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541 Benson Rd, Middlebury
$465,000
3 Beds ⋅ 3 Baths ⋅ 24161555 MLS
Rare Two-Home Compound in Middlebury - Ideal for Investment or Owner-Occupant! An extraordinary opportunity for investors or owner-occupants looking to offset their mortgage! This unique property at 541 Benson Road features TWO distinct, detached dwellings on a private .8-acre lot, offering a total of 3 bedrooms, 3 full baths, and 4 garage bays. Unit 1: The Main Residence (2BR/2BA) This beautifully appointed home features an open-concept layout with gleaming hardwood floors and high-end finishes. Chef's Kitchen: U-shaped layout with oak cabinets, granite countertops, stainless steel appliances (gas stove), and a large pantry. Main Level: Includes a spacious bedroom and a brand-new spa-like bathroom with a custom tiled walk-in shower and separate soaking tub. Upper Level: A private primary suite retreat finished in warm natural pine, featuring abundant closet space, a full ensuite bath, and a charming built-in reading nook/office area. Central Air, pellet stove for efficient heating, and a massive 3-car attached garage for ample storage or workshop space. Unit 2: Detached Carriage House (1BR/1BA) A completely separate, legal-style dwelling perfect for rental income, multi-generational living, or a professional home office. Living Space: Features a functional galley kitchen with gas cooking, a bright living area, and a private bedroom. Amenities: Full bathroom with a tiled shower and its own dedicated 1-car garage/workshop located directly be

541 Benson Rd, Middlebury
11 Upper Whittemore, 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
18 E Ridge Dr, 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
190 Allerton Farms Rd, 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
863 Whittemore Rd, 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
271 Shadduck Rd, Middlebury
$435,000
3 Beds ⋅ 2 Baths ⋅ 24168911 MLS
Charming and well-maintained raised ranch offering a bright open floor plan and thoughtful updates throughout. Features include a modern kitchen with granite countertops, stainless steel appliances, and a breakfast bar, along with beautiful hardwood flooring. The home also offers a private primary suite, multiple living spaces, and cozy fireplaces perfect for colder months. Enjoy outdoor living on the spacious deck overlooking the yard. A wonderful opportunity with comfort, style, and convenience in mind.

271 Shadduck Rd, Middlebury
192 Breakneck Hill Rd, Middlebury
$435,000
4 Beds ⋅ 2 Baths ⋅ 24166198 MLS
Welcome to this Charming Well Maintained 4 bedroom ranch. 2 full baths. This inviting home features a large bright living room with picture window overlooking beautiful landscaped yard. Beautiful hardwood floors through out. Needs some updating. Finished room in lower level with walk out leading to patio. Two Car Garage. Central Air. Public Sewer. House generator stays. Well Water. Don't miss out on making this Middlebury gem your own.

192 Breakneck Hill Rd, Middlebury
818 Middlebury Rd, 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
115 Porter Ave, Middlebury
$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
301 Steinmann Ave, 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
32 Yale 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
146 Richardson Dr, 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
89 Sandy Beach Road Unit 89, Middlebury
$375,000
2 Beds ⋅ 1 Baths ⋅ 24203525 MLS
Rare opportunity to own direct waterfront on beautiful Lake Quassapaug! Located in the desirable Tylers Cove community, this charming two-bedroom cottage sits just 50 feet from the water and features its own private dock and yard with direct lake frontage. The cottage is ready for a new owner to bring their ideas and updates-renovate the existing home, explore the possibilities of rebuilding, or simply enjoy it as a classic summer retreat. A special opportunity to experience lakefront living, boating, swimming, and relaxing by the water on one of the area's most beautiful lakes.

89 Sandy Beach Road Unit 89, Middlebury
348 Kelly Rd, 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
555 Whittemore Rd, 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
12 Yale Ave, Middlebury
$325,000
2 Beds ⋅ 1 Baths ⋅ 24113785 MLS
Picture-perfect and completely updated, this classic New England Cape delivers far more than its footprint suggests. A paver walkway, lamppost, and lush hosta gardens frame a storybook exterior with black shutters and stone front steps - genuine curb appeal on one of Middlebury's most established streets. Inside, the open floor plan connects a sun-filled living area to a fully renovated kitchen featuring a quartz-topped center island with seating, two-tone cabinetry with brass hardware, stainless appliances, and a wall of windows overlooking the green backdrop beyond. Crown molding, designer lighting, and thoughtful finishes carry throughout - every detail has been done, so you simply move in. Two bedrooms and a full bath complete this efficient, light-filled layout. Steps from the Middlebury Greenway Trail with easy Route 64 and I-84 access, and served by the award-winning Region 15 school district. A turnkey Connecticut gem.

12 Yale Ave, Middlebury
587 Shadduck Rd, Middlebury
$310,000
2 Beds ⋅ 1 Baths ⋅ 24124473 MLS
Welcome to 587 Shadduck Road, Middlebury, CT! This inviting two-bedroom, one-bathroom Cape-style home offers comfort, character, and a highly desirable location. Directly across the street, enjoy access to the Larkin State Park Trail, perfect for walking, running, or biking. Inside, the kitchen is bright and functional, featuring two windows that bring in natural light, warm wood cabinetry, and plenty of counter space. The living room boasts a cozy wood-burning fireplace, ideal for relaxing evenings. Upstairs, you'll find two spacious bedrooms with beautiful hardwood floors and abundant natural light. Additional highlights include a full bath with a tub/shower, a two-car attached garage, and a spacious yard that provides ample room for outdoor enjoyment, gardening, or entertaining. Conveniently located near major highways, shopping, and dining, this home combines everyday convenience with the peaceful charm of its natural surroundings.

587 Shadduck Rd, Middlebury
125 Shadduck Rd, Middlebury
$305,000
2 Beds ⋅ 2 Baths ⋅ 24193924 MLS
Welcome to this Middlebury home offering the perfect blend of comfort, functionality, and a desirable location. The home's refreshed interior provides move-in-ready feel designed for everyday living. The property is an excellent opportunity for buyers looking for a home that is ready to enjoy. The home sits on a level lot and is situated directly next to a small brook.

125 Shadduck Rd, Middlebury
314 Porter Ave, Middlebury
$300,000
3 Beds ⋅ 2 Baths ⋅ 24161984 MLS
A classic Middlebury Cape Cod offering strong potential. This 3bedroom, 2bath home sits on a 0.34acre lot and features 1,440 sq. ft. of living space plus a 900 sq. ft. basement. With an average physical condition rating and many original features, it's a handyman's dream-perfect for those looking to update, customize, and build equity. Traditional gableroof styling, aluminum siding, and a two story layout provide a solid foundation for renovation, with opportunities to refresh interiors, modernize systems, and enhance exterior elements. A great chance to transform a welllocated property into a personalized home in desirable Middlebury.

314 Porter Ave, Middlebury
73 Yale Ave, Middlebury
$300,000
2 Beds ⋅ 2 Baths ⋅ 24132707 MLS
This cozy comfortable 2 bed, 2 bath ranch offers the convience of one level living, with a private back yard and plenty of parking. Located close to the business center and RT 84.

73 Yale Ave, Middlebury
1252 Straits Tpke, Middlebury
$245,000
4 Beds ⋅ 1 Baths ⋅ 24162190 MLS
SUBJECT TO PROBATE APPROVAL, AS-IS, WHERE-IS CONDITION NO FHA, CHFA OR VA LENDING AVAILABLE. NEEDS WORK. LOTS OF HARDWOOD FLOORS, DETACHED 2 CAR GARAGE WORKSHOP AND STORAGE LOFT. LARGE ROOMS, SHARED DRIVEWAY,

1252 Straits Tpke, Middlebury
3 Pommel Ln Unit 3, Middlebury
$238,700
2 Beds ⋅ 2 Baths ⋅ 24134740 MLS ⋅ Steeplechase,Steeplechase Of Middlebury BLDG.
Fantastic opportunity to own this well-maintained 2-bedroom, 2-bath duplex with a 1-car garage in the desirable Steeplechase community! This is one of the affordable units, subject to income restrictions and an application process through the Town of Middlebury (application attached). Pride of ownership shows-original owners have lovingly cared for this home and completed many updates, including new windows, new hardwood floors throughout, roof, A/C, water heater, furnace, exterior paint, and new kitchen counters. Each owner is responsible for exterior maintenance. Enjoy economical natural gas heat, city water, and sewer. Move right in and make this your home before it's gone! AS-IS and the seller will not negotiate on price.

3 Pommel Ln Unit 3, Middlebury
152 Glenwood Ave, Middlebury
$224,000
2 Beds ⋅ 1 Baths ⋅ 24146106 MLS
2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your style do not forget Lake Quassapaug, Middlebury Greenway, or Hop Brook Lake. See all that Middlebury Living has to offer. EMD 10% cash 1% Financed or 1k minimum whichever is greater. Under FinCens new RRE Rule, transfers will be subject to reporting when buyers use entities or trusts to take title to residential real estate, when the transaction is all cash, privately financed or HELOC.

152 Glenwood Ave, Middlebury
35 Nutmeg Rd Unit Apt D1, Middlebury
$222,500
1 Beds ⋅ 1 Baths ⋅ 24150979 MLS ⋅ Middlebury Commons BLDG.
Middlebury Commons, Highly desirable 55+ community conveniently located to town center and all of its amenities. Bright second floor unit has primary BR with walk-in closet plus den/office that can serve as 2nd BR. Eat-in kitchen, laundry area, LR/DR combo with french door to deck overlooking private rear yard. Move right into this beautiful unit.

35 Nutmeg Rd Unit Apt D1, Middlebury
1070 Long Meadow Rd, Middlebury
$200,000
24131706 MLS
Welcome to the perfect location for your dream home in beautiful Middlebury, CT. This level, build-ready lot is ideally situated on a quiet private cul-de-sac road, offering the peace and privacy you've been looking for. Backing up to protected open space, the property provides a serene natural setting surrounded by mature trees and nature. The lot has already been cleared, saving you time and money in the building process. Whether you're planning a peaceful retreat or a spacious home, this prime piece of land offers the ideal setting. Enjoy the tranquility of a private location while still being conveniently close to schools, shopping, and major highways. Opportunities like this in Middlebury don't come often-don't miss your chance to build exactly what you've been dreaming of!

1070 Long Meadow Rd, Middlebury
288 Watertown Rd Unit Lot 5, Middlebury
$190,000
24050731 MLS
Gorgeous 1.13 acre lot in a brand new subdivision. Level and on a private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD. Shared maintenance for private driveway. Flood insurance may be required once home is built. Please check w insurance agent.

288 Watertown Rd Unit Lot 5, Middlebury
390 Middlebury Rd Unit 3, Middlebury
$100,000
1 Baths ⋅ 24162922 MLS
Professional Office Suite for Sale in Middlebury. Position your business for success in this well-located and highly functional office condo. Suite 3 at 390 Middlebury Road is a total of 850 SF and offers four private offices, with three currently occupied by professionals-providing immediate income-and one office ideal for an owner-user. The layout is well-suited for a variety of professional uses including therapy, legal, financial services, accounting, cosmetology, or consulting. There is a shared men and woman's bathroom on the same floor. The property benefits from a convenient location surrounded by retail, dining, and other professional offices, making it attractive and easily accessible for both clients and staff. Additional highlights include ample on-site parking and excellent highway connectivity with quick access to I-84 and Route 8, supporting strong accessibility. A strong opportunity to own a versatile, income-producing office suite in a desirable Middlebury location.

390 Middlebury Rd Unit 3, Middlebury
440 Lake Shore Dr, Middlebury
$85,000
24090742 MLS
Build your dream cottage on this waterfront building lot on the desirable Long Meadow Pond. The lot is located near the end of a low traffic cul-de-sac. It is a great opportunity

440 Lake Shore Dr, Middlebury
Ferndale Avenue, Middlebury
$70,000
24084578 MLS
For Sale: Unique Development Opportunity Offering a rare opportunity to acquire a three-lot subdivision in Middlebury. This property consists of three separate parcels that must be sold together. While previously approved, buyers are responsible for verifying the current status of approvals and conducting their own due diligence. The site presents some challenges due to significant ledge, which may require blasting. However, water and sewer connections are available in the street, adding convenience for development. A promising opportunity for investors, builders, or developers looking to create something special. Serious inquiries only. I'm working on getting the subdivision maps. Agents Please do not let your clients walk this property alone. Thank you

Ferndale Avenue, Middlebury

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