Homes for Sale near Memorial Middle School

The home you have been waiting for is waiting for you at 90 Fenn Road, Middlebury. Need room for inlaws? teens? an office? You can have it right here, tucked on 1.67 acres in a desirable Middlebury location. As you enter the spacious tiled foyer and look around, a formal sunken living room greets you on one side and a formal dining room on the other. You will notice the oak flooring in both

Donna Bannon BHGRE Gaetano Marra Homes

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 20 Hunting Ridge Road (aka Lot 11) is to be built. It is one level living at its finest! Features includes hardwood floors throughout, gas fireplace with stone surround, gourmet kitchen with large center island, convenient office in addition to 3 bedrooms and a 2 car attached garage. The primary bedroom boasts walk-in

Jodi Dawley Real Estate Two

Welcome to this beautifully updated home which offers modern comfort, high-end finishes & peace of mind with several upgrades already completed! Located in Middlebury's South Street neighborhood this Colonial is 3300 sq ft on a 1.85 acre lot. Step in to a bright & inviting foyer feat. a high ceiling, a custom wood & glass front door & a stunning custom handrail leading the expansive 4 bedrooms.

Jackie Desmarais Showcase Realty, Inc.

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

Welcome Home to Middlebury's newest 23 lot subdivision-Hunting Ridge Estates. 6 Deer Run Road (aka Lot 15) 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

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

Under construction with planned 2026 completion. Photos represent a comparable home built with the same floor plan. This 4-bedroom Colonial offers approximately 3,134 sq ft on a 2-acre lot, designed with an open, well-proportioned layout and thoughtful details throughout. Hardwood and tile floors span the home. A spacious great room featuring a fireplace, coffered ceilings, and built-in dry bar

Gina French Showcase Realty, Inc.

Under Construction in One of Middlebury's Most Desirable Neighborhoods! Welcome to the Avalon Farms community-known for its beautiful homes, manicured lawns, and thoughtfully designed landscaping that create a truly picturesque setting. The Cambridge model blends classic design with today's most sought-after features, offering a bright and open floor plan perfect for modern living. The spacious

Jonna Dibble BHGRE Gaetano Marra Homes

Large Colonial with charm and character ready to call home! Offering privacy on its fabulous 4 acres with magical views and abundant sunlight. The home offers four large bedrooms with ample light that will surely please. The formal living room complete with a large picture window and marble fireplace will serve as a great place to relax at the end of a long day. The dining room is ready to host

Frank Durante William Raveis Real Estate

A private hilltop retreat at the end of a quiet cul-de-sac, this stunning 8-room contemporary is set well back from the road on a picturesque knoll, offering exceptional privacy and a peaceful natural setting. Custom built and proudly maintained by its original owner, the home features soaring ceilings, expansive rooms, and walls of windows that flood the interior with natural light. The open,

Lynn LaForme Regency Real Estate, LLC

Elegant cape with refined main-level living in Middlebury. Timeless charm and thoughtful design come together in this classic home that lives beautifully like a ranch with expanded main level. The main level offers a spacious primary bedroom with a full bath and walk-in shower, complemented by a second bedroom or private office. Designed for both gracious entertaining and everyday comfort, the

Lori Geraci BHGRE Gaetano Marra Homes

Under construction with anticipated June 2026 completion. Photos show a comparable home with the same floor plan. This 4-bedroom Colonial offers approximately 3,286 square feet on a 1.5-acre lot with an open, functional layout and durable finishes throughout. Hardwood and tile flooring span the home. The main level features a great room with a fireplace, a built-in dry bar, and opens directly to

Gina French Showcase Realty, Inc.

Welcome to 36 Highridge Road, a beautifully maintained home in one of Middlebury's most desirable neighborhoods. Built in 2018 and lovingly cared for by its original and only owner, this property offers the perfect blend of modern construction, thoughtful upgrades, and low-maintenance living. Step inside to find a thoughtfully designed interior enhanced with upgraded molding, elegant cabinetry,

John Pistorino RE/MAX RISE

2 Bedroom, 1bath, ranch styled home on 0.2 acre lot. Eat in kitchen with breakfast bar leading into living room and dining area. This is a wonderful opportunity to indulge in Middlebury's rural New England charm and suburban high-end amenities. Access to I 84, RT 8, and public transportation makes commuting to lower Fairfield County, NYC or Boston appealing. But if staying local is more your

Don Orsini West View Properties, LLC

Lovely 3-bedroom, 2-bath ranch set on 1.61 private acres. This well-maintained home features hardwood floors throughout, a 2-car garage, and two fireplaces-one with a pellet stove insert. The lower level offers excellent potential for a spacious family room with a fireplace, walk-out access, and direct entry to the garage-perfect for additional living or entertaining space. Recent septic

DANIEL MULVIHILL Mulvihill Realty LLC

Impeccably remodeled "Cummings" style townhouse set within the highly sought-after Ridgewood at Middlebury community, offering refined living spaces and thoughtful modern updates throughout. The main level has been beautifully redesigned to create an open, airy flow between the living and dining areas and a chef-inspired kitchen featuring a quartz center island, double ovens, granite countertops,

Jodi Dawley Real Estate Two

Charm abounds in this remodeled classic cape with 2 car garage, central air, and massive 1st floor master suite! Remodeled eat-in-kitchen with granite countertops, stainless steel appliances, tile backsplash and breakfast bar. Living room with fireplace and hardwood floors. Dining room with hardwood floors. Luxurious master suite with built-ins, walk-in california closet, and large remodeled

John Donato Jr Showcase Realty, Inc.

Charming Cape in Middlebury with over 5 acres of land! This enchanting Cape features original character with hardwood floors flowing throughout its 3 comfortable bedrooms and 1.5 baths. For the outdoor enthusiast, the grounds are a rare find: a horse stable complete with a tack room awaits your equine companions, while a inground pool offers a private oasis for summer entertaining. With the added

Arben Belica William Raveis Real Estate

Welcome to luxury condo living in one of Middlebury's most sought-after communities, RIDGEWOOD. Built in 2018, this stunning 2-3 bedroom, 2.5 bath home offers over 2,600 SqFt of beautifully designed living space, plus an additional ~800 sq ft in a newly remodeled walkout lower level. Step inside to soaring cathedral ceilings, gleaming hardwood floors, and an open-concept layout filled with

Jay Irvine Serhant Connecticut, LLC

Discover refined comfort and timeless elegance in this beautifully appointed Cheshire model, nestled within the highly sought-after Brookside of Middlebury community. This exceptional 4-bedroom, 2 full and 2 half bath home is truly move-in ready. Open-concept floor plan that instantly impresses. The stylish kitchen features granite countertops, new modern LG appliances, and seamless flow into the

Shagufta Zahid S Factor Realty Group LLC

Not Your Typical Cape Style Home! This Beautifully Maintained 3 BD Home in Middlebury is Situated on 1.70 Acres and Exemplifies all the Love and Care Taken by its Owner! Surrounded by Lush Mature Landscaping, This Home Offers a Serenity Inspired Outdoor Living Spaces! Enjoy the Sounds of Birds while Sitting on Your Rear Patio. Or Host Dinner Parties in the Enclosed Sunroom on a Cool Summer

Bethany Lydem Stone Crest Realty LLC

Charming and well-maintained raised ranch offering a bright open floor plan and thoughtful updates throughout. Features include a modern kitchen with granite countertops, stainless steel appliances, and a breakfast bar, along with beautiful hardwood flooring. The home also offers a private primary suite, multiple living spaces, and cozy fireplaces perfect for colder months. Enjoy outdoor living

Stephen Mele Houlihan Lawrence

4 UNITS IN MIDDLEBURY-NOT ONLY "NEXT TO IMPOSSIBLE" TO FIND, BUT UNBELIEVABLY PRICED AT $599900! THIS "ONCE IN A LIFETIME" OPPORTUNITY CAN BE YOURS! LIVE IN ONE, AND COLLECT RENT FROM THE OTHER THREE UNITS, OR, ADD THIS ONE TO YOUR INVESTMENT PORTFOLIO AND "WATCH IT GROW"! One parcel (.41 ACRE), ON "PARKLIKE" GROUNDS WITH THE ATMOSPHERE OF NATURE ON A SHORT, NO-THRU STREET, consists of a

Judith Caputo Advantage Realty Group, Inc.

A private retreat where New England Charm meets Resort Style Living. Tucked along an interior driveway in the heart of Southbury, this architecturally striking wood & stone Cape offers the perfect blend of timeless design and modern luxury. A welcoming bluestone porch sets the tone for the warm, elevated lifestyle this home delivers. Inside, a dramatic two story foyer leads to a sun-filled

MaryAnne Betso Coldwell Banker Realty

Broadview Estate - A masterpiece in colonial revival design -Perched gracefully on the gentle hilltops of Middlebury! The Cameron Clark design is well preserved and displays a high quality of workmanship and materials, as well as the gracious proportions and classically inspired details inherent of the colonial revival. This residence is one of the finest examples of this style. Together the

Kary Apanovitch Coldwell Banker Realty