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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

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

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

36 W Poplar Rd, Middletown
$659,000
5 Beds ⋅ 3 Baths ⋅ 24210098 MLS
Welcome to 36 West Poplar Road, a beautifully appointed custom home built in 2014 and ideally situated in the desirable Poplar Estates subdivision. Lightly lived in and meticulously maintained, this impressive home offers quality craftsmanship, generous living spaces, and the convenience of public utilities. A handsome bluestone walkway and welcoming front entrance set the tone as you arrive, while the three-car attached garage provides plenty of space for vehicles and storage. Step inside to gleaming hardwood floors and a freshly painted interior filled with natural light. All-new custom window blinds add a polished finishing touch throughout the home. The thoughtfully designed floor plan features a spacious first-floor primary suite, offering the ease and flexibility of main-level living while still providing ample additional space for family and guests. The custom design, beautiful finishes, and exceptional condition make this home truly move-in ready. Adding tremendous potential is the huge walkout lower level, offering an abundance of space ready to be finished for additional living areas, a recreation room, home gym, office, guest quarters, or whatever best suits your lifestyle. Set within an established neighborhood yet convenient to Middletown's shopping, dining, highways, and amenities, this exceptional property combines newer construction, custom details, public utilities, and room to grow-a wonderful opportunity in Poplar Estates.

36 W Poplar Rd, Middletown

25 Wanda Ln, Middletown
$579,900
4 Beds ⋅ 3 Baths ⋅ 24208360 MLS
NEW PRICE - $579,900! Beautiful 4-Bedroom Colonial | Solar Energy Savings | Private Pool | Newly Expanded Driveway! Welcome to 25 Wanda Lane, Middletown! This beautiful and spacious 4-bedroom, 2.5-bath Colonial offers approximately 2,226 sq. ft. of above-ground living space, situated on approximately 0.35 acres. Built in 2000, this home combines comfortable family living, energy savings, and great outdoor entertaining spaces. MAJOR ENERGY-SAVING ADVANTAGE - LARGE SOLAR SYSTEM! Enjoy the benefits of an existing large solar energy system that generates substantial electricity throughout the year. Monthly Eversource statements document solar generation and electricity credits, helping offset household electricity costs and providing the potential for significant annual savings. NEWLY COMPLETED DRIVEWAY EXPANSION! A major recent exterior improvement features an expanded driveway with attractive decorative pavers and newly installed retaining wall blocks. This improvement provides additional paved parking space, enhances curb appeal, and creates a more attractive approach to the home and attached two-car garage. Inside, the home features a welcoming two-story foyer, hardwood floors, a kitchen with granite countertops and pantry, a cozy fireplace, and generous living and dining areas. The spacious primary bedroom suite includes a walk-in closet. Additional conveniences include central air conditioning, main-level laundry, and an attached two-car garage. The par

25 Wanda Ln, 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

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

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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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