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12 Copper Beech Dr, Middletown
$920,000
4 Beds ⋅ 4 Baths ⋅ 24172407 MLS
Welcome to a luxury home that delivers elegance, comfort, privacy, and lifestyle in every detail. From the dramatic two-story foyer to the expansive open floor plan, this meticulously maintained residence immediately makes a statement. Soaring ceilings, gleaming hardwood floors, custom crown molding, built-ins, a propane gas fireplace, and spectacular floor-to-ceiling windows fill the home with warmth, light, and sophistication. The gourmet kitchen is designed for both everyday living and unforgettable entertaining, featuring granite counters, stainless steel appliances, wall oven, tile backsplash, center island breakfast bar, dining area with sliders to a relaxing two-tier deck, plus a butler-style side bar connecting beautifully to the formal dining and living rooms. The first-floor primary suite feels like a private retreat with two walk-in closets and a luxurious bath with jetted tub and separate shower. A main-level office offers the perfect work-from-home space, while the second floor features three spacious bedrooms and a huge bonus room ideal for a home theater, media lounge, game room, or guest space. Set on 1.04 acres in a small cul-de-sac neighborhood, the open fenced yard offers space to relax, play, entertain, and enjoy your own full-size basketball court. Add in a 2,400 sq ft basement, oversized 3-car garage, Generac generator, fully paid solar system, central air, and the ability to walk to Dooley Pond too! Don't wait on this one!

12 Copper Beech Dr, Middletown

193 Scarborough Ln, Middletown
$900,000
4 Beds ⋅ 5 Baths ⋅ 24180844 MLS
Exceptional quality and craftsmanship define this highly sought-after home in Scarborough Lane within Highland Farms, located in the desirable Westfield area of Middletown. Offering 11 beautifully appointed rooms, this residence showcases premium finishes and thoughtful details throughout. The main level features 9-foot ceilings and an open-concept layout, with the spacious family room flowing seamlessly into the kitchen. Notable upgrades include Andersen windows, a double-sided gas fireplace shared between the family room and office, whole-house speaker wiring, durable 2x6 construction, and 14-inch steel I-beams in the lower level. The luxurious primary suite offers a tray ceiling, dual walk-in closets, and a well-appointed bath with double vanities and a Jacuzzi tub. Additional highlights include three-zone heating, a heated three-car garage with utility sink, and a versatile lower level with a private entrance that offers potential for an in-law suite. Situated on 1.4 acres, the property is serviced by city sewer and private well water, providing an ideal combination of convenience and privacy. A truly outstanding home with exceptional amenities and quality throughout.

193 Scarborough Ln, Middletown

504 Main St, Middletown
$850,000
10 Baths ⋅ 24133406 MLS
Escape overpriced city markets of Manhattan, Brooklyn, Bridgeport and Stamford and invest in opportunity of Middletown, Connecticut. Just two hours from Manhattan, 504 Main Street offers rare versatility and long-term upside: a restored 1888 brick landmark with six total units - two prime commercial storefronts and four bright, character-filled apartments overlooking Middletown's vibrant Main Street. The building blends historic charm with smart upgrades, sun-soaked interiors, renovated kitchens and baths, in unit laundry in 2 units and soaring ceilings amplify the space and craftsmanship. A geothermal HVAC system with Nest controls keeps operating costs low, and private off-street parking is an added bonus for tenants or owner. 2 store fronts offer a long term committed tenant on one side and flexibilty on the other side. Steps from acclaimed dining, boutique shops, live music, CT river, year-round community events, and Wesleyan University, this property draws a consistent, quality tenant base - from professors and grad students to professionals seeking charm, community and convenience. 504 Main is a compelling alternative to inflated city assets - a chance to own income-producing property, bring your business here or make your home here! Middletown's main street was named one of America's "Most Romantic Main Streets, highlighting its love affair with food, river vistas and New England charm. Also highlighted in the New York Times praising its vibrance and accessibly to NYC

504 Main St, Middletown

66 Sachem Dr, Middletown
$803,000
5 Beds ⋅ 5 Baths ⋅ 24171598 MLS
STUNNING 5-bedroom, 4.5-bath Colonial set on almost 2 private acres in a peaceful cul-de-sac setting. Enter into an elegant dining space with a sun-filled bay window, which flows into a phenomenal, fully remodeled kitchen with shaker-style cabinetry, quartz countertops, an impressive 9-foot island, and plenty of space for casual dining or a cozy sitting area. The kitchen opens to a large family room with a wood-burning fireplace and sliders leading out to the deck-perfect for indoor-outdoor entertaining.The main-level (very large) primary bedroom suite is truly exceptional with two walk-in closets, a spa-like bath, and a flexible adjoining room perfect for a home office, nursery, or dressing area and sliders out to the deck Finishing out the main level is a laundry area, half-bath and tons of closet space. Hardwood floors throughout this level. Head upstairs and find a SECOND primary bedroom suite with plenty of closet space and a large, fully remodeled bath with walk-in shower. Two additional bedrooms and a full bath finish out this floor. One of the many stand-out features of this home is the fantastic in-law apartment with it's own separate entrance. Includes a bedroom, full bath with washer/dryer hook-up, office & a kitchen/living room combo with sliders out to a private deck, (even central air!). Ideal for extended family, guests, or flexible living arrangements. The fully finished lower level provides even more living space.

66 Sachem Dr, Middletown

33 Knoll Ridge Ct, Middletown
$770,000
4 Beds ⋅ 3 Baths ⋅ 24174481 MLS
This beautifully designed home offers the perfect blend of comfort, flexibility, and multigenerational living. The main level features impressive 9-foot ceilings that create an open, airy feel . The kitchen has loads of counters as well as an island and dining area which leads to a large trex deck boasting a panoramic view. A spacious primary suite serves as a private retreat with a separate office, exercise area, or sitting room ideal for working from home. There are 3 more bedrooms with one conveniently located on the main floor. There are 3 full baths positioned throughout the home to accommodate family and visitors with ease. The lower level is a 1200 square foot in-law suite with an open style kitchen, living room, dining area as well as 2 bedrooms with another bathroom -- perfect for family, guests, or potential rental opportunities. This home is ideal for today's modern lifestyle.

33 Knoll Ridge Ct, Middletown

250 Sisk St, Middletown
$762,004
3 Beds ⋅ 3 Baths ⋅ 24072900 MLS
3 beautiful home sites in a fantastic location of the Westfield section of Middletown. This beautiful Cape offers it all. You will enjoy the classic historic Cape look on the exterior, framed by a brick center chimney. The inside is wow! You walk into an oversized entry boasting an open staircase offering vaulted ceilings in entry and 2 story front/flex room. You will make your way to the back of the home which is one entire great room offering corner fireplace, large open kitchen and amazing 13'x12.5' dining room with 6 big beautiful windows letting the outside in. The first floor primary suite is the entire left side of the home with amazing closet space, oversized bathroom and shower and soaking tub. Upstairs offers 2 large bedrooms and an oversized full bath with each bedroom having its own bathroom entrance with optional upstairs office/4th bedroom. This design is truly a winner combining the historic charm of the 1700/1800's with amazing open dramatic floor plan with first floor primary. Some additional standard features include granite counters, onsite finished hardwood floors throughout on first and second floor, gas fireplace, decks, white cabinetry. The list goes on! Public sewer, public water.

250 Sisk St, Middletown

135 Saddle Hill Dr, Middletown
$760,000
5 Beds ⋅ 3 Baths ⋅ 24165569 MLS
Some homes check the boxes. This one checks the boxes and gives you the backyard everyone wishes they had. Set in a sought-after neighborhood of beautifully maintained homes, this farmhouse-style Colonial offers the perfect mix of charm, comfort, and resort-style living. The backyard is truly unforgettable with a gunite pool featuring a jacuzzi and waterfall, spacious patio for entertaining, and firepit area made for everything from summer parties to quiet nights at home. Inside, the open floor plan was designed for the way people live today. The remodeled kitchen is the heart of the home, flowing seamlessly into the main living spaces and making it easy to stay connected whether you are hosting a holiday, helping with homework, or enjoying a casual night in. Hardwood floors throughout the first floor add warmth and timeless appeal. A bright sunroom offers the perfect spot for morning coffee, reading, or simply taking in views of the backyard year-round. The home offers five bedrooms in total, giving you the flexibility for guest rooms, home offices, playrooms, or workout space. Upstairs, the primary suite feels like a private escape with a custom walk-in closet and spa-inspired bath with jacuzzi tub. Beautifully updated and thoughtfully designed, this is more than just a home. It is the backdrop for pool parties, holiday traditions, and everyday moments that become lifelong memories.

135 Saddle Hill Dr, Middletown

236 Maple Shade Rd, Middletown
$759,000
3 Beds ⋅ 3 Baths ⋅ 24189442 MLS
Welcome to South Farms, where "staycation" is a way of life. This custom-built home is made for lazy mornings on the wraparound porch and sunny afternoons by the pool - all behind a brand-new full privacy fence with an acre of land. The grounds bloom spring through fall, and a charming chicken coop with its own shed adds hobby-farm charm. Inside, an open-concept layout shines with soaring cathedral ceilings, skylights, and a dramatic floor-to-ceiling fireplace. The kitchen boasts new appliances and flows into a breakfast bar and dining area made for gathering. A flexible downstairs den works as a fourth bedroom, playroom, office, or media room. Spacious full sized unfinished basement perfect for pool table and endless storage. The main floor primary bedroom suite offers a fully renovated bathroom and French doors leading to your own backyard oasis. A heated in-ground pool, lush plantings, and a footbridge over a koi pond to a pool house complete with a half bath! Upstairs, a sunny loft overlooks the living room; two bedrooms feature built-in window seats, and a huge room ready for anything; gym, playroom, extra bedroom; you name it. City sewer means no septic to worry about. Homes like this don't come around often. Come make it yours.

236 Maple Shade Rd, Middletown

128 Webster Ln, Middletown
$747,925
2 Beds ⋅ 2 Baths ⋅ 24135736 MLS
Founders' Ridge Award-Winning 55+ Adult Community! Introducing our model home, the "KIRBY II at 128 Webster Lane has 1,555 square feet of one-level living in the highly sought-after Westfield section of Middletown. This home features many high-end upgrades, including 9-foot ceilings, white wood cabinets with quartz countertops, hardwood floors in the living areas and bedrooms, and tile In the bathrooms and laundry. Enjoy an expanded 12 x 18 deck and patio and front porch, plus elegant crown molding and shadow boxes in the entry hall and custom tiled showers. The home is equipped with natural gas and central A/C for your comfort. Available for late 2025 occupancy. Some photos of Similar homes Agent/Owner related.

128 Webster Ln, Middletown

51 Snipes Ter, Middletown
$710,000
4 Beds ⋅ 4 Baths ⋅ 24178710 MLS
HIGHEST AND BEST OFFERS DUE WEDNESDAY AUG 12th by 10AM!! Exceptional 4 bedroom, 3.5 bath Split Level offering over 2,800 sq ft of beautifully maintained living space, perfectly situated on a quiet cul-de-sac in one of Middletown's desirable neighborhoods. Conveniently located just minutes from vibrant Main Street Middletown, you'll enjoy easy access to popular restaurants, shops, local amenities, & major highways for an effortless commute. The heart of the home is the spacious kitchen featuring a large center island, ideal for entertaining & gathering w/ family & friends. Hardwood floors flow throughout the home, leading to a dramatic living room w/ vaulted ceilings & a cozy gas fireplace. A formal dining room provides the perfect setting for holiday gatherings & special occasions. The expansive primary suite features vaulted ceilings, a walk-in closet w/ convenient laundry, & a luxurious ensuite bath complete w/ a soaking tub, separate shower, & double vanity. Three additional generously sized bedrooms include one w/ a private full bath, while a second full hallway bath serves the remaining bedrooms. Outdoor living is equally impressive w/ a large deck featuring an awning & propane hookup for grilling. The backyard is designed for summer enjoyment w/ an inground pool surrounded by brick pavers & a pool house for storage. The partially finished walk-out basement provides additional living space, 1/2 bath, & direct access to the pool area. Continued ...

51 Snipes Ter, Middletown

72 Annello Way, Middletown
$700,000
4 Beds ⋅ 3 Baths ⋅ 24179890 MLS
Tucked at the end of a quiet cul-de-sac in Middletown's desirable Westfield section, this beautifully maintained home offers the perfect blend of comfort, flexibility, and space. The welcoming floor plan is designed for both everyday living and entertaining, featuring a spacious kitchen with granite countertops, center island, stainless steel appliances, abundant cabinetry, and a sunny dining area that opens to the family room with soaring ceilings and a gas fireplace. A formal dining room is ready for holiday gatherings and special occasions, while a first-floor office provides the ideal work-from-home space or quiet retreat. The first-floor primary suite offers convenience and privacy with a walk-in closet and spacious bath. Upstairs are three additional bedrooms, a full bath, and a versatile bonus room that can adapt to your needs. Step outside and enjoy the backyard, complete with a Trex deck, expansive paver patio, and plenty of space for outdoor dining, entertaining, or simply relaxing. Hardwood floors, detailed moldings, central air, and a two-car garage add to the home's appeal. Conveniently located near shopping, dining, parks, golf, and commuter routes, this exceptional property offers the space and lifestyle today's buyers are looking for. Because the best spaces in a home aren't measured in square feet-they're measured in the memories made there.

72 Annello Way, Middletown

87 Wanda Ln, Middletown
$675,000
4 Beds ⋅ 3 Baths ⋅ 24144673 MLS
Set on a beautifully landscaped 0.37-acre lot in a quiet cul-de-sac setting, this spacious Colonial offers 4 bedrooms, 2.5 bathrooms, and approximately 3,500 square feet of living space. Built in 2003 and surrounded by similar well-sized homes, the property offers a strong blend of space, layout, and neighborhood consistency. Thoughtfully designed for both everyday living and entertaining, the home features multiple living areas, generously sized rooms, and flexible space throughout. The upper level is highlighted by a private primary suite wing occupying its own section of the home, complete with a spacious bedroom, full bath, walk in closet, and an adjoining bonus room ideal for an office, nursery, sitting room, or additional flex space. One of the secondary bedrooms features direct access to a separate full bath with hall entry, offering a practical setup for guests or extended stays. Laundry is conveniently located on the same level as the bedrooms, adding to the home's everyday functionality. The finished lower level provides additional versatility for a recreation room, home office, gym, or playroom. An attached 3 car garage offers ample storage and convenience. Step outside to the patio and enjoy the backyard setting with an open rear view that enhances the overall feel of the property. A well-sized home offering space, flexibility, and a strong setting within an established neighborhood.

87 Wanda Ln, Middletown

60 Watch Hill Dr, Middletown
$660,000
4 Beds ⋅ 3 Baths ⋅ 24177306 MLS
Welcome to the peaceful and charming Watch Hill Estates community, where elevated living meets timeless elegance. Perched high atop a scenic hill, this stunning Colonial offers sweeping panoramic views stretching across Middletown and Durham, creating a truly breathtaking everyday backdrop. Meticulously maintained and completely turnkey, this exceptional residence blends refined comfort with classic design. The main level unfolds beautifully with an open concept living room that flows seamlessly into an inviting family room centered around a cozy gas fireplace. A formal dining room, also ideal as a private office, complements the thoughtfully designed eat-in kitchen, featuring granite countertops, stainless steel appliances, and abundant space for gathering. Upstairs, four generously sized bedrooms provide comfort and versatility, including a luxurious primary suite with a spa-inspired en-suite bath. Rich hardwood flooring enhances much of the home, while tasteful tile accents complete the beautifully appointed interior. Step outside to your own private retreat, where a multi-tiered deck and beautiful landscaped grounds create the perfect setting for entertaining, relaxing, or simply taking in the serene countryside vistas. This is a rare opportunity to own a home where style, comfort, and spectacular scenery come together seamlessly in one unforgettable setting. *Buyer unable to secure financing; property available again.*

60 Watch Hill Dr, Middletown

220 Coleman Rd, Middletown
$660,000
3 Beds ⋅ 3 Baths ⋅ 24174229 MLS
Positioned on a beautifully landscaped lot, this impressive brick home combines timeless design with exceptional indoor & outdoor living. The main level showcases hardwood floors throughout, soaring ceilings & an open floor plan centered around a stunning floor-to-ceiling stone fireplace. The kitchen is thoughtfully designed with granite countertops, limestone backsplash & stainless steel appliances, flowing seamlessly into the spacious living & family room areas. The first-floor primary suite offers comfort & convenience, while two additional full bathrooms provide flexibility for family & guests. Enjoy the efficiency of central air, forced hot air & supplemental baseboard heating. The full basement features 9-foot ceilings & a fireplace, presenting outstanding potential for future finished living space. Step outside to a professionally landscaped, fully fenced backyard complete with a patio, fire pit & hot tub, perfect for entertaining or relaxing. A beautiful covered porch adds even more charm to this exceptional home. A standout blend of space, quality craftsmanship & lifestyle amenities, this home is designed to impress from the moment you arrive.

220 Coleman Rd, Middletown

37 Cranberry Ln, Middletown
$650,000
3 Beds ⋅ 4 Baths ⋅ 24177178 MLS
Set on a beautiful, private lot in one of Middletown's most desirable neighborhoods, 37 Cranberry Lane offers the perfect blend of space, style, and comfort. This impressive Contemporary Colonial features soaring cathedral ceilings, sun-filled spaces, and an open layout designed for both everyday living and effortless entertaining. The spacious kitchen and living areas flow seamlessly to an oversized freshly painted deck overlooking the expansive backyard-ideal for summer gatherings, outdoor dining, or simply enjoying the peaceful setting. Upstairs, you'll find three generously sized bedrooms including a spacious primary suite with a beautifully appointed ensuite bath and abundant closet space. Convenient huge second-floor laundry adds to the home's thoughtful functionality. The finished lower level provides exceptional flexible living space perfect for a home office, gym, playroom, media room, or guest overflow. Meticulously maintained throughout, the home also features furnace and air conditioning condensers along with central air for year-round comfort that was updated in the last 5 years. A wonderful opportunity to enjoy space, privacy, and a neighborhood setting that feels tucked away while remaining convenient to everything Middletown has to offer.

37 Cranberry Ln, Middletown

46 Tavern Cir, Middletown
$636,000
4 Beds ⋅ 4 Baths ⋅ 24185842 MLS
Fantastic home located in Westfield Hills community with plenty of space to roam. This 3/4 bedroom home offers it all. The first floor boasts a large open kitchen with good size eating area, formal dining room, front to back great room and first floor family room with fireplace. All of this leading out to a stunning landscaped yard for enjoying those summer outings or just a relaxing Zen moment. Upstairs offers 2 large bedrooms and an oversized primary with large ensuite, huge walk in closet, additional sitting area, office or nursery. The beautiful finished lower level will impress with a fantastic kitchen setup, family room and additional bedroom and bath and laundry with its own private access. One will enjoy laundry on the first floor and a 2nd laundry in finished lower level for a complete in law situation. All sits on a professionally landscaped lot with fire pit, pergola/gazebo and shed backing to woods. Short drive to downtown Middletown offering an array of restaurants from fine dining to pizza, Main Street shopping includes local venues and many shops and boutiques and a scenic CT River boardwalk. Only about 30 minute ride to some of CT's most beautiful beaches and shoreline towns. Highest and Best offers by July 1st, 2026 by 10:00am. No escalation clauses please.

46 Tavern Cir, Middletown

10 Talias Trl, Middletown
$620,000
4 Beds ⋅ 3 Baths ⋅ 24160499 MLS
Welcome home to 10 Talias Trail....start Spring in a new home and start "planting" new memories! This is a large 4 bedroom 2.5 bath custom-built Colonial nestled on a quiet cul-de-sac. The bright open floor plan has hardwood floors, 9 ft ceilings and custom touches thru out. The bright and spacious kitchen has plenty of cabinet and counter space, a large peninsula, granite counters and is a great spot to enjoy breakfast and ease into your day. There is a charming breakfast nook for a large kitchen table for informal dining which opens up to the fireplaced family room brimming with natural light. The formal dining room is the perfect size for family and friends to gather. Also included on the main level is an office space or extra bedroom or formal living room, if needed. Upstairs you will find 4 large bedrooms; an inviting master bedroom suite ... the hardwood floors throughout are an added upgrade and the 2nd floor laundry room is convenient and a necessity for today's busy lifestyles. The backyard is level with plenty of open space for a pool, barbeque pit or even a swing set. If you are looking for an outdoor space that is perfect for summer living, this home is just what you are looking for...!!! Close to all major highways, medical centers and shopping. Also Middletown is just 40 mins away from the shoreline and approx. 2 hours away from New York or Boston. Please note there are video cameras inside and outside of the home. Please note this an AS-IS sale

10 Talias Trl, Middletown

67 Wildwood Ln, Middletown
$611,000
4 Beds ⋅ 3 Baths ⋅ 24164926 MLS
Rarely does a home of this caliber become available in the prestigious South Farms district of Middletown. Tucked away at the end of a private cul-de-sac, 67 Wildwood Ln. is a masterpiece of craftsmanship, custom-built by the renowned Jean Gullitti. This exceptional property has been meticulously maintained by its original owners, offering a unique opportunity to own a "one-family" home with a legacy of care and pride of ownership. The interior features a sprawling layout with 4 bedrooms and 2.5 baths. At the heart of the home is a gourmet kitchen designed for the serious chef, boasting granite countertops and a large center island equipped with a gas cooktop. The main level flows effortlessly, while the finished basement provides the ultimate flex space for a home gym, media room, play area or 5th bedroom. Practical needs are easily met by the oversized two-car garage, which offers ample room for vehicles and a workshop. The outdoor living space is equally impressive, featuring a high-end Trex and paver patio that overlooks the lush, manicured grounds. This private backyard retreat is perfect for both quiet relaxation or summer entertaining. Surrounded by the peace of a boutique neighborhood, this home offers the perfect balance of seclusion and community. From the premium materials to the unbeatable location, this residence represents the gold standard of Middletown living. Do not miss your chance to be the second chapter in the story of this magnificent home!

67 Wildwood Ln, Middletown

11 Webster Ln Unit 6, Middletown
$610,000
3 Beds ⋅ 3 Baths ⋅ 24173887 MLS
Beautifully maintained single-family home located in a desirable 55+ community offering comfort, style & easy living. This open floor plan features a stunning kitchen with granite countertops, abundant cabinetry & a natural gas fireplace that creates a warm, inviting living space. Hardwood floors extend throughout the main level, including the spacious primary suite complete with a walk-in closet. The finished lower level adds exceptional versatility with a sitting area, additional bedroom & half bath with space/potential to be converted into a full bath. Additional features include natural gas heat, central air, forced hot air, whole-house generator & a beautiful outdoor patio perfect for relaxing or entertaining. Conveniently located with easy access to major highways, shopping, restaurants, golf courses, medical facilities & everyday conveniences, making it easy to enjoy both a peaceful lifestyle & nearby amenities.

11 Webster Ln Unit 6, Middletown

1446 Randolph Rd, Middletown
$603,000
3 Beds ⋅ 3 Baths ⋅ 24204996 MLS
Set well back from the road on 4.6 secluded acres, this beautifully maintained ranch combines generous one-level living with a bright, welcoming feel throughout. Large windows on all sides bring in abundant natural light and frame views of the expansive landscaping, lawn, and surrounding trees. The spacious remodeled kitchen anchors the home's everyday living, with beautifully crafted cabinetry, substantial granite countertops, a large custom center island, and generous workspace, complemented by expansive backyard views and seamless flow to the outdoor living space. The private bedroom wing includes a generous remodeled primary suite with hardwood floors, 3 spacious closets, and a modern private bath designed for the comfort, style, and functionality today's buyers expect. Just beyond the primary suite, a dedicated office with extensive built-ins offers flexible space for working from home, studying, meetings, or enjoying a hobby. The living and dining rooms flow together with warm hickory floors and custom millwork, while a thoughtfully designed mudroom/pantry just off the kitchen adds character and function with built-in cubbies and cabinetry. Outside, the broad, open lawn offers room to gather, play, garden, or enjoy the private setting. A Trex deck and paver patio extend the living space outdoors, creating an inviting place to relax or entertain. Meticulously cared for and truly move-in ready, this home feels spacious, comfortable, and private from the moment you arrive.

1446 Randolph Rd, Middletown

123 Round Hill Rd, Middletown
$600,000
3 Beds ⋅ 2 Baths ⋅ 24165620 MLS
**HIGHEST & BEST DUE BY 5 pm MONDAY 5/18** 123 Round Hill Rd in Middletown is a 3-bedroom, 2-bath ranch set on 6.62 private acres offering 2,064 sq ft of single-level living with thoughtful updates and long-term functionality throughout. Built in 2001, the home features new and refinished hardwood floors, new carpet in the secondary bedrooms, central air, a mud room, and geothermal heating designed for efficient year-round comfort. The heated tile floor in the primary bathroom adds comfort to the main suite, while two fireplaces create additional gathering space on both the main level and lower level. Auto-on lights in every closet, and low-level hallway lights show more the thoughtfulness and care that the owners put into the home when they designed it as their forever home. The full unfinished basement offers additional 2000+ square feet of potential living space with its higher ceilings, a fireplace, and plumbing for an additional bathroom - perfect for recreation, a workshop, gym, or possible in-law use. The home is equipped with 400 amp electrical service, including a dedicated 200 amp service to the garage. The attached garage was designed with the future installation of a vehicle lift in mind, with additional poured concrete in the left bay to support the setup. An RV hookup located on the side of the home adds flexibility for recreational vehicles or additional utility needs. The roof was replaced in 2018 and includes a transferable warranty.

123 Round Hill Rd, Middletown

324 Washington St, Middletown
$582,000
6 Beds ⋅ 3 Baths ⋅ 24179488 MLS
Highest & Best 06/08/26 8:00PM. Rarely does an opportunity come along that offers this level of flexibility, lifestyle, and income potential all in one exceptional property. Completely renovated from top to bottom just a few years ago, this stunning home combines modern finishes, thoughtful design, and turnkey convenience with virtually every major component already updated - allowing you to focus on enjoying the property rather than maintaining it. Whether you're seeking a spacious owner-occupied residence, a multigenerational setup, or a high-performing investment, the possibilities here are remarkable. The current upper-level short-term rental is generating over $50,000 annually and has become a favorite among guests thanks to its unique character, custom artwork, inviting atmosphere, and unbeatable location. Situated in one of Middletown's most desirable areas, you'll enjoy the ability to walk to Wesleyan University, vibrant downtown Middletown, award-winning restaurants, boutique shopping, breweries, entertainment venues, and the scenic Connecticut River waterfront and Riverwalk. Commuters will appreciate convenient access to Routes 9, 66, 91, and other major thoroughfares. Outside, the property continues to impress with extensive parking, a newly paved driveway, beautiful landscaping, multiple new decks, private patio spaces, and a luxurious outdoor retreat featuring a hot tub lounge area complete with television, privacy shades, and a resort-like feel perfect.

324 Washington St, Middletown

175 Ridgewood Rd, Middletown
$580,000
4 Beds ⋅ 3 Baths ⋅ 24204752 MLS
Looking for the feel of new construction without the new-construction price tag? This exceptional 3-year-old home offers the best of both worlds, featuring upgrades, modern finishes & all the amenities you could ask for-without the wait or expense of building from scratch. From the whole-house generator & custom under-cabinet lighting to the smart-home features & security systems, this home has been designed with comfort, convenience & peace of mind in mind. An extended driveway provides ample parking, while the covered front entry with Trex decking welcomes you home. Beautiful front landscaping adds to the home's curb appeal. Inside, you'll discover a unique and highly versatile floor plan featuring 2 primary suites. The 1st suite is located off the entry and offers an en-suite bathroom, walk-in close/office. A 2nd bedroom is located across the hall. Continue into the main living area, where an inviting open-concept design seamlessly connects the kitchen, dining area & living room. This is the heart of the home & an ideal space for entertaining. The spacious kitchen features a large center island with seating & the living room offers a cozy fireplace. Toward the rear of the home, you'll find the 2nd primary suite w/an en-suite full bathroom for added privacy. A 4th bedroom & 3rd full bathroom are located nearby, along w/a separate laundry room.

175 Ridgewood Rd, Middletown

265 Briarwood Ln, Middletown
$576,000
3 Beds ⋅ 3 Baths ⋅ 24175571 MLS
Welcome to a lifestyle that blends neighborhood charm with everyday convenience in one of Middletown's most connected and vibrant locations. Nestled within a planned community, this completely updated 3-bedroom, 2.5-bath home offers the perfect balance of comfortable living, modern style, and easy access to everything the area has to offer. From the moment you step inside, you'll appreciate that everything has already been done - simply move in and enjoy. The fully remodeled kitchen serves as the heart of the home with crisp cabinetry, beautiful quartz countertops, stainless appliances, an oversized island for gathering, and finishes that blend timeless design with everyday function. Hardwood floors and inviting living spaces create warmth and flexibility throughout, while the thoughtful layout offers room to entertain, work from home, or simply relax and unwind. Upstairs, the spacious primary suite provides a peaceful retreat complete with a beautifully remodeled bathroom designed with comfort and style in mind. Additional bedrooms offer flexibility for guests, hobbies, office space, or changing lifestyle needs. Major updates throughout the home provide peace of mind, including a roof only 4 years old, allowing the next owner to enjoy a truly turnkey experience. Outside your door, enjoy the feeling of a true neighborhood community while being just minutes from Middletown's thriving downtown filled with local restaurants, coffee shops, arts, live music, Wesleyan

265 Briarwood Ln, Middletown

220 Randolph Rd, Middletown
$565,000
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

26 Tuscany Hills Dr Unit 26, Middletown
$565,000
2 Beds ⋅ 2 Baths ⋅ 24188433 MLS ⋅ Tuscany Hills Condominium BLDG.
Welcome to 26 Tuscany Hills Drive, a beautifully maintained single-family ranch home loaded with charm and upgrades in this pet-friendly, 55+ active adult community! Rich hardwood floors grace the main living areas, while plush carpeting in both bedrooms adds warmth and comfort, creating an inviting atmosphere you'll love coming home to. The spacious living room features a cozy propane fireplace and opens seamlessly to the dining area and eat-in kitchen, creating an ideal space for everyday living and entertaining. The kitchen is well-appointed with beautiful cabinetry, granite countertops, and abundant workspace for cooking and baking. Just beyond, you'll find the convenient laundry area and access to the attached two-car garage. Situated on a desirable corner lot, the delightful sunroom with vaulted ceilings opens through sliders to a newly stained deck overlooking a private backyard bordered by mature pine trees. The primary suite features a stunning tray ceiling, generous walk-in closet, and an en-suite bath with a step-in shower. The second bedroom is adjacent to a full bath, making it ideal for guests or a home office. A full unfinished basement provides exceptional storage and endless possibilities for future expansion. Tuscany Hills offers an active lifestyle with two community gazebos, holiday celebrations, book clubs, card games, and a variety of social events. Don't miss this wonderful opportunity to enjoy easy, low-maintenance living in a welcoming community!

26 Tuscany Hills Dr Unit 26, Middletown

121 Bartholomew Rd, Middletown
$560,000
3 Beds ⋅ 3 Baths ⋅ 24171969 MLS
Amazing home! This beautiful abode sits on a 1.23 acre Currier & Ives setting. One will be impressed with the gorgeous landscaping, gardens and wooded, private setting. The oversized deck and fenced-in yard is the icing on the cake. The architectural detailing on the exterior offers brick facade, gables and sloped roof lines that sets the stage for the amazing interior of this home. One will walk into an oversized, grand 2-story entry with open staircase, front vaulted office/flex room, oversized center dining room - all of this leads into an amazing vaulted great room with fireplace and large, completely remodeled, stunning kitchen. The multiple windows is just perfect for this setting, letting the outside in with picturesque views. The upstairs will impress with a large sitting area loft overlooking the great room and entry. The primary suite offers an en suite for the ultimate in relaxation and pampering. For energy efficiency, one will enjoy the paid off solar system and EV charging station in garage. Many updates including new state-of-the-art kitchen, newer roof, newer hot water heater. This property is truly amazing - do not miss out! Minutes away from downtown Middletown offering an array of restaurants from fine dining to pizza, Main Street shopping and CT River boardwalk. A short drive to some of CT's most beautiful shoreline towns and beaches. Easy access to highways for great commuting.

121 Bartholomew Rd, Middletown

650 Ridgewood Rd, Middletown
$555,000
3 Beds ⋅ 2 Baths ⋅ 24176671 MLS
Get ready to fall in love with this beautiful newer construction ranch that perfectly blends modern style with easy, carefree living! Bright, open, and filled with natural light, this home welcomes you with gorgeous hardwood floors throughout and an open floor plan made for everyday living and entertaining alike. The stylish kitchen is truly the heart of the home, featuring granite countertops, stainless steel appliances, and plenty of room for gathering with family and friends. The spacious primary suite is your own private escape, complete with a full bath and plenty of room to relax and recharge. Two additional oversized bedrooms and a second full bathroom offer space for everyone, whether you need guest rooms, a home office, or playroom. Main floor laundry and direct access to the attached garage make life easy and convenient. Need more space? The full walkout basement is bursting with potential and ready to become the ultimate family room, home gym or game room! Outside, the back deck is the perfect spot to sip your morning coffee while taking in stunning mountain views and spectacular sunrise skies. Add in the peace of mind of a home completed in 2020 with a full house generator, central ac, natural gas fuel, and you've found a home that checks every box - and then some!

650 Ridgewood Rd, Middletown

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