Refine Search
Map
Sort by
$409,000
3 Beds ⋅ 2 Baths ⋅ 24134353 MLS
PRICED RIGHT FOR IMMEDIATE SALE! SNOOZE YOU LOSE! THIS IS "NATURES LOVERS DREAM HOME", PERFECT FOR BIRD WATCHERS, ON OPEN & GLORIOUS 1.80 ACRES WITH MATURE FRUIT/NUTS/BERRIES/BUSHES & WILLOW TREES, TO NAME A FEW! ALMOST 1500 S.F. OF LIVING! A BEAUTIFUL BABBLING BROOK. FOR PEACE AND SERENITY CAN BE SEEN FROM THE OVERSIZED COVERED DECK, AS YOU ENJOY YOUR MORNING COFFEE OR STRESS-FREE EVENING RELAXATION! CIRCULAR DRIVEWAY! GREENWAY FOR WALKING AND BIKING RIGHT AROUND THE CORNER. SOLAR PANELS FOR ENERGY EFFICIENCY, NEWER ROOF IN 2015, FURNACE IN 2016, & HOT WATER HEATER 2018. NESTLED AWAY, YET CONVENIENTLY LOCATED TO RESTAURANTS, SHOPPING AND I-84/RT 8. WHAT ARE YOU WAITING FOR???? HURRY ON THIS ONE...IT IS SURE TO GO FAST!! MORE PHOTOS TO FOLLOW SHORTLY.

115 Porter Ave, Middlebury
$405,000
4 Beds ⋅ 4 Baths ⋅ 170611536 MLS
You Will Find At The Top of the Hill a Private Hideaway This 5 level split has a cozy place for each member to cuddle up with a good book. This home features 3144 sq. ft., 2.09 acres, on a cul de sac, a living room with a fireplace and hardwood floors, formal dining room with hardwood floors, eat in kitchen, 4 bedrooms, a master suite and 3 additional bedrooms, 2 full bathrooms and 2 half baths, a large family room with a fireplace, bar and a slider to the backyard and in the lower level a perfect space for a game room or home office. The exterior has a large screen in porch with a deck attached and 3 car garage. We are excited to offer this home and eager to find a perfect match !!!

142 Ravenwood Dr, Middlebury
$400,000
3 Beds ⋅ 2 Baths ⋅ 24167075 MLS
Pleased to present this charming, turn-key colonial home which offers a warm and inviting atmosphere. This three-bedroom residence features a spacious kitchen that connects seamlessly to the dining room, which is alongside a large family room highlighted by a high efficiency fieldstone fireplace. Additional features include: A four-season sunroom leading to an outdoor grilling and relaxation area. A full walk-in laundry room with ample storage. A finished lower level with half bath, providing the potential for a full bath as previously planned by the seller. Recent upgrades including a newer roof and a two-zone, high efficiency heating and cooling system. Meticulously maintained for over 20 years, this home showcases exceptional charm, complemented by a beautifully landscaped yard. Walk to town via the Greenway, dine at multiple restaurants, shop or visit Lake Quassapaug. So much to see - schedule your showing today!

301 Steinmann Ave, Middlebury
$390,000
3 Beds ⋅ 2 Baths ⋅ 24138445 MLS
The best value in Middlebury! Welcome to 32 Yale Avenue, a home with inviting curb appeal in a desirable neighborhood just steps from the scenic Greenway Trails. This spacious property combines architectural interest with modern amenities. Inside, you'll find generous living and dining rooms with hardwood floors throughout and a cozy fireplace for added charm. A versatile first floor bedroom is complemented by two additional bedrooms upstairs, with a full bath on each level for convenience. The full basement and garage provides abundant storage. The spacious yard includes a back deck with views across the property, a gazebo and an oversized shed/outbuilding that can serve as a hobby space, mancave/she-shed or great additional storage for contractor's equipment. With city water and sewer, this move-in ready home blends comfort, functionality, and outdoor enjoyment in a quiet setting- come take a look!

32 Yale Ave, Middlebury
$390,000
3 Beds ⋅ 2 Baths ⋅ 24068595 MLS
This inviting 3-bedroom, 1.5-bathroom home with a home office space allows comfort and convenience in a fantastic location. The spacious layout includes an eat-in kitchen with room to personalize, plus modern updates like newer windows that bring in plenty of natural light. Relax and unwind on the enclosed front porch/mudroom, a perfect spot to enjoy your morning coffee. Located just a short stroll from the Middlebury Greenway, you'll have easy access to scenic walks and biking to Lake Quassy!

10 Yale Ave, Middlebury
$389,900
3 Beds ⋅ 2 Baths ⋅ 170620123 MLS
Welcome to Christian Road in Middlebury. One-level country living at its finest, come see this charming Ranch with 3 Bedrooms,2 full baths, a living room dining room, eat-in kitchen. All good-size rooms, a large 2-car garage, and a beautiful level lot consisting of 2.14 acres. You will love this home and it's coziness as soon as you walk in. Super close to Route 64, I-84 and Route 8.. an abundance of restaurants, banking, shopping, park, and great school system. Come see all that Middlebury has to offer!!

43 Christian Rd, Middlebury
$385,000
2 Beds ⋅ 1 Baths ⋅ 24053754 MLS
Well-maintained and tastefully updated home with an inviting floor plan. The formal living room features a warming fireplace, trey ceiling, chair rail, and hardwood flooring. Large Andersen picture windows bathe the room in natural light, creating an elegant and welcoming atmosphere perfect for entertaining. The family room boasts hardwood flooring, a large Andersen picture window, and a coffered ceiling, providing a comfortable and relaxing ambiance. The updated kitchen showcases granite countertops, white cabinetry, a coffered ceiling, and atrium doors leading to the deck and leveled backyard, making it a delightful space for culinary creations and gatherings. The home comprises two generously sized bedrooms with hardwood flooring and ample closet space. The primary bedroom features a coffered ceiling, adding a touch of elegance. The updated bathroom offers a large linen closet for convenient storage of towels, sheets, and bathroom essentials. Additional notable features include central air conditioning, newer Andersen doors and windows, a generator, and a water filtration system, ensuring comfort and convenience. Situated in a desirable neighborhood, this home is conveniently located near schools, shopping areas, and major highways, providing easy access to various amenities.

74 E Ridge Dr, Middlebury
$385,000
3 Beds ⋅ 2 Baths ⋅ 24063472 MLS
Start your new chapter here in the desirable town of Middlebury. All the charming appointments you would expect from an early 1900's home. Generous sized bedrooms & closets including one bedroom on the main floor. Hardwood flooring throughout. There is 1600 sq feet plus an ADDITIONAL 200+ heated square feet in the enclosed rear porch which has a full view of the expansive backyard. Lower level has a fireplace & the start of a half bath for a foreseeable finished lower level. Within the last 5 years the oil & water tanks have been replaced, the chimneys were extended, a basement system was installed, replacement windows completed, refrigerator & range were replaced, & just 2 months ago a new boiler was installed. A storage shed sits at the back of the property & just beyond is lightly wooded privacy that abuts to town of Middlebury land. A quaint enclave of roads makes for a family friendly neighborhood but still close to shopping, restaurants, & the highway. Middlebury is part of award winning Region 15 schools & home to Lake Quassapaug Amusement Park. Middlebury Recreation Area (MRA) offers seasonal passes to the lake for residents only. What a great place to spend your summers! Previous buyers flailed & then bailed. Their loss can be your gain. Seller to connect house to public water PRIOR to closing.

66 White Ave, Middlebury
$385,000
3 Beds ⋅ 2 Baths ⋅ 24077995 MLS
This one-level home is nestled on a quiet, walkable street, backs up to a peaceful, wooded setting and is located in a sought-after neighborhood. The bright eat-in kitchen boasts a breakfast bar, plus a large window overlooking the backyard, providing a serene view. The spacious living room features hardwood floors and another large window, filling the space with natural light. This home offers three cozy bedrooms with hardwood floors, along with a full bathroom featuring double sinks, all located on the main level. The walk-out basement includes a family room with a large window, an additional full bathroom, a utility room, and a garage perfect for storing bikes and lawn equipment. The backyard is private and backs up to the woods, with an asphalt basketball pad and patio. Recent updates include 12-yea-old siding, a 12-year-old roof, and a newer hot water heater. With a personal touch, this home is ready to shine. The home needs some work, being sold as-is.

43 Merideth Rd, Middlebury
$385,000
3 Beds ⋅ 1 Baths ⋅ 24110397 MLS
Welcome to 225 Whittemore Road in Middlebury, CT, where charm meets convenience in this cozy solid 3-bedroom, 2-bathroom brick cape. Situated with easy access to Route 8 and I-84, this home is a perfect retreat close to 3 parks and the greenway for outdoor recreation enthusiasts. Step inside to discover an inviting living room featuring a gas stove, creating a warm and welcoming ambiance. The updated kitchen is a chef's delight, offering a functional space to prepare delicious meals and entertain guests with ease. Two bedrooms on the main level provide convenience and comfort, while an additional bedroom on the upper level offers privacy and flexibility for various living arrangements. Moving outside, the property boasts a large level fenced-in yard, perfect for hosting gatherings or enjoying peaceful moments in the outdoors. Relax by the firepit on cool evenings, unwind on the front covered porch, or soak up the sun on the patio - the options for outdoor living are endless. The two-car garage provides ample parking and storage space, while the public sewer adds convenience to everyday living. Nestled on 0.92 acres of land, this home exudes a sense of tranquility and privacy, making it a true oasis in a convenient location. With its Cape Cod architectural style and red brick exterior, this property offers a timeless appeal and a welcoming atmosphere. Don't miss this opportunity to own a piece of Middlebury's charm and make this delightful home your own. Schedule a showing

225 Whittemore Rd, Middlebury
$383,000
3 Beds ⋅ 3 Baths ⋅ 24060925 MLS
Fabulous park-like grounds in beautiful neighborhood. This is a home needing complete professional rehab. Custom built with generous room sizes. Use your vision to picture this restored to its original elegance. Extensive work required, but will be absolutely stunning when finished. There is a 294sf beautiful room attached to home with fireplace. Room is not heated and could be used for three seasons without heat. Owners will consider CASH ONLY "AS IS WHERE IS" offers, and will not look at any other type of offers. Owners will not do any repairs. All offers must be in by December 1 noon, with proof of funds. Broker must receive Hold Harmless before any entry into house. Do not enter unless HH has been sent to Broker Screenshot of signed doc ok, or email copy. NO showings after 4pm

828 Breakneck Hill Rd, Middlebury
$380,000
2 Beds ⋅ 2 Baths ⋅ 24127393 MLS
Timeless charm and warmth fill this beautifully maintained 3 bed, 1.5 bath Middlebury home. The main level showcases original hardwood floors, custom built-ins, and a spacious living room centered around a working Heatilator fireplace - an inviting spot to gather and unwind. The formal dining room features elegant built-ins and a picturesque bay window that fills the space with natural light, creating a bright and welcoming atmosphere. The kitchen offers generous cabinet storage, classic wood cabinetry, and a clean, functional layout with a view overlooking the yard. Just off the living area, a versatile main-floor room opens to a private deck, perfect as a guest room, office, or reading nook. Upstairs, the primary suite impresses with a walk-in closet, built-in storage, and a cozy sitting area - a peaceful retreat to start and end your day. Outside, the backyard is designed for enjoyment and relaxation, complete with a large deck, an above-ground pool, and a patio surrounded by trees and greenery - ideal for summer gatherings or quiet evenings outdoors. Nestled in a desirable neighborhood close to parks, schools, and local amenities, this home combines character, comfort, and convenience in one inviting package.

146 Richardson Dr, Middlebury
$380,000
3 Beds ⋅ 2 Baths ⋅ 170609862 MLS
The most adorable home with many updates. Freshly painted inside and out, updated kitchen with granite counters, new flooring and stainless appliances, new propane line for the stove. There are also refinished hardwood floors up and down, plus updated electrical service and generator hook up. Brand new septic fields just installed, and the house has public water. Great deck, relaxing side yard with firepit and lots of pretty landscaping. Conveniently located for commuting, shopping and a few restaurants within walking distance. On the upper level you will find three bedrooms with full bath and walk-in storage closet. Main level has a living room with fireplace, dining room, updated kitchen, 1/2 bath and office area which leads to the deck. Come see all this adorable home has to offer and also comes with a 1-year home warranty. Located in the beautiful town of Middlebury Connecticut, with Region 15 schools, great shops, restaurants, parks & walking trails. The driveway access is shared, but this house also has a garage and parking at the bottom.

1424 Middlebury Rd, Middlebury
$375,000
3 Beds ⋅ 3 Baths ⋅ 24054588 MLS
Solid Ranch home on almost 2 acres ready for your updates and touches! A true handyman special, bring this diamond in the rough back to its glory! Can be lived in while you renovate. Covered front porch opens to entrance foyer with large closet, connects formal living room and dining room. Hardwood floors flow throughout. Living room has a wood burning fireplace, and picture window; dining room has large bay window, both overlooking the front yard. Eat-in kitchen with lots of cabinet space & ceiling fan. Full bath with stall shower off kitchen. Large heated breezeway connects kitchen with garage, is more of a 4-season room, has glass door to backyard and sunporch feel. Good flex and flow throughout house: the primary bedroom, with skylight and ceiling fan, could also be family room, with access to large partially fenced backyard. The other 2 bedrooms share a Jack'n'Jill bathroom with ample linen closet. Expansive basement has laundry hook-ups and could be heated by a wood burning stove; finish in 1889 sq ft! Enjoy large backyard - perfect for entertaining and relaxing with pretty gazebo and patio. Two car garage has attic space, and outdoor shed also has plenty of storage. Lots of parking in the large driveway. Newer roof, HVAC system, double oil tanks yield discount with larger fills. Across the street from Meadowview Park & Lake Elise! Enjoy Middlebury schools, Quassy Amusement & WaterPark! Please submit interest on GHAR form; EDM to Estate of Michael David Winkel

1738 Middlebury Rd, Middlebury
$375,000
3 Beds ⋅ 2 Baths ⋅ 170591550 MLS
Welcome to this promising 3-bedroom, 1.5 -bathroom home with incredible potential, ideally situated near major highways for easy commuting. This property boosts an oversized 2-car garage in addition to a sun room and full sized basement which can be finished for added living and entertaining space. This property is waiting your creative vision and TLC to transform it into the perfect dream home. It has a generous backyard space perfect for gardening, entertaining, or expansion possibilities. This property offers a fantastic investment opportunity for those looking to add value through renovations and upgrades. With some repairs and updates, this home has the potential to be a showcase property. Don't miss out on this fantastic opportunity to create your dream home in a fantastic location! Due to needed repairs, this property will have to go 203k, cash or hard money as it will not qualify for conventional or traditional FHA financing.

1600 Straits Tpke, Middlebury
$375,000
3 Beds ⋅ 2 Baths ⋅ 24062438 MLS
Great opportunity to purchase a home in Middlebury. This 3 bedroom Ranch Style home is in a great location near shopping and easy access to I84. 3 Bedrooms, Primary Bedroom with 1/2 bath, spacious living room with fireplace open to the dining area with slider to a generous sized Trex deck. Also, off the dining area you'll find the updated kitchen with a breakfast island to enjoy your morning coffee. Lower level walkout features extra space for media room/workout area plus a2 car garage and public water/sewer.

91 Richardson Dr, Middlebury
$375,000
4 Beds ⋅ 2 Baths ⋅ 170601535 MLS
Charming Middlebury Cape. This warm and inviting home is the perfect home to create cherish memories, for years to come. Freshly painted this home offers a bright eat-in Kitchen w/full appliances, formal dining room opens to a spacious living room, ideal space for hosting gatherings. Four spacious bedroom, with primary bedroom on the main level and full bath. Upper level bedroom provides flexibility for family, guest or home office. Beautiful hardwood floors thought-out the main level, Additional finished lower level is thoughtfully designed, to include a family room with fireplace, kitchen, built-ins and a full bath, This space offers endless possibility. Cair and 1 car garage. Improvements include, new electric 200 amp service, new well pump 5 Years, New furnace 2 years, Cair Compressor 12 years old, washer Dryer 5 months old, Newer Windows 2010, Roof 2010. Attractive field-stone wall adorns the landscape leading to the home. This house is ready for your personal touches call it home and start making memories. Call for a private showing. Inspections are for Informational purpose only.

1418 Straits Tpke Sts, Middlebury
$370,000
2 Beds ⋅ 1 Baths ⋅ 24088264 MLS
Welcome to this charming Cape Cod-style home nestled in the heart of Middlebury, CT. Warm hardwood floors flow throughout the main living spaces, adding a timeless touch of elegance. Begin your day-or unwind at the end of it-in the inviting three-season front porch, the perfect spot to curl up with a good book. Step inside through a cozy entryway where you can hang your coat before choosing to head into the spacious living room, dining room, or upstairs to the generously sized bedrooms. The bright kitchen features a tiled floor, ceiling fan, updated appliances, and plenty of room for a table for casual dining. Each bedroom offers ample closet space and ceiling fans for year-round comfort. The home is equipped with updated windows and a roof installed in 2008. Efficient radiator heat powered by an oil-burning furnace and continuous hot water ensure warmth and comfort during the colder months. While the basement remains unfinished, it offers great storage space and features a convenient hatchway leading to the backyard. Outside, you'll find a private deck overlooking a large backyard-perfect for entertaining or simply enjoying the outdoors. Additional highlights include an oversized detached garage offering plenty of space for storage or a workshop.

259 White Ave, Middlebury
$370,000
2 Beds ⋅ 1 Baths ⋅ 24046489 MLS
You will be very happy living in this well maintained Ranch on a Pretty and Level lot. This home is a perfect condo alternative and more!! Situated on a level .60 acre lot in a desirable subdivision in Middlebury. There is a large, eat in kitchen with a bay window which brings in the nice sunshine. There is a new Stainless Steel Refrigerator and Oven/Range, plenty of cabinet space and a tiled kitchen floor. Off of the kitchen is the Formal Dining Room with a bay window and Formal Living Room featuring a Bay Window. The bedrooms have good closet space and there is an entrance to the bathroom from the primary bedroom. The basement if full with high ceilings so it will be easy to finish off. There is a bulkhead for outside access to the peaceful backyard. Relax and Enjoy the front open porch area on a nice day. You'll love this convenient location, close to highway, schools, great restaurants, walking trail, parks and shopping of all sorts! Make sure you don't miss the opportunity to see this wonderful home so you can have it as your own, Home Sweet Home.

111 Acme Dr, Middlebury
$370,000
2 Beds ⋅ 1 Baths ⋅ 24046093 MLS
Simple living at its finest! This completely renovated ranch offers the ease of one floor living with many upgrades. The open floor plans welcomes an open space to entertain. The ample kitchen hosts plenty cabinet space for all of your cooking essentials, with a brand new center island, granite countertops, newer cabinets that reach the tall ceilings, newer appliances, plus a large picture window framing the gorgeous backyard view! Easy to care for vinyl flooring carries throughout the home. A washer and dryer nook is conveniently located right next to the bedrooms. The primary bedroom features built-in side tables, plus a walk-in closet. The second bedroom offers a space for an office, yoga room or guest bedroom. Each room is topped with sleek ceiling fans, plus the home can be cooled with a brand new ductless air conditioner, which can also work as an efficient heater. The lower level of the home holds a newer furnace, newer 200 amp electrical box, a brand new hot water heater and brand new well tank, plus a workbench. You can enjoy the quiet outdoors as much as the indoors with the private patio and raised garden beds. The two car garage is perfect for your cars or storage. Newer roof over the house and a brand new well pump. Located in a quaint neighborhood, with easy access to I84 and walking distance to the Middlebury Greenway, plus award winning Region 15 Schools! Make this house your next home!

22 Yale Ave, Middlebury
$365,000
2 Beds ⋅ 1 Baths ⋅ 24088875 MLS
Lake Shore Drive is just a short walk from the beautifully preserved Long Meadow Pond, a 117-plus acre body of water known for its fishing and kayaking. This home is perfectly in keeping with this idyllic setting, as it is a quintessentially charming ranch, a style of home known for its open and inviting floor plan. There is a confidence in your investment that comes with purchasing a newly renovated home; the knowledge that there will be little maintenance allows one to settle in and enjoy the space. Thoughtful and timeless are the home's details, such as the bluestone patio, hardwood floors, and bright white kitchen. Located in the southern part of Middlebury, you are a short drive from the area's amenities as well as highway access.

203 Lake Shore Dr, Middlebury
$360,000
2 Beds ⋅ 1 Baths ⋅ 24146072 MLS
Charming Cape Cod home ideally located just a minute from Memorial Middle School and close to everything Middlebury has to offer. This home features hardwood floors throughout, creating a warm and timeless feel from the moment you step inside. The eat in kitchen offers a comfortable space for everyday meals, while the 12x12 deck overlooks a nice yard--perfect for outdoor dining in summer and snowman making in winter! The attic has been finished and provides 372 sq ft of additional living space-ideal for home office, guest area or teen room. Whether you are looking for your first home or a smart downsizing option, this well-maintained property combines classic charm, functional space and an unbeatable location!

348 Kelly Rd, Middlebury
$360,000
3 Beds ⋅ 3 Baths ⋅ 170594563 MLS
CHARMING COLONIAL LOCATED ON A QUIET CUL-DE-SAC! FULLY UPDATED SEMI OPEN CONCEPT LAYOUT! Direct, private lake access to Long Meadow Pond just across the street from this property! THIS HOME COMES WITH AN ADDITIONAL .27 ACRE LOT ABUTTING THE WATER. Total acreage altogether is .47 of an acre with both lots combined. Enjoy activities year round from fishing, kayaking, swimming, sail boating and even ice fishing! DREAM kitchen with newer stainless steal appliances, island with breakfast bar, granite counter-tops, crown molding and STUNNING built-in hutch with shelving and storage in kitchen. Living room with french doors leading to wrap-around deck perfect for entertaining. 3 well appointed bedrooms with plenty of closet space and 2 full bathrooms. Primary bedroom with full bathroom on-suite. Relax and unwind year round at this property. This home also boasts a city sewer connection, new roof, newer furnace, newer 200 amp, new leaf guards, electrical service, generator hook-up, 2-zone heating, walk-in pantry off kitchen, newer driveway, windows and so much more. MOVE QUICK!

259 Lake Shore Dr, Middlebury
$350,000
3 Beds ⋅ 2 Baths ⋅ 170576019 MLS
This 1940's cape features gleaming hardwood floors throughout and is beaming with character. Tucked away on a quiet street with likewise homes, this home offers curb appeal, a breezeway and a one car garage. Step inside into a formal dining room with a built-in cabinet, a charming and bright eat-in-kitchen and a large living room with a fireplace, plus a bonus den at the back of the home featuring sliders to the back deck. The upper level hosts three bedrooms and a full bath. A walkup attic offers easy storage. The lower level is finished and a perfect spot for a play room or theater room. The backyard is ready for summer fun with a hot tub, heated above ground and sprawling backyard. Located close to I84 and Route 8, steps from the Middlebury Greenway and Bristol Park. Enjoy all of what Middlebury has to offer!

267 White Ave, Middlebury
$345,000
2 Beds ⋅ 2 Baths ⋅ 24115490 MLS
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!

119 Christian Rd, Middlebury
$342,000
1 Beds ⋅ 2 Baths ⋅ 24071540 MLS
Welcome to this charming 1-bedroom house with incredible potential! This home is ready for you to move right in, featuring lots of new updates. The main living areas include an inviting living room, a dining area, and kitchen which features all-new appliances, perfect for cooking your favorite meals. With 2 full bathrooms, this home offers plenty of space for comfort and convenience. There are 2 additional rooms, including a spacious loft which are ideal for a home office, den, or personal retreat. The outside area features a brand-new Trex deck, which is an ideal spot to relax or entertain while surrounded by the beauty of the lightly wooded lot. With all of these recent upgrades, this home is a great place to settle in and enjoy the peace and quiet. Don't miss out on this exceptional property-schedule a tour today and start imagining the possibilities! (Highest and Best Offer by Sunday, February 9, 2025 at 6 PM).

28 Yale Ave, Middlebury
$340,000
4 Beds ⋅ 3 Baths ⋅ 24181461 MLS
Welcome to this charming Cape Cod home, situated on a 0.34-acre corner lot in the highly desirable town of Middlebury. This home offers 1,855 square feet of comfortable living space with 4 bedrooms and 2.5 baths. The heart of the home features updated oversized country kitchen, with cabinets galore, stainless steel refrigerator, dishwaher and microwave and a gas range. Formal Living Room and Formal Dining Room for your gatherings and entertaining. Newer windows, doors. Remodeled and updated bathrooms. First floor laundry room and bedroom for your convenience. Also, an in-law apartment provides added flexibility for extended family, guests, or potential rental income. The in-law was originally the two car garage that can be converted back! Enjoy all that Middlebury has to offer, including its small-town charm, highly rated schools, wonderful parks, popular restaurants, lake, tennis courts,health club, walking and riding trails, health club and convenient access to Route 8 and I-84.

555 Whittemore Rd, Middlebury
$335,000
3 Beds ⋅ 3 Baths ⋅ 24021506 MLS
Attention cape lovers!!! This cozy, well maintained cape offers an open and inviting main level with a large living room, french doors leading out to the backyard and private garden patio with cascading waterfall, an updated kitchen with hickory cabinets, granite countertops, stainless steel appliances, and a breakfast bar which extends to the sun-filled dining room. Hardwood floors throughout and updated tile in the kitchen. Upstairs, you will be welcomed with a freshly painted and updated full bath with blue tooth technology, a spacious primary bedroom along with 2 additional bedrooms. Outside you will find plenty of sunshine amongst the manicured lawn, various flowers, and trees! This yard offers space to run and play, privacy, a shed with electricity and a lovely patio great for outdoor dining and entertaining! Brand new roof and gutters (2024), freshly power-washed vinyl siding, and regular maintenance has kept this home beautiful and comfortable. Close to parks, walking/biking trails, shopping, dining, schools and so much more! Centrally located and conveniently only minutes away from 84 and close to Route 8. A commuters dream!

294 Porter Ave, Middlebury
$333,000
3 Beds ⋅ 2 Baths ⋅ 170582585 MLS
Turn key, single level home in desirable Middlebury! Set back from the road and offering plenty of level backyard space, this three bedroom two bath home has much to offer. Beautiful hardwood floors throughout much of the living space, large kitchen with new appliances, flooring, granite countertops, custom cabinets, and recessed lighting. The spacious living room offers plenty of natural light, and large stone gas fireplace. Separate dining room, currently used as an office and home theater, provides additional options for entertaining! Down the hallway you will find three generous sized bedrooms with ample closet space. Home includes rear deck for grilling and full basement with walk out, workshop area and plenty of room for storage. Too many improvements to mention! See full list of improvements in attachments, including install of central air. Located close to all major conveniences and area schools, there is nothing to do but move right in!

2006 Straits Tpke, Middlebury
$331,900
3 Beds ⋅ 1 Baths ⋅ 24033449 MLS
REQUESTING HIGHEST AND BEST BY 8/16 AT 6:00PM. Charming Middlebury Cape in a desirable neighborhood close to the Greenway walking path and town center w /hiking trails right behind your private fenced in backyard. This home features 3 bedrooms, 1 full bathroom, public sewer and water, a new furnace and a Generac generator. Perfect home for those seeking comfort convenience and a welcoming community.

185 Porter Ave, Middlebury

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.