Middlebury, CT Homes

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  /40

  $689,900

  • 3 Beds
  • 4 Baths
  • 3,432 Sq Ft

  33 Ridgewood Dr Unit 33, Middlebury, CT 06762

  Walls of windows! Spectacular, light filled end unit at an award-winning townhome community in Middlebury. Turnkey! Primary bedroom on main level with newly renovated en suite bath. Gorgeous updated kitchen with modern appliances. 2 guest bedrooms on 2nd floor with large shared Jack & Jill bath. Spacious loft for bonus space or home office. Finished lower level flex space for playroom, home

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 871-0910

  33 Ridgewood Dr Unit 33, Middlebury, CT 06762
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  Explore Middlebury

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  /11

  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • House for Rent

  173 Christian Rd, Middlebury, CT 06762

  Property Id: 2064532Perfect year round residence or weekend retreat. This newly renovated 1b/1ba cottage offers plenty of storage and a large covered carport. Vaulted ceilings, ductless heating/cooling, washer & dryer and room for the grill behind the house.Walk to the lake for day fun and enjoy all water sports or experience a magical sunset... an abundance of peaceful country

  173 Christian Rd, Middlebury, CT 06762
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  $225,000 Sold Sep 16, 2025

  • Land
  • 3.07 Acres
  • $73,290 per Acre

  • 330 Days On Market

  288 Watertown Rd Unit Lot 3, Middlebury, CT 06762

  Gorgeous 3.07 acre lot in a brand new subdivision. Level and on the end of the cul de sac private road. Proposed 4 Bedroom home with well and septic and underground utilities. Build your dream home! We can arrange a builder or modular homes as well. Frontage of lot disclosed in mls is frontage on Watertown Rd. Frontage on private drive is per maps. Assessment and Taxes TBD. Shared maintenance for

  John Donato Jr Showcase Realty, Inc.

  288 Watertown Rd Unit Lot 3, Middlebury, CT 06762
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  Est $240,320 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft

  35 Nutmeg Rd Unit B5, Middlebury, CT 06762

  35 Nutmeg Rd Unit B5, Middlebury, CT 06762
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  /4

  $75,000 Pending

  • Land
  • 1.64 Acres
  • $45,732 per Acre

  0 Ferndale Ave, Middlebury, CT 06762

  For Sale: Unique Development Opportunity Offering a rare opportunity to acquire a three-lot subdivision in Middlebury. This property consists of three separate parcels that must be sold together. While previously approved, buyers are responsible for verifying the current status of approvals and conducting their own due diligence. The site presents some challenges due to significant ledge, which

  

  Ken Demirs

  Regency Real Estate, LLC

  (475) 258-7617

  0 Ferndale Ave, Middlebury, CT 06762
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  /23

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  Unlisted Address

  Spacious and well-maintained 2 bed, 1 bath second-floor apartment in the heart of Middlebury. This turn-key rental features hardwood floors throughout, abundant natural light, and an eat-in kitchen with plenty of cabinet space and sliding doors leading to a large private deck overlooking the backyard. The inviting living room offers hardwood floors and storage closet, while both bedrooms include

  Jay Irvine Serhant Connecticut, LLC

  Unlisted Address
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  $345,000 Sold Sep 10, 2025

  • 866 Sq Ft
  • $398/SF
  • 11 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1936

  119 Christian Rd, Middlebury, CT 06762

  Nestled in one of Middlebury's 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 room complete with a cozy wood stove. The bright, airy kitchen flows seamlessly from the living space, making it ideal

  David Aurigemma Regency Real Estate, LLC

  119 Christian Rd, Middlebury, CT 06762
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762

  47 Ridgewood Dr Unit 47, Middlebury, CT 06762
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  /40

  $799,000

  • 4 Beds
  • 4 Baths
  • 3,360 Sq Ft

  200 N Farm Rd, Middlebury, CT 06762

  Nestled in the serene & sought-after North Farm Road neighborhood of Middlebury, this property offers approximatley 3,360 sq ft of living space on a generous 2.54 acre lot! This custom designed home will have you living in your own VT style home with a blend of privacy & convenient access to town! As you enter the home you will notice the great room with the floor to ceiling custom stone hearth

  Jackie Desmarais Showcase Realty, Inc.

  200 N Farm Rd, Middlebury, CT 06762
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  /29

  $4,250 per month

  • 3 Beds
  • 3.5 Baths
  • 3,190 Sq Ft
  • House for Rent

  8 Dogwood Ct, Middlebury, CT 06762

  This beautiful, light-filled end unit in Ridgewood of Middlebury is available for lease immediately! The spacious and thoughtfully designed floor plan makes this home perfect for entertaining. Dramatic high ceilings and large, bright windows open the space even further. The home features three spacious bedrooms, including a luxurious first-floor Primary with a large walk-in closet, access to the

  Matthew Perrin West View Properties, LLC

  8 Dogwood Ct, Middlebury, CT 06762
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  $1,375,000 Sold Sep 04, 2025

  • 6,175 Sq Ft
  • $223/SF
  • 103 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 2001

  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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  Not Listed For Sale

  6 Burr Hall Rd, Middlebury, CT 06762

  6 Burr Hall Rd, Middlebury, CT 06762
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  /40

  $669,900

  • 3 Beds
  • 4 Baths
  • 3,488 Sq Ft

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762

  No detail has been overlooked in the stunning remodel of this elegant home in Benson Woods, Middlebury's premier active adult community. Perched on a premium lot with serene views of the Eight Mile River, this residence offers 3-4 bedrooms, 2 full baths, and 2 half baths across a thoughtfully designed layout. Step inside to discover custom interior trim, rich wood flooring, and a chef's kitchen

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  117 Periwinkle Dr Unit 117, Middlebury, CT 06762
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  $536,000 Sold Aug 28, 2025

  • 2,088 Sq Ft
  • $257/SF
  • 104 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1954

  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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  Est $1,525,090 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,363 Sq Ft

  397 White Deer Rock Rd, Middlebury, CT 06762

  397 White Deer Rock Rd, Middlebury, CT 06762
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  /40

  $829,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,711 Sq Ft

  1 Hampshire Ct, Middlebury, CT 06762

  Welcome to Avalon Farms in Middlebury, one of the area's most desirable single-family home communities. This exceptional residence offers 4 bedrooms, 3.5 baths, and 3,711 sq. ft. of living space, perfectly combining comfort, style, and functionality. Set on one of the few lots overlooking the serene community pond, this home invites you in with a dramatic two-story foyer. The spacious first-floor

  Patricia Forbes Berkshire Hathaway NE Prop.

  1 Hampshire Ct, Middlebury, CT 06762
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  $499,900 Sold Aug 26, 2025

  • 2,360 Sq Ft
  • $212/SF
  • 150 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1934

  58 Shadduck Rd, Middlebury, CT 06762

  PRICED TO SELL! DO NOT MISS YOUR OPPORTUNITY TO LIVE IN THE AMAZING TOWN OF MIDDLEBURY IN THIS BEAUTIFUL COLONIAL THAT NEEDS NOTHING BUT TO MOVE RIGHT IN! ACT QUICK! 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

  Amber Segetti RE/MAX RISE

  58 Shadduck Rd, Middlebury, CT 06762
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  Est $425,732 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,434 Sq Ft

  23 Atwood St, Middlebury, CT 06762

  23 Atwood St, Middlebury, CT 06762
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  /40

  $575,000

  • 3 Beds
  • 3.5 Baths
  • 3,103 Sq Ft

  2 Dogwood Ct, Middlebury, CT 06762

  Beautiful 3-bedroom, 3.5-bath 3179 Sqft townhouse with a 1-car garage located on of the best best private streets in the highly sought-after Ridgewood community. The resort style complex people are raving about! This spacious home offers a flexible layout perfect for modern living. The main level features hardwood floors, a half bath, a bright living room, a dining area, and an eat-in kitchen

  Jay Irvine Serhant Connecticut, LLC

  2 Dogwood Ct, Middlebury, CT 06762
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  $679,000 Sold Aug 21, 2025

  • 2,988 Sq Ft
  • $227/SF
  • 28 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1984

  100 Fairhaven Dr, Middlebury, CT 06762

  Welcome home to this beautiful 4-bedroom, 2.5-bath colonial located at the end of a private cul-de-sac in a desirable neighborhood, just minutes from the highway. Inside, you'll find a bright and welcoming layout filled with natural light and hardwood floors throughout. The family room features custom built-ins and a cozy gas fireplace, while the formal living room offers a classic brick

  Tom Dorso Mapleridge Realty

  100 Fairhaven Dr, Middlebury, CT 06762
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  Est $539,823 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  436 Judd Rd, Southbury, CT 06488

  436 Judd Rd, Southbury, CT 06488
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  /38

  $717,000

  • 3 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  111 Dwyer Rd, Middlebury, CT 06762

  Elegant Saltbox Colonial in Sought-After Middlebury, Nestled on 2.44 secluded acres, this tasteful saltbox colonial boasts park-like grounds with a private, tree-lined driveway leading to professionally landscaped gardens. Enjoy blooming trees and bushes from spring to fall, creating a picturesque setting. Outdoor living is enhanced with a slate patio, built-in barbecue, and bocce court, perfect

  Mary Ann Hebert BHGRE Gaetano Marra Homes

  111 Dwyer Rd, Middlebury, CT 06762
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  $485,000 Sold Aug 20, 2025

  • 2,534 Sq Ft
  • $191/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1935

  101 Shadduck Rd, Middlebury, CT 06762

  Beautiful 3-Bedroom home with first floor Primary Suite on nearly half acre lot! Welcome to your dream home! This charming 3-bedroom, 2 Full Bath residence combines modern updates with timeless character. Step inside to discover newly, refinished hardwood floors & fresh paint throughout, creating a bright & inviting space ready for you to move right in. The first-floor primary suite offer privacy

  Jackie Desmarais Showcase Realty, Inc.

  101 Shadduck Rd, Middlebury, CT 06762
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  Est $632,180 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  740 Whittemore Rd, Middlebury, CT 06762

  740 Whittemore Rd, Middlebury, CT 06762
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  /40

  $900,000

  • 4 Beds
  • 2.5 Baths
  • 3,142 Sq Ft

  87 Falcon Crest Rd, Middlebury, CT 06762

  4 Bedroom home on cul-de-sac road with direct waterfront on Mirey Dam Pond! Gorgeous views from many rooms in the house. Immerse yourself in the serene setting and manicured yard. Eat-in-kitchen with pantry, Corian countertops, custom cherry cabinets, tile floor and backsplash, stainless steel appliances, vaulted ceiling, and pond views! Family room with hardwood floors, gas fireplace, crown

  John Donato Jr Showcase Realty, Inc.

  87 Falcon Crest Rd, Middlebury, CT 06762
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  $460,000 Sold Aug 15, 2025

  • 1,842 Sq Ft
  • $250/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  74 Joy Rd, Middlebury, CT 06762

  Gorgeous ranch located on a private cul-de-sac in Middlebury! This fully updated three bedroom ranch features hardwood floors throughout the entire main level, oversized eat in kitchen with quartz countertops and stainless-steel appliances, new windows, brand new central air, and a Buderus oil furnace. Your completely finished lower level has a full bathroom with walk out to the fenced in

  Tom Dorso Mapleridge Realty

  74 Joy Rd, Middlebury, CT 06762
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  Est $547,189 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,611 Sq Ft

  212 Breakneck Hill Rd, Middlebury, CT 06762

  212 Breakneck Hill Rd, Middlebury, CT 06762
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  /40

  $939,000

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

  383 Leonard Rd, Middlebury, CT 06762

  *HOME WARRANTY* Welcome to your dream home - a beautifully designed 3,220 sq ft new construction offering warmth, space, and flexibility for today's modern family. With 4 generous bedrooms and 3.5 baths, this home invites you to live, laugh, and grow in comfort. The heart of the home is the open-concept main level, where the kitchen, dining, and living areas come together around a cozy electric

  Koco Pela William Raveis Real Estate

  383 Leonard Rd, Middlebury, CT 06762
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  $591,251 Sold Aug 15, 2025

  • 2,923 Sq Ft
  • $202/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762

  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 appointed attached

  Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 35 24070506, Middlebury, CT 06762
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  Est $585,959 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  108 White Ave, Middlebury, CT 06762

  108 White Ave, Middlebury, CT 06762
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  /28

  $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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  $547,460 Sold Aug 15, 2025

  • 1,950 Sq Ft
  • $281/SF
  • 163 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  0 N Benson Rd Unit 37, Middlebury, CT 06762

  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 appointed attached

  Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 37, Middlebury, CT 06762
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  Est $492,718 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,552 Sq Ft

  28 Jensen Dr, Middlebury, CT 06762

  28 Jensen Dr, Middlebury, CT 06762
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  /2

  $729,900 Open Sun 11AM - 1PM

  • 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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  $520,000 Sold Aug 13, 2025

  • 2,248 Sq Ft
  • $231/SF
  • 70 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1937

  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.

  1 Stevens Rd, Middlebury, CT 06762
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  Est $412,549 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  109 Yale Ave, Middlebury, CT 06762

  109 Yale Ave, Middlebury, CT 06762
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  /26

  $695,000 Pending

  • 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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  $520,000 Sold Aug 08, 2025

  • 2,130 Sq Ft
  • $244/SF
  • 117 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  29 Winding Trail Unit 29, Middlebury, CT 06762

  Beautiful luxury Portman Condo in Sought-After Ridgewood Community. Stunning 3-bed, 2.5-bath 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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  Est $429,453 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,236 Sq Ft

  145 Algin Dr, Middlebury, CT 06762

  145 Algin Dr, Middlebury, CT 06762
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  /9

  $548,828 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,462 Sq Ft

  0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762

  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 appointed attached

  Renee Meuse Lovley Century 21 AllPoints Realty

  0 N Benson Rd Unit 55 24086408, Middlebury, CT 06762

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