Middletown Homes with Colonial Style

Welcome to Middletown, Connecticut – a charming city nestled in the heart of Middlesex County that beautifully blends rich history with modern living. Known for its vibrant downtown, lush parks, and welcoming community, Middletown offers a wonderful quality of life for families, professionals, and retirees alike. With a rich cultural scene, including theaters, art galleries, and a variety of dining options, there's always something to explore and enjoy.

One of the standout features of Middletown is its stunning collection of Colonial-style homes. These architectural gems reflect the city's storied past, showcasing elegant lines, symmetrical facades, and classic details that evoke a sense of timelessness. Each Colonial home tells a story, from the stately brick exteriors to the inviting front porches, making them a perfect choice for those who appreciate history and character in their living spaces.

Living in a Colonial-style home in Middletown means embracing both comfort and style. These homes often feature spacious layouts, large windows that fill the rooms with natural light, and beautifully landscaped yards that are perfect for family gatherings or quiet evenings. The neighborhoods are friendly and well-maintained, offering a sense of community that is hard to find elsewhere.

Whether you're a first-time homebuyer or looking to settle down in a historic yet vibrant city, Middletown's Colonial homes provide an ideal backdrop for your next chapter. Come discover the charm and warmth of Middletown, where your dream home awaits!

Newest Middletown Homes with Colonial Style

$425,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24216846 MLS

Don't miss this pristine and charming Gambrel Colonial on a perfect level half acre, offering a quiet setting, gorgeous views, generous outdoor living spaces, and tasteful renovations in every room. Infused with beautiful natural light, this right-sized home offers 1718 sf with loads of windows (11 have been replaced by this owner), 3 bedrooms, and 2 bathrooms. The main floor space takes full advantage of its front-to-back design with two living/family rooms anchored by a central combined kitchen and dining room. The kitchen was renovated in 2026 with new LifeProof flooring, solid surface counters, subway tile backsplash, paint, and lighting. With separate coffee bar area and pantry and cool exposed brick, the kitchen offers great storage and is large enough for a long dining table, and can accommodate an island too! The family room features a wood-burning fireplace for cozy nights. The second floor offers a full bathroom and 3 generously sized bedrooms and spacious hallway, all updated with paint and featuring new flooring. The large remodeled full bath (2024) features marble tile tub surround and gorgeous hexagonal floor tile. More to love: half bath (remodeled 2023); new A/C (2023); new paver patio, garage doors, and shed (2021); new siding (2020); full basement; underground pet fence; and generator-ready.

400 Coleman Rd, Middletown

$460,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24214279 MLS

Step Back in Time - with Comfort and Charm! Built in 1881, this lovingly maintained antique home is filled with character, warmth, and timeless beauty. Nestled on 2.62 acres of peaceful, picturesque grounds, this special property offers a rare blend of history, privacy, and possibility. Step inside and discover 1,964 sq. ft. of inviting living space where the craftsmanship of a bygone era shines through. Rich woodwork, vintage hardware, charming built-ins, and delightful architectural details create an atmosphere that simply cannot be replicated in today's homes. Each room tells a story, offering warmth, character, and a sense of nostalgia. The partially finished attic offers exciting possibilities for expanded living space, a creative studio, or a home office, allowing the next owner to imagine what could be. Outside, enjoy the beauty of mature trees, picturesque surroundings, and plenty of room to roam. Whether relaxing in the peaceful setting, enjoying nature, or envisioning your own outdoor retreat, the possibilities are endless. A detached garage and charming garden shed complement this wonderful property. More than just a house, this is a home that has been cherished through the years and is ready for its next chapter. Warm, welcoming, and full of soul, it awaits someone who appreciates the beauty and individuality of an antique home. Come experience the magic of this 1881 gem.

1040 Washington St, Middletown

$525,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212608 MLS

Welcome to 37 Valley Drive! Offering over 2,400 square feet of living space, this spacious 4-bedroom, 2.5-bath home features a versatile floor plan, distinctive architectural details, and numerous recent improvements! The main level offers a generously sized kitchen opening to an impressive great room featuring soaring vaulted ceilings, skylights, and a cozy fireplace. A bright and inviting sunroom provides additional living space with vaulted ceilings, skylights, and newly installed flooring. You'll also find an expansive bonus room, currently enjoyed as a billiards room, featuring beautiful exposed beams and plenty of space for entertaining, recreation, a home theater, or additional gathering space. An additional bedroom and living area provide flexibility for guests, a home office, or a potential extended-family arrangement with some finishing touches. Upstairs, the primary bedroom features its own private full bathroom, while the additional bedrooms share a beautifully updated second full bathroom. Exposed beams in the bedrooms add warmth and architectural character throughout the upper level. Recent improvements include fresh interior paint and new flooring in the upstairs bedrooms. Additional highlights include a roof approximately 6 years old, a newer hot water heater approximately 3 years old, central air conditioning, and a whole-house generator for added peace of mind. Step outside onto the beautiful newly constructed deck, perfect for entertaining, dining, or

37 Valley Dr, Middletown

$589,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24210931 MLS

Homes in Sonoma Woods don't come available often, and Unit 35 offers one of the largest models in this sought-after 55+ Middletown community. With 2 bedrooms, 2.5 baths, walkout basement with an exercise or craft room, and nearly 2,000 sq ft of living space, this home delivers the ease of condo living without giving up the space you want. The comfortable main level features a fireplace and a heated sunroom overlooking the back of the property, creating additional year-round living space and leading directly onto the deck for relaxing or entertaining. The full walkout basement offers more than 1,000 sq ft, with a portion already finished for even more usable space while still providing plenty of room for storage, hobbies, a workshop or future possibilities. An attached garage, natural gas heat and central air add everyday convenience. Built in 2005, this spacious unit offers a great opportunity for buyers looking to right-size without feeling like they have to squeeze into their next home. With limited turnover in Sonoma Woods, opportunities like this can be hard to find. If you've been waiting for a home in this community, could Unit 35 be the one worth making a move for?

35 Sonoma Ln Unit 35, Middletown

$349,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24213576 MLS

Welcome to this spacious Colonial-style home offering over 2,500 square feet of living space. Featuring 4 bedrooms, central air conditioning, a generously sized kitchen with an eat-in area, and a separate dining area, this home offers plenty of room for comfortable living and entertaining. Originally designed as a side-by-side property, the home has been converted into a single-family residence, offering a unique layout with ample space and possibilities. Conveniently located near major highways, restaurants, shopping, and other local amenities, this property combines space, convenience, and opportunity. Don't miss the chance to make this home your own!

477 Hunting Hill Ave, Middletown

$349,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24212644 MLS

Welcome to 95 Hunting Hill Ave, a charming and very well-cared-for 3-bedroom, 1.5-bath home surrounded by beautiful, established gardens. Inside, you'll find inviting living spaces and a versatile sunroom/den that has been freshly painted with brand-new flooring-perfect for an office, playroom, or cozy sitting area. Step outside to enjoy the backyard patio and peaceful garden setting. Conveniently located near downtown Middletown, Wesleyan University, restaurants, shopping, and nearby parks and trails. A lovingly maintained home ready for its next chapter!

95 Hunting Hill Ave, Middletown

$379,999

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$339,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210969 MLS

This is home is located convenient to Shopping center and route 9. First floor main bedroom. Addition four bedrooms on the upper level and a full bath one of the bedroom does not have a closet. Builtin hutch in the dinning area. Living room with fireplace. (never used) Hardwood floors under carpeting. Handicap Ramp A detached two car garage. Property to be sold in "as is" condition, Contingent upon probate approval. Easy to show

42 Saybrook Rd, Middletown

$599,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24208360 MLS

**PRICE REDUCTION!! Beautiful and spacious 4-bedroom Colonial in a desirable Middletown neighborhood. This approximately 2,313-sq-ft home features a large master bedroom suite with walk-in closet, remodeled granite kitchen, pantry closet, hardwood floors, two-story foyer, fireplace, generous living spaces, central air, main-level laundry, and a 2-car attached garage. The finished lower level provides valuable additional about 650-sq-ft living, recreation and office space. Outside, enjoy your own private summer retreat with a large deck and backyard swimming pool, perfect for entertaining or relaxing with family and friends. Situated on approximately 0.35 acres with convenient access to shopping, dining, schools, parks and major roads. Driveway is being expanded with pavers and concrete retaining wall blocks. A wonderful opportunity to own a spacious Middletown home with the outdoor amenities buyers are looking for!

25 Wanda Ln, Middletown

$379,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24207911 MLS

Welcome to 74 Boston Rd in Middletown, CT, a beautifully renovated home that has been gutted down to the studs and rebuilt with nearly everything brand new. This spacious property offers 4 bedrooms plus a bonus room previously used as a children's bedroom, along with 2 full bathrooms. Designed to feel like new construction, the home features a new roof with new plywood and shingles, new siding with insulation, new interior framing, drywall, flooring, doors, brand-new energy-efficient LED light fixtures, recessed lighting in the living room, dining room, and large laundry room, plus double-pane windows throughout. The updated kitchen includes new cabinets, quartz countertops, refrigerator, dishwasher, microwave, stove/oven range, and faucet. Both bathrooms include new vanities, faucets, toilets, porcelain tile flooring, and porcelain tile shower walls. Brand New Driveway. Major upgrades also include new insulation inside the walls, all-new plumbing pipes, a brand-new gas line, a new tankless high-efficiency gas boiler for heat and hot water, a brand-new 200 AMP electrical panel, and all new electrical wiring, outlets, and switches. Permits were pulled for electrical, HVAC, plumbing, and general construction, and all permits were successfully closed with inspections passed. Sitting on a huge 0.97-acre lot with a brook behind the yard, this move-in-ready home offers modern comfort, space, and peace of mind, like a new construction would.

74 Boston Rd, Middletown

$329,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205306 MLS

Well maintained 3 bedroom home with flexible floor plan. 1 bedroom on the first floor, as well as 2 full baths, Living room, and eat-in kitchen. The second floor has 2 additional bedrooms. 1st Floor Laundry. New Furnace. Splits for air condioning. 200 amp elec. Panel w/ Generator hook up. New detached 3 car garage with loft are above.

64 Ryan St, Middletown

$349,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24206199 MLS

FULLY UPDATED & TURN KEY! Welcome to 672 East Main Street, a beautifully renovated home offering extensive update inside and out. This meticulously maintained property features a new roof, siding, windows, front door, flooring, interior paint, kitchen cabinets, updated kitchen and bathrooms, and so much more. Enjoy the convenience of a dedicated washer and dryer located on the main floor, making everyday living easy and convenient without the need to go up or down. Outside, enjoy new landscaping, a new concrete walkway, and a new back patio, creating a fresh and welcoming exterior. Located close to everything, with easy access to Route 9 and just minutes from Downtown Middletown, you'll enjoy convenient access to shopping, dining, entertainment, and everyday amenities. With so many major improvements already completed, this home is truly move-in ready and turn-key. Just unpack, settle in, and enjoy!

672 E Main St, Middletown

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Middletown Homes with Colonial Style

Newest Middletown Homes with Colonial Style

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