Middlebury CT Real Estate & Homes for Sale

Step in to timeless elegance with this beautifully restored 5 bedroom, 2.5 bath home with solid oak flooring throughout, and a 2 car detached garage nestled on a lush, landscaped 1 acre lot just a short walk to the town green, the Middlebury Library and the scenic Middlebury Greenway. Built in 1941, this classic residence blends vintage charm with modern comforts, offering generous living spaces, thoughtful updates throughout and underground utilities while still maintaining a classic look. Enjoy the beauty of mature plantings and fruit trees that frame the property creating a private oasis just minutes from the heart of town, Westover School and the Crest Rd. Preserve Land Trust. Whether you are relaxing on the built in bluestone porch, entertaining in the spacious living room around the Soap Stone fire place or exploring the gardens, this home offers a rare combination of character, location & charm! Don't miss a chance to own a piece of history in one of the area's most desirable neighborhoods. 10 mins to I84, 2 hrs to NYC and 2.5 hrs to Boston.

Welcome to this beautifully maintained colonial home offering space, style, and location !With 4 generously sized bedrooms and 2.5 baths, this home is perfect for everyday living and entertaining. The spacious kitchen is fully applianced and features heated tile floors, breakfast bar, and eating area. The mudroom and Primary Bath also have heated floors. A second floor bathroom features a laundry shoot to the first floor bathroom!With a prime location on the Middlebury Memorial Day parade route; you will be enjoying this beautiful yard on parade day! Step inside to find large, light filled rooms throughout, including a spacious primary suite complete with an updated primary on suite w/a walk-in shower. The heart of the home extends to the outdoors with a low maintenance composite deck-with a built in area for a hot tub already prewired for convenience and a stunning bluestone patio. There is a cedar closet in the attic to store those winter sweaters and a large rec-room in the lower level with a brick fireplace and still has plenty of storage/work shop/workout area! The large 2 car garage includes an EV 240V electric car charging station. Gardeners will appreciate the raised garden beds & gardening shed. All on a nearly 1 acre lot close to restaurants and Middlebury Greenway!

Discover timeless grace and style in this stunning 4 -bedroom home, nestled in the highly sought-after Brookside of Middlebury. From the moment you step inside, you will be captivated by its graceful open floor plan and refined finishes. The beautiful two-story foyer seamlessly flows into an elegant dining room and a fabulous kitchen featuring SS appliances, granite countertops and high bar area - perfect for gathering and entertaining. The flow continues thru to the casual dining area -framed by an attractive bay window - and the spectacular family room with cathedral ceiling and cozy fireplace with a perfect view of the great, flat back yard. Fabulous first floor primary suite features a luxurious remodeled bathroom with soaking tub, shower stall and double sink, two spacious walk-in closets and an attached den. The attractive, wide staircase leads to the second floor with a large loft, three generously sized bedrooms and beautiful, remodeled full bath with double sinks. Meticulously maintained, this home boast gleaming hardwood floors, fresh interior paint and recently updated kitchen appliances. Located within the award-winning Pomperaug School District and offering convenient proximity to New York, this exceptional property blends comfort, elegance and convenience.

Discover timeless grace and style in this stunning 4 -bedroom home, nestled in the highly sought-after Brookside of Middlebury. From the moment you step inside, you will be captivated by its graceful open floor plan and refined finishes. The beautiful two-story foyer seamlessly flows into an elegant dining room and a fabulous kitchen featuring SS appliances, granite countertops and high bar area - perfect for gathering and entertaining. The flow continues thru to the casual dining area -framed by an attractive bay window - and the spectacular family room with cathedral ceiling and cozy fireplace with a perfect view of the great, flat back yard. Fabulous first floor primary suite features a luxurious remodeled bathroom with soaking tub, shower stall and double sink, two spacious walk-in closets and an attached den. The attractive, wide staircase leads to the second floor with a large loft, three generously sized bedrooms and beautiful, remodeled full bath with double sinks. Meticulously maintained, this home boast gleaming hardwood floors, fresh interior paint and recently updated kitchen appliances. Located within the award-winning Pomperaug School District and offering convenient proximity to New York, this exceptional property blends comfort, elegance and convenience.

Welcome home to this warm and inviting 3-bedroom, 2.5-bathroom townhome, offering just under 1,900 square feet of beautifully finished living space. From the moment you step into the charming two-story foyer, you'll be greeted by an abundance of natural light and a sense of openness that continues throughout the home. The spacious, open-concept layout seamlessly connects the kitchen, dining area, and cozy family room, making it perfect for both everyday living and entertaining. Vaulted ceilings add an airy, welcoming feel, while large windows bring in even more light. The main-level primary suite provides a peaceful retreat with plenty of space to relax and unwind. Upstairs, you'll find two additional bedrooms and a full bathroom, ideal for family, guests, or a home office. The unfinished basement offers a fantastic opportunity to create even more living space-whether you envision a rec room, home gym, or a media lounge, the possibilities are endless. A two-car attached garage and a thoughtfully designed layout add to the home's comfort and convenience. Located in a vibrant community that features a basketball court, multiple pools, and a playground, you'll have plenty of opportunities to enjoy the outdoors and stay active close to home. Don't miss your chance to experience everything this lovely townhome and neighborhood have to offer!

Located in a desirable neighborhood setting, this beautifully appointed home offers refined living with the flexibility to suit any stage of life. Step inside to a grand two-story foyer that sets the tone for the home's spacious, light-filled interior. The main-level primary suite features a tray ceiling and spa-inspired bathroom with a double vanity, walk-in shower, and jetted soaking tub-creating the perfect private retreat. At the heart of the home, a soaring cathedral-ceiling great room with a wood-burning fireplace provides a cozy yet open space for gatherings. The updated eat-in kitchen boasts Marble countertops, high end appliances, including sub zero double refrigerator and freezer, Bosch dishwasher, a wolf oven, and a warming tray, an oversized island, wet bar, and seamless access to a mudroom and attached garage-designed with daily living in mind. A formal dining room flows easily into the kitchen and living areas, offering both elegance and functionality. Upstairs, two generous bedrooms each feature en suite bathrooms, connected by a lofted walkway that overlooks the great room below. Whether you're seeking one-level living or room to grow, this home offers comfort, space, and community-all in one.

Welcome to this expansive and exquisitely renovated Colonial estate, where timeless charm meets modern luxury. Boasting 5 spacious bedrooms and 5 elegantly appointed bathrooms, enhanced by a fully finished lower level offering potential for an in-law apartment or guest suite. Designed with flexibility and functionality in mind, the home features multiple flex rooms that can easily serve as dedicated home offices, creative studios, or fitness spaces-perfect for today's dynamic lifestyles. The large open floor plan seamlessly connects the gourmet kitchen, formal dining, and airy living areas, creating an ideal environment for entertaining or simply enjoying everyday living with ease and elegance. Step outside to your private backyard oasis-featuring a tranquil koi pond, an oversized outdoor pool, a dedicated lap pool for fitness enthusiasts, and a relaxing hot tub tucked beneath mature trees. Whether you're hosting guests or seeking a quiet escape, this outdoor retreat delivers a true sense of serenity and luxury. This one-of-a-kind property offers space, versatility, and high-end comfort-perfect for those who value refined living in a serene, resort-like setting.

Welcome to 105 Jericho Road - a charming home tucked away on a quiet cul-de-sac in the highly sought-after town of Middlebury! This spacious property offers over 1,400 square feet of comfortable living space, featuring 3 bedrooms and 2.5 bathrooms. The main level includes a large eat-in kitchen, ideal for family meals or entertaining guests, and a sun-filled living room complete with a cozy fireplace - perfect for relaxing evenings. The finished basement provides additional flexibility and is currently being used as a nursery, home gym, and recreation offering plenty of room to suit your lifestyle. A half bath is conveniently located downstairs as well. Outside, enjoy a long driveway, 2-car garage, and a large, flat backyard that's perfect for gatherings, games, and outdoor fun. Whether you're hosting summer BBQs or simply enjoying some quiet time outdoors, this yard is ready for it all. Don't miss your chance to live in one of Middlebury's most desirable neighborhoods.

Welcome to 61 Stonybrook Road-a spacious and light-filled contemporary ranch nestled on 1.38 wooded acres in a peaceful Middlebury setting. With over 2,800 square feet of living space, this 4-bedroom, 2.5-bath home offers the perfect blend of modern design and natural beauty. Soaring vaulted ceilings and gleaming hardwood floors create a warm and open atmosphere. Ideal for both everyday living and entertaining, the home's thoughtful design brings the outdoors in with large windows framing the wooded surroundings and large wrap around deck. The inviting living room features a cozy fireplace, perfect for relaxing evenings, while the generously sized primary suite includes an ensuite bath for added comfort and privacy. With a total of nine rooms, there's plenty of flexible space for entertaining, home offices, or quiet retreats. Enjoy the serenity of this private oasis while still being just minutes from schools, shopping, entertainment and commuter routes. There is an oversized detached 2 car garage perfect for your cars, workstation and extra storage Nestled in a community known for its highly regarded schools and small-town appeal, this home offers the best of both tranquility and convenience.

Here's your chance to build the home you've always dreamed of at 7 White Birch Lane, a to-be-built 3,325 SF custom residence located on one of the most desirable cul-de-sac lots in Middlebury. With 4 bedrooms, 3.5 baths, and a 2-car garage, this home offers both elegance and flexibility-crafted with the quality and attention to detail you deserve. Enjoy hardwood flooring throughout and the tile of your choosing in all bathrooms, with generous allowances for appliances, countertops, lighting, fixtures, and more-giving you the power to personalize every inch of your home to suit your taste and lifestyle. The unfinished basement opens the door to endless possibilities-whether you envision a media room, gym, home office, guest suite, or expansive entertainment space, the choice is entirely yours. Don't settle for someone else's vision-work directly with the builder and make 7 White Birch Lane your custom masterpiece. Minutes to I-84, Lake Quassapaug, Quassy Park & amazing local dining. Book your appointment with the builder today!

Welcome to 4 White Birch Lane, a to-be-built, fully customizable 2,750 SF home offering the perfect blend of luxury, flexibility, and modern design. This 4-bedroom, 3.5-bath home includes a 2-car garage and a spacious walk-out basement ready for future finishing-ideal for added living space, a home office, gym, or media room. Enjoy hardwood flooring throughout, with stylish tile in all bathrooms and laundry room. Generous builder allowances let you personalize everything from countertops and cabinetry to lighting, paint colors, and fixtures, so your home truly reflects your style and preferences. Set in a desirable Middlebury location, this home offers the unique opportunity to work directly with the builder and make your vision a reality. Minutes to I-84, Lake Quassapaug, Quassy Park & amazing local dining. Make an appointment with the builder-start customizing your dream home at 4 White Birch Lane today!

Design your dream home from the ground up at 1 White Birch Lane, a to-be-built, fully customizable residence in beautiful Middlebury CT. This thoughtfully designed 2,450 SF home will feature 3 spacious bedrooms, 2.5 baths, and a 2-car garage, all crafted with exceptional attention to detail and quality. Enjoy hardwood flooring throughout, with tile in all bathrooms and laundry room, creating a seamless blend of style and durability. The unfinished basement offers endless potential for future expansion-perfect for a home gym, media room, or additional living space. With generous allowances for countertops, appliances, lighting, and finishes, you have the freedom to make every detail your own, from paint colors to fixtures. Located in a peaceful, desirable neighborhood, this is your chance to create a custom home that fits your lifestyle today-and grows with you tomorrow. Minutes to I-84, Lake Quassapaug, Quassy Park & amazing local dining. Now scheduling appointments with the builder-start planning your perfect home at 1 White Birch Lane!

Welcome to 6 White Birch Lane in Middlebury, an exceptional 3,700 sq ft custom home set on the largest lot at the end of the cul-de-sac, offering privacy, space and sophistication in one of Middlebury's most sought-after neighborhoods. This stunning 4-bedroom, 3.5-bath residence is designed for modern living with high-end finishes and timeless elegance throughout. Enjoy hardwood flooring in every room and beautiful tile in all bathrooms and laundry room. The spacious layout includes a 3-car garage, flexible living areas, plus generous allowances for countertops, appliances, lighting, and more-giving you the freedom to choose the finishes that reflect your personal style. This is a rare opportunity to build your dream home on a premier lot, surrounded by quality craftsmanship and nestled in a peaceful cul-de-sac setting. Perfectly positioned for both relaxation and convenience, this home sits just minutes from I-84, Route 63, and Route 64, providing easy commuting access to major destinations. Enjoy the best of the area with nearby attractions like Lake Quassapaug, Quassy Amusement & Waterpark, and the scenic Larkin State Park Trail. Indulge in a variety of local dining favorites including Vyne Restaurant & Bar, 1754 House, Brewbury Kitchen & Tap, and the award-winning Local Gourmet Cafe. Don't miss your chance to customize a home that truly stands out in space, style, and setting. Book your appointment with the builder today-your dream home starts here!

Welcome to 11 White Birch Lane - a rare opportunity to create your ideal home in one of Middlebury's most desirable neighborhoods. This to-be-built, customizable residence will offer 4 spacious bedrooms, 4.1 luxurious baths, a 3-car garage, and an open-concept layout designed for modern living. From the beautiful hardwood floors and stunning kitchen island to the generous allowances for tile & stone, appliances, lighting, and more-you'll have the freedom to personalize every detail to match your vision, including paint colors, fixtures, and finishes. Perfectly positioned for convenience, this home sits just minutes from I-84, Route 63, and Route 64, providing easy commuting access to major destinations. Enjoy the best of the area with nearby attractions like Lake Quassapaug, Quassy Amusement & Waterpark, and the scenic Larkin State Park Trail. Indulge in a variety of local dining favorites including Vyne Restaurant & Bar, 1754 House, Brewbury Kitchen & Tap, and the award-winning Local Gourmet Cafe. Don't miss your chance to own a custom-built home with close proximity to nature, dining, and top commuter routes. Schedule an appointment now to meet with the Builder and start designing your dream home today!

Welcome to 6 Brookside Drive in Middlebury, CT-a beautifully maintained 3,745 sq ft colonial-style home in the desirable Brookside subdivision. This versatile residence offers 4 bedrooms and 4 bathrooms across three finished levels, ideal for multigenerational living. The open-concept main floor features vaulted ceilings, a gas fireplace, a gourmet eat-in kitchen with smart appliances, and a spacious primary suite with a luxurious ensuite bath. Upstairs includes two bedrooms, a full bath, and a loft overlooking the living room. The finished lower level offers in-law potential with a kitchenette, full bath, living/dining space, and a private bedroom with walk-in closet. Additional amenities include hardwood floors, custom window treatments, laundry/mudroom, central air, natural gas heat, city utilities, a two-car garage, generator setup with portable generator included, gutter guards, and an oversized covered deck. Conveniently located near Routes 8 and I-84, shopping, dining, and entertainment.

Welcome to 6 Brookside Drive in Middlebury, CT-a beautifully maintained 3,745 sq ft colonial-style home in the desirable Brookside subdivision. This versatile residence offers 4 bedrooms and 4 bathrooms across three finished levels, ideal for multigenerational living. The open-concept main floor features vaulted ceilings, a gas fireplace, a gourmet eat-in kitchen with smart appliances, and a spacious primary suite with a luxurious ensuite bath. Upstairs includes two bedrooms, a full bath, and a loft overlooking the living room. The finished lower level offers in-law potential with a kitchenette, full bath, living/dining space, and a private bedroom with walk-in closet. Additional amenities include hardwood floors, custom window treatments, laundry/mudroom, central air, natural gas heat, city utilities, a two-car garage, generator setup with portable generator included, gutter guards, and an oversized covered deck. Conveniently located near Routes 8 and I-84, shopping, dining, and entertainment.

This well maintained home offers lots of space for the expanding family or simply one level living for the downsizer with guests to entertain. Truly a MUST SEE! Remodeled kitchen, gleaming oak floors, fireplaced dining room for those traditional holidays. Large Open Great Room with lots of Natural Sunlight. Full Walk Up Attic for possible expansion if needed. Lower level boasts a full bathroom with jacuzzi tub and shower, an efficiency kitchen, large 25'x29' living area with an additional 21'x16' room, (presently being used as a bedroom). Walk out to oversized 2 car garage with workshop area. All situated on a lovely Groomed landscape corner lot in a modest neighborhood conveniently located within minutes of local amenities yet, only 40 minutes to NY City.

NEW CONSTRUCTION split level with possible in-law 3220 sqft, 4 bedrooms, 3.5 baths, open floor plan on main level with kitchen, dinning/living room with a electric fireplace. A large size kitchen with granite countertops, plenty of cabinets, tiled backsplash, double oven, a large island for cooking or eating. The dining area next to the kitchen leads to a sliding door to outside trex deck(16x12), which connects thru stairs to a nice patio and walkway around the house, making easy for outside entertaining. Lower level featuring a family room, bedroom with 1/2 bath (if needed can be turned to full), mud or rec/play room. A full basement with epoxy flooring is wide open can be used for a lot of storage, can be finished or other uses. Upper level featuring a huge primary bedroom with walk in closet with build shelvings and beautifully designed bathroom with shower, soaking tub, double sinks. The other 2 large bedrooms (15.5x14) have double closets with sensor lighting and their own full nicely designed bathrooms. Laundry room is located on the hallway and includes washer, dryer. The whole house has natural hardwood flooring. The house has a wired, gas powered generator for emergency outage. The whole house has spray foam insulation, which makes it very energy efficient on cooling and heating. Most of the backyard is flat and the rest is wooded area, 2 oversized car garages with epoxy flooring can fit pickup truck and you have more room for shelving and storage

Welcome Home! Nestled in one of Middlebury's most desirable neighborhoods, this beautiful home, with over 5200 square feet of living area, offers the perfect blend of comfort, elegance and functionality. Designed with the entertainer in mind, the spacious dining room flows into a top-of-the-line kitchen featuring a Viking stove, double ovens built into a large island, a restaurant-style stainless steel refrigerator,freezer and a dishwasher--everything a home chef could dream of! Gather in the inviting living room, complete with a grand stone fireplace and charming wall to wall bookshelves, creating the perfect space to relax or host guests. The mudroom, with its cozy radiant heated floors, leads into a bright and airy three-season sunroom--an ideal spot to enjoy your private, fully fenced backyard and patio. Upstairs, the serene primary suite offers a generaous closet, a spa-like bathroom with a walk-inshower and a luxurious soaking jacuzzi tub. Down the hall, you will find 2 additional bedrooms spacious bedrooms, each with its own bathroom, plus 2 more versatile rooms that can easily be transformed into extra space for guests, office or play area. The finished lower level provides even more living space and offers a pool table, lounge area, home gym and plenty of storage. Additional highlights include a 2 car garage, large shed, whole house generator as well as central air and so much more.

Nestled in one of Middlebury's most sought-after neighborhoods, this well-maintained two-bedroom ranch blends comfort, convenience, and charm. Step inside through the inviting enclosed front porch-perfect for morning coffee or evening relaxation-into a warm and welcoming living room complete with a cozy wood stove. The bright, airy kitchen flows seamlessly from the living space, making it ideal for both everyday living and entertaining guests. The primary bedroom features a generous walk-in closet, offering ample storage. A nicely remodeled full bathroom and a separate laundry room add to the home's thoughtful layout. Enjoy peaceful summer evenings on the back deck overlooking a private, serene backyard. Some key updates include a newer 30-year roof with transferable warranty, recently repointed chimney with fresh brickwork, and a new well holding tank. Schedule your showing today!

Welcome to 115 Marney Drive! This spacious split level home has so much to offer to a family of any size! Not only does it have 3 bedrooms and 2.5 baths, it also has a large living room and dining area great for entertainment. The lower level has a finished bedroom and den with fireplace for additional guests. This house has had many updates since 2018 including a new roof and gutters with gutter guard, two full bathrooms and a new kitchen. Situated on a quiet cul-de-sac with a beautiful deck and two car garage, this house checks all the boxes.

Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The gourmet kitchen features granite countertops, stainless steel appliances, a gas cooktop, tile backsplash, and an island with breakfast bar seating, flowing seamlessly into the spacious living room with a gas fireplace and access to a private deck and backyard-perfect for entertaining. The luxurious primary suite impresses with vaulted ceilings, a walk-in closet, and a spa-like bath with a double vanity, soaking tub, and shower. Two additional bedrooms, one with vaulted ceilings and a walk-in closet, and a full bath complete the upper level. The unfinished 900+ SqFt basement offers endless potential. Enjoy resort-style amenities, including a clubhouse with an entertainment area, kitchen, gym, pool, indoor basketball court, tennis court, and playground. This home combines elegance, comfort, and convenience. You very rarely get a unit with a large side yard and private flat wooded backyard. If you like to entertain, or engage in yard activities, this is the unit to buy! Private desirable town, 1.3 hrs from NYC, easy access to highways. Schedule your showing today!

Meticulously maintained and completely renovated in 2024, this move-in-ready home is a true masterpiece of thoughtful design. Located in one of Middlebury's most desirable neighborhoods, this 4 bedroom, 3 full bath home is a gem not to be missed. From the moment you step inside, you feel the warmth and coziness of the home combined with the ease of modern living. The updated kitchen boasts granite countertops, GE Cafe appliances, a Sub-Zero refrigerator and a center island perfect for everyday living and entertaining. Enjoy elevated finishes like coffered ceilings, custom millwork and hardwood floors. The first floor provides the convenient opportunity for a 4th bedroom, office or play area. The full bath upgrade on the main level enables freedom and function for privacy or busy family life. A generous side entry mud room seamlessly links the garage, main living area, and the private outdoor patio. The spacious family and dining rooms create a comfortable and connected flow off the kitchen for everyday living, and effortless entertaining. Upstairs, the spacious primary suite includes a walk in closet and en-suite bath. Two additional large sized bedrooms share a full hallway bath with plenty of room to have your own space. Located in a vibrant, established neighborhood with a strong community feel, and just minutes away from town where you can find your favorite shops and restaurants along with the scenic Greenway trail, this home is a true must see!

Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features a vaulted breakfast area surrounded by windows, granite countertops, and stainless steel appliances. The first-floor primary suite boasts a generous walk-in closet and a full bath. Upstairs, a beautifully finished loft area offers another full bath, a walk-in closet, and two additional bedrooms. The lower level is a showstopper, featuring a built-in wet bar, plenty of space for entertaining, and direct access to a private outdoor patio. A private library/office and an additional full bath complete this level. Enjoy an unbeatable location just a short walk to the clubhouse, which includes an outdoor pool, gym, indoor basketball court, and tennis courts. With easy access to I-84, top-rated schools, and fantastic restaurants-plus just 30 minutes to the train to NYC-this home truly has it all! Don't miss this rare opportunity to own the original model home!

Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile backsplash. Stainless steel appliances and gleaming hardwood floors extend through the great room and dining room, creating a seamless flow. The main level offers a luxurious primary bedroom suite with an attached spa-like bath, an office, a powder room, and a convenient laundry area. Upstairs, discover a versatile loft, a second bedroom, and a full bath - perfect for guests or additional living space. This home is equipped with a chair lift from the garage and is prepped for a future elevator, ensuring accessibility for years to come. The HOA covers full lawn maintenance and snow removal right up to your front door, providing hassle-free living. Located minutes from Edgewood for tennis or pickleball, and close to scenic Lake Quassapaug - ideal for boating or picnicking at the Middlebury Recreation Area. Enjoy easy access to fine dining, shopping, and I-84, with NYC just 90 miles away and Boston a two-hour drive.