Middlebury, CT Homes for Sale

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  $549,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  1 Stevens Rd, Middlebury, CT 06762

  First Time on the Market - Classic 1930s Colonial in Prime In-Town Location Step into timeless elegance with this rare, stately 1930s Colonial, offered to the open market for the first time. Full of classic charm, the home features original moldings, custom built-ins, and enduring craftsmanship throughout. The main level offers a spacious front-to-back living room with a fireplace and gleaming

  

  Tim Drakeley

  Drakeley Real Estate, Inc.

  (475) 265-6768

  1 Stevens Rd, Middlebury, CT 06762
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  $799,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,674 Sq Ft

  77 Crest Rd, Middlebury, CT 06762

  Privacy, charm and timeless craftsmanship only begin to describe all that 77 Crest Rd has to offer. Nestled in the Hamlet of Middlebury's Historic District, this 2,600+ sq ft Contemporary Craftsman boasts flexible living with 4 full bedrooms, 3.5 baths, Large living room, and Large family room with 1/2 bath. 2 Blue Stone patios and a Belgian block patio perfectly placed alongside the newly

  Blair Patterson William Raveis Real Estate

  77 Crest Rd, Middlebury, CT 06762
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  $939,000 Open Sun 11AM - 1:30PM

  • 4 Beds
  • 3.5 Baths
  • 3,220 Sq Ft

  383 Leonard Rd, Middlebury, CT 06762

  NEW CONSTRUCTION split level with possible in-law 3220 sqft, 4 bedrooms, 3.5 baths, open floor plan on main level with kitchen, dinning/living room with a electric fireplace. A large size kitchen with granite countertops, plenty of cabinets, tiled backsplash, double oven, a large island for cooking or eating. The dining area next to the kitchen leads to a sliding door to outside trex deck(16x12),

  Koco Pela William Raveis Real Estate

  383 Leonard Rd, Middlebury, CT 06762
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  $885,000

  • 3 Beds
  • 3.5 Baths
  • 5,292 Sq Ft

  130 Upper Whittemore Rd, Middlebury, CT 06762

  Welcome Home! Nestled in one of Middlebury's most desirable neighborhoods, this beautiful home, with over 5200 square feet of living area, offers the perfect blend of comfort, elegance and functionality. Designed with the entertainer in mind, the spacious dining room flows into a top-of-the-line kitchen featuring a Viking stove, double ovens built into a large island, a restaurant-style stainless

  Donna Bannon BHGRE Bannon & Hebert

  130 Upper Whittemore Rd, Middlebury, CT 06762
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  $695,000

  • 4 Beds
  • 2.5 Baths
  • 2,570 Sq Ft

  55 Westwood Dr, Middlebury, CT 06762

  Middlebury Modern. Authentic c.1962 Mid-Century Modern Designed by Noted Architect Andrew S Cohen as his Personal Residence. This Largely Untouched Modernist is Set Quietly on Nearly 1-Acre. Walls of Glass & Dark Stone Floors Showcase the Signature Elements of the Era. 4 Bedrooms, 2.5 Baths Include an en-suite Primary Bedroom with Dressing Room & Balcony. Large Eat-in Kitchen Adjacent to Family

  Graham Klemm Klemm Real Estate Inc

  55 Westwood Dr, Middlebury, CT 06762
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  $949,500 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  4 White Birch Ln, Middlebury, CT 06762

  Welcome to 4 White Birch Lane, a to-be-built, fully customizable 2,750 SF home offering the perfect blend of luxury, flexibility, and modern design. This 4-bedroom, 3.5-bath home includes a 2-car garage and a spacious walk-out basement ready for future finishing-ideal for added living space, a home office, gym, or media room. Enjoy hardwood flooring throughout, with stylish tile in all bathrooms

  Donna Kennedy Keller Williams Realty

  4 White Birch Ln, Middlebury, CT 06762
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  $721,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  3 Pine Ridge Unit 23, Middlebury, CT 06762

  Welcome to Granite Woods - 2024 HOBI Award Winner for Best Detached 55+ Community. Only six homes remain in this in-town neighborhood featuring 24 detached Cape-style homes in the heart of Middlebury Village. Enjoy the peace, privacy, and independence of a stand-alone home with no shared walls, all within a low-maintenance community designed for active 55+ living. Ideally located, Granite Woods

  Robert Michaud Michaud Real Estate

  3 Pine Ridge Unit 23, Middlebury, CT 06762
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  $899,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,878 Sq Ft

  22 Somerset Dr, Middlebury, CT 06762

  TO BE BUILT. One of the most desirable neighborhoods in Middlebury! The Avalon Farms community is comprised of lovely homes, manicured lawns, and beautiful gardens resulting in a unique aesthetic. The Cambridge model showcases a classic design combined with today's "must haves" that will meet all your expectations of an open floor plan. The great room with a cathedral ceiling, fireplace, and

  Ellie Gollenberg BHGRE Bannon & Hebert

  22 Somerset Dr, Middlebury, CT 06762
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  $759,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  15 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 15 Hunting Ridge Rd(aka Lot 4) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

  Jodi Dawley Real Estate Two

  15 Hunting Ridge Rd, Middlebury, CT 06762
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  $759,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,466 Sq Ft

  28 Hunting Ridge Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 28 Hunting Ridge Road (aka Lot 7) is ready to move in to!! This home is a 2400+ sq ft 4 bedroom colonial. Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

  Jodi Dawley Real Estate Two

  28 Hunting Ridge Rd, Middlebury, CT 06762
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  $729,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  2 Deer Run Rd, Middlebury, CT 06762

  Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 2 Deer Run Road (aka Lot 13) is just beginning construction and will be one level living at its finest! Please see attached plans and specs. There are several other lots and plans to choose from or will build to suit! City water and sewer.

  Jodi Dawley Real Estate Two

  2 Deer Run Rd, Middlebury, CT 06762
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  $485,000 Open Sun 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  1 Yale Ave, Middlebury, CT 06762

  Charming Cape in prime neighborhood location. Ideally set just off the Middlebury Greenway Trail, this beautiful home offers comfort, space, and convenience. The updated kitchen features granite countertops, stainless steel appliances, white cabinetry, and ample space for cooking and dining. A bright, inviting living room provides the perfect space to relax. The main-level primary suite is

  Elizabeth Newnham William Pitt Sotheby's Int'l

  1 Yale Ave, Middlebury, CT 06762
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  $649,900

  • 4 Beds
  • 2.5 Baths
  • 3,224 Sq Ft

  1 Independence Cir, Middlebury, CT 06762

  Welcome to this beautiful 4 bedroom, 2.5 bath colonial in the highly sought after complex at Brookside of Middlebury. As you enter, the main floor boasts a large office, bright living room and formal dining room perfect for entertaining with its great flow. Kitchen continues that flow with granite covered island and countertops, gas stovetop with overhead microwave, and gas wall oven along with

  Carol D'Amato Regency Real Estate, LLC

  1 Independence Cir, Middlebury, CT 06762
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  $649,900

  • 4 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  1 Chatham Ct, Middlebury, CT 06762

  Discover timeless grace and style in this stunning 4 -bedroom home, nestled in the highly sought-after Brookside of Middlebury. From the moment you step inside, you will be captivated by its graceful open floor plan and refined finishes. The beautiful two-story foyer seamlessly flows into an elegant dining room and a fabulous kitchen featuring SS appliances, granite countertops and high bar area

  Norinne Byrne Calcagni Real Estate

  1 Chatham Ct, Middlebury, CT 06762
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  $539,900

  • 3 Beds
  • 2.5 Baths
  • 1,882 Sq Ft

  17 Highridge Rd Unit 17, Middlebury, CT 06762

  Welcome home to this warm and inviting 3-bedroom, 2.5-bathroom townhome, offering just under 1,900 square feet of beautifully finished living space. From the moment you step into the charming two-story foyer, you'll be greeted by an abundance of natural light and a sense of openness that continues throughout the home. The spacious, open-concept layout seamlessly connects the kitchen, dining area,

  Kayla O'Grady William Raveis Real Estate

  17 Highridge Rd Unit 17, Middlebury, CT 06762
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  $1,475,000

  • 4 Beds
  • 5 Baths
  • 6,175 Sq Ft

  122 Mirey Dam Rd, Middlebury, CT 06762

  Welcome to this expansive and exquisitely renovated Colonial estate, where timeless charm meets modern luxury. Boasting 5 spacious bedrooms and 5 elegantly appointed bathrooms, enhanced by a fully finished lower level offering potential for an in-law apartment or guest suite. Designed with flexibility and functionality in mind, the home features multiple flex rooms that can easily serve as

  Jennifer Jones Coldwell Banker Realty

  122 Mirey Dam Rd, Middlebury, CT 06762
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  $625,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft

  61 Stony Brook Rd, Middlebury, CT 06762

  Welcome to 61 Stonybrook Road-a spacious and light-filled contemporary ranch nestled on 1.38 wooded acres in a peaceful Middlebury setting. With over 2,800 square feet of living space, this 4-bedroom, 2.5-bath home offers the perfect blend of modern design and natural beauty. Soaring vaulted ceilings and gleaming hardwood floors create a warm and open atmosphere. Ideal for both everyday living

  Maria Cohen William Raveis Real Estate

  61 Stony Brook Rd, Middlebury, CT 06762
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  $216,000

  • Land
  • 1.04 Acres
  • $207,692 per Acre

  28 Pine Hollow Dr, Middlebury, CT 06762

  Non-conforming conforming two Barns on property.

  Derek Greene Derek Greene

  28 Pine Hollow Dr, Middlebury, CT 06762
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  $660,000

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  6 Brookside Dr, Middlebury, CT 06762

  Welcome to 6 Brookside Drive in Middlebury, CT-a beautifully maintained 3,745 sq ft colonial-style home in the desirable Brookside subdivision. This versatile residence offers 4 bedrooms and 4 bathrooms across three finished levels, ideal for multigenerational living. The open-concept main floor features vaulted ceilings, a gas fireplace, a gourmet eat-in kitchen with smart appliances, and a

  Nutan Pawar DreamHomes Realty LLC

  6 Brookside Dr, Middlebury, CT 06762
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  $660,000

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  6 Brookside Dr, Middlebury, CT 06762

  Welcome to 6 Brookside Drive in Middlebury, CT-a beautifully maintained 3,745 sq ft colonial-style home in the desirable Brookside subdivision. This versatile residence offers 4 bedrooms and 4 bathrooms across three finished levels, ideal for multigenerational living. The open-concept main floor features vaulted ceilings, a gas fireplace, a gourmet eat-in kitchen with smart appliances, and a

  Nutan Pawar DreamHomes Realty LLC

  6 Brookside Dr, Middlebury, CT 06762
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  $579,900

  • 3 Beds
  • 2 Baths
  • 2,560 Sq Ft

  297 Whittemore Rd, Middlebury, CT 06762

  DRASTIC PRICE DROP!!! Seller is Motivated!!! This well maintained home offers lots of space for the expanding family or simply one level living for the downsizer with guests to entertain. Truly a MUST SEE! Remodeled kitchen, gleaming oak floors, fireplace dining room for those traditional holidays. Large Open Great Room with lots of Natural Sunlight. Full Walk Up Attic for possible expansion if

  Susan Belmonte Coldwell Banker Realty

  297 Whittemore Rd, Middlebury, CT 06762
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  $699,900

  • Land
  • 6 Acres
  • $116,070 per Acre

  Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762

  This is an exceptional opportunity to create your dream home in an area of fine homes. Three lots, sold as a package, provide over six acres of stunning land in one of Middlebury's most desirable neighborhoods. Extending the road will be necessary for the three separate lots unless they are combined into a single parcel. Enjoy picturesque views of Mirey Pond.

  Mary Ann Hebert BHGRE Bannon & Hebert

  Lots 12,13, 14 Mirey Dam Rd, Middlebury, CT 06762
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  $85,000

  • Land
  • 0.45 Acre
  • $188,889 per Acre

  440 Lake Shore Dr, Middlebury, CT 06762

  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

  Florence DeDampierre W. Raveis Lifestyles Realty

  440 Lake Shore Dr, Middlebury, CT 06762
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  $489,900

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  115 Marney Dr, Middlebury, CT 06762

  Welcome to 115 Marney Drive! This spacious split level home has so much to offer to a family of any size! Not only does it have 3 bedrooms and 2.5 baths, it also has a large living room and dining area great for entertainment. The lower level has a finished bedroom and den with fireplace for additional guests. This house has had many updates since 2018 including a new roof and gutters with gutter

  Allysa DeRosa Mapleridge Realty

  115 Marney Dr, Middlebury, CT 06762
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  $560,000

  • 3 Beds
  • 2.5 Baths
  • 2,122 Sq Ft

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762

  Luxury living in this stunning 2122+ SqFt Portman ELITE END unit in sought Ridgewood community. This 3-bed, 2.5-bath home boasts exquisite upgrades, including a 3-foot extended bump out on both floors, hardwood floors, 9-ft ceilings, recessed lighting, custom crown, chair trail and mantle molding w/ custom beams. The open floor plan brings tons of natural light, offering serene forest views. The

  Jay Irvine Serhant Connecticut, LLC

  39 Ridgewood Dr Unit 39, Middlebury, CT 06762
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  $589,000

  • 4 Beds
  • 3 Baths
  • 2,088 Sq Ft

  76 Three Mile Hill Rd, Middlebury, CT 06762

  Meticulously maintained and completely renovated in 2024, this move-in-ready home is a true masterpiece of thoughtful design. Located in one of Middlebury's most desirable neighborhoods, this 4 bedroom, 3 full bath home is a gem not to be missed. From the moment you step inside, you feel the warmth and coziness of the home combined with the ease of modern living. The updated kitchen boasts

  Lisa Clarke Dave Jones Realty, LLC

  76 Three Mile Hill Rd, Middlebury, CT 06762
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  $640,000

  • 3 Beds
  • 3.5 Baths
  • 3,477 Sq Ft

  1 Dogwood Ct Unit 1, Middlebury, CT 06762

  Wow-this is it! The original model home is back on the market for the first time, offering exceptional quality and design. This desirable Dickinson-style home, originally built as the model, is impeccably finished on all three levels. The spacious dining area flows seamlessly into a vaulted living room with a cozy fireplace and sliders leading to a private deck. The light-filled kitchen features

  Joyce Drakeley Drakeley Real Estate, Inc.

  1 Dogwood Ct Unit 1, Middlebury, CT 06762
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  $569,900

  • 2 Beds
  • 2.5 Baths
  • 2,593 Sq Ft

  112 Periwinkle Dr Unit 112, Middlebury, CT 06762

  Welcome to Benson Woods - an exclusive community of 78 single-family homes designed for active adults. This beautifully maintained home boasts an open floor plan, featuring a great room with a cozy fireplace and soaring cathedral ceilings. The eat-in kitchen is a chef's delight, complete with a spacious island, dining area, white shaker-style cabinets, granite countertops, and a stylish tile

  Mary Ann Hebert BHGRE Bannon & Hebert

  112 Periwinkle Dr Unit 112, Middlebury, CT 06762
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  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,882 Sq Ft

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762

  Welcome to this luxury end-unit condo built in 2022 w/ 3-Bed, 2.5-Bath in Sought-After Ridgewood.1882 Sqft w/ 4 extension to floor plan. This beautifully designed living space, offers 1 level living that many look for. Equipped w/ cathedral ceilings and a first-floor primary bedroom suite for ultimate convenience and a very rare unit. The gourmet kitchen boasts quartz countertops, stainless steel

  Jay Irvine Serhant Connecticut, LLC

  180 Ridgewood Dr Unit 219, Middlebury, CT 06762
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  $549,900

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  29 Winding Trail Unit 29, Middlebury, CT 06762

  Beautiful Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath condo built by Toll Brothers, nestled on a private cul-de-sac in unique location. Over 2,100 sqft designed modern living space, this home includes a 4-foot bump-out for added size. Entering the home, the first floor features an open floor plan w/ hardwood floors, white cabinetry, stainless steel appliances,

  Jay Irvine Serhant Connecticut, LLC

  29 Winding Trail Unit 29, Middlebury, CT 06762
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  $659,000

  • 4 Beds
  • 3.5 Baths
  • 3,195 Sq Ft

  1 Winding Trail Unit 1, Middlebury, CT 06762

  Don't wait to see this turn key home in the desirable Ridgewood of Middlbury, one of the areas newest and most picturesque communities. This is a unique end unit, The Emerson Model, situated in a private, quiet cornet lot. As you enter the home, you'll view the open living room/dining room, with a gas fireplace and plenty of light. The attached kitchen includes granite countertops, large cherry

  Scott Hellriegel Berkshire Hathaway NE Prop.

  1 Winding Trail Unit 1, Middlebury, CT 06762
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  $549,900

  • 3 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  58 Shadduck Rd, Middlebury, CT 06762

  DON'T MISS OUT, BACK ON MARKET!!!! This beautifully renovated colonial seamlessly blends classic elegance with modern updates. Featuring gleaming hardwood floors, an open-concept main level, and a bright kitchen with a center island, this home offers a perfect space for entertaining and everyday living. The primary suite includes a luxurious en suite bath and walk-in closets, complemented by

  Amber Segetti RE/MAX RISE

  58 Shadduck Rd, Middlebury, CT 06762
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  $499,950

  • 3 Beds
  • 3.5 Baths
  • 1,596 Sq Ft

  28 Maple Dr, Middlebury, CT 06762

  Welcome to 28 Maple Drive, a classic gem in the heart of Middlebury, Connecticut, where charm and comfort meet timeless design. This meticulously maintained single-family home, built in 1950, offers 1,596 square feet of thoughtfully designed living space. With 3 spacious bedrooms, 3.5 bathrooms, and a warm, inviting layout, this home is perfect for both entertaining and everyday living. A fully

  Dean Giatas William Raveis Real Estate

  28 Maple Dr, Middlebury, CT 06762
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  $50,000

  • Land
  • 0.84 Acre
  • $59,524 per Acre

  0 Lake Shore Dr, Middlebury, CT 06762

  Four lots for sale as a package deal! Total Acreage 0.84 THREE of the lots CAN NOT be built on but you can have an abundance of land and privacy around the single family structure you build! Nestled in a desirable area of Middlebury don't miss your opportunity to create a home of your own.

  Rosania Melo Century 21 Scala Group

  0 Lake Shore Dr, Middlebury, CT 06762
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  $599,000

  • 4 Beds
  • 3.5 Baths
  • 2,691 Sq Ft

  66 Artillery Rd, Middlebury, CT 06762

  Antique lovers alert! Enjoy this quintessential 1803 Colonial on 1.026 acres, nestled within the picturesque conservation protected 7.3 acre land containing Fenn Pond. You'll own a piece of history, with the privacy, character and tradition of its era, including wide board floors, 7 fireplaces, and front and back staircases. Delightful finds everywhere! The magical setting contains stone walls,

  Mary Helen Levine Mary Helen Levine Real Estate LLC

  66 Artillery Rd, Middlebury, CT 06762
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  $199,009

  • Land
  • 4.67 Acres
  • $42,614 per Acre

  75 Gleneagle Rd, Middlebury, CT 06762

  LOCATION, LOCATION, LOCATION!!! ONLY LOT FOR SALE IN THIS PRIVATE, 11 LOT SUBDIVISION OF QUALITY-BUILT HIGH END HOMES. SUBDIVISION HAS THE UNIQUE BONUSES OF PUBLIC WATER & SEWER (ALREADY EXTENDED TO LOT) AND CLOSE PROXIMITY TO LOCAL RETAIL AND HIGHWAYS. 4.67 ACRE SITE TUCKED AWAY AT THE END OF A TURN-AROUND TO THE LEFT OF THE ELABORATE GAZEEBO AND LAND TRUST PROPERTY.

  Scott Tedesco Tedesco Real Estate

  75 Gleneagle Rd, Middlebury, CT 06762
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  $274,900

  • Land
  • 3.33 Acres
  • $82,553 per Acre

  19 Deer Run Rd, Middlebury, CT 06762

  Welcome to Hunting Ridge Estates, a premier 23-lot subdivision offering the perfect blend of privacy and natural beauty. This spacious 3.33-acre rear lot provides ample space to build your dream home in a peaceful, upscale setting. With multiple lot options available, you can choose the one that best suits your vision. Whether you prefer to bring your own builder or take advantage of our

  Jodi Dawley Real Estate Two

  19 Deer Run Rd, Middlebury, CT 06762
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  $509,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762

  Only 4 Units Remaining! An address that elevates your lifestyle - Aberdeen Estates at Benson Woods is a premier 55+ Adult Community located in the charming town of Middlebury. This under construction neighborhood will be comprised of 32 attached townhomes across 11 buildings offering a two-story design and unique details crafted just for adults over 55. Experience effortless living in beautifully

  Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 47 24099635, Middlebury, CT 06762
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  $1,099,750 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  7 White Birch Ln, Middlebury, CT 06762

  Here's your chance to build the home you've always dreamed of at 7 White Birch Lane, a to-be-built 3,325 SF custom residence located on one of the most desirable cul-de-sac lots in Middlebury. With 4 bedrooms, 3.5 baths, and a 2-car garage, this home offers both elegance and flexibility-crafted with the quality and attention to detail you deserve. Enjoy hardwood flooring throughout and the tile

  Donna Kennedy Keller Williams Realty

  7 White Birch Ln, Middlebury, CT 06762
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  $1,249,500 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  6 White Birch Ln, Middlebury, CT 06762

  Welcome to 6 White Birch Lane in Middlebury, an exceptional 3,700 sq ft custom home set on the largest lot at the end of the cul-de-sac, offering privacy, space and sophistication in one of Middlebury's most sought-after neighborhoods. This stunning 4-bedroom, 3.5-bath residence is designed for modern living with high-end finishes and timeless elegance throughout. Enjoy hardwood flooring in every

  Donna Kennedy Keller Williams Realty

  6 White Birch Ln, Middlebury, CT 06762

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