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$450,000
3 Beds 2 Baths 24007242 MLS
Pride in ownership is clearly evident in this immaculately maintained home. Remodeled kitchen with new cabinetry, granite, stainless and double farmhouse sink is tastefully updated and wide open to dining room. Hardwood throughout main level including 3 bedrooms. Elegant first floor bath is updated with double sinks and opens to hallway and primary bedroom. Lower level boasts 2 large rooms perfect for guests, additional entertaining space plus home office with closet and full bath. New roof in 2021 and new boiler in 2007. Enjoy the outdoors with Trex deck leading to patio. Yard is slightly sloping and level yard complete with firepit and shed. Minutes to schools, shopping and I84 for easy commute. Nothing to do but move in! Video surveillance in home. Sign consent form prior to entry.

192 Porter Ave, Middlebury

$449,900
2 Beds 3 Baths 24101800 MLS
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!

190 Allerton Farms Rd, Middlebury

$445,000
3 Beds 3 Baths 24010349 MLS
Spacious & beautiful split level home in Middlebury! Plenty of room for everyone! This property features a large foyer leading to a family room with a fireplace, French doors to a gym or office area with sliders to the back yard. Also on this level is another room which can be used as an office or guest room attached to a nice 1/2 bath. The main level is an open concept of living room, dining room and large kitchen with breakfast bar! The bedroom level has 3 nice size bedrooms to include the large primary bedroom with a small deck perfect for enjoying a cup of coffee! The primary bath features a soaking tub, walk in shower & 2 spacious closets. The main bathroom has been recently remodeled. A 2 car garage, public water/sewer & central air are just some of the features provided with this home!

47 White Ave, Middlebury

$444,000
3 Beds 2 Baths 24172026 MLS
"Highest and Best offers due Monday, 5/10 at 1:00 PM". Nestled in the desirable town of Middlebury and within walking distance to Westover School, this home suits a variety of lifestyles. Perfect blend of space and manageable living! Ideal for buyers seeking privacy and land without overwhelming upkeep, this well-maintained split-level home offers 1.3 acres of usable land with a comfortable, efficient layout. The main level features a welcoming living room with a fireplace and hardwood floors, flowing into a dining area and an eat-in kitchen with granite counters, stainless steel appliances, and tile flooring. A 10x12 three-season room just off the kitchen offers a great space to relax or entertain while enjoying views of the private, lightly wooded lot. Upstairs are three bedrooms with hardwood floors and a full bath with tile flooring and a new vanity. The lower level provides additional living space with a rec/play room, half bath, and flexible bonus area with laundry. Fresh paint in some rooms adds a refreshed feel. New Roof installed Jan 2026. Additional features include a heated garage, attic storage, usable yard space, shed, and garden area-perfect for first-time or move-up buyers seeking space and convenience. Schedule your showing today and discover all the potential this home has to offer!

863 Whittemore Rd, Middlebury

$440,000
3 Beds 3 Baths 24092040 MLS
Charming, Fully Renovated Cape in Desirable Middlebury Welcome to this stunningly remodeled 1950s Cape, perfectly blending timeless charm with modern finishes. Located in the heart of Middlebury, known for its award-winning schools, scenic Greenway, and proximity to town, shops, and restaurants, this home has been thoughtfully upgraded inside and out. Step into an open-concept main level featuring gleaming hardwood floors and a spacious living room with a cozy fireplace, perfect for entertaining or relaxing nights in. The remodeled kitchen is a chef's dream, boasting stainless steel appliances, an oversized center island, and seamless flow into the living space. The first floor also offers the convenience of a primary bedroom suite complete with a beautifully updated full bath, a stylish half bath, and a dedicated laundry area. Upstairs, you'll find two generously sized bedrooms, a full bath, and an abundance of closet space and storage. Additional highlights include: * One-car garage * Immaculate, professionally landscaped yard * Brand-new roof, windows, furnace, and central air * Newly installed walkway and stairs * Large storage shed * Unfinished basement offering great potential This move-in ready gem combines quality, comfort, and location. Don't miss your chance to call this Middlebury masterpiece your new home!

69 Nick Rd, Middlebury

$440,000
3 Beds 3 Baths 24039846 MLS
Set on a private road, this move in ready 3 bedroom Raised Ranch has plenty of space for living both inside and out. The eat in kitchen features pullout cabinets and pantry, space for meal prep and has tastefully been redone. Access to the private two tier rear deck from the kitchen. Bright living room with wood fireplace adjoins the dining room for a great open feel. On the main level, there are 3 bedrooms in total, including the primary bedroom with full bath as well as an additional full bath. All bedrooms have ceiling fans and nice closet space. On the walk out level, there is a spacious family room with built-ins and a gas fireplace. The laundry room is conveniently located off the family room and includes a half bath and utility sink. Cedar closets and a summer kitchen can be found on the partially finished side of the walk out space. House generator fueled by propane is an added bonus! This house is on a private road close to a lovely pond.

31 Stony Brook Rd, Middlebury

$440,000
2 Beds 3 Baths 24047400 MLS Ridgewood At Middlebury BLDG.
Experience luxury living Middlebury with this maintenance-free luxury condo at Ridgewood! This light-filled end unit offers 4 levels of spacious living, starting with an eat-in kitchen featuring granite countertops, a breakfast bar, gas range, and ample storage. The large bay window floods the space with natural light. Adjacent is an open-concept living and dining room with a cozy gas fireplace and access to a private Trex deck, perfect for unwinding amidst lush, serene landscaping. This open floor offers plenty of space for entertaining guests. Upstairs, you'll find two generously sized bedrooms a primary bedroom with a walk-in closet and a full en-suite bath overlooking peaceful wooded views. The second bedroom across from the primary has ample room with a second full bathroom outside of it. A convenient stackable washer/dryer is also located on this level. Head up to the finished loft, ideal as a guest room or home office, complete with skylights for added brightness. The finished lower level/ basement is perfect for a game room, rec space, or watching your favorite shows, with easy access to the garage. Residents of Ridgewood enjoy access to a luxurious clubhouse, heated in-ground pool, tennis courts, gym, indoor basketball court, movie theater. Beautifully maintained grounds. With close proximity to I-84, 1.3 hr to NYC and just minutes from historic Middlebury, Woodbury, and Southbury, you'll have endless options for dining and shopping. Seller will be doing 1031 exchang

23 Ridgewood Dr Unit 23, Middlebury

$432,500
3 Beds 2 Baths 24070875 MLS
Step into this charming Cape brimming with character and modern updates! Nestled in the highly desirable town of Middlebury, renowned for its award-winning schools, this home offers unique charm and stands out as one of a kind. As you enter through the front door, you're welcomed by a warm and inviting living area featuring a cozy fireplace with a woodstove insert and custom built-ins. The open-concept kitchen and dining area make preparing family meals a delight. The updated kitchen boasts all newer appliances, a breakfast bar, and ample space for entertaining, allowing guests to seamlessly mingle with those in the kitchen. A fully updated bathroom completes the first floor. For the garage enthusiast, the attached two-car garage offers plenty of space and convenient direct access to the kitchen. The second floor is equally impressive showcasing a newly renovated bathroom and a very spacious primary bedroom with a large closet-the perfect oasis for relaxation. To top it off it, this home has been meticulously maintained, with many updates including a new roof, water heater, propane heating system, light fixtures, bathrooms, fence and freshly painted throughout within the last seven years. Located close to Middlebury Greenway, excellent restaurants, shopping, and scenic trails, this home truly has it all. Don't miss the chance to make this one-of-a-kind gem your own! Highest & Best by Monday, February 3rd at 8 PM.

377 Porter Ave, Middlebury

$430,026
3 Beds 2 Baths 24019820 MLS
Large Cape in in an excellent location, less than 1/4 mile to Middlebury Rd and the Middlebury Greenway. This 3 bedroom 1.5 bath has been kept in excellent condition. The 3 bedrooms upstairs all have hardwood floors, and you will find original built ins and a full bath. Dining and living rooms are hardwood floors as well. The eat in kitchen has a breakfast nook, granite counters and exits to the breezeway. The living room has a fireplace, and the huge family room exits to a brand new composite deck. Improvements/features include a brand new driveway, new Trex deck, gutter guards, basement waterproof system, oil tank, well pump, water softener, new dishwasher, washer & dryer, new bilco doors, recent paint, newer garage door and flat 1/2 acre lot.

138 Regan Rd, Middlebury

$425,000
3 Beds 3 Baths 170595736 MLS
BEAUTIFULLY RENOVATED THREE BEDROOM CAPE! This home has been fully updated with detailed trimwork, stone counters, built-ins, new roof, siding, all mechanicals including central air. The kitchen is detailed with stainless appliances, plenty of storage, and beverage cooler. A great entertainment space, the kitchen flows through to an eating area, with access to the backyard and into the living room. The living room has a very large custom built-in entertainment cabinet spanning an entire wall. From there you can pass a bedroom which can also be used as an office or playroom. A dining room includes a wood fireplace with gas piping run for future gas log. Also on first floor you will find a powder room with laundry. The second floor has a master bedroom and bath in addition to a second bedroom and another full common bath. Back downstairs and out to the backyard, you exit onto a covered porch. Stepping down you are on a beautifully crafted stone patio with a stone propane fire pit and three available propane hookups for grilling. Down a few more steps and you are in the yard with another fire pit area and included playscape. The newly sided garage is a perfect space for a workshop or storage. This quiet neighborhood is great for an evening stroll or morning jog. Easy access to route 84. Current photos of garage do not represent new siding, which was installed days ago.

252 White Ave, Middlebury

$425,000
3 Beds 2 Baths 170607171 MLS
14 month home warranty included! Impeccably renovated and updated home loaded with charm and character. Pull into the brand-new double driveway and you will be greeted by the new siding, French Doors and new exterior lighting. The new paver walkway edged in Belgium Block will lead the way to the home of your dreams. As you enter the home you will instantly appreciate gleaning from the new hardwood floors. The open floor plan is showcased by the brand-new kitchen (cabinets, Quartz counter tops, stainless steel sink, GE Stainless Steel Appliances and recessed lighting). Come see what New England living is about. Sit back on the large deck and enjoy a cocktail or curl up to a book as you enjoy the spacious backyard. The bedrooms are spacious, and the primary bedroom has a newly appointed gas fireplace to keep even the chilliest of nights warm! The spacious primary bathroom has a new vanity and an oversized soaking tub. Head downstairs and you are greeted by a large space for entertaining complete with a stone fireplace (just add a wood/gas or pellet stove). This is a must see home, schedule your showing in advance.

36 Middlebury Ter, Middlebury

$425,000
2 Beds 2 Baths 24009406 MLS
Impeccably restored two bedroom Cape in the heart of Middlebury, CT! Sitting on a corner lot, this cute as a button home has much to offer. Park in the newly installed brick paver driveway and enter through the garage or use the Bluestone walkway to the front door. Inside you will find a tastefully remodeled kitchen featuring quartz countertops, center island, new appliances, a gleaming backsplash and newly constructed pantry for your storage needs. Directly off the kitchen, get ready to barbeque on the new rear deck! The first floor also features large dining room with slider to a side 10 x 10 deck (restored). Looking to work from home or need an additional dwelling room? Currently used as an office, the additional room on the first floor could fit a single bed and does have a closet. A relocated half bath on the first floor has been expanded and updated for your convenience. Lastly on the main level is the graciously sized living room with masonry fireplace. Maintenance free Mohawk vinyl flooring lines the main level. Upstairs find two bedrooms featuring two closets each and refinished oak flooring. Both bedrooms share an upgraded full bath. See full list of improvements! Located just a few steps away from town parks, schools and Middlebury's Greenway biking, running and walking route, jump right into this vibrant community! Don't miss out on this charming Cape located close to all major conveniences and award winning restaurants!

44 Middlebury Ter, Middlebury

$425,000
3 Beds 2 Baths 24101631 MLS
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.

1 Yale Ave, Middlebury

$425,000
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 Rd, Middlebury

$422,000
3 Beds 1 Baths 24086501 MLS
Charming Move-In Ready Ranch in the Heart of Middlebury Welcome home to this beautifully updated ranch-style gem, ideally located in the heart of Middlebury. Set on a quiet street just steps from the scenic Middlebury Greenway Trail, this home offers comfort, style, and convenience all in one. The recently renovated eat-in kitchen is a showstopper, featuring granite countertops, subway tile backsplash, wainscoting, and newer Samsung stainless steel appliances-perfect for everyday living and entertaining. The main level boasts freshly painted bedrooms, hardwood floors throughout, a bright and spacious living room with a wood-burning fireplace, and a completely updated full bathroom. Head downstairs to the fully finished lower level, where you'll find a cozy Jtul wood stove, a wet bar, and a half bath-an ideal space for relaxing, hosting, or even a home office. Located minutes from local dining, shopping, and major routes (Rt. 8 and I-84), and nestled in the award-winning Region 15 school district, this home truly has it all. Don't miss your chance to make this Middlebury beauty your own-schedule your private showing today!

64 Joy Rd, Middlebury

$420,000
2 Beds 1 Baths 24008908 MLS
Perfect opportunity to own a loved and fully renovated house in the heart of Middlebury. Gorgeous warm hardwood floor welcome you to this delightful property. New kitchen, new roof, new appliances, new deck, new utilities and so much more. Large open level lot, completely fenced and landscaped. Freshly painted and hardwood floors refinished. Additional half bath recently added to a beautifully finished basement adds to the extra appeal of this dynamite home. Absolutely move in condition. Lovely area with large mature trees. Expansion possibilities are endless, property is located adjacent to luxury properties and antique homes. Super easy access to 1-84, Rt8 and all other commuting routes. Do not miss out on what will be a fabulous home for the new buyer!

14 Lubec Rd, Middlebury

$420,000
3 Beds 2 Baths 170593815 MLS
Unicorn sightings are rare, but finding your perfect home on a peaceful dead-end street is like hitting the jackpot! This raised ranch gem has three bedrooms and two bathrooms – your personal haven. Your culinary dreams come alive in the eat-in kitchen while the living room wraps you in coziness. An extra space on the main level? It’s your canvas – think big office or movie marathon central. Downstairs, the fully finished basement is the ultimate playground. Game night? Movie night? It's all up to you. Outside, the party continues with an inground pool and a deck perfect for sun-soaked gatherings. New roof, dazzling hardwood floors, and fresh siding make this home shine even brighter... speaking of brightness - windows AND doors are new. *** HIGHEST AND BEST BY TUESDAY 29th AT 5pm *** Ready for the adventure? Your suburban sanctuary is waiting!

96 Algin Dr, Middlebury

$420,000
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 Dr, Middlebury

$416,000
2 Beds 1 Baths 24177692 MLS
Tucked away on a beautifully secluded setting, this storybook Cape blends timeless charm with thoughtful updates throughout. The distinctive wood and stone exterior creates unforgettable curb appeal, while the inviting interior offers warmth, character, and functionality. The sun filled living room features hardwood floors, exposed beamed ceilings, and a stunning fireplace with insert, creating the perfect gathering space. French doors lead to a bright sunroom with newly installed flooring, ideal for relaxing or working from home. The formal dining room showcases a built in hutch and hardwood floors, while the charming country kitchen offers built in bench seating, stainless steel appliances, and an induction stove perfect for everyday living and entertaining alike. Additional highlights include a walk up attic offering future expansion potential for a primary suite, a newly updated bathroom floor, interior and exterior painting completed in 2026, a recently replaced roof, and connection to public sewer. Plenty of extra parking along the side lot. Conveniently located close to restaurants, shopping, banking, and major highways while still offering a peaceful private setting. Best and final is Monday 6/1 at noon.

818 Middlebury Rd, Middlebury

$415,000
3 Beds 2 Baths 24071697 MLS
Price Improvement!! DIRECT WATER FRONT PROPERTY with water access and rights just waiting for new owners right in time for Spring! This 3 bed, 2 full bath recently remodeled home boasts custom cabinets, granite counters & island with a breakfast bar, stainless steel appliances, custom built-ins and views of the private Long Meadow Pond. Hiking trails abound with Larkin State Park as your backdrop which sweeps around the pond abutting the cul-de-sac street the home sits on. The top floor has a small office or bedroom and generous sized Primary Suite, walk-in closet, full bath and sliders leading to a TREX terrace with SOARING views. The 2nd floor is an open concept living/dining/kitchen with side entrance, sliders leading to another Trex Deck with a large pantry. Another FULL Bathroom w/ tub finish out the level. The third floor houses the 3rd bedroom or family room/playroom, a dedicated laundry room and utility closet with door to yet ANOTHER TREX deck and walkway to an oversized double landing wood deck and planting beds leading to the cleared land down to the water. Detached garage, wired electric with a workshop and lower room for an in-law or extra living space. Minutes to Southbury/Middlebury Hamlet or Naugatuck for shopping & entertaining yet feels worlds away from civilization. Bring your fishing boat, canoe, kayak for years of summer memories and evenings relaxing on your VERY OWN PRIVATE BEACH with TWO fire p

460 Lake Shore Dr, Middlebury

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