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9 Magnolia Ave, Middletown
$285,000
4 Beds ⋅ 1 Baths ⋅ 24217261 MLS
Welcome to 9 Magnolia Place, a charming and well-maintained Middletown home offering an impressive list of thoughtful updates inside and out. Tucked along a quiet dead end, this 4-bedroom home combines character, comfort and many of the major improvements buyers appreciate. Recent updates include new kitchen cabinetry, new quartz countertops, sink and faucet, a metal range hood, and fresh interior paint throughout nearly every room, both hallways and the upper staircase. Approximately a year and a half ago, the first 10 feet of the exterior sewer line were replaced, another valuable improvement to the property. Additional improvements over the years include newer vinyl siding with insulation, energy-efficient double-pane replacement windows, a designer front entry door and surrounding structure, added attic/crawl-space and ceiling insulation, and an updated large shower/bath with generous built-in shelving. The home is equipped with an oil-fired Crown heating system, an above-ground oil tank, a newer A.O. Smith water heater and solar panels. The roof features high-performance asphalt shingles, reported by the seller to carry a 50-year rating and designed for winds up to 130 mph, along with updated gutters. Outside, enjoy a partially fenced backyard, storage shed and a wonderful covered rear deck overlooking the yard-a comfortable spot for morning coffee, outdoor dining or simply relaxing. A full unfinished basement with hatchway access provides additional storage

9 Magnolia Ave, Middletown

37 Valley Dr, Middletown
$525,000
4 Beds ⋅ 3 Baths ⋅ 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

219 Pearl St, Middletown
$274,900
4 Beds ⋅ 2 Baths ⋅ 24213164 MLS
*Highest & best offers due by Tuesday 10/20 at 5 PM* Downtown convenience, classic character, and two-family potential come together at 219 Pearl Street! Wesleyan University is just a few blocks away, and Main Street's restaurants, shops, and local favorites are within walking distance! Russell Library, parks, public transportation, and convenient access to Route 9 add to the appeal. Two apartments on separate floors offer flexibility for investors or owner-occupants looking to offset housing costs with rental income. Both kitchens feature quartz countertops, with stainless steel appliances and a stackable washer/dryer in the first-floor unit. Wood flooring and generous windows bring warmth and natural light, while the second-floor screened-in porch offers a place to relax. A HUGE walk-up attic is a standout feature, offering abundant storage and exciting finishing potential for a buyer with the right vision. The sewer line was relined in 2021, a major infrastructure improvement! The paved driveway provides plenty of off-street parking, and the level rear yard adds outdoor space to enjoy. An unfinished basement, public water and sewer, natural gas, and a Navien tankless water heater installed in 2020 round out the features. Whether you're looking to house hack, generate rental income, or explore the home's untapped potential, this downtown two-family deserves a look. Make it yours today, this one won't last!

219 Pearl St, Middletown

74 Boston Rd, Middletown
$379,000
4 Beds ⋅ 2 Baths ⋅ 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

85 Freeman Rd, Middletown
$749,900
4 Beds ⋅ 3 Baths ⋅ 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

85 Oakcliff Rd, Middletown
$555,000
4 Beds ⋅ 3 Baths ⋅ 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

1409 Millbrook Rd, Middletown
$1,295,000
4 Beds ⋅ 4 Baths ⋅ 24187574 MLS
Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring, ceiling fans throughout, and a dramatic two-sided fireplace that serves as a focal point for multiple living areas. German-engineered windows with roll shutters & premium German doors provide exceptional quality. Kitchen features new appliances & an open concept. 2 bedrooms with full bathrooms on the main level offer one-floor living options. The lower level includes 2 oversized garages providing abundant storage, workshop space, and room for recreational equipment. A wood/storage shed adds even more utility. This home is in pristine condition with brand new well, new water heater, and 2 central air units. The property consists of three separately deeded parcels presenting a rare opportunity for future investment, development, or resale. The land features rolling acreage, mature trees, open spaces, and a picturesque man-made pond. Whether you're seeking a private retreat, recreational haven, family compound, or property with investment upside, this one-of-a-kind estate delivers stunning natural beauty, exceptional craftsmanship, and limitless possibilities.

1409 Millbrook Rd, Middletown

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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