The Matthews TeamWilliam Raveis

The Matthews Team

Middlebury CT Real Estate

Lake in Middlebury ConnecticutLocated approximately 90 miles north of New York City, Middlebury is a great escape from the non-stop activity of New York City. With easy access to the surrounding towns of Waterbury, Watertown, Woodbury, Southbury, and Naugatuck, Middlebury is comfortably accessible to restaurants, shops, and activities for the entire family. Middlebury’s Lake Quassapaug is a local favorite, with Quassy Amusement Park being right on the shore prompting a day filled with water activities, fun, & games for the whole family. Browse current Middlebury CT real estate listings below.

Middlebury Real Estate for Sale

Contact The Matthews Team at 860-868-0511 with any questions or to schedule a private tour.

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7 E. Farm Road Middlebury CT 06762

Middlebury, CT7 E. Farm Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 170453155

  • Single Family
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 9,478
  • Acreage 7.99

Old-world elegance with dynamic views of Atwater Pond. This estate includes 3 building lots acquired to buffer and provide seclusion, along with a bordering land trust. This European Inspired Country Manor is designed with artful detail and a grand size similar to distinguished French and English manors. Enter into the grand sweeping foyer with 20' ceilings, marble and porcelain floors, and the impressive custom curved stairway. Continue and find outstanding details everywhere. With the authentic French stone floor reproduction and other French and English influences, this marvelous home is art that surrounds you. The splendid living room boasts a circa 1776 antique French chestnut mantel accenting a hand-built limestone fireplace. The 12' ceilings with hand sculptured beams magnify the exhilarating sense of space felt throughout this stunning manor. The striking conservatory encompassed by a dynamic amount of glass illuminates the bluestone floors and brick trim. A focus point of the elegant dining room is the double-tier octagonal tray ceiling along with the custom hand-painted stencils continued from the living room through to the kitchen. The flow of the living space extends out onto the wide bluestone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The three lots can be used to add more gardens, add a pool and pool guest house, all while providing exquisite views of Atwood Pond ... continued in the addendum

Listed by Deborah A Laemmerhirt of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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135 Crest Road Middlebury CT 06762

Middlebury, CT135 Crest Road

Price$1,724,900

Est. Mortgage: $/month

Under Agreement

MLS Number 170491053

  • Single Family
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 4,864
  • Acreage 3.05

Remarkable & completely updated Mid-Century Modern engulfed by Nature in the coveted 'Bury's' of Ct. A silent oasis leaving the towns church bells and birds as the only thing to hear, yet walking distance to renowned restaurants and bars. Upon entry to this vibrant and streamlined masterpiece, you are greeted by the Great Room with sunken & main level dual-entertaining spaces flanked with a 9-foot wall of glass sliding doors that span the length of the home, inviting inside the 3+ acres of the property and the 14+ acres of natural land trust that abuts the back of the house. Step onto 900+sq ft of IPE decking overlooking meandering decks to a sunken lagoon style heated in-ground gunite pool WITH pool house including kitchen & bath. Back on the far end of the deck you will find built in BBQ & access to the STUNNING cathedral-ceiling/glass atrium chef's kitchen w/ double industrial Sub-Zeros and top of the line appliances. Perfect for a dinner of 4 or staffed for 100 guests. Primary BR Suite has a private sitting room w/ fireplace and deck access. The generous PBR suite, cornered in windows with powered automatic sun shades boasts breathtaking westrerly views of the property and pool and stunning sunsets. The floating king bed is abutted with glass lined closets that lead to the heated floor, open, Japanese bathroom complete with private picture window and electric shade that reveals even more views. 85 Miles to NYC, and 10 miles to Oxford Airport, this stunner is a MUST SEE!

Listed by Blair Patterson of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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51 Abbott Farms Road Middlebury CT 06762

Middlebury, CT51 Abbott Farms Road

Price$1,599,900

Est. Mortgage: $/month

MLS Number 170493074

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6,746
  • Acreage 4.1

Stately and elegant, this custom-built Georgian Colonial is on the market for the first time. A sweeping staircase is the focal point of the 17 ft two story foyer. A formal living room with one of five fireplaces opens to a bright music room, perfect for a grand piano. Formal dining room boasts trey ceiling, fireplace with gas log and an elegant butler's pantry. The remodeled gourmet kitchen features Viking dual fuel six burner oven range, built in convection microwave and subzero fridge. An expansive center island, beautiful Wood-Mode cabinets and a walk-in pantry open to a spacious breakfast room. The sunken family room with coffered ceiling and a distinctive limestone fireplace is the informal heart of the home. Inspired by the library at the Mayflower Inn, this room is a showstopper! Dramatic two stories of cherry paneled walls, built in bookcases, desk and cabinets. From the master bedroom ensuite, enter the loft overlooking the library and the second-floor balcony. A well thought out floor plan includes 3 more generous sized bedrooms plus a second floor bonus room or playroom and a large walk in space waiting to be finished or perfect for extra storage. Beautiful four acres of manicured grounds include granite curbing on the circular drive, a stunning patio with hot tub in the private back yard and room for a pool and tennis court. Distant views of Lake Quassapaug. Close to Middlebury Greenway and great restaurants. 90 miles from NYC. Welcome to Middlebury!

Listed by Mary Ann Hebert and Jonna Dibble of BHGRE Bannon & Hebert

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 East Farm Road Middlebury CT 06762

Middlebury, CT7 East Farm Road

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170251554

  • Single Family
  • Bedrooms 4
  • Bathroom 7
  • Square Feet 9,478
  • Acreage 1.97

Old world elegance on Atwater Pond. This European Inspired Country Manor is designed with the artful detail and a grand size similar to distinguished French and English manors. Enter into the grand sweeping foyer with 20' ceilings, marble and porcelain floors and the impressive custom curved stairway. Continue and find outstanding details everywhere. With the authentic French stone floor reproduction, and other French and English influences, this marvelous home is to a level of art. The splendid living room boasts a circa 1776 antique French chestnut mantel accenting a hand build limestone fireplace. The 12' ceilings with hand sculptured beams magnify the exhilarating sense of space felt throughout this stunning manor. The striking conservatory encompassed by a dynamic amount of glass illuminates the blue stone floors and brick trim. A focus point of the elegant dining room is the double tier octagonal tray ceiling along with the custom hand painted stencils continued from the living room through to the kitchen. The flow of the living space extends out onto the wide blue stone terrace with private views of the magnificent and fragrant perennial gardens framed with brick and stone. The captivating French country kitchen equipped with custom cabinets, high end appliances, center island breakfast bar continues to provide a great space for entertaining and relaxing. The Library is appointed with walnut panels surrounding a superb fireplace detailed ... continued in addendum

Listed by Deborah A Laemmerhirt of Keller Williams Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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15 Sandy Beach Road Middlebury CT 06762

Middlebury, CT15 Sandy Beach Road

Price$1,400,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170471828

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,936
  • Acreage 0.66

Exquisite waterfront two bedroom, two bath main residence with separate 1 bedroom cottage/studio with full bath on Lake Quassapaug. This 1952 home has been beautifully renovated into a classic cedar shingle Nantucket style house. Designed with the utmost attention, the home embodies the epitome of the New England coastline with simple, casual, and bright spaces highlighted by light colors and natural wood floors. An abundance of windows overlook the lake and multiple French doors open to the rear bluestone patio for a gorgeous view of the water and evening sunsets. Quality finishes throughout include Marvin windows and doors, Buderus hydro air system, Simpson doors, Waterworks, Franke, Artemide, Visual comfort, and Louis Poulsen. The chef's eat-in kitchen includes Viking, Subzero, KitchenAid, Bosch and honed marble countertops. A converted boathouse on the water's edge is now a private heated/cooled cottage with full bath, perfect for an additional bedroom, artist studio or office. It has its own patio with firepit, outdoor shower and amazing view! There is a dock and private beach. Professionally landscaped, the grounds include gorgeous specimen trees, flowering bushes, vegetable garden, cherry tree, pear tree and apple trees. To make this property even sweeter... you have your own protected blueberry patch! A must see.

Listed by Maria Taylor and Claudine McHugh of Klemm Real Estate Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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305 Burr Hall Road Middlebury CT 06762

Middlebury, CT305 Burr Hall Road

Price$1,399,900

Est. Mortgage: $/month

MLS Number 170491098

  • Single Family
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,465
  • Acreage 3.38

A place for everyone! Warm and inviting cottage style colonial in one of Middlebury's finest cul de sac locations just minutes from golf, town center. major routes and all of Middlebury's award-winning schools. Built with all the best quality, this home that can't be reproduced in today's construction climate at the current value. This meticulously maintained home checks all the boxes. Light filled eat in kitchen with bay window open to family room with fireplace, formal living room with fireplace, cozy first floor study, formal dining room, gorgeous first floor primary bedroom suite, upper level play room and four second floor bedrooms with en-suite baths. Conveniently located towards the end of Burr Hall, this home is tucked away to offer total privacy, abutting some open space and a small brook preventing any future development within sight. The exterior includes a circular driveway lined with cobble stone, many gorgeous plantings that have been lovingly cared for, a back deck off the living room along with a back patio out the lower-level walkout and room for a pool! An ideal home for generational living with room for expansion in the lower level or just keep the full sized gym that exists now. A well built and extremely well cared for home, that is move in ready for a new owner that is looking to upgrade.

Listed by Timothy Drakeley of Drakeley Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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92 Chesham Drive Middlebury CT 06762

Middlebury, CT92 Chesham Drive

Price$1,300,000

Est. Mortgage: $/month

MLS Number 170485326

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 4,424
  • Acreage 3.78

Picture yourself living in this enchanting hilltop retreat, enjoying fantastic views of the countryside while surrounded by peaceful nature. As you ascend the illuminated driveway you'll be greeted by lush mature and exotic gardens and privacy evergreens. Entering this custom, architect-designed home requires only one step from all entry points and is accessible throughout the main floor from the 3-foot-wide solid doors to the 4-foot-wide staircase. One step up from the main garage right to the kitchen makes shopping a breeze. With the primary suite on the main level and the beautiful laundry room next door, you may never want to leave the first floor. The living room features a cathedral indigenous stone wood-burning fireplace, while the other 3 fireplaces (primary suite, dining room and game room) are all gas. The flex room is currently used as a handy kennel and has potential for many other uses, such as a split master or nursery. Downstairs with third garage is a getaway for kids, in-laws and guests as the game room has its own pull-out Sub-Zero refrigerator/freezer and is prepped for a Miele MasterChef oven. The two bedrooms downstairs, each with its own full bath, are on either side of the game room allowing privacy for all. The ipe decking allows for decades of enjoyment while you watch hot air balloons, wildlife and fireworks from three surrounding towns.

Listed by Tom Carroll of ROVI Homes

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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98 Leonard Road Middlebury CT 06762

Middlebury, CT98 Leonard Road

Price$1,200,000

Est. Mortgage: $/month

MLS Number 170485670

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,357
  • Acreage 12.27

Welcome to Daffodil Farm! This beautifully restored home is situated on 12+ acres with a newly paved driveway leading up to this stately 4 BR home with 3.5 BA's & a 2 car garage. As you enter the home you will be drawn to the large foyer & sophisticated design this home offers with an oversized FLR with a cozy FPLC, HW floors & beautiful built in, custom, window shutters. Just off the LR is a spacious light filled sunroom that leads to the stone patio with custom built outdoor FPLC & pizza oven for the cook! The office is amazing with original woodwork & the perfect 1/2 BA.The FDR has a traditional built-in hutch & large enough for entertaining family & friends. The DR also has French doors, custom shutters & allows you access to the large patio to enjoy your morning coffee or simply take in the view! The Kitchen has been updated with a gas stove, SS appliances & features a cozy, sunny work nook. The kitchen opens to a comfortable large family room for which everyone will hang out in! Upstairs there are 4 large BR's with HW flooring. The primary BR has a walk-in closet & a FBA fully updated. There is also a large bedroom with built in work stations & a FBA with shower perfect for guests! 2 other BR's add to the spaciousness of the second floor. The views from the back of the house look over the Daffodils this time of year. C/A, newer roof, 2 outbuildings for storage & many more updates bring out the charm of this gorgeous home! Please call today for your private showing!

Listed by Jackie Desmarais of Showcase Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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192 Watertown Road Middlebury CT 06762

Middlebury, CT192 Watertown Road

Price$1,000,000

Est. Mortgage: $/month

MLS Number 170497575

  • Single Family
  • Bedrooms 3
  • Bathroom 5
  • Square Feet 5,073
  • Acreage 4.59

4823sqft Remodeled Colonial trimmed to the 9s complete w 4 car garage, 5 fireplaces, gorgeous patio for entertaining, outbuilding w bar & 4.59acres of land! Custom trim & hardwood floors throughout. Remodeled eat-in-kitchen w country craft cabinets, granite countertops, oversized island w breakfast bar, stainless steel double ovens, Viking propane cooktop, warming drawer, beverage fridge, large pantry closet & dining space w fireplace. Sun drenched family room w wainescoating, corner fireplace, bay window, crown molding. Dining room w wood paneling, corner fireplace & french doors. Library w corner fireplace, built-in bookshelves & crown molding. Office w shiplap & crown molding. Powder room. 3-season sunroom w gorgeous bluestone floors could be used year round w mini-split system for heating & cooling. Master suite w trey ceilings, 2 walk-in closets w built-ins, 2 balconies & attached full bath w tiled stand up shower, soaking tub, granite countertops & marble floors. 2nd & 3rd bedrooms both amply sized & serviced by remodeled full bath. Large guest suite w attached full bath & possible separate entry. Finished lower level rec room w additional 1/2 bath. Lower garage currently being used as home gym. Strong mechanicals including hydro air heat, central air cooling, security system, generator hookup, irrigation, sound system. Gorgeous & manicured lot are the cherry on top! Private patio, firepit & fenced area perfect for pets. Outbuilding w custom bar. This home has it all!!

Listed by John Donato Jr of Showcase Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

122 Mirey Dam Road Middlebury CT 06762

Middlebury, CT122 Mirey Dam Road

Price$985,000

Est. Mortgage: $/month

Under Agreement

MLS Number 170492132

  • Single Family
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 6,175
  • Acreage 2.69

So much to love in this custom-built stately Georgian Colonial with impressive curb-appeal that begins the moment you arrive at the stone wall entrance, and the front door opens to your two-story grand entry Foyer with chandelier, marble floor and staircase. An oasis awaits in this secluded and private setting that includes a stress-relaxing Hot-tub and In-ground Swimming pool for summertime fun! Attention to detail abounds in this gracious layout with it's oversized rooms and light open views of manicured grounds and pool. Chef's kitchen with large center island and Wolf range has plenty of space for entertaining & dining with huge Family Room and Eat-In-Kitchen with walkout to deck and rear patio area. Special occasions are an ease, hosting from your oversized Formal Dining Room with it's stunning chandelier centerpiece. High-end luxury details are found throughout this home; granite counters in baths and kitchen, Chef's kitchen appliances, fine moldings and woodworking details and gorgeous Premier Bath fixtures and marble. There is plenty of space for storage with double walk-in closets in the Premier Bedroom Suite and built-ins in other rooms and amazing lower level storage space with easy access. A solar energy efficient home. Take a look at our aerial pictures to see the ultimate privacy this setting offers, yet with all the conveniences of local nearby shopping readily close-by with easy access to 84 and all points north and south CT for commuting and to New York City.

Listed by Vincent Capuano of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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69 Gleneagle Road Middlebury CT 06762

Middlebury, CT69 Gleneagle Road

Price$850,000

Est. Mortgage: $/month

MLS Number 170494121

  • Single Family
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,220
  • Acreage 1.15

Welcome to 69 Gleneagle Rd, situated in a neighborhood of stately homes. Sited at the end of a quiet cul-de-sac, this elegant custom-built Georgian Colonial encompasses 1.17 acres connecting to wooded land trust property. Natural light and spacious rooms abound in this single owner 5 bedroom + 5 bath home. Enter through the spacious two-story foyer featuring a custom curved staircase, captains walk, and marble flooring sourced from Danby, VT. Entertain in the sunken great room with soaring ceilings, stone fireplace, wet bar, and French doors leading to a bluestone patio. It's easy to imagine eating in the sun-filled, open concept kitchen including a dedicated breakfast nook and walk in pantry. The kitchen opens to a rear deck above the level fenced in yard with southern exposure; perfect for a pool. Two half baths, a dedicated laundry room, and elegant formal dining and living rooms complete this flowing main level that is both comfortable and entertainment oriented. On the second level is a generous and bright primary suite with hardwood flooring, trey ceiling, and oversized walk-in closet. The private bathroom features separate vanities, whirlpool tub, shower, and custom millwork. Completing the second level is a guest room with en suite private bathroom, another separate full bath featuring double sinks, soaking tub + shower, and three additional bedrooms. 90 minutes to NYC Award winning Region 15 school system. A perfect place to call home.

Listed by Heather Dever of Showcase Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

191 Falcon Crest Road Middlebury CT 06762

Middlebury, CT191 Falcon Crest Road

Price$845,000

Est. Mortgage: $/month

MLS Number 170496587

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,905
  • Acreage 3.63

STUNNING NEIGHBORHOOD AND LOCATED ON DESIRABLE CUL-DE-SAC! Your dreams come true the moment you drive down the scenic, secluded driveway. This spectacular Colonial Farmhouse is situated on 3.63 private acres surrounded by a land trust with walking trails. Custom built, single owner home, has a place for everyone. Enjoy light filled rooms, family room with 2-story windows, double sliders, GRAND stone floor-to-ceiling fireplace and built-in entertainment center. Beautiful kitchen which includes custom cherry cabinets, granite countertops, island with butcher block top, stainless steel appliances, chefs stove, breakfast bar and spacious eat-in area. Off of the kitchen, enjoy hosting holidays with the additional space of the homes formal dining and living rooms. Finishing off the main level are a full bathroom, separate office and mudroom with lots of storage. All upper level bedrooms, all light & bright with ample closet space. Primary bedroom with on-suite and sitting area is separated by catwalk overlooking family room from other bedrooms. FINISHED LOWER LEVEL includes large recreation area, half bathroom, walk-in closet, storage area and exercise room. Relax and enjoy your nicely finished outdoor living space with beautiful grounds and 2nd sitting area with built-in firepit. Bonus feature with a HUGE storage area above detached garage. All this only minutes from I-84, 1.45 to Manhattan and 15m to Oxford airport. WELCOME HOME!

Listed by David Aurigemma of Regency Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.81% last updated on Jun 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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 2022 SmartMLS, Inc.