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$599,900
4 Beds ⋅ 2 Baths ⋅ 24162489 MLS
Step back in time while enjoying the comfort of modern updates in this distinctive 1868 home in Middletown's desirable South Farms area. Set on a property rich in character, history, and functionality, this unique home offers 3 bedrooms, 1 1/2 baths, an upstairs office, and a completely remodeled kitchen area. The full-height basement features a granite foundation, poured concrete floor, and floor drains, along with an updated electrical panel. The property itself is truly special, framed by magnificent pine trees believed to be among some of the oldest in Middletown. The grounds and collection of outbuildings give this property a presence and versatility that is hard to find today. The three-story barn includes an insulated bonus room on the third floor, while the heated one-car garage offers a concrete floor and insulated office space-ideal for a workshop, studio, home business, or hobby space. A second one-car garage provides a concrete floor, attic storage, and a dedicated gardening area with shelving. There is also a three-bay open shed, including one bay with a concrete slab, plus a corn shed and the property's original outhouse, adding an authentic connection to its past. Whether you're drawn to historic homes, need room for hobbies and projects, appreciate extensive storage, or simply want a property with a story to tell, this South Farms offering is a rare find. It's a unique combination of historic character, practical improvements, beautiful grounds, and excepti

110 Freeman Rd, Middletown
$589,900
2 Beds ⋅ 2 Baths ⋅ 24123204 MLS
Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "MARTIN II," Under CONSTRUCTION! Now with many new UPGRADES - available for occupancy in early 2027 Located in the highly sought-after Westfield section of Middletown, this beautiful 1,430 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design: Enjoy the sophistication of wood cabinetry with granite countertops and a walk-in pantry. Hardwood floors flow through out the main living areas, while tile flooring is featured in the baths and laundry room. A deck at the rear of the home creates the perfect space to relax and entertain. The home is equipped with natural gas and central A/C for year-round comfort. Some photos similar and depict some upgrades. Agent/Owner related. Come see why our motto is "Choose a Carefree Lifestyle!"

137 Webster Ln Unit 2-42, Middletown
$585,000
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
$579,000
4 Beds ⋅ 3 Baths ⋅ 24200663 MLS
Welcome to 220 Randolph Rd - This spacious 4-bedroom, 2.5-bath Colonial offers the rare opportunity to enjoy 2.53 acres of privacy in the heart of Middletown. The first floor features a welcoming living room with a propane fireplace, an open-concept eat-in kitchen, and a convenient primary suite complete with a walk-in closet and a large en-suite bathroom featuring both a shower and jetted tub. A half bath and easily accessible laundry area complete the main level. Upstairs, you'll find three additional bedrooms, a full bathroom with double sinks, and a versatile bonus loft space at the top of the stairs-perfect for a play area, reading nook, home office, or whatever suits your needs. The second-level flooring is ready for your personal touch, offering the opportunity to make the space truly your own. The spacious, stand-up attic offers abundant storage and the opportunity to be transformed into a bonus room or additional living space. The basement provides even more room to grow, with ample space and the potential to be finished to suit your needs. Outside, the property truly shines. Set far back from the road and surrounded by both woods and farmland, the expansive backyard creates a private retreat where you can enjoy summer barbecues and gatherings.

220 Randolph Rd, Middletown
$554,900
3 Beds ⋅ 3 Baths ⋅ 24196131 MLS
Beautifully updated Saltbox Colonial in Middletown's Westfield neighborhood! This 3-bedroom, 2.5-bath home offers a spacious, open floor plan with the perfect balance of classic charm and modern updates. The updated kitchen featuring granite countertops, stainless steel appliances, and a bright eat-in dining area with cathedral ceilings and a slider leading to the expansive deck-ideal for indoor and outdoor entertaining. The kitchen flows seamlessly into the impressive family room with soaring cathedral ceilings, a custom fireplace with a pellet stove, and a second slider providing even more access to the deck and backyard. Hardwood floors run throughout the first floor, which also features a formal living room and formal dining room, offering flexible spaces for gatherings and everyday living. Upstairs, the spacious primary suite is a true retreat with an updated full bath, and dual closets. An open hallway overlooks the family room below, adding to the home's bright and airy feel. Two additional generously sized bedrooms and a full bath complete the second floor. The fully finished lower level provides exceptional space, perfect for a playroom, recreation room, home office, gym, or media room. You'll also find a dedicated laundry room and a cedar closet for additional storage. Outside, enjoy the expansive deck overlooking the fully fenced backyard-perfect for summer entertaining. Enjoy evening strolls or bike rides through the 3 cul-de-sacs of Sylvan Run.

897 East St, Middletown
$539,999
3 Beds ⋅ 3 Baths ⋅ 24191099 MLS
Welcome to this beautifully updated 3-bedroom Contemporary- ranch style home, privately set on a lush .92-acre lot. A charming wraparound covered porch creates an inviting first impression and a wonderful place to relax. Inside, vaulted ceilings, abundant natural light, fresh paint and new luxury vinyl flooring enhance more than 1,600 square feet of above-grade living space, with an additional 800+ square feet on the lower level. The home offers 2 full and 1 half baths, including a primary bathroom upgraded in 2022. More than $70,000 in recent improvements include a new upper-level balcony, siding, refinished deck, Driveway, new appliances and a washing machine installed in 2025. Additional updates include a 30-year architectural roof installed in 2004, replacement shingles adjacent to the rear balcony in 2026, a new central-air condenser installed in 2016 and two 100-amp electrical panels, including one installed in 2018. The versatile lower level features a heated family room with a fireplace, a new sliding door and existing plumbing, creating exciting possibilities for an en-suite guest area, potential in-law, home office, studio or salon. Buyers should perform their own diligence regarding any intended use and applicable municipal requirements and approvals. The outdoor space has been beautifully refreshed with more than $5,000 in new landscaping and a brand-new saltwater above-ground pool installed just three weeks ago...

1512 Country Club Rd, Middletown

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