Middlebury Real Estate | Middlebury Properties for Sale

This custom arts and crafts bungalow, designed and built for its current owners, is perfectly sited on 14.85 tranquil acres, highlighting a gorgeous view and is accessed by a long gated private driveway. It is a home for someone who loves nature, stone and wood in a very private setting. The timeless design and easy layout are embellished by fine craftsmanship and quality materials which include quarter-sawn white oak floors, doors and trim with 9’ ceilings. The foyer entryway leads to a study, pantry and mudroom with half bath. The living room fireplace was crafted with stone carefully selected from the property. The sun filled kitchen with casual dining includes Crown Point cabinetry, Wolf, Subzero and Bosch appliances with access to the terrace, gardens and conservatory. The main floor primary suite has his/her closets, laundry room, full bath and terrace access. Upstairs is the family room, office nook, two bedrooms and full bath. A walk-out lower level has recreation space, wine room, sauna and gym as well as Veissmann mechanicals, with hydronic 5-zoned radiant heated floors throughout, audio system, Unico central A/C system and 12kw Kohler generator. Multiple outbuildings include two heated garages with epoxy floors, equipment barn (can fit 2 cars) with greenhouse, potting and wood sheds, outdoor fireplace and shower, electric awnings and an in-ground rainwater cistern for garden irrigation. Turnkey mint.

397 White Deer Rock Road, Middlebury

$1,590,000

170600317 MLS

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.

100 North Benson Road, Middlebury

$669,500

2 Beds ⋅ 2 Baths ⋅ 170600691 MLS ⋅ Benson Woods BLDG.

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!

409 Chestnut Circle Unit 79, Middlebury

$655,500

2 Beds ⋅ 2 Baths ⋅ 170600544 MLS ⋅ Benson Woods BLDG.

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!

407 Chestnut Circle Unit 78, Middlebury

$649,500

2 Beds ⋅ 2 Baths ⋅ 170600279 MLS ⋅ Benson Woods BLDG.

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!

405 Chestnut Circle Unit 77, Middlebury

$1,300,000

4 Beds ⋅ 4 Baths ⋅ 170597325 MLS

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!

106 Judd Hill Road, Middlebury

$369,900

3 Beds ⋅ 2 Baths ⋅ 170597361 MLS

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.

1424 Middlebury Road, Middlebury

$1,500,000

4 Beds ⋅ 7 Baths ⋅ 170594586 MLS

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.

7 East Farm Road, Middlebury

$800,000

3 Beds ⋅ 2 Baths ⋅ 170596129 MLS

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.

27 Sandy Beach Road, Middlebury

$550,000

3 Beds ⋅ 3 Baths ⋅ 170595703 MLS ⋅ Ridgewood At Middlebury BLDG.

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.

47 Ridgewood Drive Unit 47, Middlebury

$665,600

2 Beds ⋅ 2 Baths ⋅ 170597815 MLS ⋅ Benson Woods BLDG.

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! Call for details!!

403 Chestnut Circle Unit 76, Middlebury

$779,900

4 Beds ⋅ 3 Baths ⋅ 170596575 MLS

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.

28 Hunting Ridge Road, Middlebury

$550,000

3 Beds ⋅ 3 Baths ⋅ 170592308 MLS ⋅ Ridgewood At Middlebury BLDG.

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.

1 Fairview Lane Unit 1, Middlebury

$479,000

3 Beds ⋅ 3 Baths ⋅ 170594649 MLS

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!

530 Whittemore Road, Middlebury

$499,900

3 Beds ⋅ 3 Baths ⋅ 170593670 MLS ⋅ Steeplechase BLDG.

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.)

5 Pommel Lane, Middlebury

$78,999

170593868 MLS

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.

271 Steinmann Avenue, Middlebury

$799,900

3 Beds ⋅ 4 Baths ⋅ 170594073 MLS

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.

588 Charcoal Avenue, Middlebury

$1,999,900

5 Beds ⋅ 7 Baths ⋅ 170507932 MLS

Exquisite Country Cape situated along one of Middlebury's most picturesque roads. This 5800 sq.ft. Cape is a true gem, boasting a gunite pool, acres of open meadow bounded by stone walls, distant city views & beautiful backyard w/ patio, perfect for hosting summer soirees. Recently renovated, this sprawling home offers a fabulous eat-in kitchen w/ spacious island and a generous dining area featuring a vaulted ceiling w/ exposed hand-hewn beams & FP. A cased opening leads to a sun porch with 3 walls of glass offering seamless access to a private patio.The main level is a showcase of elegance & functionality featuring a formal LR w/ FP & built-ins, a gracious DR w/ corner built-ins, a paneled 1st floor office complete w/ FP & wet bar & a sumptuous primary BR suite. Almost every room treats you to breathtaking distant views of the patio & inviting in-ground pool. The upper level offers a quaint loft area & 3 beautifully appointed BR’s, two of which have en suite baths, resulting in a total of 3 full baths on this floor. The pristine exterior boasts the hallmark Middlebury stone walls adorning the front, fencing, terraced patios, in-ground pool, practice golf range for enthusiasts & acres of lush meadow for your enjoyment. Additional amenities include a 2nd first-floor BR suite, an attached 3 car garage & a drive-under garage that provides multi-car storage space in the basement. Situated in the highly sought-after South Street location, this property is an exceptional find.

700 South Street, Middlebury

$450,000

3 Beds ⋅ 3 Baths ⋅ 170593338 MLS

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 sizable new pressure treated deck, retractable fixed awning with power remote 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 a brand-new asphalt driveway on .89 acre lot. Don’t miss the opportunity to call this beautiful property home. Seller is highly motivated! Call today to schedule a private showing.

159 Acme Drive, Middlebury

$929,000

5 Beds ⋅ 5 Baths ⋅ 170592684 MLS

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.

275 Burr Hall Road, Middlebury

$895,900

5 Beds ⋅ 3 Baths ⋅ 170592375 MLS

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.

34 Breakneck Hill Road, Middlebury

$850,000

3 Beds ⋅ 3 Baths ⋅ 170591262 MLS

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.

294 Christian Road, Middlebury

$579,000

6 Beds ⋅ 4 Baths ⋅ 170591012 MLS

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.

660 Whittemore Road, Middlebury

$424,900

3 Beds ⋅ 2 Baths ⋅ 170590343 MLS

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!

100 Bayberry Terrace, Middlebury

$520,000

3 Beds ⋅ 3 Baths ⋅ 170589526 MLS

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!

17 Caveson Court, Middlebury

$1,300,000

3 Beds ⋅ 4 Baths ⋅ 170581926 MLS

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. ...

17 Beacon Hill Road, Middlebury

$2,000,000

4 Beds ⋅ 6 Baths ⋅ 170580842 MLS

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!

40 Winthrop Drive, Middlebury

$179,900

170575742 MLS

Welcome home to Middlebury's newest 23 lot subdivision- Hunting Ridge Estates. There are several lots to choose from starting at $165,900 or will build to suit starting at $675,000.

11 Hunting Ridge (lot 3) Road, Middlebury

$699,900

3 Beds ⋅ 2 Baths ⋅ 170574902 MLS

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 3 Hunting Ridge Road (aka Lot 1) is just beginning construction and will be one level living at its finest! 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.

3 Hunting Ridge Road, Middlebury

$799,900

4 Beds ⋅ 3 Baths ⋅ 170575054 MLS

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 7 Hunting Ridge Road (aka Lot 2) is under construction and will be a 2600+ 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.

7 Hunting Ridge Road, Middlebury

$109,000

170572361 MLS

Beautiful lot with water views. It is on the water on the beautiful Long Meadow pond, in Middlebury. It is a perefct spot to built your dream house.

440 Lake Shore Drive, Middlebury

$570,000

4 Beds ⋅ 3 Baths ⋅ 170567658 MLS

Welcome to your new home in beautiful historic Middlebury CT. Built in 2020, 420 Bioski Road is a 5-bedroom 3 Full Bath beauty that sits on just under one acre of land. The open concept main level with living room access to the deck is perfect for entertaining. The main level also has 2 bedrooms, perfect for guests or a home office. The kitchen which can also be accessed from the attached 2 car garage, is outfitted with matching stainless-steel appliances, including a smart refrigerator. The master bedroom totes an additional living space that can be used as a spacious walk-in closet and a large on-suite with a standalone jetted tub. Middlebury hosts Quassy Amusement Park, Lake Quassapaug, Edgewood Bath and Tennis, High Field Club, The John Largay Preserve Middlebury Land Trust, and a plethora of restaurants and bars. Don't hesitate to take a look today, this property won't last long. SOLD AS IS CONDITION

420 Bioski Road, Middlebury

$925,000

3 Beds ⋅ 4 Baths ⋅ 170523627 MLS

Custom built home on a 1.54 ac lot. You enter this home through a grand foyer with a custom chandelier on a lift. The chef's kitchen has custom cabinets, granite tops, breakfast island, dining area, all stainless steel appls including a gas Wolf range, 3 oven's & a sub-zero refrig. FDR with tray ceiling. FLR with wood fireplace. The 1st fl family rm has a wet bar with a viking refrig/wine cooler. There is a butler's pantry with a washer/dryer & ice machine. The 2nd fl features a Primary bedroom suite with tray ceiling, a full bath with jacuzzi, an 8 head walk-in shower, a huge walk in closet & an office or workout rm. There are also 2 other generous sized bdrms. A huge bonus room with a gas fireplace, bar & a media system finishes the 2nd floor. There is also a heated 3 car gar. This home offers white oak hardwood flooring throughout, crown molding, 3 zone hydro warm air furnace, 3 central ac units, central vac, 9' ceilings on the 1st fl, surround system throughout, security cameras & alarm system and a sprinkler system for the front & side yards. As you walk outside from the home onto a trex deck you are greeted with a 18 x 36 inground pool with a new heater, pump & filter. Stamped concrete, black iron fencing and a waterfall complete the pool area. There is also a screened in lighted gazebo overlooking the pool. There is an additional 38 acre parcel attached to this property that can be purchased separately for $469,000.

400 Watertown Road, Middlebury

$149,900

170560564 MLS

A NEARLY 5 ACRE LOT ON THE CUL-DE-SAC W/ BEAUTIFUL GAZEEBO OF ONE OF MIDDLEBURY'S PREMIER SUBDIVISION. WATER & SEWER LATERALS ALREADY ON THE SITE. UNDERGROUND ELECTRICAL ON SITE AS WELL. WETLANDS APPROVAL IN PLACE. STREET OF LARGE, CUSTOM, LUXURY HOMES. A PLACE TO BUILD THE HOME OF YOUR DREAMS!!!

75 Gleneagle Road, Middlebury

$220,000

170497652 MLS

Still looking for that perfect home? Wonderful opportunity to build your custom home in Middlebury. Public water and sewer available. 4 newly subdivided lots, first time on the market. Great location, easy access to shopping, schools, and restaurants. 2 Lots available # Lot #121A 5.00 acres $220,000; Lot #121B 6.5 acres $220,000. Each available lot has sewer assessment paid. Sold#317B 2.56 acres and Lot 317 A 2.4 acres.

121 B Kelly Road Unit 121B, Middlebury

$220,000

170497650 MLS

Still looking for that perfect home? Wonderful opportunity to build your custom home in Middlebury. Public water and sewer available. 4 newly subdivided lots, first time on the market. Great location, easy access to shopping, schools, and restaurants. Lots available: Lot #121A 5.00 acres $220,000; Lot #121B 6.5 acres $220,000. Both lots 121 A and 121 B have sewer assessments that have been paid. ***Lots Sold: 317B 2.56 acres and Lot 317A with 2.4 acres.

121 A Kelly Road, Middlebury

$839,500

170526797 MLS

TURN THE KEY AND START COUNTING YOUR RETURNS WHEN YOU ARE THE OWNER OF MIDDLEBURY'S FAVORITE FAMILY RESTAURANT DESTINATION! THIS 40+ YEAR TOWN LANDMARK FEATURES HIGH VISIBILITY CORNER LOCATION WITH PARKING FOR 60+ VEHICHLES MINUTES TO TOWN CENTER, NAUGATUCK AND WATERBURY BUSINESS DISTRICTS, QUASSY AMUSEMENT PARK WITH EASY ACCESS TO RT 8 AND I-84. RECENTLY RENOVATED INTERIOR OFFERS SEATING CAPACITY OF 160+, SEPARATE BANQUET ROOM FOR ALL FAMILY, BUSINESS AND CORPORATE GATHERING, FULL LIQUOR LICENSE, WIFI AND 75" TV FOR ENTERTAINMENT AND PRESENTATIONS, CENTRAL A/C, COMPRESSOR, BROILER AND OVENS, DISHWASHER, ICE MACHINE, ICE CREAM UNIT PLUS WALK IN COOLER AND FREEZER WITH HUGE LOWER LEVEL FOR INVENTORY AND STORAGE. DETAILED FINANCIALS AND P & L PROVIDED WITH EXECUTED CONFIDENTIALITY AGREEMENT.

725 Straits Turnpike, Middlebury

$1,050,000

5 Beds ⋅ 7 Baths ⋅ 170527394 MLS

Stunning Colonial design with three floors of idyllic living space. Gorgeous five bedroom, six full & a half bathroom, custom built with classic features. Beautiful architectural details throughout, including a huge foyer, uniquely designed floor plan on each level, spacious rooms, built-ins, huge ground & upper-level patio, hardwood flooring & more. All surrounded by five acres & privacy. Come and bring your ideas to add, creating the perfect home for you and your lifestyle. Although part of a quiet subdivision, this house was designed and built by a separate architect and contractor for the sellers. The great room boasts two walls of windows and is open to the informal dining area. The sizeable kitchen, boasting distinctive cabinets, a fabulous center island and an abundance of counterspace. Features that please even the most persnickety chefs! Microwave not operational. The Master Suite is off a long hallway. A span of built-ins along one wall creates a chic expansive space. True architectural attention to every detail. Upstairs there are three bedroom suites off a large central space. One, a potential second master & the other two with a wall of windows opening to a huge terrace. The lower level boasts an au pair suite with second kitchen. You will be amazed with the space and storage in this home. Conveniently located near I 84 for commuting access. Area amenities nearby, local private schools include The Taft School and Westover School.

54 Falcon Crest Road, Middlebury

$299,900

170544991 MLS

Wonderful opportunity to own 13.46 beautiful acres in Middlebury! This was previously an approved 2 lot subdivision (expired.) Located in Middlebury, CT - "small town living at its finest." This picturesque lot lot is surrounded by stone fences, majestic trees and babbling brooks! Loads of privacy yet so close to route 84-perfect for commuters or investor who wants to develop the property. Survey maps available upon request.

Sandy Hill Road, Middlebury

$2,999,000

7 Beds ⋅ 8 Baths ⋅ 170527314 MLS

This estate, originally known as Broadview estate, originated as a summer home designed by Charles Cameron Clark a prominent architect from New York City. Broadview is an idyllic New England style country estate set on over 12 acres draped across the gentle hilltops of Middlebury with beautiful sunset vistas. The property includes a seventeen room main house, 2 guest cottages and a pool house. Both guest homes have 2 bedrooms and loft sleeping area. These buildings sit on a sprawling property includes lovely manicured lawns and gardens, a 55 foot length heated pool, separate hot tub, firepit and tennis court. The estate was renovated in 2002 and again, more recently in 2017. The main home features both formal and informal settings, exquisite millwork, hardwood floors. The chef quality kitchen with marble counters, large butler’s pantry, breakfast nook and informal dining room complete the kitchen area. There is easy access to a temperature/humidity controlled 800 bottle wine cellar. Pass through the French doors to the library and beyond to a raised paneled Great room with vaulted ceilings and stone fireplace. On the other side of the kitchen is the formal dining room, gracious sized living room both with working fireplaces. Hanging off the living room is a private office and a light filled conservatory overlooking the beautiful gardens. 2 half baths and laundry complete this level.

775 South Street, Middlebury

$629,000

2 Beds ⋅ 3 Baths ⋅ 170535160 MLS ⋅ Benson Woods BLDG.

Quick delivery Simsbury Elite with loads of upgrades in Phase 1!! There is still some time to make your selections on this homesite in prime location! Upgrades include full bath in loft, larger great room, rough plumbing in basement for full bath, & 10" foundation walls with walk-out lower level. Premium lot!! Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Need more time? We have just opened up our next phase - 5 premium homes on private circle. Call for specs and plans!

315 Hemlock Lane Unit 74, Middlebury

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