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$499,000
2 Beds ⋅ 2 Baths ⋅ 170527688 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham Elite style is our single level attached home with the loft option. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

108 Periwinkle Dr Unit 18, Middlebury
$495,650
3 Beds ⋅ 2 Baths ⋅ 24163920 MLS
Welcome to this charming and beautifully maintained 3BR ranch, perfectly situated on a quiet cul-de-sac. Offering the ease of one-level living, this inviting home features an open living room and dining room layout enhanced by gleaming hardwood floors, a cozy fireplace and abundant natural light. The updated kitchen boasts a large granite center island that is ideal for cooking gathering and entertaining. Just off the main living space is bright four season room that provides the perfect place to relax year-round. Step outside to a spacious two-tiered deck over-looking private rear yard, offering a peaceful setting for outdoor dining, entertaining or simply unwinding. The lower level has excellent potential for future expansion and is perfect for creating additional living space, a home office or recreation area. The homes low maintenance exterior and two-car garage add to its overall appeal and convenience. A wonderful combination of comfort and style, this home is ready to welcome its next owner! Seller requests highest and best by Wed 4/15 @12:00 pm

18 Freedom Rd, Middlebury
$495,000
3 Beds ⋅ 3 Baths ⋅ 24131737 MLS
Tucked on a quiet street in the heart of Middlebury, this beautifully maintained Cape is where comfort meets craftsmanship. Step inside to a sunlit living room anchored by gleaming hardwood floors and a cozy gas fireplace-the perfect place to unwind after a long day. The thoughtfully designed first-floor primary suite offers a serene escape, complete with a full bath and walk-in closet. The granite-topped eat-in kitchen blends function and style, ideal for both everyday meals and weekend gatherings. Upstairs, you'll be pleasantly surprised by the spacious landing-no tight ceilings here-and two generous bedrooms flanking a well-appointed full bath. Downstairs, a partially finished basement provides room for hobbies, workouts, or movie nights. With central air, a brand-new roof, and public sewer, this home is as practical as it is inviting. Outside, lush landscaping and a maintenance-free exterior make enjoying your surroundings effortless. Timeless design, modern updates, and that unmistakable feeling of "home"-you'll find it all at 116 Yale Avenue, Middlebury.

116 Yale Ave, Middlebury
$495,000
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 Ln, Middlebury
$495,000
4 Beds ⋅ 2 Baths ⋅ 24129568 MLS
Welcome to this stunning Colonial that's full of charm and curb appeal! Step inside to a spacious kitchen with abundant storage, a cozy breakfast nook, and an adjoining dining room perfect for gatherings. The kitchen flows seamlessly into a bright, sun-filled living room and out to a two-tier deck (upper deck is trex & the lower level is pressure treated wood) is overlooking a peaceful wooded backyard-an ideal spot to relax or entertain. The main level also features hardwood floors throughout, a full bath, dining room and a dedicated laundry area for everyday convenience. Upstairs, you'll find four comfortable bedrooms, a full bath with an attractive soaker tub, and a private primary suite with its own balcony. Beautiful crown moulding throughout the home. The partially finished basement offers flexible, light-filled space for play, hobbies, or a home office, along with a well-appointed utility and workshop area that walks out to the backyard. Recent updates include: Central air (upstairs, 2021), refinished kitchen hardwood floors, roof replaced with a 50-year warranty (transferable by DiGiorgi), newer Marvin windows, newer boiler, trex decking and a generator hookup. With a two-car detached garage and plenty of parking, this home blends beauty, comfort, and practicality. Public water & sewer! Don't miss your chance to make it yours!

182 Bayberry Ter, Middlebury
$493,000
3 Beds ⋅ 3 Baths ⋅ 24087751 MLS ⋅ Ridgewood BLDG.
Enjoy living a relaxing and luxurious lifestyle in a most desirable community. As you step into this beautifully appointed, light filled townhome, you can appreciate the open floorplan. This Portman model offers hardwood flooring on the main level and features an eat-in kitchen open to the living/dining room with a gas fireplace for ambiance and warmth. Accessible from the kitchen dining area, the TREX deck allows for al fresco dining overlooking a peaceful backyard setting. It is complete with stairs to conveniently access the rear community space. The second floor offers 3 bedrooms, 2 full baths and a laundry room. The spacious primary bedroom suite features a luxurious full bath with a vaulted ceiling and an enclosed shower. Its cathedral ceiling gives the primary bedroom volumes of space, and there is plenty of space in the walk-in closet. The two additional bedrooms are spacious with plenty of closet space. The full basement with a full-size window allows for lots of light and storage, or it can be finished for additional living space. And the 2-car garage is attached for ease of entry. Enjoy all the amenities which Ridgewood has to offer while living a carefree, low maintenance lifestyle.

43 Ridgewood Dr Unit 43, Middlebury
$490,000
3 Beds ⋅ 3 Baths ⋅ 24086849 MLS
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.

115 Marney Dr, Middlebury
$489,000
2 Beds ⋅ 2 Baths ⋅ 170573612 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham style is our single level attached home. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

304 Hemlock Way Unit 68, Middlebury
$489,000
2 Beds ⋅ 3 Baths ⋅ 170608353 MLS ⋅ Steeplechase BLDG.
Do not miss this lovely 2 BR cape in desirable Steeplechase. Move right in and enjoy the open floorplan with combination living/dining room with wood flooring and lots of light. It leads to the enclosed screened porchoverlooking the private rear yard with lovely plantings. Prep meals &enjoy them in the eat in kitchen. Enjoy the fireplace in the family room/den as you gather around. For ease of living, there is a first floor bedroom and full bath as well as laundry facilities. On the upper level, a spacious bedroom, full bath and loft that offers many opportunities as an office, sitting area or whatever you need. On a practical level, there is a spacious 2 car garage with just 2 steps to the house and a full basement that is accessible through the main house or through the garage.

13 Hackamore Cir, Middlebury
$487,400
2 Beds ⋅ 3 Baths ⋅ 24011457 MLS ⋅ Steeplechase BLDG.
Lovely 2 bedroom stand alone home features first floor bedroom, full bath and laundry access. The living room seamlessly transitions into the dining area, creating an open space perfect for gatherings. Natural light floods through the windows, creating a bright and cheerful ambiance. The nearby eat-in kitchen is spacious and well-equipped. The family room, complete with a cozy gas fireplace, offers a relaxed setting for unwinding or hosting guests. The door leading to the deck offers a relaxing spot to enjoy the outdoors. Completing the main level is a half bathroom. The upper-level bedroom provides privacy and comfort. Adjacent to it is a full bath. The loft area offers versatility, serving as a home office, study space, or even a cozy reading nook. The spacious two-car garage provides additional storage for tools and outdoor equipment. The full basement, with its walk-out access to the backyard, offers endless possibilities. Whether it's a home gym, entertainment area, workshop or craft area.

5 Kimberwick Ct Unit 5, Middlebury
$485,000
4 Beds ⋅ 3 Baths ⋅ 24185992 MLS
Character, charm, and exceptional flexibility come together in this one-of-a-kind Middlebury home. Offering far more space than meets the eye, this property blends timeless craftsmanship with a versatile layout designed to fit today's evolving lifestyle. The main home features expansive living and dining spaces, a full bath, a main-level bedroom, and an additional flexible-use room ideal for a home office, den, guest space, or hobby room. Upstairs, you'll find two generously sized bedrooms with abundant closet space and a convenient half bath. A standout feature is the potential in-law setup, complete with its own living area, bedroom, and full bath, providing endless possibilities for multi-generational living, extended guests, or added privacy. Throughout the home, you'll appreciate the details that make this property truly special-from beautiful built-ins and custom trim work to the character and craftsmanship rarely found today. Outside, enjoy a spacious backyard designed for both relaxation and entertaining, featuring a large above-ground pool with surrounding deck space, perfect for summer gatherings and enjoying the outdoors. The lower level offers additional storage, garage space, and a workshop area complete with a workbench, ideal for hobbyists, craftsmen, or anyone in need of extra room. This is not your average Cape-style home. With its generous living space, unique layout, and endless possibilities, this home it ready for its next chapter!

413 Watertown Rd, Middlebury
$485,000
3 Beds ⋅ 2 Baths ⋅ 24109477 MLS
Beautiful 3-Bedroom home with first floor Primary Suite on nearly half acre lot! Welcome to your dream home! This charming 3-bedroom, 2 Full Bath residence combines modern updates with timeless character. Step inside to discover newly, refinished hardwood floors & fresh paint throughout, creating a bright & inviting space ready for you to move right in. The first-floor primary suite offer privacy & comfort, with a spacious walk-in closet. The layout is thoughtfully designed with both a formal living room & a formal dining room perfect for entertaining. Enjoy a warm & open atmosphere in the great room with sliders that open to an oversized deck-ideal for outdoor dining & relaxation. You'll also find the perfect work-from-home space in the dedicated office. C/A, city water/sewer, 1 car garage all located in a desirable neighborhood, this home offers the perfect blend of comfort, function, & style. Don't miss your chance to own this beautifully maintained home!

101 Shadduck Rd, Middlebury
$482,500
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 Ct, Middlebury
$480,000
4 Beds ⋅ 2 Baths ⋅ 24065893 MLS
Discover this charming stucco ranch, nestled on a spacious 0.66-acre lot just five minutes from Route 84. This inviting home features four bedrooms and two full, fully remodeled bathrooms. Enjoy modern comforts with central air conditioning, making it an ideal retreat in any season. The property boasts a convenient horseshoe driveway and is situated on a peaceful dead-end road, offering privacy and tranquility. Don't miss the opportunity to make this stunning property your new home!

36 Aveline Ave, Middlebury
$480,000
3 Beds ⋅ 3 Baths ⋅ 170625129 MLS
Back on Market. Buyer got cold feet and backed out. Fully Renovated, gorgeous 3 bed 3 bath Colonial with over 2,000 sqft of living space! Additional square footage in the partial finished basement makes for a great bonus room! With hardwood floors throughout, the main level presents an open floor plan connecting the kitchen, living, and dining spaces. The living room includes a wood-burning fireplace and windows that fill the room with natural light. The kitchen, with high-quality finishes, opens to a deck overlooking the backyard. The beautifully renovated large pantry and full bath complete the main level. The second level has two spacious bedrooms and full bathroom with custom-built shower. The practicality of the laundry room on this level adds a modern touch. The third level provides a private spacious third bedroom suite with another full bathroom. Additional updates include a new roof (2021), new driveway (2023), and new mechanicals, and professional landscaping to include a new environmentally friendly stone driveway and walkways, flowering self sufficient trees and shrubs, custom fence and two outbuildings. Don't miss the chance to make this your home! Subject to seller finding suitable housing and actively looking.

530 Whittemore Rd, Middlebury
$480,000
3 Beds ⋅ 3 Baths ⋅ 24104870 MLS
Wake up with a smile in this spacious 2-3 bedroom cape style home in a quiet neighborhood. Originally built in 1950, it was re built and expanded in 2011, and it has a great deal to offer, including an expansive 17' X 9' entry that leads to the 26' X 16' living room. In addition the eat in kitchen has access to the deck overlooking the private yard. This home also features a dining room, a sunroom as well as a possible first floor bedroom. On the second level, there is a spacious, bright loft area as well as 2 bedrooms and a full bath. There are oak floors throughout the living area and tile in kitchen and baths. Plenty of space to enjoy life and to entertain. Public water and sewer. All this on a quiet street in a convenient location. (Sale is subject to Probate Court approval.)

30 Nick Rd, Middlebury
$480,000
2 Beds ⋅ 2 Baths ⋅ 170526661 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham style is our single level attached home. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

106 Periwinkle Dr Unit 17, Middlebury
$479,000
4 Beds ⋅ 4 Baths ⋅ 24072300 MLS
Come see this Westside 4-bedroom beauty boasting over 1,800 sq. ft. of classic Colonial elegance. You'll fall in love with the charming wrap-around front porch, perfect for relaxing afternoons! Inside, you'll find a formal living and dining room with stunning natural woodwork and gleaming hardwood floors throughout. The bright, eat-in kitchen features tile flooring and comes fully equipped with appliances-ideal for preparing family meals or entertaining guests. All bedrooms are generously sized, perfect for a growing family, and the finished attic offers endless possibilities as a playroom, home office, or workout space. Enjoy the modern touches of updated bathrooms and energy-efficient features, including solar panels and a gas tankless hot water unit. Stay comfortable year-round with a super-efficient gas hot-air system and central A/C. Outside, the fenced-in backyard with a patio is perfect for gatherings, gardening, or simply enjoying your outdoor space. The full basement includes a workshop area for your hobbies or projects. Located close to restaurants, shopping, banking, and all major highways, this home combines timeless charm with convenience. Homes with this level of character and upgrades at this price point don't last long-schedule your showing today!

835 Whittemore Rd, Middlebury
$477,000
2 Beds ⋅ 2 Baths ⋅ 170580811 MLS ⋅ Benson Woods BLDG.
Debating between a house or a condo? Benson Woods (over 55 community) offers the best of both worlds! Each of our 4 flexible floor plans offer modern amenities coupled with New England Charm. The Durham style is our single level attached home. All homes afford single level living at its finest with second floor loft and 3rd bedroom options. They will feature quaint farm style porches, 2 car attached garages, open floor plans, full basements and some luxurious options! Great location close to town, shopping, restaurants, golf and major highways. Now taking reservations for Phase 1-

306 Hemlock Way Unit 69, Middlebury
$475,000
3 Beds ⋅ 2 Baths ⋅ 24167472 MLS
Not Your Typical Cape Style Home! This Beautifully Maintained 3 BD Home in Middlebury is Situated on 1.70 Acres and Exemplifies all the Love and Care Taken by its Owner! Surrounded by Lush Mature Landscaping, This Home Offers a Serenity Inspired Outdoor Living Spaces! Enjoy the Sounds of Birds while Sitting on Your Rear Patio. Or Host Dinner Parties in the Enclosed Sunroom on a Cool Summer evening. Enjoy the Beautiful Mixture of Gorgeous Modern Updates Seamlessly Intergraded with Stunning Hardwood floors, and Beautiful Built-Ins. Impressive Fully Appliance Eat-in Kitchen with Stainless Steel Gas Oven range, Dishwasher and Refrigerator, Updated Cabinetry with Crown Molding and Relaxing Breakfast Bar to Sit and Have Morning Coffee with Friends. Host Dinner Parties in the Formal Dining room or Holiday Celebrations in the Oversized Fireplaced Living room Featuring Large Picture Windows Overlooking Beautiful Side Yard with Babbling Brook. Foyer Entry Allows Ample room for Coats, Shoes and Storage Closet, Plus Convenient First Floor Full Bath with Soaking Tub. Second Floor Offers 3 Beautiful Bedrooms, Full Bath, Built-in Shelving, Walk-in Closet in Primary Bedroom. Additional Amenities: Over Sized 2 car Detached garage with walkup to Oversized Storage area (or Convert to Media room or Office). Home Offers Whole House Generac Generator, Ductwork in Place...Could Add CA. Do not walk property or drive on Driveway(s) without an appointment!

420 Charcoal Ave, Middlebury
$475,000
3 Beds ⋅ 4 Baths ⋅ 24145459 MLS
Located in desirable Middlebury, Connecticut, this spacious 3-bedroom home offers 3 full and 1 half baths, including a primary bedroom with its own private bath. The well-designed, flexible layout features a finished walk-out basement providing exceptional additional living and entertaining space, complete with one of two inviting fireplaces that add warmth and character throughout the home. Recent updates include a brand new furnace, offering added comfort and peace of mind. Step outside to a large, private, slightly wooded backyard-perfect for relaxing, entertaining, or enjoying peaceful outdoor living. Conveniently located close to town shopping, restaurants, and everyday amenities, with easy access to Route 8 and I-84, this home offers an ideal blend of privacy, comfort, and convenience. A must-see opportunity.

637 Watertown Rd, Middlebury
$467,000
3 Beds ⋅ 2 Baths ⋅ 24189880 MLS
*Please submit your offers by Monday July 20th at 2:00pm.* Welcome to 24 Steinmann Avenue, where charm, thoughtful updates, and exceptional outdoor living come together in one of Middlebury's most desirable locations. This inviting Cape offers a flexible layout that lives larger than expected. The renovated kitchen features butcher block countertops, updated appliances, hardwood floors, recessed lighting, a breakfast bar, and a GE Kitchen Hub, flowing seamlessly into the dining room. The cozy living room boasts refinished hardwood floors, custom built-ins, a wood plank ceiling, recessed lighting, and an energy-efficient pellet stove. A spacious first-floor primary suite with an en-suite bath and convenient laundry offers easy one-level living, while two bright bedrooms and a full bath complete the second floor. Recent improvements include refinished hardwood floors, updated electrical, security cameras, and a new electric pool heater. Outside, enjoy your own private retreat with a heated in-ground pool, patio, firepit space, and pool room - perfect for relaxing or entertaining. The oversized fenced driveway provides ample parking and direct access to the Middlebury Greenway for walking, running, and biking. Combining timeless character, modern updates, and outstanding outdoor amenities, this move-in ready home is one you won't want to miss! 1-Year home warranty included with sale.

24 Steinmann Ave, Middlebury
$465,000
3 Beds ⋅ 3 Baths ⋅ 24106201 MLS
Welcome home to this turn key entertainers dream in highly desirable Middlebury CT. Set far back on a secluded and expansive peaceful fenced in lot, outdoor living is private and tranquil. From the moment you enter this home your attention will be drawn to the high end kitchen and bathroom finishes, custom railings and lighting, and shiplap accent wall, noting every detail has been curated. Granite countertops, stainless steel appliances with a double oven, and a breakfast bar with seating makes this kitchen a show stopper. The main level continues with an expansive living room and dining room filled with natural light that is accentuated by a statement fireplace and exposed wood beams. The primary suite features a full en suite bathroom with custom tiles, floating vanity, and walk in closet. 2 additional bedrooms and a full bathroom with gorgeous fixtures, tiles, and soaking tub complete the upper level. Versatility and functionality are perfectly blended thanks to an incredible lower level featuring an entire second kitchen, bathroom with curbless shower, fireplace and laundry! Need an in-law suite, flex space, or airbnb? - All possible with this customizable layout. With an oversized 2 car garage, numerous closets, storage, entertaining, and living are waiting for you.

1996 Straits Tpke, Middlebury
$465,000
3 Beds ⋅ 2 Baths ⋅ 24021545 MLS
This wonderful Split Level is located in the heart of the charming Three Mile Hill neighborhood. Let's start with what makes this home so special! City Water and City Sewers, 2 Full and Newly Remodeled Baths, Updated Stainless Steel Kitchen Appliances, 2 Floor to Ceiling Fireplaces (on the main and lower levels), Large Lower Level Family Room, and Recessed Lighting. If that isn't enough to make you want to run to this home, here's what else you get. As you enter this charming home, you walk into a welcoming foyer which leads directly to an expansive living room. Steps off of the living room is the large eat-in kitchen which leads directly to a roomy back deck thru the large sliding glass doors. Ascending a few steps from the living space, you'll find the upper level and the roomy sleeping quarters. Three bedrooms, each a sanctuary of peace and tranquility, offer you peace and solitude after a busy day. Descending to the lower level is the cozy and over-sized walk out family room. This expansive space extends seamlessly to a versatile fully enclosed porch with endless possibilities. Another true allure of this split-level gem is the amazing property. Step outside into the backyard oasis, where a lush expanse of greenery invites outdoor relaxation and entertainment. The combination of this house and property will make this place somewhere you'll be proud to say - "I'm Home". Be sure to make an appointment today to see all that this home has to offer. You won't be disappointed

2 Northwood Dr, Middlebury
$461,500
4 Beds ⋅ 2 Baths ⋅ 24059989 MLS
Welcome to this beautiful Cape Cod home, offering 1,958 square feet of living space with a traditional layout and classic charm. Nestled in a peaceful neighborhood in Middlebury, this home is perfect for those seeking comfort and functionality. The home features two spacious bedrooms located upstairs and two additional bedrooms on the main level, providing flexible living options. Two full bathrooms, on each floor, ensure convenience and privacy for family members and guests. The formal dining room includes built-in cabinetry, making it ideal for entertaining or enjoying family meals. The cozy living room, with a fireplace and built-in shelving, creates a warm ambiance perfect for relaxing or hosting guests. Adjacent to the dining room is a light-filled sunroom for savoring your morning coffee or enjoying a peaceful retreat. The detached three-car garage also has ample space for vehicles, storage, or a workshop. This residence boasts plenty of space and character, just waiting for your finishing touches. Take a look at this lovely home and make it yours today! Subject to Probate approval. ** listing includes abutting rear 1.16 parcel as reflected in total 1.92 acres**

130 Christian Rd, Middlebury
$461,000
3 Beds ⋅ 1 Baths ⋅ 24136109 MLS
Discover your dream home at 11 Upper Whittemore Rd, a stunningly renovated Brick Ranch nestled on a private, dead-end street with over 1.37 acres of beautiful land. This oasis boasts an unbeatable location because it provides both seclusion and connectivity: you're just moments from the recreational fun of Lake Quassapaug and Quassy Amusement Park, and the property offers easy access to major highways for simple commuting. Step inside to find a brand-new, modern kitchen featuring Carrara-style quartz countertops, stainless steel appliances, and gorgeous subway tile. Recessed lighting illuminates the entire home, highlighting gleaming hardwood floors, new crown molding, trim, and doors. The fully renovated bathroom completes the luxury, offering a beautifully tiled shower and an oversized vanity. This home is built for low-maintenance living with a brick exterior and features a brand new well holding tank. One of the key features is a fantastic oversized shed/garage-perfect for a workshop or storage. Home is being finished and sold as is, this is a rare chance to secure a high-end, private retreat in a prime Middlebury spot!

11 Upper Whittemore, Middlebury
$460,000
3 Beds ⋅ 2 Baths ⋅ 24107316 MLS
Gorgeous ranch located on a private cul-de-sac in Middlebury! This fully updated three bedroom ranch features hardwood floors throughout the entire main level, oversized eat in kitchen with quartz countertops and stainless-steel appliances, new windows, brand new central air, and a Buderus oil furnace. Your completely finished lower level has a full bathroom with walk out to the fenced in backyard. This space is perfect for further entertainment or a potential in-law set up. Laundry is located on the main floor bathroom that has also been updated. This home is located steps from the scenic Middlebury Greenway walking trail. Simply a must see!

74 Joy Rd, Middlebury
$458,000
3 Beds ⋅ 2 Baths ⋅ 170622814 MLS
Welcome Home to this Charming Cape Cod Style Home in Middlebury, CT. Inside and out this special home, with its many improvements, is private oasis for any family to make their own. Enter the home through the inviting mudroom with beautiful brick flooring, and plenty of storage space. The attractive and brightly lit kitchen, with adjoining dining room, was renovated in 2020 and includes new appliances, butcher block counter tops and hardware, breakfast or coffee bar, hardwood floors, recessed lighting, and its own GE Kitchen HUB. The living room has a new wood plank ceiling, recessed lighting, built-ins and hardwood floors. To complete this cozy space there is an energy efficient pellet stove that heats much of the home. The primary bedroom, with ensuite, is located on the first floor with the laundry area conveniently located in this space. Two light and airy additional bedrooms and full bath are located on the second floor. Summer is right around the corner. Exit the oversized fenced-in driveway directly onto the Middlebury Greenway. To complete this property there is a pool room, a private patio area to enjoy your morning coffee or afternoon cocktails, an in-ground heated pool with newly installed pool steps and liner, and new diatomaceous earth pool filter. End your perfect day gathered around the firepit. Priced to Sell! Don’t miss out on an opportunity to see this lovely home in Middlebury, CT.

24 Steinmann Ave, Middlebury
$456,000
3 Beds ⋅ 3 Baths ⋅ 24119687 MLS
Lovingly Maintained Home in Desirable Middlebury Location Nestled in one of Middlebury's most sought-after neighborhoods, this lovingly maintained home offers comfort, convenience, and timeless charm on a level, private lot-perfect for relaxing or entertaining. Located in a top-rated, award-winning school district, this home is ideal for families seeking both community and quality education. Enjoy peace of mind with low-maintenance vinyl siding, energy-efficient vinyl windows, a 10-year-old roof, and gutter guards already in place. Inside, the home boasts gleaming hardwood floors throughout the main level, including under the carpeted bedrooms. The primary bedroom features a private half bath, while two additional generously sized bedrooms and a well pointed full bath complete the main floor. The heart of the home is the open-concept kitchen, showcasing beautiful maple cabinetry, stainless steel appliances, and seamless flow into the dining and living areas. The spacious living room is filled with natural light thanks to a large picture window and opens directly into the dining room, where French doors lead out to a good-sized Trex deck-perfect for outdoor dining and gatherings. The finished lower level offers valuable space, complete with a laundry room, an additional half bath, and direct access to the two-car garage. A separate entry door makes this level versatile for a home office, guest suite, or recreation area. This home truly has it all!

18 E Ridge Dr, Middlebury
$454,000
3 Beds ⋅ 3 Baths ⋅ 24078439 MLS
Charming custom home with a barn on a flat lot! This spacious, custom-built home offers character, functionality, and endless potential. Situated on a beautiful level lot, the property includes a barn with a loft-perfect for storage, a workshop, or creative possibilities. Inside, you'll find a living room with a stone fireplace, a first-floor office, an eat-in kitchen, and a formal dining room. A full utility bathroom with laundry and a sunroom overlooking the backyard add to the home's versatility. Upstairs, three bedrooms with hardwood floors are accompanied by a full guest bathroom and a half bath in the primary bedroom. Additional features include upgraded 200-amp electric service and a basement housing all mechanicals (low ceiling height). Sold as-is-don't miss this unique opportunity! Middlebury is conveniently located near I-84, making travel easy to Waterbury (10-15 min), New Haven (30-40 min), Hartford (40-50 min), and NYC (~90 min). The community offers seasonal events, local farmers' markets and town gatherings.

679 Christian Rd, Middlebury

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