Connecticut Realtor with experience and knowledge of residential and commercial property in Middlebury

6/12/2025 3:00:04 PM
Active
1 Dogwood Court Middlebury CT
1 Dogwood Court

Middlebury, Connecticut 06762

$630,000 | Active

3 Beds | 4 Baths | 3477 Sqft | 0 Acres | 70 Days on Market

Property Type: Condo/Co-Op For Sale

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 int...

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6/12/2025 12:39:48 PM
Under Contract
180 Ridgewood Drive Middlebury CT
180 Ridgewood Drive

Middlebury, Connecticut 06762

$575,000 | Under Contract

3 Beds | 3 Baths | 1882 Sqft | 0 Acres | 68 Days on Market

Property Type: Condo/Co-Op For Sale

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 bedr...

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6/12/2025 1:40:20 AM
Under Contract CTS
17 Highridge Road Middlebury CT
17 Highridge Road

Middlebury, Connecticut 06762

$539,900 | Under Contract - Continue

3 Beds | 3 Baths | 1882 Sqft | 0 Acres | 21 Days on Market

Property Type: Condo/Co-Op For Sale

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, youll be greeted by an abundance of natural light and a sense of openne...

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6/10/2025 8:44:02 PM
Under Contract
69 Nick Road Middlebury CT
69 Nick Road

Middlebury, Connecticut 06762

$419,900 | Under Contract

3 Beds | 3 Baths | 1414 Sqft | 0.61 Acres | 3 Days on Market

Property Type: Single Family For Sale

Charming, Fully Renovated Cape in Desirable Middlebury Welcome to this stunningly remodeled 1950s Cape, perfectly blending timeless charm with modern finishes. Located in the heart of Middlebury, known for its award-winning schools, scenic Greenway, and proximity to town, shops,...

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6/10/2025 6:23:36 PM
Active
190 Allerton Farms Road Middlebury CT
190 Allerton Farms Road

Middlebury, Connecticut 06762

$539,900 | Active

2 Beds | 3 Baths | 1744 Sqft | 0.73 Acres | 3 Days on Market

Property Type: Single Family For Sale

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 finish...

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6/9/2025 3:50:14 PM
Active
76 Three Mile Hill Road Middlebury CT
76 Three Mile Hill Road

Middlebury, Connecticut 06762

$549,000 | Active

4 Beds | 3 Baths | 2088 Sqft | 0.82 Acres | 70 Days on Market

Property Type: Single Family For Sale

Meticulously maintained and completely renovated in 2024, this move-in-ready home is a true masterpiece of thoughtful design. Located in one of Middleburys most desirable neighborhoods, this 4 bedroom, 3 full bath home is a gem not to be missed. From the moment you step inside, ...

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6/6/2025 1:36:58 PM
Active
297 Whittemore Road Middlebury CT
297 Whittemore Road

Middlebury, Connecticut 06762

$579,900 | Active

3 Beds | 2 Baths | 2560 Sqft | 0.59 Acres | 36 Days on Market

Property Type: Single Family For Sale

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 tr...

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6/5/2025 1:28:51 PM
Active
1 Yale Avenue Middlebury CT
1 Yale Avenue

Middlebury, Connecticut 06762

$485,000 | Active

3 Beds | 2 Baths | 1788 Sqft | 0.29 Acres | 8 Days on Market

Property Type: Single Family For Sale

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...

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6/5/2025 4:05:03 AM
Active
77 Crest Road Middlebury CT
77 Crest Road

Middlebury, Connecticut 06762

$799,000 | Active

4 Beds | 4 Baths | 2674 Sqft | 1.5 Acres | 8 Days on Market

Property Type: Single Family For Sale

Privacy, charm and timeless craftsmanship only begin to describe all that 77 Crest Rd has to offer. Nestled in the Hamlet of Middleburys Historic District, this 2,600+ sq ft Contemporary Craftsman boasts flexible living with 4 full bedrooms, 3.5 baths, Large living room, and Larg...

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6/3/2025 4:36:44 PM
Active
58 Shadduck Road Middlebury CT
58 Shadduck Road

Middlebury, Connecticut 06762

$549,900 | Active

3 Beds | 3 Baths | 2360 Sqft | 0.97 Acres | 77 Days on Market

Property Type: Single Family For Sale

DONT 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 entertai...

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6/3/2025 2:35:12 PM
Active
1 Stevens Road Middlebury CT
1 Stevens Road

Middlebury, Connecticut 06762

$549,900 | Active

3 Beds | 3 Baths | 2248 Sqft | 0.28 Acres | 20 Days on Market

Property Type: Single Family For Sale

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 endurin...

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6/3/2025 12:39:02 PM
Under Contract CTS
222 Crest Road Middlebury CT
222 Crest Road

Middlebury, Connecticut 06762

$739,000 | Under Contract - Continue

5 Beds | 3 Baths | 2442 Sqft | 1.05 Acres | 21 Days on Market

Property Type: Single Family For Sale

Step in to timeless elegance with this beautifully restored 5 bedroom, 2.5 bath home with solid oak flooring throughout, and a 2 car detached garage nestled on a lush, landscaped 1 acre lot just a short walk to the town green, the Middlebury Library and the scenic Middlebury Gree...

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6/3/2025 1:06:56 AM
Active
61 Stony Brook Road Middlebury CT
61 Stony Brook Road

Middlebury, Connecticut 06762

$625,000 | Active

4 Beds | 3 Baths | 2804 Sqft | 1.38 Acres | 28 Days on Market

Property Type: Single Family For Sale

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. Soa...

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5/31/2025 11:42:03 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$560,753 | Under Contract

3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

5 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 ...

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5/31/2025 8:10:04 PM
Under Contract
119 Christian Road Middlebury CT
119 Christian Road

Middlebury, Connecticut 06762

$340,000 | Under Contract

2 Beds | 2 Baths | 866 Sqft | 0.39 Acres | 15 Days on Market

Property Type: Single Family For Sale

Nestled in one of Middleburys most sought-after neighborhoods, this well-maintained two-bedroom ranch blends comfort, convenience, and charm. Step inside through the inviting enclosed front porch-perfect for morning coffee or evening relaxation-into a warm and welcoming living ro...

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5/30/2025 5:41:18 PM
Active
1 Independence Circle Middlebury CT
1 Independence Circle

Middlebury, Connecticut 06762

$649,900 | Active

4 Beds | 3 Baths | 3224 Sqft | 0 Acres | 14 Days on Market

Property Type: Single Family For Sale

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...

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5/30/2025 4:48:37 PM
Active
1 Independence Circle Middlebury CT
1 Independence Circle

Middlebury, Connecticut 06762

$649,900 | Active

4 Beds | 3 Baths | 3224 Sqft | 0 Acres | 14 Days on Market

Property Type: Condo/Co-Op For Sale

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...

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5/29/2025 6:17:13 PM
Under Contract CTS
18 Deer Run Road Middlebury CT
18 Deer Run Road

Middlebury, Connecticut 06762

$799,900 | Under Contract - Continue

3 Beds | 3 Baths | 2190 Sqft | 3.47 Acres | 17 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 18 Deer Run Road (aka Lot 20) 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...

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5/29/2025 1:27:01 PM
Active
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$509,900 | Active

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 15 Days on Market

Property Type: Condo/Co-Op For Sale

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 offe...

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5/28/2025 8:55:43 PM
Under Contract CTS
34 Avalon Drive Middlebury CT
34 Avalon Drive

Middlebury, Connecticut 06762

$785,000 | Under Contract - Continue

3 Beds | 4 Baths | 3374 Sqft | 0.71 Acres | 29 Days on Market

Property Type: Single Family For Sale

Located in a desirable neighborhood setting, this beautifully appointed home offers refined living with the flexibility to suit any stage of life. Step inside to a grand two-story foyer that sets the tone for the homes spacious, light-filled interior. The main-level primary suite...

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5/28/2025 12:45:18 AM
Active
55 Westwood Drive Middlebury CT
55 Westwood Drive

Middlebury, Connecticut 06762

$695,000 | Active

4 Beds | 3 Baths | 2570 Sqft | 0.98 Acres | 95 Days on Market

Property Type: Single Family For Sale

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...

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5/27/2025 9:00:16 PM
Under Contract
15 Brookside Drive Middlebury CT
15 Brookside Drive

Middlebury, Connecticut 06762

$679,000 | Under Contract

3 Beds | 3 Baths | 3308 Sqft | 1 Acres | 39 Days on Market

Property Type: Single Family For Sale

This stunning colonial home features a beautifully landscaped level lot with an expansive side yard. As you approach, you are welcomed by a charming covered front porch that leads into a grand two-story foyer with a winding staircase and abundant natural light from the second-sto...

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5/26/2025 2:47:27 AM
Under Contract CTS
190 Bronson Drive Middlebury CT
190 Bronson Drive

Middlebury, Connecticut 06762

$675,000 | Under Contract - Continue

4 Beds | 3 Baths | 2850 Sqft | 0.97 Acres | 24 Days on Market

Property Type: Single Family For Sale

Welcome to this beautifully maintained 4 bedroom 2.5 bath colonial home offering space and style in a sought after location! Enter from the oversized 2 car garage into the mudroom with ample storage. Beyond the large eat-in kitchen and formal dining room is the family room that ...

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5/24/2025 3:18:06 PM
Under Contract CTS
126 Colonial Avenue Middlebury CT
126 Colonial Avenue

Middlebury, Connecticut 06762

$635,000 | Under Contract - Continue

3 Beds | 2 Baths | 2531 Sqft | 2.4 Acres | 99 Days on Market

Property Type: Single Family For Sale

Built in 1911, this four square colonial has so many fabulous vintage qualities including a beautiful, generously sized front entry, arched doorways, custom moldings and so much more. The main level offers a spacious eat in kitchen, formal living and dining rooms as well as a 21 ...

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5/20/2025 3:08:44 PM
Active
115 Marney Drive Middlebury CT
115 Marney Drive

Middlebury, Connecticut 06762

$489,900 | Active

3 Beds | 3 Baths | 1682 Sqft | 0.41 Acres | 62 Days on Market

Property Type: Single Family For Sale

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 f...

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5/19/2025 9:35:10 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$522,128 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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5/19/2025 3:23:15 PM
Active
28 Maple Drive Middlebury CT
28 Maple Drive

Middlebury, Connecticut 06762

$499,950 | Active

3 Beds | 4 Baths | 1596 Sqft | 2.31 Acres | 133 Days on Market

Property Type: Single Family For Sale

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...

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5/16/2025 4:26:45 PM
Active
1 Chatham Court Middlebury CT
1 Chatham Court

Middlebury, Connecticut 06762

$649,900 | Active

4 Beds | 3 Baths | 2950 Sqft | 0 Acres | 28 Days on Market

Property Type: Single Family For Sale

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 f...

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5/16/2025 4:13:23 PM
Active
1 Chatham Court Middlebury CT
1 Chatham Court

Middlebury, Connecticut 06762

$649,900 | Active

4 Beds | 3 Baths | 2950 Sqft | 0 Acres | 28 Days on Market

Property Type: Condo/Co-Op For Sale

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 f...

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5/16/2025 2:38:22 AM
Active
29 Winding Trail Middlebury CT
29 Winding Trail

Middlebury, Connecticut 06762

$549,900 | Active

3 Beds | 3 Baths | 2130 Sqft | 0 Acres | 72 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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5/15/2025 12:47:20 AM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$533,416 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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5/14/2025 11:13:15 PM
Active
122 Mirey Dam Road Middlebury CT
122 Mirey Dam Road

Middlebury, Connecticut 06762

$1,475,000 | Active

4 Beds | 5 Baths | 6175 Sqft | 2.69 Acres | 30 Days on Market

Property Type: Single Family For Sale

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. De...

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5/14/2025 3:46:09 PM
Under Contract CTS
17 Deer Run Road Middlebury CT
17 Deer Run Road

Middlebury, Connecticut 06762

$759,900 | Under Contract - Continue

4 Beds | 3 Baths | 2466 Sqft | 1.27 Acres | 95 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 17 Deer Run Road (aka Lot 22) is ready to move in to! It is 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 sui...

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5/14/2025 2:50:03 PM
Under Contract CTS
94 Upper Whittemore Road Middlebury CT
94 Upper Whittemore Road

Middlebury, Connecticut 06762

$539,900 | Under Contract - Continue

3 Beds | 2 Baths | 2024 Sqft | 1.8 Acres | 36 Days on Market

Property Type: Single Family For Sale

Nestled along a designated scenic route just seconds from Lake Quassapaug, this custom-built Craftsman-style split-level home offers a rare blend of timeless character and modern comfort. The main-level features rich hardwood floors and a luxurious primary suite, complete with an...

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5/12/2025 3:59:37 PM
Under Contract
18 Hunting Ridge Road Middlebury CT
18 Hunting Ridge Road

Middlebury, Connecticut 06762

$799,900 | Under Contract

4 Beds | 3 Baths | 2700 Sqft | 1.06 Acres | 298 Days on Market

Property Type: Single Family For Sale

Welcome home to Middleburys newest 23 lot subdivision- Hunting Ridge Estates. This home is currently under construction and will be a 2700 four bedroom colonial featuring hardwood flooring throughout, upgraded trim, walk-in pantry and an attached garage. Still time to customize!!...

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5/9/2025 1:59:16 PM
Active
7 White Birch Lane Middlebury CT
7 White Birch Lane

Middlebury, Connecticut 06762

$1,099,750 | Active

4 Beds | 4 Baths | 3325 Sqft | 1.4048 Acres | 35 Days on Market

Property Type: Single Family For Sale

Heres your chance to build the home youve 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 flexib...

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5/9/2025 12:04:11 AM
Under Contract CTS
1440 Straits Turnpike Middlebury CT
1440 Straits Turnpike

Middlebury, Connecticut 06762

$499,900 | Under Contract - Continue

3 Beds | 3 Baths | 2046 Sqft | 0.37 Acres | 40 Days on Market

Property Type: Single Family For Sale

Pride of ownership abounds in this custom built cape! Main level offers living room with fireplace and pellet insert, crown moldings and hardwood flooring with open flow into the dining room appointed with French doors with transom, crown moldings and hardwood flooring, eating s...

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5/8/2025 3:30:24 PM
Active
4 White Birch Lane Middlebury CT
4 White Birch Lane

Middlebury, Connecticut 06762

$949,500 | Active

4 Beds | 4 Baths | 2750 Sqft | 1.243 Acres | 36 Days on Market

Property Type: Single Family For Sale

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 l...

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5/8/2025 3:09:55 PM
Active
1 White Brich Lane Middlebury CT
1 White Brich Lane

Middlebury, Connecticut 06762

$869,500 | Active

3 Beds | 3 Baths | 2450 Sqft | 1.3692 Acres | 36 Days on Market

Property Type: Single Family For Sale

Design your dream home from the ground up at 1 White Birch Lane, a to-be-built, fully customizable residence in beautiful Middlebury CT. This thoughtfully designed 2,450 SF home will feature 3 spacious bedrooms, 2.5 baths, and a 2-car garage, all crafted with exceptional attentio...

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5/7/2025 11:59:57 PM
Active
6 White Birch Lane Middlebury CT
6 White Birch Lane

Middlebury, Connecticut 06762

$1,249,500 | Active

4 Beds | 4 Baths | 3700 Sqft | 2.6825 Acres | 37 Days on Market

Property Type: Single Family For Sale

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 Middleburys most sought-after neighborhoods. This stunning 4-bedroom, 3.5-bath residence i...

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5/7/2025 6:21:34 PM
Active
11 White Birch Lane Middlebury CT
11 White Birch Lane

Middlebury, Connecticut 06762

$999,500 | Active

4 Beds | 5 Baths | 3000 Sqft | 1.6803 Acres | 37 Days on Market

Property Type: Single Family For Sale

Welcome to 11 White Birch Lane - a rare opportunity to create your ideal home in one of Middleburys most desirable neighborhoods. This to-be-built, customizable residence will offer 4 spacious bedrooms, 4.1 luxurious baths, a 3-car garage, and an open-concept layout designed for ...

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5/7/2025 4:28:47 PM
Under Contract
405 Chestnut Circle Middlebury CT
405 Chestnut Circle

Middlebury, Connecticut 06762

$649,500 | Under Contract

2 Beds | 3 Baths | 2292 Sqft | 0 Acres | 99 Days on Market

Property Type: Condo/Co-Op For Sale

Welcome to our final phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over...

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5/6/2025 2:26:43 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$522,128 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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5/5/2025 1:44:21 PM
Active
6 Brookside Drive Middlebury CT
6 Brookside Drive

Middlebury, Connecticut 06762

$660,000 | Active

3 Beds | 3 Baths | 2240 Sqft | 0 Acres | 39 Days on Market

Property Type: Condo/Co-Op For Sale

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-co...

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5/5/2025 11:09:18 AM
Active
6 Brookside Drive Middlebury CT
6 Brookside Drive

Middlebury, Connecticut 06762

$660,000 | Active

3 Beds | 3 Baths | 2240 Sqft | 1 Acres | 39 Days on Market

Property Type: Single Family For Sale

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-co...

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5/5/2025 5:47:58 AM
Active
130 Upper Whittemore Road Middlebury CT
130 Upper Whittemore Road

Middlebury, Connecticut 06762

$885,000 | Active

3 Beds | 4 Baths | 5292 Sqft | 1.62 Acres | 39 Days on Market

Property Type: Single Family For Sale

Welcome Home! Nestled in one of Middleburys 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 ...

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5/1/2025 12:48:33 PM
Under Contract CTS
203 Lake Shore Drive Middlebury CT
203 Lake Shore Drive

Middlebury, Connecticut 06762

$375,000 | Under Contract - Continue

2 Beds | 1 Baths | 1344 Sqft | 0.44 Acres | 51 Days on Market

Property Type: Single Family For Sale

Lake Shore Drive is just a short walk from the beautifully preserved Long Meadow Pond, a 117-plus acre body of water known for its fishing and kayaking. This home is perfectly in keeping with this idyllic setting, as it is a quintessentially charming ranch, a style of home known ...

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5/1/2025 2:01:31 AM
Active
383 Leonard Road Middlebury CT
383 Leonard Road

Middlebury, Connecticut 06762

$939,000 | Active

4 Beds | 4 Baths | 3220 Sqft | 1.23 Acres | 44 Days on Market

Property Type: Single Family For Sale

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...

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4/28/2025 5:13:03 PM
Under Contract CTS
64 Joy Road Middlebury CT
64 Joy Road

Middlebury, Connecticut 06762

$399,000 | Under Contract - Continue

3 Beds | 1 Baths | 1688 Sqft | 0.46 Acres | 53 Days on Market

Property Type: Single Family For Sale

Charming Move-In Ready Ranch in the Heart of Middlebury Welcome home to this beautifully updated ranch-style gem, ideally located in the heart of Middlebury. Set on a quiet street just steps from the scenic Middlebury Greenway Trail, this home offers comfort, style, and convenien...

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4/22/2025 7:08:50 PM
Under Contract CTS
14 Deer Run Road Middlebury CT
14 Deer Run Road

Middlebury, Connecticut 06762

$699,000 | Under Contract - Continue

3 Beds | 2 Baths | 1877 Sqft | 1.18 Acres | 60 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 14 Deer Run Rd(aka Lot 19) 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 bu...

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4/22/2025 1:34:00 AM
Active
66 Artillery Road Middlebury CT
66 Artillery Road

Middlebury, Connecticut 06762

$599,000 | Active

4 Beds | 4 Baths | 2691 Sqft | 1.02 Acres | 246 Days on Market

Property Type: Single Family For Sale

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. Youll own a piece of history, with the privacy, character and tradition of its era, including wide board floors,...

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4/21/2025 9:26:46 PM
Under Contract CTS
116 Bronson Drive Middlebury CT
116 Bronson Drive

Middlebury, Connecticut 06762

$600,000 | Under Contract - Continue

3 Beds | 3 Baths | 2262 Sqft | 1.04 Acres | 60 Days on Market

Property Type: Single Family For Sale

Welcome to this beautifully updated home, perfectly located in the heart of Middlebury! This charming single-story property offers 3 spacious bedrooms and 3 full-sized bathrooms, making it an ideal home for those looking for main-level living. Enjoy the vibrant atmosphere of th...

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4/17/2025 9:56:12 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$525,438 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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4/17/2025 9:49:34 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$499,900 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 132 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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4/17/2025 7:25:43 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$509,900 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 163 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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4/9/2025 6:47:58 PM
Active
106 Judd Hill Road Middlebury CT
106 Judd Hill Road

Middlebury, Connecticut 06762

$1,219,900 | Active

4 Beds | 4 Baths | 4696 Sqft | 1.67 Acres | 141 Days on Market

Property Type: Single Family For Sale

Sitting pretty at 4,200 square feet, this exquisite property is designed for those ready to embrace a luxury lifestyle, offering the perfect setting for anyone looking to expand their living space. Crafted with attention to detail, every corner of this 10-room home radiates sophi...

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4/8/2025 5:07:20 PM
Active
39 Ridgewood Drive Middlebury CT
39 Ridgewood Drive

Middlebury, Connecticut 06762

$560,000 | Active

3 Beds | 3 Baths | 2122 Sqft | 0 Acres | 66 Days on Market

Property Type: Condo/Co-Op For Sale

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 a...

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4/7/2025 6:32:47 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$519,900 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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4/7/2025 3:07:27 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$548,828 | Under Contract

3 Beds | 3 Baths | 2462 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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4/3/2025 8:26:18 PM
Active
112 Periwinkle Drive Middlebury CT
112 Periwinkle Drive

Middlebury, Connecticut 06762

$569,900 | Active

2 Beds | 3 Baths | 2593 Sqft | 0 Acres | 71 Days on Market

Property Type: Condo/Co-Op For Sale

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 chefs delight, ...

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4/1/2025 12:58:40 PM
Active
1 Winding Trail Middlebury CT
1 Winding Trail

Middlebury, Connecticut 06762

$659,000 | Active

4 Beds | 4 Baths | 3195 Sqft | 0 Acres | 73 Days on Market

Property Type: Condo/Co-Op For Sale

Dont 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, youll view the open living room/din...

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3/24/2025 6:15:22 PM
Active
3 Pine Ridge Middlebury CT
3 Pine Ridge

Middlebury, Connecticut 06762

$721,000 | Active

2 Beds | 3 Baths | 2290 Sqft | 0 Acres | 81 Days on Market

Property Type: Condo/Co-Op For Sale

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 n...

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3/21/2025 8:28:19 PM
Active
1 Pine Ridge Middlebury CT
1 Pine Ridge

Middlebury, Connecticut 06762

$619,000 | Active

2 Beds | 2 Baths | 1600 Sqft | 0 Acres | 84 Days on Market

Property Type: Condo/Co-Op For Sale

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 n...

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3/12/2025 2:40:49 PM
Active
15 Hunting Ridge Road Middlebury CT
15 Hunting Ridge Road

Middlebury, Connecticut 06762

$759,900 | Active

3 Beds | 3 Baths | 2190 Sqft | 0.92 Acres | 93 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys 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 wil...

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3/10/2025 5:33:35 PM
Active
28 Hunting Ridge Road Middlebury CT
28 Hunting Ridge Road

Middlebury, Connecticut 06762

$759,900 | Active

4 Beds | 3 Baths | 2466 Sqft | 2.8 Acres | 95 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys 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 wil...

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3/3/2025 6:45:45 PM
Under Contract CTS
11 Hunting Ridge Road Middlebury CT
11 Hunting Ridge Road

Middlebury, Connecticut 06762

$799,900 | Under Contract - Continue

4 Beds | 3 Baths | 2700 Sqft | 1.31 Acres | 235 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 11 Hunting Ridge Road (aka Lot 3) is to be built. It is a 2700 sq ft colonial with 2 car attached garage.Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen w...

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2/27/2025 9:43:49 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$545,400 | Under Contract

3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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2/27/2025 7:27:05 PM
Under Contract
407 Chestnut Circle Middlebury CT
407 Chestnut Circle

Middlebury, Connecticut 06762

$655,500 | Under Contract

2 Beds | 2 Baths | 2292 Sqft | 0 Acres | 519 Days on Market

Property Type: Condo/Co-Op For Sale

Welcome to our next phase!!! Chestnut Circle consists of 5 Simsbury Elite homes on a private circle! These homesites have many upgraded options including walk-out basements, expanded great rooms, premium locations and more! Debating between a house or a condo? Benson Woods (over ...

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2/24/2025 10:16:12 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$505,834 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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2/23/2025 8:38:32 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$499,900 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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1/30/2025 11:19:00 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$546,936 | Under Contract

3 Beds | 3 Baths | 2252 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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1/23/2025 9:50:04 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$591,251 | Under Contract

3 Beds | 3 Baths | 2923 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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1/5/2025 3:14:57 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$509,300 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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12/13/2024 10:35:04 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$511,000 | Under Contract

3 Beds | 3 Baths | 1950 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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11/22/2024 5:37:50 PM
Under Contract
 Benson Road Middlebury CT
Benson Road

Middlebury, Connecticut 06762

$541,566 | Under Contract

3 Beds | 3 Baths | 2206 Sqft | 0 Acres | 0 Days on Market

Property Type: Condo/Co-Op For Sale

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 ...

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9/23/2024 6:42:47 PM
Under Contract
3 Hunting Ridge Road Middlebury CT
3 Hunting Ridge Road

Middlebury, Connecticut 06762

$624,900 | Under Contract

3 Beds | 2 Baths | 1700 Sqft | 1.31 Acres | 73 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys newest 23 lot subdivision-Hunting Ridge Estates. 3 Hunting Ridge Road (aka Lot 1) is now complete and ready for occupancy! It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet ki...

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8/19/2024 7:07:23 PM
Active
294 Christian Road Middlebury CT
294 Christian Road

Middlebury, Connecticut 06762

$899,000 | Active

3 Beds | 3 Baths | 2878 Sqft | 1.05 Acres | 664 Days on Market

Property Type: Single Family For Sale

New construction designed to impress the most discerning buyer. The Cambridge Model with 2,878 sq. ft. offers a grand two-story foyer leading to the great room with majestic soaring ceilings, fireplace and beautiful windows giving the space a light and airy feeling. The kitchen a...

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7/12/2024 5:20:07 PM
Active
2 Deer Run Road Middlebury CT
2 Deer Run Road

Middlebury, Connecticut 06762

$729,900 | Active

3 Beds | 3 Baths | 2190 Sqft | 0.92 Acres | 336 Days on Market

Property Type: Single Family For Sale

Welcome Home to Middleburys 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 ...

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6/14/2024 3:30:12 PM
Active
22 Somerset Drive Middlebury CT
22 Somerset Drive

Middlebury, Connecticut 06762

$899,000 | Active

3 Beds | 3 Baths | 2878 Sqft | 0.8 Acres | 364 Days on Market

Property Type: Single Family For Sale

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 todays must haves that...

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