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153 Main St, Middlefield
$101,000
2 Beds ⋅ 1 Baths ⋅ 24210134 MLS
Attention investors, contractors and renovation enthusiasts! This 2-bedroom, 1-bath home offering 1,218 square feet on .31 acres presents an opportunity for a complete renovation or potential teardown. The property is in distressed condition and requires extensive repairs throughout. Condition of the foundation, well, septic, mechanical systems and utilities are unknown. Property is being sold strictly AS-IS, WHERE-IS, with any personal property and contents remaining at the time of closing to convey with the property. Seller will not make repairs, improvements or concessions. Property will not qualify for traditional financing. Buyer and buyer's representatives are responsible for all due diligence regarding the property, its condition and potential future use. Bring your vision and explore the possibilities this property may offer.

153 Main St, Middlefield

88 Peters Ln, Middlefield
$350,000
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

75 Main St, Middlefield
$405,000
3 Beds ⋅ 2 Baths ⋅ 24182229 MLS
Classic 1906 Colonial charm meets thoughtful updates in the storybook village of Rockfall. A window-wrapped front sun porch welcomes you home, while to the side of the home a screened porch with exposed timber rafters feels like a treehouse over the yard, an outdoor living room for three seasons. Inside, wide-plank pine floors and natural wood trim carry authentic turn of the century character through the bright living room and a dining room warmed by a wood stove. The updated kitchen delivers with white shaker cabinetry, deep green subway tile, a butcher block island with seating, farmhouse sink, and stainless appliances, while a built-in hutch and mudroom drop zone keep daily life organized. Upstairs, three comfortable bedrooms with ceiling fans share an updated full bath, and the walk-up unfinished attic adds abundant storage and room to dream. Outside, 0.44 level acres offer a tree-ringed backyard, patio area, private driveway with parking for six, and a detached one-car garage. Moments from Wadsworth Falls State Park with its scenic falls, swimming area, and trails along the Coginchaug River, and minutes to Lyman Orchards and downtown Middletown. Well and septic, updated baths, and a turnkey blend of character and comfort ready for its next century.

75 Main St, Middlefield

25 Aresco Dr, Middlefield
$463,000
3 Beds ⋅ 2 Baths ⋅ 24200331 MLS
Welcome to 25 Aresco Drive, a warm and inviting ranch located on a cul de sac in the Rockfall section of Middlefield. This beautiful, well cared for home offers comfortable one level living with hardwood floors throughout most of the home, including hardwood under the carpeting. The spacious living room features a wood-burning fireplace and large picture window, creating a bright and welcoming space. The heated sunroom with vaulted ceiling and skylight is the perfect spot to relax and enjoy year-round. Step outside to a covered deck overlooking the spacious yard and above-ground pool, ideal for summer entertaining. The partially finished lower level offers additional flexible living space for a home office, media room, rec room, workout space or craft area, along with a full bathroom. Additional features include central air, central vacuum, generator hookup, invisible fence, and attached garage. Move-in ready and conveniently located near Peckham Park, Beseck Lake, Lyman Orchards, Wadsworth Falls State Park, and Powder Ridge Mountain Park and Resort, with nearby hiking and golf. Come see all that this home has to offer! Please submit highest and best offer by Tuesday, 8/25/26, at 2:00 pm

25 Aresco Dr, Middlefield

10 Crestview Dr Unit 10, Middlefield
$660,000
3 Beds ⋅ 3 Baths ⋅ 24201402 MLS ⋅ Crestview BLDG.
Welcome to 10 Crestview Drive, a truly exceptional home nestled within a sought-after 55+ community offering peace, privacy, and serene surroundings, all while being just minutes from downtown Middletown. This beautifully maintained property offers the best of both worlds with convenient one-level living and an expansive finished walk-out lower level featuring a full in-law apartment. Step inside to gleaming hardwood floors and impressive tall ceilings that create a bright, spacious feel throughout. A charming den with French doors provides the perfect retreat for reading, relaxing, or working from home. The spacious formal dining room is ideal for hosting gatherings and entertaining guests. At the heart of the home, the updated kitchen features granite countertops, stainless steel appliances, and a cozy breakfast nook, flowing seamlessly into the beautiful living room highlighted by a propane fireplace. Just off the living room, step into the screened-in sun porch and take in the peaceful surroundings. The porch leads to an open portion of the deck, complete with the perfect space for your grill. The spacious primary suite is truly a standout, featuring a walk-in closet and a luxurious en-suite bathroom with granite countertops, dual sinks, a jetted tub, and a separate stand-up shower. The main level is completed by a second bedroom, an additional full bathroom with new tile, and a recently updated laundry room with a brand-new washer + dryer and a granite countertop.

10 Crestview Dr Unit 10, Middlefield

6 Sunrise Rdg, Middlefield
$425,000
3 Beds ⋅ 2 Baths ⋅ 24197100 MLS
Nestled on a cul-de-sac in one of Rockfall's most desirable neighborhoods, and the only street in town with city sewer available, this charming Cape is it's own private oasis backed by a 16 acre farm. Freshly painted and move-in ready, this 3 bedroom, 2 bath home features a flexible floor plan with potential for a 4th bedroom and possible in-law setup in the walk-out lower level currently being used as a primary suite. The updated kitchen showcases granite counters, tile backsplash and stainless steel appliances and opens seamlessly to the dining area with a slider leading to a large deck, perfect for entertaining or relaxing. Or spend time lounging in the front sunporch that conveniently connects to the attached garage. The inviting living room is full of New England charm with beautiful hardwood floors and a cozy wood stove to keep you warm during the cold fall and winter nights. A 2nd sunporch overlooking the backyard is lined with windows making it a great sitting room, office space or even a 4th bedroom with a large walk-in closet. Upstairs is 2 carpeted bedrooms with built-ins and skylights. The main level is complete with a full bath with a vaulted ceiling and skylight. The lower level boasts an amazing primary suite with a walk-in closet and slider to the backyard, laundry room and plenty of storage room. Additional features include a 2 year old roof, forced hot air, generator hookup with generator included, and conveniently tucked away while still close to everythi

6 Sunrise Rdg, Middlefield

169 Cedar St, Middlefield
$333,000
2 Beds ⋅ 1 Baths ⋅ 24160022 MLS
Under $300K in Middlefield - a rare opportunity to own, update, and build real equity. Located in the desirable Rockfall section, this one-level ranch offers comfortable living today with the chance to personalize and enhance over time. While cosmetic updates will unlock the home's full potential, one of the most important improvements has already been completed - the septic system was fully replaced just a few years ago (not just the tank), providing significant long-term value and peace of mind.The living room is bright and inviting, featuring large windows that bring in natural light along with a classic fireplace that adds warmth and character. The eat-in kitchen offers good space and functionality for daily living, with clear opportunity for future updates to flooring, cabinetry, and countertops. Two nicely sized bedrooms complete the main level, making true one-floor living easy and practical. A rebuilt chimney with wood stove adds both charm and efficiency. Outside, enjoy a pleasant yard with room to relax, garden, or entertain. A two-car garage offers valuable storage. Lifestyle is a true highlight here. Middlefield is known as a recreation crossroads, with close proximity to Powder Ridge Mountain Park, Lake Beseck, Lyman Orchards, and Wadsworth Falls State Park. Plus, easy access to Washington Street in Middletown puts shopping, dining, and everyday conveniences just minutes away. This is a smart opportunity to invest in both home and lifestyle.

169 Cedar St, Middlefield

32 Maple St, Middlefield
$397,000
3 Beds ⋅ 2 Baths ⋅ 24180014 MLS
Charming and versatile Cape offering 3 bedrooms, 2 full baths, and a 1-car garage. The flexible floor plan features a first-floor bedroom and full bath, perfect for guests, a home office, or one-level living. Upstairs you'll find two additional bedrooms and a second full bath. The updated kitchen is designed for both function and style, featuring an open pantry area that is ideal for a coffee bar, additional cabinetry, or extra storage. Laundry hookups are conveniently located on the main level, with a second hookup available in the lower level. Just off the dining room, a bright and inviting sunroom provides the perfect spot to relax with your morning coffee, read a book, or enjoy additional living space throughout the seasons. Step outside to enjoy the large, fully fenced backyard-perfect for entertaining, gardening, or giving your four-legged friends plenty of room to run and play. Located in the desirable Rockfall section of Middlefield, this home offers easy access to year-round recreation. Enjoy nearby golf courses, boating on Lake Beseck, hiking and outdoor adventures, and skiing, snowboarding, concerts, and seasonal events at Powder Ridge Mountain Park. Whether you're looking for outdoor fun, relaxation, or a convenient location, this home offers something for everyone. OFFER DEADLINE 6/28 BY NOON.

32 Maple St, Middlefield

12 Garden Hill Rd, Middlefield
$425,000
3 Beds ⋅ 1 Baths ⋅ 24184090 MLS
***MULTIPLE OFFERS - HIGHEST & BEST DEADLINE - SUNDAY 5PM*** Welcome to 12 Garden Hill Road - a charming 3-bedroom ranch nestled on a quiet cul-de-sac in Middlefield's desirable Rockfall neighborhood. Set on 0.61 acres of level, park-like land, this move-in ready home offers the perfect blend of privacy and comfort. Inside, an open floor plan connects the living, dining, and kitchen spaces. The living room features a bay window that floods the space with natural light, while rich hardwood floors flow throughout. The updated kitchen boasts white cabinetry, dark quartz countertops, and a peninsula. Sliding doors off the dining area open to a private backyard and deck - perfect for entertaining. The primary bedroom includes a walk-in closet, and a full unfinished basement offers excellent storage and future potential. An attached garage, main-level laundry hookups (will involve minor plumbing to put back), and pull-down attic round out the practical features. Close to parks, lakes, golf, and library. Feeds into Coginchaug Regional School District, RSD13. Easy Route 9, 91, and 15 access. Low taxes at $5,269/year. Don't miss this one!

12 Garden Hill Rd, Middlefield

53 Cedar St, Middlefield
$551,000
3 Beds ⋅ 2 Baths ⋅ 24169577 MLS
This is the kind of home that instantly feels like home. Built in 1900, it blends timeless charm with a warm, lived-in character you simply can't recreate. Inside, you'll find inviting spaces filled with natural light-from the sun-drenched wood-paneled family room with skylights and garden views, to the cozy living areas and an updated kitchen with a large center island that naturally becomes the heart of the home. But what truly sets this property apart is the lifestyle it offers. Step outside and you're surrounded by a homestead-inspired setting-gardens ready for planting, blooming flowers, open yard space, and even a chicken coop for those looking to embrace a more connected way of living. It's peaceful, private, and full of possibility. The detached garage features an exceptional bonus: a beautifully finished studio space is additional 621 sq ft to enjoy! Complete with a full bath and kitchenette. Whether you need a home office, creative space, guest suite, or the ultimate hangout spot, this flexible area delivers. Solar panels add an energy-efficient touch, bringing modern convenience into this character-filled home. A place to slow down, spread out, and live a little differently... in all the best ways.

53 Cedar St, Middlefield

341 Main St, Middlefield
$500,000
3 Beds ⋅ 3 Baths ⋅ 24169869 MLS
Enjoy the privacy of being set back over 500 feet from the road in this beautifully updated raised ranch on 1.5 acre in the heart of Middlefield. It features a newly renovated master bathroom (2024) and kitchen (2025) with elegant quartz countertops, recessed lighting, stainless steel appliances, beverage cooler, and oversized island which flows into the living room in an open concept design that is perfect for entertaining guests or nights by the fire. Walk out to your 600 sqft stamped concrete back patio and enjoy the surroundings of nature, as well as the peaceful ambience of the large water feature. The lower level is finished and heated, adding approx 550 square feet of living space ideal for a gym, home office, play area, or rec room. Enter the 600 square foot utility room either from the two car garage or via the side driveway to find lots of storage and space ideal for a project-oriented person, with heat available for year-round use. Enjoy central air in the summer, and never fear the price of oil in the winter as the house also features an envied outdoor wood boiler, providing hydronic heat to the whole home and hot water heater. Located just minutes from Lyman Orchards and Wadsworth Falls State Park, shopping and dining while living the country life in a quiet neighborhood. Highest and Best Monday 4/27 at 9pm

341 Main St, Middlefield

107 Main St, Middlefield
$382,500
3 Beds ⋅ 2 Baths ⋅ 24160572 MLS
Welcome to this quaint New England farmhouse tucked away in the charming village of Rockfall, where small-town charm meets everyday convenience. This inviting 3-bedroom, 2-bathroom home is full of warmth and character, offering the cozy feel you expect from a classic farmhouse with the space you need for modern living. Add the custom woodworking of a master carpenter and this is a winner for sure. Be sure to find the hidden space in the dinning room and the large closet upstairs. Enjoy being just a short walk from beautiful Wadsworth Falls State Park, perfect for hiking, biking, picnics, or relaxing family days surrounded by nature. Whether you love the outdoors or simply appreciate peaceful surroundings, this location is hard to beat. The property also features a dreamy detached 4 car garage, ideal for storage, hobbies or workshop. The electric service to the garage will support many hobbies. With its timeless style, scenic setting, and welcoming feel, this home captures the true spirit of New England living. Don't miss the opportunity to own a piece of classic charm in one of the area's most beloved locations.

107 Main St, Middlefield

40 Sylvan Rdg Unit 40, Middlefield
$340,000
2 Beds ⋅ 4 Baths ⋅ 24147045 MLS ⋅ Sylvan Ridge BLDG.
Rarely available, desirable end-unit townhouse in Sylvan Ridge Condo Association, tucked away on a cul-de-sac. This three level home offers 2 BRs, 2 full baths and 2 half baths. It has a partially finished and heated walkout basement that provides excellent additional living room or flex space. The beautiful, remodeled kitchen features custom soft close cabinets, under cabinet lighting, SS appliances, granite countertops and a large center island. It opens seamlessly to the main living areas, perfect for entertaining. The open floor plan is filled with natural light and highlights a warm and inviting family room with vaulted ceilings and a cozy wood burning fireplace. Upstairs you will find two spacious bedrooms. The guest bedroom and the primary en-suite with a large walk-in closet and private full bath. Enjoy multiple private outdoor spaces that face the natural setting of the wooded cul-de-sac. These include, a patio, porch and deck, ideal for relaxing in this serene environment. This private end unit comes with a detached garage accessable from your private patio. This home is conveniently located near shopping, downtown Middletown, minutes away from Wesleyan Univerity, and routes 66, 9, and 91. This is a unique opportunity to get in on a very rare special unit, in a small complex set in a beautiful wooded location (24 units). Sold as-is

40 Sylvan Rdg Unit 40, Middlefield

9 Sunset Dr, Middlefield
$369,000
3 Beds ⋅ 2 Baths ⋅ 24137436 MLS
Charming All-Brick Ranch in the Heart of Rockfall! Welcome home to this beautiful 1,760 sq. ft. all-brick ranch - a perfect blend of classic charm and comfort! Nestled on a perfectly level .45-acre lot, this home offers easy living inside and out. Step inside to find a bright, spacious living room featuring hardwood floors, built-in hutches, and a cozy gas log fireplace - perfect for relaxing evenings or hosting friends. The large eat-in kitchen is the heart of the home, with oak cabinets, a center island, and plenty of dining space for family gatherings. You'll find three generous bedrooms, one with its own half bath and convenient laundry closet. Most of the home boasts hardwood floors, adding warmth and timeless appeal. Love to entertain? The spacious breezeway opens seamlessly into a large three-season room, complete with a wood-burning fireplace - the perfect spot to enjoy morning coffee or crisp fall nights. Step outside to your 12'x20' Trex deck with vinyl railings, overlooking the expansive, level backyard - ideal for barbecues, games, or peaceful relaxation. A two-car garage, handy shed, and an unfinished basement with another fireplace round out this fantastic property, offering endless potential for storage or future living space. Why Rockfall? Rockfall, Connecticut is a hidden gem in Middlesex County - known for its small-town charm, scenic nature trails, and proximity to Wadsworth Falls State Park, where you can hike, swim, and picnic by the waterfalls.

9 Sunset Dr, Middlefield

4 Lorraine Ter, Middlefield
$404,900
3 Beds ⋅ 2 Baths ⋅ 24147630 MLS
Welcome home to this spacious and move-in-ready 1,600 square foot ranch, perfectly situated on a corner lot. Designed with family living in mind, this home features a beautifully updated kitchen and brand-new flooring throughout, creating a clean and comfortable space for everyday life. The large bonus room offers endless possibilities-ideal as a playroom, teen hangout, in-law space, or family room. With 1.5 bathrooms and central air, there's room and comfort for everyone. The roof was replaced down to the plywood in 2023. Step outside to a partially fenced backyard where kids and pets can play safely, and enjoy summer fun in the newer above-ground pool with deck-perfect for family gatherings and weekend relaxation. A wonderful place to make lasting memories.

4 Lorraine Ter, Middlefield

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