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150 Millbrook Rd, Middletown
$340,000
4 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24203998 MLS
Set on approximately 5.2 acres in Middletown, this historic 4-bedroom home offers a unique opportunity to enjoy space, privacy, and the character of an older property. Built in 1760, the home offers approximately 1,680 square feet of living space and plenty of room to explore the possibilities. The expansive parcel provides a peaceful setting with ample outdoor space for gardening, recreation, entertaining, or simply enjoying the privacy of your own property. Inside, the home offers four bedrooms and one full bath, providing a flexible layout with plenty of potential to make the space your own. The generous acreage creates opportunities for those looking for more land while still being conveniently located in Middletown. Whether you're looking for a property with history, land, or the opportunity to bring your own vision to life, 150 Millbrook Road is worth a look. Come see the property and discover its potential for yourself.

150 Millbrook Rd, Middletown
400 Coleman Rd, Middletown
$425,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE 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 Infused with beautiful natural light, this right-sized home offers 1718 sf with loads of windows (11 have been replaced by this owner), 3 bedrooms, and 2 bathrooms.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
1040 Washington St, 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
37 Valley Dr, 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
35 Sonoma Ln Unit 35, 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
477 Hunting Hill Ave, 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
95 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
66 Durant St, 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
42 Saybrook Rd, 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
25 Wanda Ln, 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
74 Boston Rd, 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
672 E Main 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
85 Freeman Rd, Middletown
$749,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204169 MLS
NEW CONSTRUCTION MODERN COLONIAL Beautiful 4-bedroom, 21/2-bath Modern Colonial privately situated on 1.8 acres of rolling country hills. Currently under construction to be complete mid Nov. Exterior features include vinyl siding, Harvey windows, architectural shingles, Trex front porch with white railings, & paved driveway not yet complete. The lot will be professionally graded, topsoiled, and seeded. The approximately 2,232 sq. ft. home features 31/4" natural-finish white oak flooring, tile baths, square-edge flat trim, recessed lighting, & inset floor registers. The kitchen offers white shaker cabinets, quartz counters, navy-blue eat-at island, stainless farmhouse sink, built-in hood, propane stove, & an appliance allowance. The family room features a gas fireplace. The primary suite includes a coffered ceiling with crown molding, walk-in closet with custom shelving,& bath with double vanity, quartz counter, and walk-in rain-head shower. Four bedrooms include a flexible 4th bedroom/bonus room, plus second-floor laundry. Additional features include white bathroom vanities, quartz bath counters, hydro-air heating/cooling, Insta-hot combination boiler/hot water system, 200-amp service, well & septic, oversized 2-car garage with openers, unfinished basement, and Trex rear deck. Adjacent 2.8-acre lot also available, with plans for a home in the same Modern Colonial style. AI-enhanced photos of anticipated finished home/landscaping- actual appearances may vary

85 Freeman Rd, Middletown
130 Spencer Dr, Middletown
$349,000
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201926 MLS
Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown
23 Brookview Ln, Middletown
$605,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24201081 MLS
Welcome to 23 Brookview Lane, a spacious Colonial tucked into the desirable Westfield section of Middletown. Set in a beautiful residential community, this home offers a great combination of space, privacy, and a comfortable layout with plenty of room to grow. Inside, beautiful hardwood floors run through much of the main living area, while the fireplace creates a warm focal point and a perfect place to gather. The kitchen and dining areas offer plenty of room for everyday living and entertaining, with direct access to the rear deck overlooking the backyard. Upstairs, you'll find spacious bedrooms and a primary suite complete with its own private full bathroom and walk-in closet, giving the homeowners a comfortable space of their own. The additional bedrooms offer plenty of flexibility for family, guests, or a home office. Downstairs, the fully finished walk-out lower level adds another dimension to the home and can easily serve as a second family room, recreation space, office, gym, or playroom. One of the highlights of the property is the outdoor setting. Step out onto the deck and enjoy views of the private, lightly wooded backyard, creating a peaceful setting for morning coffee, summer gatherings, or simply relaxing at the end of the day. The attached two-car garage and sizable private driveway provide ample parking and additional convenience. Located just minutes from Spencer School, Middletown High School, shopping, restaurants, parks, and major commuter routes, Broo

23 Brookview Ln, Middletown
85 Oakcliff Rd, Middletown
$555,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24198723 MLS
Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

85 Oakcliff Rd, Middletown
20 Chimney Hill Rd, Middletown
$649,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197740 MLS
Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

20 Chimney Hill Rd, Middletown
166 Mccormick Ln, Middletown
$649,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193869 MLS
Welcome to this beautifully maintained 4+-bedroom, 2.5-bath Colonial conveniently located in the heart of Middletown. Freshly painted and move-in ready, this home offers the rare combination of generous living space, flexible room options, entertaining areas, and valuable recent updates-including a new roof in 2025. The spacious eat-in kitchen features a center island and bright breakfast nook with skylight, opening directly into a welcoming great room with a fireplace and built-in sound system. It's an ideal layout for both everyday living and entertaining. But the feature you'll want to see is the approximately 500-square-foot first-floor fifth bedroom/media room. With a projector and surround sound already in place, it's perfect for movie nights, watching the big game, or hosting friends. Because of its size and location, it can easily be transformed into a first-floor primary suite, guest suite, home office, gym, playroom, or recreation space. Upstairs, four generously sized bedrooms provide plenty of room for family, guests, or dedicated work-from-home space. A separate living room and formal dining room offer even more flexibility for entertaining.

166 Mccormick Ln, Middletown

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