Middlebury CT Real Estate & Homes for Sale

Custom-Built Ranch - A Rare Find in Middlebury! Discover this exceptional custom-built ranch featuring 2 bedrooms and 2.5 baths. A large country kitchen, formal dining room, sunken living room and great room complete the main level of the home. The walk-out lower level is finished, offering a summer kitchen, spacious family room, and convenient laundry area-perfect for entertaining or extended stays! Step outside to enjoy the beautifully level backyard, ideal for relaxation or outdoor activities. For car enthusiasts or those needing extra space, this home boasts a heated one car attached garage plus an oversized two-car detached garage-providing ample storage for vehicles, hobbies, or a workshop. Close to the Naugatuck line, easy access to shopping, restaurants, hiking and golf. Don't miss this one!

Charming Cape in prime neighborhood location. Ideally set just off the Middlebury Greenway Trail, this beautiful home offers comfort, space, and convenience. The updated kitchen features granite countertops, stainless steel appliances, white cabinetry, and ample space for cooking and dining. A bright, inviting living room provides the perfect space to relax. The main-level primary suite is spacious and features a vaulted ceiling, full bath, walk-in closet, slider to the deck, sitting area/nursery and private office. Upstairs, you'll find two large bedrooms with hardwood floors and a full bath (with vaulted ceiling/skylight). The lower level features an exercise/storage area plus mechanical room. Recent updates include a new roof (2024), mini-split heating and cooling system (2020), refinished hardwood floors (2nd floor), and water heater (2023). Enjoy the fenced backyard, ample parking, and a corner lot location in wonderful neighborhood. Conveniently located minutes from shopping, parks, Lake Quassapaug, Quassy Amusement Park and highway access, this home offers terrific value in a prime setting.

Privacy, charm and timeless craftsmanship only begin to describe all that 77 Crest Rd has to offer. Nestled in the Hamlet of Middlebury's Historic District, this 2,600+ sq ft Contemporary Craftsman boasts flexible living with 4 full bedrooms, 3.5 baths, Large living room, and Large family room with 1/2 bath. 2 Blue Stone patios and a Belgian block patio perfectly placed alongside the newly renovated in-ground, gunite Saltwater swimming pool with newer mechanicals, fence, waterfall and SURROUNDED by the 9+ acre Crest Preserve, one of Middlebury's 62 Land Trusts designed to keep with the town's history of nature preservation. Original, winding hand-carved staircases, colonial wood shutters, reading nooks, finished attic and original hardwood floors throughout, blend seamlessly with the detail oriented modern updates this home craved. Inside the FRESHLY Painted Interior you'll find updated bathrooms, gas insert fireplace, electric, A/C, chefs' kitchen w/ granite counters, double oven and new stainless-steel appliances looking out picture windows to your pool oasis, patios, backyard and Soaring land trust views. The OVERSIZED window-wall in the living room picture frames the landscaped front yard with mature perennials and Japanese maples. Outside, new siding, roof, barn lighting, chimney, and landscaping make this a true Gem of a home. Listen to the town church bells while entertaining or just peacefully enjoying this magical 1.5-acre location.

Welcome to this beautiful 4 bedroom, 2.5 bath colonial in the highly sought after complex at Brookside of Middlebury. As you enter, the main floor boasts a large office, bright living room and formal dining room perfect for entertaining with its great flow. Kitchen continues that flow with granite covered island and countertops, gas stovetop with overhead microwave, and gas wall oven along with counter depth stainless steel refrigerator and dishwasher. Enjoy cooking in the kitchen while guests gather round the fireplace in the great room with its expansive cathedral ceiling. Continue through the sliding glass doors to the Trex deck and outdoor private patio surrounded by extensive landscaping and sweeping lawn. Upstairs you will enter the double doors to the primary ensuite with tiled shower and whirlpool tub. Overlook to great room and 3 more bedrooms, as well as a laundry room complete the 2nd fl. The 671 sq ft of finished permitted basement completes this home with a theater including a 100" screen with speakers and a separate area for just hanging out playing Foosball or video games. A great home to live your dream life with top-rated schools, lovely parks and recreational areas in a small town atmosphere. Agent is related to owner.

Welcome to this beautiful 4 bedroom, 2.5 bath colonial in the highly sought after complex at Brookside of Middlebury. As you enter, the main floor boasts a large office, bright living room and formal dining room perfect for entertaining with its great flow. Kitchen continues that flow with granite covered island and countertops, gas stovetop with overhead microwave, and gas wall oven along with counter depth stainless steel refrigerator and dishwasher. Enjoy cooking in the kitchen while guests gather round the fireplace in the great room with its expansive cathedral ceiling. Continue through the sliding glass doors to the Trex deck and outdoor private patio surrounded by extensive landscaping and sweeping lawn. Upstairs you will enter the double doors to the primary ensuite with tiled shower and whirlpool tub. Overlook to great room and 3 more bedrooms, as well as a laundry room complete the 2nd fl. The 671 sq ft of finished permitted basement completes this home with a theater including a 100" screen with speakers and a separate area for just hanging out playing Foosball or video games. A great home to live your dream life with top-rated schools, lovely parks and recreational areas in a small town atmosphere. Agent is related to owner.

Only 4 Units Remaining! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully appointed attached townhomes offering 1,950 SF of living space, 3 bedrooms, 2.5 baths, featuring a first floor primary bedroom suite, grand vaulted open living and dining spaces, beautifully designed kitchen and baths, a full basement, 2 car attached garage, backyard patio, natural gas, and option to finish the second level bonus room. While situated in a quaint historic community, Aberdeen Estates offers the best of both worlds, being within minutes of fine restaurants, parks and rec, health facilities, shopping, and easy access to Interstate-84. Model unit coming July 2025. Phase 2 occupancy starting early 2026. A Planned Unit Development (PUD). Developed by Newport Realty Group. Agent related.

First Time on the Market - Classic 1930s Colonial in Prime In-Town Location Step into timeless elegance with this rare, stately 1930s Colonial, offered to the open market for the first time. Full of classic charm, the home features original moldings, custom built-ins, and enduring craftsmanship throughout. The main level offers a spacious front-to-back living room with a fireplace and gleaming hardwood floors, a formal dining room perfect for entertaining, a cozy eat-in kitchen, and a thoughtfully added family room providing extra space for everyday living. Upstairs, you'll find three generously sized bedrooms, two full baths, and a bright second-floor landing with additional built-ins. A walk-up attic offers abundant storage or potential future expansion. Set in a hidden gem of a neighborhood, this home sits along the historic trolley bed trail, offering direct access to local shops, restaurants, and all the amenities of in-town living.

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 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 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.

DRASTIC PRICE DROP!!! Seller is Motivated!!! 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, fireplace 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.

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!