Middlefield Real Estate

Welcome to Middlefield, Connecticut—a hidden gem nestled in the heart of Middlesex County. This charming town offers a delightful blend of rural tranquility and suburban convenience, making it an ideal place for families, retirees, and everyone in between. With a rich history dating back to the 18th century, Middlefield is steeped in tradition, yet it boasts modern amenities that cater to today’s lifestyle.

The town is renowned for its picturesque landscapes, featuring rolling hills, lush forests, and serene lakes. Outdoor enthusiasts will find plenty of opportunities for exploration at the nearby Wadsworth Falls State Park, where hiking trails and scenic waterfalls await. The community is also home to a variety of recreational facilities, including sports fields, playgrounds, and picnic areas, perfect for family outings and social gatherings.

Middlefield’s charming downtown area offers a selection of local shops, cafes, and eateries, creating a warm, small-town atmosphere. Residents enjoy a close-knit community with various events throughout the year, from farmers' markets to seasonal festivals, fostering a sense of belonging and connection among neighbors.

Education is a top priority in Middlefield, with access to quality schools that serve the community’s youth, preparing them for a bright future. The town’s strategic location also provides easy access to major highways, making commutes to nearby cities like Hartford and New Haven a breeze.

Whether you’re looking to settle down or invest in a piece of Connecticut’s beautiful landscape, Middlefield offers an inviting community that feels like home. Come discover the charm and warmth of this delightful town!

Newest Listings in Middlefield

$520,000

3 Beds ⋅ 3 Baths ⋅ 24203910 MLS

The tax record may say 1935, but this is far from your typical 1935 home. The original footprint represents just a small portion of the home you see today, thoughtfully renovated and expanded over the decades by its builder-owner to create a home designed for the way we live now. The spacious kitchen features a center island, abundant cabinetry, pantry and breakfast area, flowing easily into the dining room and inviting living spaces. A true standout is the impressive family room addition with vaulted ceiling, walls of windows, its own front entrance and access to the deck, creating flexible space for entertaining, relaxing, a game room, studio or whatever fits your lifestyle. The main level offers two bedrooms and an updated full bath, while upstairs, the private primary suite features a walk-in closet and spa-like bath with freestanding soaking tub and beautifully tiled glass shower. A dedicated lower-level office provides quiet work-from-home space. Outside, enjoy multiple areas to gather and unwind, including a paver patio and a fenced-in retreat with above-ground pool, spacious deck and pool clubhouse. Located in Rockfall, you're close to Lake Beseck, Powder Ridge, Lyman Orchards and Wadsworth Falls, with convenient access to shopping and highways. 1935 may be where the story started, but this home has evolved beautifully for today's lifestyle.

12 Ross Rd, Middlefield

$420,000

4 Beds ⋅ 2 Baths ⋅ 24202534 MLS

Welcome to this inviting ranch in Middlefield, a home that has been lovingly owned and cared for by the same family for many years. Originally a small cottage, the home has grown over the years with thoughtfully added spaces to accommodate a growing family, creating a unique layout filled with character and plenty of room to make it your own. The spacious living area is a true centerpiece of the home, featuring a custom-built stone fireplace. On the kitchen side, a wood-burning stove offers another option to save money on heating costs. A recently renovated sunroom, completed within the past year, sits between the garage and living room and features electric heat, making it a great space for year-round enjoyment. Outside, the property features a large two-bay garage with additional storage space above. Come see what this home has to offer your family.

24 Sunrise Rdg, Middlefield

$699,900

4 Beds ⋅ 4 Baths ⋅ 24202689 MLS

Keep your boat in the backyard! Rare opportunity to own a beautifully updated Multi family property with waterfront, exceptional outdoor spaces, and outstanding income potential. Whether you're looking for an owner-occupied investment, multigenerational living, or an income-producing property, this home offers incredible versatility. Recent improvements include a brand-new roof, new siding, a beautifully renovated second floor, and brand-new fencing, giving the property a fresh, updated feel while taking care of many of the major improvements a new owner would typically face. The main two-family residence features beautiful balconies overlooking the lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing and enjoying the view. Outside, you'll find a charming courtyard area, landscaped grounds, and inviting spaces for entertaining. Brand new Metal Dock.

157 Baileyville Rd, Middlefield

$749,000

4 Beds ⋅ 3 Baths ⋅ 24196454 MLS

Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

19 High St, Middlefield

$729,999

3 Beds ⋅ 3 Baths ⋅ 24195983 MLS

Welcome Home to Middlefield! Experience the perfect blend of modern comfort and timeless farmhouse charm in this stunning new construction ranch, thoughtfully designed for effortless one-level living. Situated on a clear, level, and fully usable one-acre lot just up the hill from beautiful Lake Beseck, this home offers the ideal combination of privacy, convenience, and style. Boasting 2,278 square feet, this spacious home features three bedrooms, 2.5 bathrooms, and an attached two-car garage. The open-concept floor plan is designed for both everyday living and entertaining, with a welcoming great room that serves as the heart of the home. Unwind in the bright and inviting sunroom, or enjoy the ease and accessibility that only single-story living can provide. Located in the thriving town of Middlefield, this property offers the best of both worlds-peaceful rural surroundings with exceptional access to major amenities. Commuters will appreciate the convenient highway access, placing New Haven just 20 minutes away and Hartford approximately 25 minutes away. Outdoor enthusiasts will love being just minutes from Lake Beseck, scenic hiking trails, championship golf courses, and nearby ski areas. Excellent schools, shopping, dining, and a variety of cultural attractions are all within easy reach, making this an exceptional place to call home. There's still time to select your finishes so don't wait long! Please note, pictures and drawings may contain optional fini

123 Way Rd, Middlefield

$342,000

2 Beds ⋅ 1 Baths ⋅ 24196110 MLS

Highest & Best are due Thursday at 10am. Welcome home to this charming ranch nestled on a beautifully landscaped, level .52-acre lot in the desirable Rockfall section of Middlefield. Offering the convenience of one-level living with room to grow, this home features gleaming hardwood floors, a welcoming living room with a classic fireplace and custom built-ins, and an updated eat-in kitchen with granite countertops, stainless steel appliances, rich wood cabinetry, tile backsplash, recessed lighting, and plenty of workspace. The screened porch is the perfect spot to enjoy your morning coffee while overlooking the peaceful backyard, while the covered patio creates an ideal space for outdoor dining and entertaining. The yard offers room for pets, gardening, or play, all surrounded by mature trees for added privacy. Two generously sized bedrooms and a full bath complete the main level. Looking for additional space? The walk-up attic offers exciting potential for future expansion, while the partially finished lower level is perfect for a family room, home office, gym, or hobby space. An under-house garage provides additional storage, and the Generac whole-house generator offers year-round peace of mind. Conveniently located just minutes from Lyman Orchards, Powder Ridge, Wadsworth Falls and everything Middlefield has to offer, with easy access Washington St and commuter routes.

88 Peters Ln, Middlefield

$625,000

4 Beds ⋅ 3 Baths ⋅ 24192216 MLS

Nestled back from the road in a serene, private setting, this impeccably maintained and professionally landscaped 4-bedroom, 2 1/2-bath Colonial offers the perfect blend of comfort, elegance and privacy. The sunken living room features a stunning stone fireplace with a majestic mantel, creating a warm focal point that can also be enjoyed from the kitchen and breakfast nook. The beautifully appointed kitchen boasts granite countertops, stainless steel appliances, a center island and plenty of space for cooking and entertaining. The formal dining room and cozy den showcase beautiful hardwood flooring, adding warmth and character throughout the main level. The expansive primary suite is a true retreat, complete with a spa-like bath featuring a hydro tub, double-sink vanity and separate shower. Just off the primary bedroom is a versatile bonus room with conveniently located laundry, ideal as a dressing room, sitting area, home office, or nursery. The private fourth bedroom, located on the third floor, makes an excellent guest suite, offering separation from the main living areas. Step outside to enjoy the Trex deck with a pergola, perfect for entertaining family and friends or simply relaxing while overlooking the fully fenced in backyard designed for both fun and tranquility. Conveniently located just minutes from shopping, dining, and everyday amenities, yet tucked away in its own peaceful oasis. Don't miss the opportunity to make it yours!

41 Harvest Woods Rd, Middlefield

$749,900

4 Beds ⋅ 3 Baths ⋅ 24190498 MLS

Nestled in the heart of scenic Middlefield, this distinctive and beautifully maintained 4 bedroom 2.5 bathroom property offers a rare blend of classic New England character and modern flexibility. Inside on the first floor, an open-concept kitchen and dining area invite gathering and entertaining, seamlessly flowing into a sunroom-style flex space with room to grow-ideal for a home office, playroom, or reading nook. A separate living room, complete with a working fireplace, creates a cozy retreat for New England winters or days on the slopes of the nearby Powder Ridge Ski Resort. For the summer, step outside and you will find a stunning in-ground pool surrounded by a spacious brick patio, perfect for lounging and outdoor dining. An attached two-car garage adds everyday convenience and a second private driveway offers access to the rear of the property and the detached barn. The true gem is this fully renovated, detached barn-an inspired space with limitless potential. Featuring whitewashed wood walls and an airy farmhouse aesthetic, the barn offers a dramatic open-plan ground level and a second floor with three rooms and a bathroom. Off of the ground level, french doors lead to a private terrace shaded by mature grapevines, ideal for al fresco dining or sunset cocktails. Whether used as a luxurious art studio, at-home gym or work-from-home suite, this space delivers unmatched versatility with its own entrance and a beautiful walkway connection to the main home and pool.

88 Powder Hill Rd, Middlefield

$399,000

24189290 MLS

Prime Land Opportunity - Baileyville Rd & Route 147, Middlefield, CT Nestled in the heart of scenic Middlefield, this exceptional 7.5 acre parcel (approx.) located at Baileyville Road this property offers a rare opportunity for developers or investors seeking to capitalize on the area's demand for year-round recreational living. Ideal for a custom home, vacation home, or small-scale residential project (subject to zoning/survey/approvals). Perfectly positioned for outdoor enthusiasts and nature lovers, the property is just minutes from two of Connecticut's most cherished destinations - Lake Beseck and Powder Ridge Mountain Park & Resort. Imagine waking up to serene woodland views, spending summer afternoons kayaking or fishing on Lake Beseck, and enjoying winter adventures skiing or snowboarding at Powder Ridge - all within a short drive from your future doorstep. Features: (1) Road frontage on Baileyville Rd Peaceful, wooded surroundings (2) Close proximity to outdoor recreation (3) Easy access to major highways and local dining. Whether you're a builder, investor, or looking to create a private getaway, this parcel offers natural beauty, lake views, and year-round recreation just minutes away. Don't miss this opportunity! NOTE: Buyer/Buyers Agent to perform their due diligence.

Baileyville Road, Middlefield

$600,000

2 Beds ⋅ 1 Baths ⋅ 24188626 MLS

Every weekend you wait is another weekend someone else gets to spend here. Wake up to spectacular sunrises over Lake Beseck, spend the day boating, swimming, kayaking or fishing, and end the evening relaxing on your private deck as the water sparkles just steps away. This direct waterfront cottage offers the lake lifestyle so many dream about, yet so few ever find. With private docks and a floating dock, you'll enjoy instant access to the lake where motorboats are welcome. Paddle the shoreline, cast a line from your dock, or take a short stroll to the town beach for another day in the sun. Inside, the charming open floor plan is filled with natural light and flows into a beautiful sunroom wrapped in walls of windows that keep the breathtaking views front and center. The Trex deck is the perfect place for morning coffee, summer gatherings, and unforgettable sunrises. Thoughtfully maintained with central air and a new roof in 2024, this home is ready to enjoy from day one. Because Lake Beseck is managed by DEEP, no flood insurance is required. Looking ahead? The home offers the potential to build up to 35 feet (subject to approvals), creating the opportunity for an even more spectacular waterfront retreat. Conveniently located just minutes from I-91 and in the heart of Connecticut's recreation corridor, you'll enjoy easy access to Powder Ridge, Lyman Orchards, and four nearby golf courses. Lake homes are more than real estate. They're where summers become tradition.

18-A Lake Shore Dr, Middlefield

$168,000

24181732 MLS

Imagine waking up every day in a town where orchards bloom, ski slopes come alive in winter, golf courses stretch across rolling hills, and hiking trails, waterfalls, and lakes are just minutes from your front door. This beautiful level, cleared lot on Cherry Hill offers the opportunity to build more than a home-it offers a lifestyle. Nestled in one of Middlefield's most convenient locations, you'll enjoy easy access to Lyman Orchards, Powder Ridge, Lake Beseck, and all the small-town charm that makes this community so special, while remaining close to major commuting routes. Bring your vision and create the home you've always dreamed of in a place where adventure, recreation, and New England beauty surround you year-round. There are no perc tests on file, and buyers are responsible for conducting their own due diligence regarding building suitability and approvals.

Cherry Hill Rd, Middlefield

$165,000

24177245 MLS

Build your vision on this residential parcel offering a great opportunity in a convenient location with easy access to nearby amenities, shopping, dining, and major routes. Public records reflect the parcel as conforming to current zoning and frontage requirements. Buyers and buyers' agents encouraged to exercise their own diligence regarding all property information, zoning, and intended use.

133 Main St, Middlefield

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