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46 Houses For Sale in Middlebury, CT

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Toll Brothers

$502,995Est. Payment
3 Beds | 3 Baths | 2,485 Sqft
Middlebury, CT 06762
House For Sale

This to-be-built home is the "Denton" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury. This Townhome plan home is priced from $502,995 and has 3 bedrooms, 2 baths, 1 half baths, is 2,485 square feet, and has a 2-car garage. The Builder describes this home as: "The unique entry to the Denton maximizes the space and flow from the foyer into the open plan dining room, great room, kitchen, and casual dining area.. A private office is also located off of the entry foyer. The second floor features a primary bedroom suite with cathedral ceiling as well as two additional bedrooms, a spacious loft, and a convenient laundry". Listing provided by newhomesource.com.

New
$260,000Est. Payment
4 Beds | 1 Bath | 1,380 Sqft
62 Three Mile Hill Road, Middlebury, CT 06762
House For Sale

This well cared for Cape in desirable Three mile hill neighborhood offers 4 bedrooms, Living Rm w hardwood floors and hardwood in 3 of the bedrooms and hallways. Main floor master bedroom. A Eat in kitchen w granite counter tops and a door that lead to the patio. Two bedrooms upstairs one has carpeting and built in drawers and book shelf. There is a basement with access to the garage, laundry and additional space. This home offers city sewer, city water, a whole house water filter and hook up and wire installed for a generator, plus a large side yard, a patio, outdoor fireplace and ornamental grasses. Optional Electric hot water heater timer for those that are energy efficient. Over a quarter acre of land ! Make this your next home. Please only buyers go inside and follow all covid guidelines, you must wear a mask and do not touch belongings. Great time to move to Middlebury!!

Toll Brothers

$552,995Est. Payment
3 Beds | 3 Baths | 2,616 Sqft
Middlebury, CT 06762
House For Sale

This to-be-built home is the "Bucknell II" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury. This Townhome plan home is priced from $552,995 and has 3 bedrooms, 2 baths, 1 half baths, is 2,616 square feet, and has a 2-car garage. The Builder describes this home as: "Two-story foyer is flanked by a formal living room and two-story dining room.. The spacious kitchen opens to the great room. The first-floor primary bedroom suite has 2 walk-in closets, tray ceiling and elegant primary bath. On the second floor there are 2 bedrooms, a hall bath and a loft to complete this townhome". Listing provided by newhomesource.com.

New
$319,900Est. Payment
3 Beds | 2 Baths | 1,644 Sqft
4 Laurel Road, Middlebury, CT 06762
House For Sale

Looking for that magical cottage in the woods? This is it! Step into the foyer of this lovely cape and be delighted by the beautiful wood staircase, arched doorways and wood floors. Family room features vaulted wood ceiling with top of the line cast iron wood stove which offers a great alternative heat source as well as ambiance. Main floor bedroom with full bath plus two additional bedrooms and newly updated bath on second floor. Enjoy your coffee on the covered front porch or the enclosed side porch. Enjoy snow shoeing and hiking in the back yard and fishing in Long Meadow Pond in the summer. Enjoy all that Middlebury has to offer in this quiet oasis.

New
$319,900Est. Payment
3 Beds | 2 Baths | 1,488 Sqft
4 Laurel Rd Washington Drive, Middlebury, CT 06762
House For Sale

Looking for that magical cottage in the woods? This is it! Step into the foyer of this lovely cape and be delighted by the beautiful wood staircase, arched doorways, and wood floors. The family room features a vaulted wood ceiling with the top-of-the-line cast iron wood stove which offers a great alternative heat source as well as ambiance. Main floor bedroom with full bath plus two additional bedrooms and newly updated bath on the second floor. Enjoy your coffee on the covered front porch or the enclosed side porch. Enjoy snowshoeing and hiking in the backyard and fishing in Long Meadow Pond in the summer. Enjoy all that Middlebury has to offer in this quiet oasis.

$649,900Est. Payment
4 Beds | 4 Baths | 4,212 Sqft
6 Plymouth Lane Unit 6, Middlebury, CT 06762
House For Sale

A RARE OPPORTUNITY to fall in love with this Stunning 4 bedroom Colonial in the sought-after Heights at Brookside Community. From the moment you step into the foyer, you will discover this is a house built for entertaining! Formal living and dining rooms with wood floors and study area or music room on the first floor. The bright kitchen with loads of cabinets and storage, granite counters, stone backsplash, and stainless steel appliances, and center island is a chef's delight! The kitchen opens to the dramatic family room with a floor-to-ceiling stone gas fireplace. The hardwood floors throughout the home are gleaming from the natural light that streams from the large windows. The master bedroom suite is a private oasis with his and her walk-in closets, a quiet dressing area, and a master bathroom that boasts double vanities walk-in shower, and a large soaker tub. Three more light and bright bedrooms and the second of 3 full baths complete the upper level. Get ready for the weekend in the lower-level media room and game room. You will also find a large, bright office with a walk-out to the backyard. Two more rooms can be used for the study area or meditation room. Storage room with wine cellar and place for an extra fridge or freezer. Don't miss out there is too much to mention in this beautiful home.

Toll Brothers

$492,995Est. Payment
2 Beds | 2 Baths | 1,627 Sqft
Middlebury, CT 06762
House For Sale

This to-be-built home is the "Bethel" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury. This Townhome plan home is priced from $492,995 and has 2 bedrooms, 2 baths, is 1,627 square feet, and has a 2-car garage. The Builder describes this home as: "The primary bedroom suite of the distinctive Bethel features a tray ceiling, two large walk-in closets, and a luxurious bath with a spacious shower with a seat, a soaking tub, a private toilet area, and a dual-sink vanity.. But it all begins with an elegant entryway with a colonnade. The large dining room of this splendid home is sure to impress your dinner guests! Additional highlights include a spacious kitchen with a cathedral ceiling, an adjoining great room with a cathedral ceiling, a tucked-away laundry, and nine-foot ceilings throughout". Listing provided by newhomesource.com.

$3,995,000Est. Payment
5 Beds | 5 Baths | 6,554 Sqft
9 Bristol Road, Middlebury, CT 06762
House For Sale

Lake living at its finest! Custom Greek Revival built from foundation up by current owners. An entertainers dream, this 5 bedroom, 4.5 bath home has 6 acres of direct frontage on Lake Quassapaug with its own drive in boathouse with power lift and private beach. Lake facing pool with separate spa and pool house with kitchen. Lakeside terrace with stone firepit. Stunning public spaces on main level including an enormous eat in kitchen with fireplace and entertainment area with projection video system. Commercial grade appliances include Traulsen refrigerator and freezer and 48" Viking range. Luxurious primary bedroom suite includes fireplace, office and its own gym with stunning lake views! An en-suite guest room, and 3 additional bedrooms with shared bath and laundry complete the second floor. 1200 square feet of heated garage space for 4 cars. Many smart home features, geothermal heat, generator, slate roof, random width hardwood flooring, just a few of the custom finishes. Room for tennis court if desired. Do not miss your chance to make this your own ultimate lake compound. Easy access from I-84, under 2 hours from NYC, 2.5 hours from Boston.

$255,000Est. Payment
3 Beds | 2 Baths | 1,050 Sqft
31 Yale Avenue, Middlebury, CT 06762
House For Sale

Charming, New England Cape nestled amongst likewise homes. New Roof, a new furnace, plus a new hot water heater gives you peace of mind for the big-budget items. Hardwood floors throughout, three bedrooms, a finished basement for extra space, a mudroom in the back to keep the mess out, and a large deck overlooking the easy-to-care-for yard. Located in the Award Winning Region 15 School District, makes this home the perfect starter home or even a downsizing home. Pick up the Middlebury Greenway Trail, at the end of the road, for an easy stroll, or bike ride to the other end of town. This house is ready for your personal touch and to welcome you home!

$424,000Est. Payment
3 Beds | 3 Baths | 2,228 Sqft
7 Pelham Way, Middlebury, CT 06762
House For Sale

Welcome to Steeplechase, a non age restricted sought after community. As you enter this 3 bedroom, 2 1/2 bath unit, you can't help but notice the soaring ceiling, the oversize windows streaming with natural light and the gleaming hardwood floors throughout. A staircase leading up to a second floor balcony overlooks the living room with fireplace that flows into the dining room. A doorway in this living /dining area brings you into a cozy family room with a gas fireplace and sliding glass doors that open out to a trex deck (portion of which is covered). Enjoy looking out at the wooded private yard with a stone wall as you sip your morning coffee. Off the family room is the the light and bright new kitchen with granite counters, a casual dining area and access to the 2 car garage. The upstairs floor features the master bedroom which has a full bath, vaulted ceiling and plenty of storage. 2 additional bedrooms with storage galore, a hall bath room and a convenient laundry area complete the second floor. Lovingly maintained, this free standing unit has been freshly painted and is ready for you to move right in. Please wear masks. .

Toll Brothers

$507,688Est. Payment
3 Beds | 3 Baths | 2,000 Sqft
161 Ridgewood Drive, Middlebury, CT 06762
House For Sale

This new construction, quick move-in home is the "Tamarack" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury at 161 Ridgewood Drive, Middlebury, CT-06762. HOT HOME: 3 bedroom first floor primary suite ready summer 2021. This Townhome inventory home is priced at $507,688 and has 3 bedrooms, 2 baths, 1 half baths, is 2,000 square feet, and has a 2-car garage. The Builder describes this home as: "Your dream home is waiting.. The first-floor offers a bedroom suite complete with a private bath and walk-in closet. The second floor offers a versatile loft space that can be suited to your needs. The walk-out basement creates a seamless indoor/outdoor entertaining space. This low-maintenance community has lawn care and snow removal provided. There s still time to personalize this beautiful home with Design Studio upgrades!MLS Number: 170352594 Disclaimer: Photos are images only and should not be relied upon to confirm applicable features". Listing provided by newhomesource.com.

Toll Brothers

$530,194Est. Payment
3 Beds | 3 Baths | 2,485 Sqft
170 Ridgewood Drive, Middlebury, CT 06762
House For Sale

This new construction, quick move-in home is the "Denton" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury at 170 Ridgewood Drive, Middlebury, CT-06762. This Townhome inventory home is priced at $530,194 and has 3 bedrooms, 2 baths, 1 half baths, is 2,485 square feet, and has a 2-car garage. The Builder describes this home as: "The unique entry to the Denton maximizes the space and flow from the foyer into the open plan dining room, great room, kitchen, and casual dining area.. A private office is also located off of the entry foyer. The second floor features a primary bedroom suite with cathedral ceiling as well as two additional bedrooms, a spacious loft, and a convenient laundry. MLS Number: 170323501 Disclaimer: Photos are images only and should not be relied upon to confirm applicable features". Listing provided by newhomesource.com.

$515,000Est. Payment
4 Beds | 3 Baths | 2,950 Sqft
13 Brookside Drive, Middlebury, CT 06762
House For Sale

The Cheshire at Brookside with many upgrades. First-floor master suite with sitting room, his & her closets, and full bath. Large, covered, screened porch 14x12 and patio for your enjoyment. Enjoy your coffee in front of the wood-burning fireplace, open living room & kitchen concept. This unit is a must-see, sunny and warm. Three second-floor bedrooms and open area for work or reading, you choose. There is a large, full basement for you to be creative with. No age restrictions. Make an appointment to see. 24-hour notice needed. NO SHOWINGS 2/25/21 - 2/27/21 Family

$349,000Est. Payment
3 Beds | 1 Bath | 1,410 Sqft
173 Christian Road, Middlebury, CT 06762
House For Sale

Where awesomeness happens! Cool landscape and privacy to be shared with friends and loved ones. Property features ample room so everyone has their own space to unplug and unwind. Home offers many upgrades: on demand hot water system, remodeled kitchen and baths, adorably redone guest house, central air, newer mechanicals, excellently maintained, completely turn key. Patio area includes grilling/cooking facility, private outdoor shower, lovely gardens overlooking a flat meadow for earthing. Walk to the lake for day fun and enjoy all water sports or experience a magical sunset... an abundance of peaceful country life within 73 miles of NYC. The charming historic Tribury area with hiking, biking paths, parks, antique and luxury shopping, theater, restaurants, and a huge variety of wellness facilities: fitness, yoga, meditation, beauty, massage-spa services, and a well renowned organic health food market. Each season in Connecticut has it's own magical aesthetics and events. Wedged between the hills of Litchfield County and coastal Fairfield County, commuting anywhere is a breeze. Perfect for full time residence, second home, or a fantastic AIRBNB opportunity. Middlebury is proud of the award winning school system and its' upward thinking about philanthropic endeavors. Come visit and see.

Toll Brothers

$561,717Est. Payment
3 Beds | 3 Baths | 2,485 Sqft
5 Fairview Lane, Middlebury, CT 06762
House For Sale

This new construction, quick move-in home is the "Denton" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury at 5 Fairview Lane, Middlebury, CT-06762. HOT HOME: Home with Many Designer Upgrades - Move in Spring 2021. This Townhome inventory home is priced at $561,717 and has 3 bedrooms, 2 baths, 1 half baths, is 2,485 square feet, and has a 2-car garage. The Builder describes this home as: "Love everything about this 3-bedroom home.. This Denton floorplan is located on a cul-de-sac. The oversized kitchen island provides a centerpiece for entertaining. A first-floor office provides the space to work from home. Gorgeous designer finishes highlight every room in this home. Enjoy scenic community amenities like walking and jogging trails throughout. Schedule an appointment today to learn more about this stunning home! MLS Number: 170301662 Disclaimer: Photos are images only and should not be relied upon to confirm applicable features". Listing provided by newhomesource.com.

$339,900Est. Payment
2 Beds | 2 Baths | 2,504 Sqft
607 Watertown Road, Middlebury, CT 06762
House For Sale

A great opportunity to own an L- shaped ranch with lots of style, lots of features and only 90 miles from NYC. This home takes advantage of the natural beauty surrounding it with its plentiful, stylish cottage style windows overlooking the rear yard, brook and wooded area.As you enter the side door, a bright L shaped kitchen greets you. It offers an efficient galley work area as well as a dining area. The spacious 25' X 16' living room with fieldstone fireplace features a beautiful fieldstone fireplace, wall to wall carpeting with hardwood under, a slider to the deck as well as a covert bar area, great for parties. Just off the living room is a dining room that overlooks the bubbling Hop Brook stream. 2 bedrooms, 2 full baths and a laundry area complete the main level. The fully finished walk out level can serve as a spacious rec room. It offers a walk out to the patio and stone wall overlooking woods and the brook. This is a fabulous spot for relaxing and observing natural beauty. The previous owner had used a bedroom on the walk out level. There is a lot of closet space there, and there is a separate area with washer and dryer. Since plumbing is currently present, perhaps one could install an addition bath on this level. Additional storage under the garage. Don't miss this fabulous opportunity!

Toll Brothers

$452,995Est. Payment
3 Beds | 3 Baths | 1,780 Sqft
Middlebury, CT 06762
House For Sale

This to-be-built home is the "Portman" plan by Toll Brothers, and is located in the community of The Ridgewood at Middlebury. This Townhome plan home is priced from $452,995 and has 3 bedrooms, 2 baths, 1 half baths, is 1,780 square feet, and has a 2-car garage. The Builder describes this home as: "The open design of the charming Portman offers plenty of space for entertaining.. And when your guests have gone, you can relax in the luxurious and spacious primary bedroom suite, which features a cathedral ceiling, a large walk-in closet, and an elegant primary bath. Additional highlights include a covered entry, an expansive great room, a formal dining room, a well-appointed kitchen, a roomy casual dining area, and a convenient second-floor laundry". Listing provided by newhomesource.com.

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