offers 1st floor primary suite, with handicap features in bath. 2nd bedroom can be den, third bedroom in lower level with 1/2 bath. Separate laundry room and powder room on main floor. Airy kitchen with SS appliances opens to living room, with fireplace, sky lights leading to private deck. This rare end unit offers privacy and many extras. Room for expansion in lower level. Come see the pool. theater, workout room, game room and more. Photos are from owner. Tenant is moving out slowly.

Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds!

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is to be built and will be a 2400+ sq ft 4 bedroom colonial. Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

This remarkable condo offers a lifestyle of comfort and convenience, along with an array of features that elevate your lifestyle Step inside this condo, and you'll immediately notice the upgrades that make it stand out. The condo is designed for modern living, offering a well-appointed kitchen with stainless steel appliances, an island, and plenty of counter space and storage. The open layout seamlessly connects the living room, dining area, and kitchen, creating a functional space ideal for both entertaining and daily living. In the living room, you'll discover a welcoming fireplace that adds both warmth and ambiance. The primary suite offers a comfortable retreat with a full bathroom with double vanities—a perfect place to unwind and recharge after a long day. The additional two bedrooms are equally inviting, giving cozy spaces for family members or guests. The finished walkout basement offers great potential for creating additional living space, whether it's a cozy retreat, a home office, or an entertainment area. Slider doors bring in ample natural light and provide easy access to the backyard, making it a versatile and inviting area. Beyond your doorstep, you'll discover a wealth of community amenities. Dive into the pool for a refreshing swim, gather with friends at the clubhouse, shoot hoops at the basketball court, or watch your kids play at the playground. The possibilities are endless.

Prepare to be Wowed as you step into a world of sophistication and comfort in this fully updated Colonial home, complete with a 1-car garage. The main level welcomes you with an open floor plan that seamlessly integrates the kitchen, living, and dining spaces, all adorned with stunning hardwood flooring. The living room features a cozy wood-burning fireplace and an abundance of windows that flood the room with natural light, providing a warm and inviting atmosphere that extends into the dining area. The gourmet kitchen has been beautifully and thoughtfully renovated. A convenient back door from the kitchen opens up to a delightful deck overlooking the serene backyard. The main level is completed with a renovated full bath. The second level boasts two generously sized bedrooms and a full bathroom w/custom-built shower and a laundry room. The journey continues to the third level, where you'll find a third bedroom and another full bathroom, ensuring ample space and privacy. The partially finished basement presents a versatile bonus room that adapts to your needs, adding extra flexibility to the living spaces. The seller's dedication to excellence is evident in the extensive updates made both inside and out, including a captivating garden, the relocation of the laundry to the second floor, upgraded mechanical systems and appliances, custom window treatments, and luxurious high-end finishes throughout. Don't miss the opportunity to make this exceptional Colonial your dream home!

Desirable Steeplechase where you can live in a lovely community surrounded by natural beauty. This 2400+ s.f. standalone home offers lots of space for comfortable living and entertaining. The front porch leads to a generously sized entry and on to the spacious FLR w/ FP that opens to the dining room. The kitchen, with white cabinetry and granite counters, is open to the family room that leads to a lovely sun room with tile floor. You can enjoy every season from this charming home. A powder room completes the main level. On the second level, 3 generously sized bedrooms, including the primary suite with an enormous walk in closet. The laundry is conveniently located on the second level. You'll appreciate the 2 steps from the attached 2 car garage to the house as well as the amount of space in the full basement. This lovely community is just the place to enjoy life.(Not an age restricted community.)

Come and built your dream home and enjoy the peaceful town of Middlebury, a town where the charm of New England meets the convenience of modern living. This prime parcel of land presents a remarkable opportunity to become a part of this vibrant community. With its picturesque landscapes, rich history, and proximity to amenities, Middlebury offers the best of both worlds. The featured land boasts a gentle slope making it an ideal canvas for your dream home or investment. Enjoy the tranquility of the area while staying well-connected to one of the best school's systems in the state, shops, and recreational facilities. Embrace the allure of Middlebury and seize the chance to own a piece of its remarkable story that promises both serenity and creative freedom.

REDUCED!! Ultimate privacy in this 8 room, 3 bedroom, 4098 SF Middlebury colonial with a contemporary flair set on a 4.94 landscaped acre lot close to Lake Quassapaug. This beautiful home was a builder's personal home for almost 40 years! As you walk in, there is a 2 story foyer with a custom oak staircase! Home features 3 bedrooms with 3 1/2 baths. Main level office area with private entrance can be converted to another master bedroom! The home has a lovely flow with oversized rooms for all your family gatherings. Hardwood floors throughout. Kitchen with granite counter tops, double ovens, eating area and a woodstove. Garden room with windows galore and a propane fireplace. Formal living room has a custom floor to ceiling stone fireplace with a raised hearth, cathedral ceilings, and skylight. Primary master bedroom suite has sliders to a balcony, walk in cedar closet, marble countertops, walk in shower and a whirlpool tub! Other features include: main level laundry, central air, 2 oil tanks, 3 car garage, and a whole house generator. 90 miles from New York City, close to wonderful restaurants & the Middlebury Greenway. Welcome Home! Owner/Agent related.

Welcome home to this beautifully updated 3-bedroom, 2.5-bathroom ranch in a well-established, Middlebury neighborhood with easy access to highways and shopping. The vintage charm and tasteful updates are noticeable as soon as you step on the new tiled front entrance. Freshly painted, with wall wainscoting in hallway, kitchen, bathroom and lower-level family room. Hardwood floors throughout most of the home. Large spacious living room with a bay window. Dining room with a wood fireplace looking into the updated kitchen which features white shaker style soft close cabinetry, large island stainless steel appliances and quartz countertops. Off the kitchen is a new sizable pressure treated deck, perfect for entertaining and evening relaxation. Updated main level bathrooms with new tiled floors. Large Primary bedroom with updated half bath, and a laundry room. This home also features a lower-level heated family room with walk out and sliding doors to potential additional living space with a full bath complete with shower. Two car garage, newer roof, newer mechanicals, 200 AMP electrical service, public water/sewer and installing a new asphalt driveway in the next few weeks on .89 acres lot. Don’t miss the opportunity to call this beautiful property home! Call today to schedule a private showing.

A remarkable opportunity awaits you at 275 Burr Hall Road, Middlebury. Built in 2002 and privately set on 5+ acres in a most desirable subdivision of elegant homes, it was built with attention to detail and quality. This fabulous home is just loaded with extras. The chef/entertainer in you will appreciate not only the size of the custom kitchen, but also all that it has to offer, including granite counters, breakfast bar, Viking stove and a generously sized dining area with access to the lovely patio with pergola. It is open to the expansive family room with one of three fireplaces. Hardwood floors throughout. The second floor features four generously sized bedrooms and a large bonus room. Lower level finished 900+ sq. ft with full bath and walk out. Fitness buffs will love the private lap pool enclosed in a heated solarium. Two car attached plus 3 car detached garage has a finished second floor space, perfect for an exercise or yoga studio. Perfect location. 90 miles from NYC, 3 hours from Boston. Close to wonderful restaurants, beautiful Lake Quassapaug, hiking, biking and nearby golf courses.

Come view this beautiful bright and spacious Colonial located on an interior lot in Middlebury, CT! Home features 5 bedrooms with 3 full bathrooms. Features include a spacious Great room with over 800 sq feet of space, which is perfect to host any special occasion. The heart of this home, the eat-in kitchen which connects to Great room and Dining room, comes with wine cooler, granite countertops and stainless-steel appliances. Home features good sized Formal Dining room with crown molding perfect for holiday gatherings. Also, on the main level comes a formal living when you walk in from the main entrance. Main floor also features good sized bedroom with good closet space. Upstairs features primary bedroom with full bath that features a jacuzzi and walk in closet. Additional 3 spacious bedrooms with ample closet space and full bathroom finish off the upstairs. Hardwood floors throughout whole home and tile in the kitchen. Central Air throughout house. Attached 3 car garage with plenty of parking on long driveway. Surrounding beautiful stone walls compliment the home outside with beautiful walkway to front door. Unfinished basement would be perfect to make it your theater room, workout room, pool table room or just to add additional space. This home is a must see!! Owner/Agent related.

New construction designed to impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with majestic soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen and heart of the home has an expansive island, granite countertops, stainless steel appliances and white shaker style cabinets. A breakfast nook for informal dining has French doors leading to the back deck. A formal dining room for those special occasions rounds out the flow for ease of entertaining. A first-floor primary suite offers two walk-in closets and a luxurious bath with oversized shower and double vanities. The second level with two generously sized bedrooms share a Jack and Jill bathroom. For those working from home, home schooling or those desiring a quiet space for listening to music or relaxing with a good book will find a den tucked away on the first floor. All hardwood floors run throughout the main level. There is a first-floor laundry, mudroom, 2 car attached garage, c/a, underground utilities, underground sprinklers, private well and public sewer. This lot, with just over an acre, has limited seasonal views of Avalon Farms pond and is part of the Avalon Farms community. Photos used are similar to new construction; pictured lighting is not included. Floor plans, elevations and proposed site plan are attached.

Welcome to this charming raised ranch nestled on a spacious 7.2-acre lot, offering a canvas of possibilities for a variety of lifestyles. Boasting potential for livestock, providing ample space for enthusiasts to create their own mini-farmstead and with the opportunity for future construction or subdivision, this property opens doors to both immediate comfort and long-term investment. As you enter, you'll appreciate the thoughtful layout featuring three bedrooms and two full bathrooms, providing ample space for family and guests. The inviting living space seamlessly flows into the well-equipped kitchen, making daily activities and entertaining a breeze. One of the highlights of this property is the deck that overlooks the serene and private yard, creating an ideal spot for relaxation and outdoor gatherings. Whether you're savoring a morning coffee or hosting a summer barbecue, the deck offers the perfect vantage point to enjoy the beauty of the natural surroundings. Completing the package is a convenient two-car garage, offering storage solutions and practicality. This property offers the perfect blend of tranquility, versatility, and potential, making it a unique find for those seeking a harmonious balance between rural living and modern comforts. Don't miss your chance to own this captivating raised ranch with endless possibilities!

Beautifully updated this unique colonial boasts 3,100+ sqft with an additional 1,200 sqft finished basement. The entire home, both inside and out, has been freshly painted for a modern look situated on a level corner lot. The stylish kitchen has stainless steel appliances, built-in hutch and center island with quartz counter tops and opens up to the living room with an art deco fireplace. Off to the side of the kitchen is the dining area with vinyl floors. Make your way up to the oversized primary bedroom ensuite with gleaming hardwood floors which includes a large walk-in closet with 2 additional closets, enough room for any wardrobe. The primary bath is tastefully decorated with double sinks, whirlpool tub and a spacious tiled shower. Just down the hall are 4 additional bedrooms all with hardwood floors. The main bath includes double sinks with tastefully tiled counter top and shower. The laundry room is conveniently located on this level with folding area with quartz counter top. The main level also offers an office and an additional bedroom maybe for guests or an in-law stay. Need more space? Let's not forget about the fully refinished basement with new vinyl floors, tons of storage and a handsomely decorated fully tiled bath and built in bar for entertaining.

Nestled at the end of a quiet cul de sac, 17 Caveson Court is the home you've been searching for! This well maintained home offers three bedrooms on the upper level, complete with two full baths. Primary bedroom with en-suite bathroom and walk in closet. Laundry is conveniently located on the upper level. The main living area flows nicely with large living room and dining room combined space, cozy family room with fireplace and large sunroom to enjoy the seasons. A well appointed kitchen with granite countertops, breakfast bar and eat in area complete the main level. Centrally located and close to I-84, shopping, restaurants and more, makes this home a must see!

Welcome to Luxury. This completely renovated custom-built home is privately nestled on a quiet cul-de-sac on over 2 acres of professionally landscaped gardens, lawns, and beautiful stone walls. Boasting Custom Marvin windows and doors, wide white oak hardwood floors, along with custom trim are what makes this home exceptional. Beautiful natural light fills all the rooms. Through the marble foyer you enter the library-office area or can step down into the stunning living room with cathedral ceilings, custom limestone fireplace and floor to ceiling windows with beautiful views of the outdoors. The living room opens to a spacious formal dining room with French doors that lead to the beautiful back yard with plenty of space for large family gatherings. You will appreciate the seamless flow of the entire first floor, which is ideal for entertaining. The chef’s kitchen features furniture-quality custom made cabinetry with all Wolf stainless steel appliances including a 6-burner cook top with indoor grill, pot filler, 3 ovens, subzero, wine cooler, warming drawer, 2 dishwashers, large pantry, 3 sinks, extra-large center Island and coffee/bar area. The eat in breakfast area has cathedral ceilings, a chandelier, and French doors leading to back yard. Continue into the large family room as well as the laundry room/hobby room/office both including custom cabinets. Off these rooms are 4 smart climate-controlled garages perfect for the car enthusiast. ...

Stunning all brick home w/ heated in-ground pool, covered outdoor dining/entertaining space and main level master set on a private lot on a cul-de-sac of similar homes. In-ground pool w/ spa, fully applianced and covered outdoor kitchen w/ entertaining area, bar, fireplace and ample room for sitting. Poolhouse. Putting greens. Gorgeous patio w/ pergula. Inside, remodeled eat-in-kitchen w/ granite countertops, large center island, Stainless Steel appliances including 6 burner Wolf stove, Subzero fridge, wine fridge, potfiller, pantry and 2 sinks. Family room w/ fireplace open to kitchen area. 2-story formal living room w/ applianced wetbar and fireplace. Grand dining room. Study w/ rich wood paneling and ceiling. Main level master suite w/ fireplace, trey ceiling, walk-in closet w/ built-ins, and attached full bath w/ marble floor, tile surround shower, double sink and jetted tub. Main level laundry room w/ granite. 2 main level powder rooms. 3 additional bedrooms upstairs all with an attached bath and ample closet space. Bonus room upstairs. Tastefully finished lower level with gorgeous trimwork and fireplace, wine room, home gym, and potential for even more finished space. High ceilings and beautiful trimwork throughout. Mechanicals include central air, propane heat, audio, generator, sec system, central vac. New roof and many very recent updates. The facade, curb appeal and entertaining area are absolutely striking. Don't miss the chance to have your own private estate!