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360 Chauncey Rd, Middletown
$345,000
3 Beds ⋅ 2 Baths ⋅ 24216264 MLS
Do you love downtown Middletown, but want to live in a quieter area? 360 Chauncey Road is the answer you're looking for! Enjoy what Middletown has to offer while being tucked away in a quiet area. This property offers 3-4 bedrooms, two full bathrooms, hardwood floors, harvey windows and a yard to enjoy. Throughout the home you'll find pockets of character that make it unique; the wood paneling on the ceilings, the bathroom trim, or the covered porch paired with a charming blue door. The eat-in kitchen has plenty of counter and cabinet space, all your needed appliances, and access to the brand new deck. The main floor bedroom is accompanied with a full bath and another potential bedroom, study, rec room, or dining room. Upstairs are the two spacious bedrooms with another full bath and crawl space storage. In the basement you'll find a ton of storage and future expandable space. Enjoy dedicated laundry space & shelving with access to outside. Outside, the back deck overlooks the level yard with plenty of tree cover for the Summer months and offering beautiful views in the Fall. Come check out 360 Chauncey Road and then head downtown to enjoy some of the incredible restaurants and shops Middletown has to offer, or hit the nearby hiking trails at Millers Pond or Crystal Lake! Updates include Brand new 2026 deck, 2021 plastic septic tank, 2022 well pump, 2026 well tank & water softener, 2019 roof, and AO Smith 2021 water heater. Take advantage of this well maintained home!

360 Chauncey Rd, Middletown

404 Newfield St, Middletown
$450,000
3 Beds ⋅ 3 Baths ⋅ 24217472 MLS
One level living with room for expansion in this spacious ranch. Three bedrooms and 3 full baths with and oversize mudroom between the house and garage give you lots of options. Oversized 2 car garage gives you plenty of room for storage in the event you may want to finish off the lower level of this home. Completely remodeled home allows you peace of mind knowing all you have to do is move in. New Windows, new roof, new gutters, new flooring in kitchen and living room and remaining floors refinished The kitchen offers lots of countertop space, cabinets, quartz countertops, island, stainless steel appliances and room for the dining table. Recessed lighting and tile back splash finish off the detail. All three bedrooms are roomy and the master bedroom offers a fully renovated master bath with tiled walk in shower. Keep the open fireplace or add a pellet or wood stove to give you that New England feel while keeping the chill off. The basement would make for great additional living space as there is already a full bath there. New Bilco door and steps to basement. Updated mechanicals including new gas boiler, city water and sewer will give you peace of mind. New roof, windows and fresh paint throughout. There is a shared driveway however there is room from survey (in photos) that was done to have a private driveway. Located near the heart of Middletown, with so many options when it comes to dining, shopping or entertainment.

404 Newfield St, Middletown

854 Long Hill Rd Unit 854, Middletown
$279,000
3 Beds ⋅ 2 Baths ⋅ 24215577 MLS ⋅ Ridgely Condo I BLDG.
**End unit? Yes, please!** More windows, more natural light, and a little extra breathing room! Welcome to 854 Long Hill Road, a spacious 3-bedroom townhouse in Middletown's desirable Wesleyan Hills-Ridgely One community. With 1,360 square feet of living space, this home has plenty of personality and room to make it your own. The generously sized living room features a wood-burning fireplace, built-in shelving, a charming bay window, and extra windows that let the sunshine in. There's even room for a dining area, because dinner deserves more than the coffee table! The oversized eat-in kitchen offers plenty of cabinet and counter space, plus sliders leading to a private deck, perfect for morning coffee, outdoor dining, or simply enjoying a little fresh air. A convenient half bath rounds out the main level. Upstairs, you'll find three comfortable bedrooms, including a spacious primary with a cozy window seat and direct access to the full bathroom. The two additional bedrooms offer flexibility for guests, a home office, or a creative space. One even has built-in bookshelves, ready for your favorite reads or collections! Need storage? The full basement has you covered, with laundry, plenty of room for life's extras. Central air and assigned parking add everyday convenience. Tucked into Wesleyan Hills community, you're just minutes from downtown Middletown, Wesleyan University, restaurants, shopping, and major commuting routes. A little charm, a lot of space, and an end-unit!

854 Long Hill Rd Unit 854, Middletown

38 Autumn Ln Unit 38, Middletown
$469,000
3 Beds ⋅ 3 Baths ⋅ 24212932 MLS ⋅ Autumn Meadows BLDG.
Welcome to Autumn Meadows, where beautiful improvements and versatile living come together! This freestanding 3-bedroom, 3-full-bath home offers no shared walls, An inviting open floor plan creates a wonderful sense of space, while three main-level bedrooms, including the primary suite, provide the ease and convenience of one-level living. The updated kitchen features quartz countertops, a generous breakfast bar, newer stainless steel appliances and abundant cabinetry. Gleaming hardwood floors, crown molding and a handsome propane fireplace enhance the living and dining areas. Sliders from the living room open to a spacious TimberTech deck overlooking a picturesque natural meadow with seasonal birdlife. Remodeled bathrooms feature stylish vanities and beautiful quartz and tile showers. The finished lower level offers over 600 square feet of additional living space with heat, central air, a full bath and hookups for a potential kitchenette. Imagine a guest retreat, recreation room, home office or possible second primary suite! Approximately 1,000 square feet of unfinished basement provides generous workshop, mechanical and storage space. The attached finished two-car garage features epoxy flooring and access to the lower walkout level. A new central A/C system installed August 2026 adds peace of mind. Convenient to downtown Middletown, Wesleyan University, Middlesex Health and major commuting routes. A truly special place to call home!

38 Autumn Ln Unit 38, Middletown

27 Rising Trail Court, Unit 27, Middletown
$199,900
3 Beds ⋅ 2 Baths ⋅ 24212390 MLS ⋅ Beacon Hill Towne Homes BLDG.
Welcome to 27 Rising Trail Court, a spacious 3-bedroom, 1.5-bath townhouse-style condo offering three levels of living space, a two-car carport, and a desirable end-unit location! Step inside to an open-concept main level featuring luxury vinyl flooring throughout, where the recently updated kitchen overlooks the dining area and sunken living room. The kitchen features granite countertops, stainless steel appliances, recessed lighting, and plenty of workspace, with a convenient half bathroom nearby. Just beyond, the sunken living room is filled with natural light from sliding glass doors that lead directly to your private back deck. Upstairs, the second floor offers two generously sized bedrooms with wall-to-wall carpeting, a dedicated laundry area, and a remodeled full bathroom featuring tile flooring, a tiled tub/shower surround, and an updated vanity. Continue to the third floor where you'll find an additional bedroom along with a large unfinished storage area offering excellent potential for additional usable space. Additional highlights include a brand-new water heater installed earlier this year, two-car covered parking, pool access, and an end-unit location situated beside the community swing set. The association also allows one dog or one cat, making this a great option for pet owners. Offered at $199,900, this is a fantastic opportunity to make the move from renting to homeownership!

27 Rising Trail Court, Unit 27, Middletown

630 Ridgewood Rd, Middletown
$550,000
3 Beds ⋅ 3 Baths ⋅ 24195246 MLS
Enjoy the best of both worlds in this newer, move-in-ready home nestled along a peaceful country road in Middletown's sought-after Westfield section. Set against beautiful open-space vistas stretching for miles, this property offers a rare sense of privacy and tranquility while remaining conveniently close to everything Middletown has to offer. The inviting open floor plan features a well-appointed kitchen with a center island, an abundance of cabinetry, pantry closet and adjoining family room, all positioned to take full advantage of the spectacular countryside views. A versatile first-floor office or dining room provides the perfect space for working from home, hobbies or guests. The convenient mudroom offers direct access to the garage, keeping everyday life organized. Upstairs, the spacious primary suite features a private full bath, while two additional generously sized bedrooms provide plenty of room for family or guests. The walkout lower level offers excellent potential for future finished living space, recreation, a home gym or simply exceptional storage. Enjoy peaceful country living without sacrificing convenience, with easy access to trendy downtown Middletown, Wesleyan University and the Connecticut Riverfront. Middletown is a vibrant and diverse community offering an impressive array of restaurants, shopping, arts, entertainment, recreation and year-round activities. A wonderful opportunity to enjoy space, views and modern living.

630 Ridgewood Rd, Middletown

66 Durant St, Middletown
$379,999
3 Beds ⋅ 2 Baths ⋅ 24211673 MLS
Welcome to this beautifully renovated, move-in ready colonial that blends classic architectural layout with modern, functional living space. This rare oversized lot could be subdivided. Recently updated, this gorgeous home offers plenty of room to entertain and relax. The Main Level: Step past the inviting front porch into a bright, airy main floor of open and versatile spaces designed for gathering and comfort. A sprawling living room centers the home, flowing seamlessly into the formal dining area perfect for hosting holiday dinners and family gatherings. The kitchen offers wonderful natural light with a breakfast nook and custom floor-to-ceiling cabinets. Sunlit Family Room: Tucked at the back of the home is a spacious family room with wood burning stove, anchored by a full bath and dedicated laundry room. Bonus Sun Room: Bathed in natural light, the attached sun room serves as a perfect home office, reading nook, or plant oasis. Outdoor Entertaining: The sun room opens up directly to a massive, custom outdoor deck, ideal for summer barbecues, outdoor lounging, and evening entertaining. The Upper Level: The primary suite provides a true sanctuary with windows that flood the room with natural light. Two additional bright bedrooms offer great closet space and share a pristine, newly updated full bath. This beautifully updated home offers ultimate peace of mind with three high-ticket upgrades: new gas furnace, new hot water heater and rooftop solar panels

66 Durant St, Middletown

184 Rolling Grn, Middletown
$609,000
3 Beds ⋅ 3 Baths ⋅ 24207436 MLS
Welcome to this gorgeous 3-bedroom, 3.5-bath Colonial nestled on a desirable cul-de-sac in a highly sought-after neighborhood. Filled with natural light, this beautifully updated home offers comfort, space, and functionality throughout. The home has been thoughtfully updated within the past two years.The inviting living room features beautiful flooring and flows seamlessly into the dining area, creating an ideal space for entertaining. The updated kitchen offers new appliances, abundant natural light, and convenient access to the sunroom-perfect for relaxing and enjoying the surroundings. The oversized family room provides plenty of space for quality time with family and friends.Upstairs, you'll find generously sized bedrooms, with updated carpeting throughout the second floor. The spacious primary suite features hardwood flooring, a ceiling fan, and a private bath with a Jacuzzi tub and separate standing shower. Additional ceiling fans throughout the home enhance comfort and airflow.The finished walkout basement adds valuable living space and includes a full bathroom, making it ideal for a media room, recreation area, home office, or entertaining space. Step outside to enjoy the beautiful backyard and patio, perfect for gatherings, outdoor dining, and summer celebrations.This wonderful home offers a great combination of updates, space, and location. The seller has spent $161,000 to keep the house updates. Don't miss the opportunity to make it your own dream home!

184 Rolling Grn, Middletown

1231 Washington St Unit 2, Middletown
$224,500
3 Beds ⋅ 1 Baths ⋅ 24205455 MLS ⋅ Woodgate BLDG.
Enjoy one of a select few of the largest townhouse end units in the complex offering 1,109 square feet of vast living space. Nestled in a popular, well-maintained community, this home combines convenience, comfort and peace of mind with nothing to do but unpack and enjoy. Recent complex-wide improvements include new roads with abundant guest parking, new siding, roofs, and decks giving the community a fresh, updated appearance. Additional highlights include a private entrance, in-unit washer and dryer, 6 panel doors, and hot water heater only four months old. Step inside to discover an inviting open floor plan featuring a spacious living room with soaring vaulted ceilings that fill the space with natural light and create an airy, welcoming atmosphere. The main level offers a remodeled kitchen with newer cabinetry, appliances and tile flooring. Enjoy an updated full bath with deep tub / shower combination, newer glass doors, plus two generously sized bedrooms, each with sliding glass doors leading to an oversized deck-perfect for morning coffee, outdoor dining, or simply relaxing. Upstairs, a third bedroom provides flexible space ideal for guests, a home office, workout room, or additional living area. Conveniently located near shopping, restaurants, major commuter routes, and just 2.2 miles to Wesleyan University, this home presents an excellent opportunity for owner-occupants and investors alike. Cash, Conventional and CHFA Conv Financing only. Special Assessment ends 10/38.

1231 Washington St Unit 2, Middletown

122 Newfield St Unit 3A, Middletown
$329,900
3 Beds ⋅ 2 Baths ⋅ 24201404 MLS ⋅ Arawana Estates BLDG.
Welcome to Arawana Estates, where historic charm meets modern comfort in a truly unique setting! Located within a beautifully converted mansion, this rarely available penthouse-style condo offers a spacious & distinctive layout filled with character & natural light. High ceilings, hardwood floors, recessed lighting, oversized windows & custom built-ins create a warm & inviting atmosphere throughout. The updated kitchen features crisp white cabinetry, leathered granite countertops with breakfast-bar seating, stainless steel appliances & a new Bosch dishwasher. Beautifully appointed baths offer granite finishes, subway tile & a relaxing soaking tub. The impressive primary bedroom is a standout, offering generous proportions, beautiful hardwood flooring, a fireplace & extensive custom built-in cabinetry & shelving. In-unit laundry & abundant storage add everyday convenience. Set within an intimate 6-unit community, Arawana Estates is surrounded by expansive lawns, mature trees, distinctive stonework & picturesque views, creating a peaceful & private setting just minutes from everything Middletown has to offer. Conveniently located near Wesleyan University, downtown Middletown, restaurants, shopping, parks, trails & public transportation. Veterans Memorial Park is also nearby, offering a community pool, splash pad & walking trails. A rare opportunity to own a one-of-a-kind residence combining historic architecture, modern updates, generous living space & beautiful surroundings.

122 Newfield St Unit 3A, Middletown

65 Murray St, Middletown
$399,900
3 Beds ⋅ 2 Baths ⋅ 24200766 MLS
Oversized Ranch with Incredible Outdoor Living! This 3 Bedroom, 2 full Bath home offers 1,236 sq. ft., a mighty 2-car attached garage, and a picture-perfect backyard oasis! The inviting foyer opens to an expansive Living Room/Dining Room combination featuring an attractive gas fireplace and sliders to an amazing deck, patio, and backyard. The bright, spacious eat-in Kitchen captures the morning sun and offers a generous breakfast nook and plenty of counter space. The laundry is conveniently located at the far end of the Kitchen. Down the hall are 3 good-sized bedrooms and a welcoming full bath. The Master Bedroom Suite features crown molding, a Master Bathroom with a walk-in shower, and a walk-in closet. Step outside to a sprawling 30' x 15' deck/patio plus an adjacent 12' x 9' patio, creating an exceptional retreat for relaxing or entertaining. The large, flat backyard gives you plenty of room to enjoy it all! The 30' long, cozy front porch is another perfect spot to relax and watch the sunrise. The basement is huge, completely open, ready for finish (Family Room, Game Room, Work Shop). Comfort and efficiency come from 2 split units for heating and A/C, plus a newer heat pump for efficient heating, cooling, and improved electric bills. There are also select baseboard units and radiant ceiling heat, with the split units providing the greatest efficiency. City water and sewer complete the package. The home you've been waiting for!

65 Murray St, Middletown

145 Monarca Dr, Middletown
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 24202531 MLS
A one-of-a-kind custom-built new construction home that must be experienced in person to be appreciated. This modern contemporary farmhouse-style ranch sits on 2.38 acres of private land, positioned at the end of a cul-de-sac on a private road. From the moment you arrive, the exterior makes a lasting impression. Stone walls frame the driveway, guiding you past a thoughtfully designed approach w/a waterfall element & circular drive. The home's facade showcases board & batten siding, stone & striking black windows, gutters & trim. A covered front entry with a custom-built on-site front door & oversized 10-ft garage doors complete the curb appeal. Inside, every detail has been carefully designed & executed. Custom paneled walls conceal hidden features, including a discreet foyer closet & a hidden half bath accessed through the paneling along w/built-in storage for convenience. The open-concept living space is breathtaking, highlighted by soaring ceilings, exposed beams & a stunning central fireplace that anchors the home. The chef's kitchen is both beautiful & functional, featuring high-end cabinetry, a farmhouse sink, a large center island w/waterfall quartz edges & additional storage below. 1 wing of the home includes 2 guest bedrooms, a full bath & a cleverly enclosed laundry area finished walnut, keeping it completely out of sight. The primary suite offers a luxurious bath w/a walk-in shower, double vanities, walk-in closet, & a unique double-seater, lay-down soaking tub.

145 Monarca Dr, Middletown

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