Refine Search
Map
Sort by
$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
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 24202531 MLS
A one-of-a-kind custom-built new construction home that must be experienced in person to be appreciated. This modern contemporary farmhouse-style ranch sits on 2.38 acres of private land, positioned at the end of a cul-de-sac on a private road. From the moment you arrive, the exterior makes a lasting impression. Stone walls frame the driveway, guiding you past a thoughtfully designed approach w/a waterfall element & circular drive. The home's facade showcases board & batten siding, stone & striking black windows, gutters & trim. A covered front entry with a custom-built on-site front door & oversized 10-ft garage doors complete the curb appeal. Inside, every detail has been carefully designed & executed. Custom paneled walls conceal hidden features, including a discreet foyer closet & a hidden half bath accessed through the paneling along w/built-in storage for convenience. The open-concept living space is breathtaking, highlighted by soaring ceilings, exposed beams & a stunning central fireplace that anchors the home. The chef's kitchen is both beautiful & functional, featuring high-end cabinetry, a farmhouse sink, a large center island w/waterfall quartz edges & additional storage below. 1 wing of the home includes 2 guest bedrooms, a full bath & a cleverly enclosed laundry area finished walnut, keeping it completely out of sight. The primary suite offers a luxurious bath w/a walk-in shower, double vanities, walk-in closet, & a unique double-seater, lay-down soaking tub.

145 Monarca Dr, Middletown
$898,000
4 Beds ⋅ 5 Baths ⋅ 24187393 MLS
Lakeshore Realty is proud to present 49 Partridge Lane, a beautifully maintained home tucked away on a quiet cul-de-sac in one of Middletown's most desirable neighborhoods. Designed for both everyday living and entertaining, this exceptional home features a bright, open floor plan, spacious living areas, and a beautifully appointed kitchen complete with premium Viking stainless steel appliances, offering both luxury and performance for the home chef. One of the property's most unique features is its location abutting the Mt. Higby Reservoir, providing a peaceful natural backdrop, enhanced privacy, and picturesque views. Enjoy direct access to nature while relaxing in your private backyard, perfect for entertaining, gardening, or unwinding after a long day. Generously sized bedrooms, well-designed living spaces, and meticulous upkeep make this home truly move-in ready. Conveniently located just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, golf courses, and major highways, you'll enjoy the perfect combination of tranquility and accessibility. With high-end finishes, a sought-after location, and the rare benefit of bordering protected natural surroundings, 49 Partridge Lane offers an outstanding opportunity to own a home that blends comfort, quality, and lifestyle. Schedule your private showing today!

49 Partridge Ln, Middletown
$779,000
6 Beds ⋅ 4 Baths ⋅ 24199581 MLS
A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to the surrounding landscape. The beautifully designed kitchen features quartz countertops, stainless steel appliances, double ovens, and generous space for gathering and entertaining. Two striking stone fireplaces serve as dramatic focal points, adding warmth, texture and character to the home's expansive living spaces. Offering six bedrooms and three-and-a-half beautifully renovated baths, the versatile floor plan provides exceptional flexibility for today's lifestyle. With its generous proportions and abundance of private and flexible spaces, the home is ideally suited for multigenerational living, extended family, guests, or those seeking dedicated space for a home office or home-based business. A fabulous loft provides yet another versatile area for a family room, office or game room. The spacious primary suite offers a walk-in closet, beautifully updated bath and private patio overlooking the peaceful surroundings. Throughout the home, meticulous details, interesting architectural elements and thoughtfully designed spaces create a sense of character rarely found in

44 Chamberlain Hill 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 & not yet complete. 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
$699,000
4 Beds ⋅ 3 Baths ⋅ 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
$689,000
2 Beds ⋅ 2 Baths ⋅ 24205132 MLS
Expect the best! Carefree living at Founders' Ridge, the premier award-winning 55+ community in Central Connecticut! Introducing the highly sought-after Kirby II model home, now available for IMMEDIATE occupancy. This is the last Kirby II available at this price point. Located in Middletown's desirable Westfield section, this thoughtfully designed 1,555-square-foot, single-level home offers an ideal blend of comfort, style, and convenience. Inside, you'll find elegant white cabinetry, quartz countertops, and a spacious walk-in pantry that combine beauty with functionality. Hardwood flooring flows throughout the main living areas, while the bathrooms and laundry room feature durable tile flooring. A bright bay window in the front room fills the space with natural light and offers sweeping views. Outside, the private rear patio provides the perfect setting for relaxing or entertaining. Additional highlights include natural gas heating and central air conditioning for year-round comfort. Some photos are of similar homes and may include optional upgrades. Agent/owner related.

Unit 2-41 Webster Ln Unit 145, Middletown
$677,000
4 Beds ⋅ 3 Baths ⋅ 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
$649,900
4 Beds ⋅ 4 Baths ⋅ 24183475 MLS
Tucked away on a quiet cul-de-sac in Middletown's South End near the Durham line, 76 Thimble Rock Road offers approximately 2,600 square feet of well-maintained living space. This 4-bedroom, 2 full, 2 half bath Colonial has been carefully cared for over the years by a single owner and is ready for its next chapter. Inside, you'll find spacious rooms, abundant natural light, hardwood flooring, and solid wood doors throughout. The floor plan provides plenty of flexibility for everyday living, entertaining, working from home, or accommodating changing needs over time. The partially finished walkout lower level adds valuable bonus space and offers a variety of potential uses, including a recreation room, home office, gym, hobby area, or possible in-law setup. Direct access to the yard makes the space feel like a natural extension of the home. Conveniently located near Middletown's amenities while offering a quieter setting, this property provides space, functionality, and quality construction in a sought-after area of town. Estate sale subject to probate court approval.

76 Thimble Rock Rd, Middletown
$625,000
3 Beds ⋅ 3 Baths ⋅ 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
$605,000
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
$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
$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
$499,999
3 Beds ⋅ 3 Baths ⋅ 24203636 MLS
This Dutch style Colonial offers a perfect blend of traditional charm and the airy feel everyone is looking for. From the moment you step inside, you see the open floor plan, creating a seamless flow that's well suited for quiet weeknights or for hosting a crowd. Access the multi-level deck off the back of the family room for outdoor enjoyment. The beautifully updated kitchen features stylish finishes and plenty of prep space for the home chef. The first floor is complete with an oversized full bathroom, and convenient mudroom space between kitchen and garage. On the second floor, a generous primary bedroom with great closet space is on one side of the hallway, with 2 secondary bedrooms on the other. A large bathroom with jetted tub and double sinks allows space for everyone's morning routine. The layout provides incredible flexibility, including a fourth bedroom located in the finished walkout lower level. With access to a full bath, this space serves as a private and comfortable guest suite or home office. The lower level adds significant versatility to the home with its laundry area, rec room with wet bar and slider that walks out to the lower-level patio with hot tub. Situated in a prime Middletown location, you're just moments away from the local park and Moody elementary school. With quick access to the highway the commute to work is a breeze. This home is ready for its next chapter!

141 Cimarron Rd, Middletown
$499,900
3 Beds ⋅ 3 Baths ⋅ 24198344 MLS
Welcome home to this beautifully maintained Contemporary Colonial, perfectly situated on a peaceful cul-de-sac in a desirable neighborhood. Offering the ideal blend of style, comfort, and functionality, this home features 2.5 baths, efficient natural gas heat, newer central air, vinyl siding, and 200-amp electrical service for added peace of mind. The remodeled kitchen is the heart of the home, designed for both everyday living and entertaining. Just beyond, the inviting living room showcases a custom hearth surrounding a cozy gas fireplace insert, creating the perfect place to gather year-round. Upstairs, the spacious primary suite offers a private full bath, walk-in closet, and a relaxing retreat at the end of the day. Ceiling fans in every room provide added comfort throughout the home. Need extra space? You'll love the incredible Great room featuring skylights that flood the area with natural light, making it ideal for a family room, home office, playroom, or fitness space. Step outside to a large deck overlooking a private backyard, beautifully complemented by mature landscaping and an in-ground sprinkler system to keep everything looking its best with ease. A two-car attached garage completes this exceptional property. If you've been searching for a move-in ready home that offers quality updates, generous living space, and a fantastic location, this Contemporary Colonial is one you won't want to miss!

69 Ledgebrook Ln, Middletown
$469,000
4 Beds ⋅ 3 Baths ⋅ 24199864 MLS
Welcome to this beautifully updated, bright and spacious home, conveniently located in a desirable Middletown neighborhood. Thoughtfully updated inside and out, this home offers an inviting layout with generous living spaces. The living room is centered around a cozy fireplace, while central heating and cooling provide year-round comfort. The kitchen is made for both everyday living and entertaining, featuring stainless steel appliances, a powerful double oven, and a center island with cooktop. The oversized primary suite is a true highlight, offering an impressive amount of space along with its own private full bath featuring a floating tub and walk in shower. Just outside the primary suite is the conveniently located in-home washer and dryer. A second generously sized bedroom features an exceptionally large closet and great lighting. The finished basement provides even more versatile living space, perfect for a family room, home office, recreation area, gym, or additional entertaining space. Outside, enjoy a spacious fully fenced backyard and patio with plenty of room for gatherings, relaxing, and outdoor entertaining. Additional updates and features include a new 40-gallon electric hot water heater and propane heating, with the leased propane tank located in the backyard. With its bright updated interior, oversized rooms, finished lower level, central air, fireplace, and fantastic outdoor space, this home offers an ideal combination of comfort, space, and conven

87 Meech Rd, Middletown
$465,000
2 Beds ⋅ 3 Baths ⋅ 24195232 MLS
Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftmanship, modern finishes, and an open concept layout ideal for everyday living and entertaining. This is a spacious 2 bedroom 2.5 bath home. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and coordinating designer fixtures throughout. Beautifully finished bathrooms, spacious living areas, prefinished engineered hardwood flooring, and abundant natural light creates a sophisticated yet inviting atmosphere. Additional features include central air, city water and sewer, washer and dryer hookups, an attached one car garage with dedicated storage, and professionally designed landscaping with blue stone steppingstones leading to the sidewalk. Ideally located in desirable Middletown, this exceptional new construction community offers low maintenance luxury living just minutes from vibrant downtown, Weslyn University, Wadsworth Falls State Park, the Connecticut River, restaurants, shopping, entertainment and major highways.

61 W St Unit 15, Middletown
$454,900
3 Beds ⋅ 2 Baths ⋅ 24203125 MLS
This charming three-bedroom, one-and-a-half-bath English Tudor sits on a landscaped corner lot and offers a wonderful mix of classic details and modern updates. The beautifully updated kitchen features white and gray cabinetry, quartz countertops, a farmhouse sink, breakfast bar, stainless steel appliances, and plenty of storage and workspace. From there, the layout flows into the dining room with its original corner hutch, followed by a tiled sunroom that leads out to the patio. The living room features hardwood flooring, built-in bookcases, and a wood-burning fireplace. A convenient half bathroom completes the main level. Upstairs, you'll find a primary bedroom with a walk-in closet, two additional bedrooms, and a tastefully renovated full bathroom. Approximately 430 square feet of finished space in the lower level includes a family room with a bar, workshop, laundry room with a utility sink, and additional storage. The property also includes a detached two-car garage and paved driveway.

147 Old Mill Rd, Middletown
$450,000
2 Beds ⋅ 2 Baths ⋅ 24196263 MLS
Welcome to 1511 Country Club Rd, a charming 2-bedroom Cape with the posability of 5- bedrooms offering comfort, character, and exceptional versatility. This inviting home features a flexible layout with a private in-law suite or separate living space-perfect for multi-generational living, guests, a private home office or income possibility. Step outside to enjoy the expansive backyard, offering plenty of room for entertaining, gardening, or relaxing. A fenced-in area provides a safe and secure space for people or pets to play, while the rest of the large yard offers endless opportunities to enjoy the outdoors. Whether you're looking for your first home, room to grow, or a property with flexible living options, this charming Cape is a wonderful place to make your next home.

1511 Country Club Rd, Middletown
$449,900
3 Beds ⋅ 2 Baths ⋅ 24199578 MLS
Welcome to 147 Ridge Rd, a stunning, completely remodeled home located in the highly desirable South Farms district of Middletown! This beautifully updated property has been renovated from top to bottom and is truly move-in ready. The heart of the home is the spectacular open-concept kitchen, featuring beautiful quartz countertops and seamless flow into a bright, light-filled living room with a decorative stone fireplace. Throughout the home, you'll find beautifully refinished hardwood floors and two beautifully updated bathrooms, each featuring elegant inlaid tile showers. The dining room features a slider to an impressive 16-foot deck, creating the perfect setting for indoor and outdoor entertaining, relaxing, and enjoying the private surroundings. Major updates include a new roof and windows, a newer furnace, and new electrical wiring and electrical panel. Every detail has been thoughtfully updated to create a comfortable, stylish, and modern home. This is a must-see property! Schedule your private showing today and experience everything 147 Ridge Rd has to offer.

147 Ridge Rd, Middletown
$429,000
3 Beds ⋅ 2 Baths ⋅ 24196637 MLS
Welcome to 76 George St, Middletown! This 1,600 SF home offers 3 bedrooms, a spacious kitchen, and plenty of potential to make the property your own. The walk-out lower level features roughed-in plumbing, creating an exciting opportunity for additional living space, a recreation area, or a possible in-law apartment. Set on nearly one acre of land, the property offers additional road frontage on Boston Rd and the potential for an additional structure, subject to zoning and approvals. With generous land, flexible space, and multiple possibilities for future use, this property offers an excellent opportunity for homeowners, investors, or those looking to create additional living space. A lease-to-own option is also available. Don't miss this unique opportunity-bring your vision and explore the possibilities!

76 George St, Middletown
$425,000
4 Beds ⋅ 2 Baths ⋅ 24197069 MLS
Welcome to 104 Bell Street - a rare find on 2.6 private acres in the heart of Middletown. This 4-bedroom, 2 full bath home offers a truly unique setting where you drive down a long, secluded driveway and cross a bridge over Sawmill Brook to arrive at your own private oasis. Fully updated throughout, this home features a renovated kitchen, updated bathrooms, new flooring, new 200-amp electrical service, new AC unit and furnace, new oil tank, an updated well system, and a resurfaced bridge. The wooded, incredibly private lot offers endless potential - whether you envision expanded outdoor living, gardens, or simply the peace and quiet of your own retreat tucked away from the world. Despite the secluded feel, the property is easy to show and conveniently located with quick access to I-91, Wesleyan University, and downtown Middletown. With so much already done, this is a move-in ready home with room to dream on 2.6 acres. Buyer to verify flood zone designation and obtain flood insurance quotes prior to purchase. Agent/Owner.

104 Bell St, Middletown
$425,000
3 Beds ⋅ 1 Baths ⋅ 24195038 MLS
Welcome to this charming 3-bedroom, 1-bath ranch nestled on the highly sought-after Higby Road. Set on a generous half-acre lot, this home offers the perfect opportunity for first-time buyers, downsizers, or anyone looking to add their personal touch. Inside, you'll find comfortable one-level living with a functional layout, hardwood floors, and a cozy fireplace. Additional features include an attached garage, partially finished basement for extra living or storage space, and a peaceful backyard with plenty of room to relax or entertain. Conveniently located near shopping, dining, parks, and major commuter routes, this home combines a desirable location with endless potential. Don't miss your chance to make this Higby Road gem your own!

104 Higby Rd, Middletown
$419,900
1 Beds ⋅ 2 Baths ⋅ 24195008 MLS
Experience elevated living in this brand-new luxury townhome, thoughtfully designed with quality craftsmanship, modern finishes, and an open-concept layout ideal for everyday living and entertaining. This spacious 1-bedroom, 1.5-bath home features a versatile loft perfect for a home office, den, or flex space. The chef-inspired kitchen showcases GE stainless steel appliances, white shaker cabinetry, premium quartz countertops, sleek black hardware, and coordinating designer fixtures throughout. Beautifully finished bathrooms, spacious living areas, and abundant natural light create a sophisticated yet inviting atmosphere. Additional features include central air, city water and sewer, washer and dryer hookups, an attached one-car garage with dedicated storage, and professionally designed landscaping with bluestone stepping stones leading to the sidewalk. Ideally located in desirable Middletown, this exceptional new construction community offers low-maintenance luxury living just minutes from vibrant downtown, Wesleyan University, Wadsworth Falls State Park, restaurants, shopping, entertainment, and major highways.

61 W St Unit 13, Middletown
$400,000
3 Beds ⋅ 2 Baths ⋅ 24192947 MLS
Tastefully updated and move-in ready, this charming 3-bedroom, 2-bath home is located in Middletown's desirable South Farms area. The spacious family room features a vaulted ceiling and brand-new skylights, creating a bright and welcoming gathering space. The updated kitchen offers abundant cabinet storage, granite countertops, stainless steel appliances, and a center island. The dining room showcases hardwood flooring, a wood-burning fireplace, and access to a four-season sunroom complete with a custom-built bar, perfect for entertaining year-round. The first floor includes a bedroom with hardwood floors, a full bath, and an additional flex room ideal for a home office, playroom, or hobby space. Upstairs you'll find two additional bedrooms and a second full bath with a stand-up shower. Relax outdoors on the back deck under the gazebo overlooking the yard. Additional highlights include a one-car under-house garage, additional room in basement perfect for workout room or storage, brand-new roof with 50 year transferable warranty, and numerous updates throughout. Conveniently located within walking distance to schools and just minutes from Main Street Middletown, shopping, dining, and major highways.

25 Garfield Ave, Middletown
$395,000
3 Beds ⋅ 3 Baths ⋅ 24194117 MLS
Welcome home to this charming property located at the end of a peaceful cul-de-sac. This residence features three bedrooms, including a primary bedroom with an ensuite full bathroom. There are two updated full bathrooms in total, along with a convenient half bath. As you enter, you'll notice the gleaming hardwood floors that flow throughout the main living areas. The kitchen is thoughtfully designed with granite countertops, maple wood cabinets, and stainless steel appliances, offering a great setup for everyday cooking. The dining area seamlessly connects to the cozy living space, which features a gas fireplace and a mini-split system, providing an additional heating and cooling option for year-round comfort. From the dining area, sliding doors open to a patio with Trex decking, complete with a retractable awning, perfect for providing shade when needed and easily rolled back for sunny days. The two-car garage provides direct access to a finished basement area that includes a half bathroom and laundry facilities, enhancing the home's functionality. Energy-efficient solar panels ensure excellent coverage, leading to no current electric bill. Step outside to discover a private walking path accessible right from your backyard. This home is fully move-in ready, waiting for you to create lasting memories.

3 Yellow Pine Cir, Middletown
$394,500
3 Beds ⋅ 2 Baths ⋅ 24195917 MLS
Welcome to 45 Annette Place! This beautifully maintained home is truly move-in ready and has so much to offer. The updated kitchen features granite countertops, stainless steel appliances, and recessed lighting, creating a bright and modern space. Hardwood floors flow throughout the living room and bedrooms, adding warmth and timeless appeal. The partially finished basement provides additional living space and is complete with a cozy pellet stove-perfect for relaxing year-round. Need room for vehicles, hobbies, or storage? The impressive 3-car garage offers endless possibilities. Outside, you'll be welcomed by beautifully landscaped grounds that add exceptional curb appeal and create a wonderful outdoor setting to enjoy. This is a home you'll be proud to own!

45 Annette Pl, Middletown

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.