Refine Search
Sort by
193 Scarborough Ln, Middletown
$900,000
4 Beds ⋅ 5 Baths ⋅ CLOSED Status ⋅ 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

33 Knoll Ridge Ct, Middletown
$770,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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

135 Saddle Hill Dr, Middletown
$760,000
5 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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

128 Webster Ln, Middletown
$747,925
2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 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

72 Annello Way, Middletown
$700,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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

175 Ridgewood Rd, Middletown
$580,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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 ⋅ CLOSED Status ⋅ 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

43 Flynn Ln, Middletown
$550,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24176340 MLS
Located in the desirable Westfield section of Middletown, this well cared for home offers one of the lowest fire taxes in town and sits on a beautiful 1.25 acre lot. Lovingly owned since 2004, the Seller has raised their family here, creating a warm and inviting home ready for its next chapter. The main level features hardwood floors and a dramatic cathedral ceiling in the living room with an Avalon pellet stove, adding both charm and efficiency. The lower level offers a spacious great room with a Ravelli pellet stove, plus a separate 12 x 16 flex space that can be used as a man cave, woman cave, office, or dressing room and includes an exceptional custom closet. Energy efficiency is a standout with owned solar installed in 2023, resulting in a total 2025 electric cost of just 625 for the year. Recent updates include siding, windows and furnace 2017, pool and deck 2022, and hot water heater 2024. Total living space is 2,563 sq ft. This is a must see property offering comfort, updates, and value in a prime location.

43 Flynn Ln, Middletown

52 Sonoma Ln Unit 52, Middletown
$540,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24196378 MLS ⋅ Sonoma Woods BLDG.
Run do not walk to see this spectacular Sonoma Woods home, Middletown's premier adult community. Architectural details offer multiple gables & stone to oversized windows. Inside impresses w/2 story entry & beautiful refinished hardwood flooring. 1st flr offers an open floor plan w/front dining room, kitchen w/beautiful cabinetry, granite & brand new cooktop. Open great room w/soaring vaulted ceilings, an open railing catwalk from above, corner gas FP that opens into a breakfast room with built ins & center island with seating. One will be able to walk out on your oversized deck which has recently been updated with composite decking & pvc railings. The first floor also offers a walkin laundry room, half bath & large primary bedroom with beautiful ensuite bath offering double sinks, granite & completely refurbished shower with new glass doors. One will enjoy the large walkin closet boasting California style builts ins and organizers. The upstairs of this abode offers specular 2 story views to below with open railings, an office with hardwood floors and French doors, either 3 bedrooms with a full bath or a 2nd bedroom with large bonus room. Very flexible! Full walkout LL offers potential for more space. Minutes away from downtown Middletown-one of the widest Main Streets in the US, boasting historical buildings, an array of restaurants from fine dining to pizza, Main Street shopping & CT River boardwalk. Only a 25-minute ride to some of CT's most beautiful shoreline and beaches.

52 Sonoma Ln Unit 52, Middletown

68 Pleasant View Dr, Middletown
$530,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24172644 MLS
From the moment you pull into the driveway, this classic brick Ranch feels like home. Tucked away in a peaceful neighborhood on nearly half an acre of lush, level land, it offers a rare sense of sanctuary where the world outside seems to slow down. With nearly 2,000 square feet of main-level living space, this is a home designed for making memories-whether it's gathering around the warmth of the wood-burning fireplace on a crisp autumn evening or enjoying the quiet glow of natural light that fills the spacious rooms. The heart of this home's charm extends far beyond the main floor, leading you into a fully finished basement that was truly built for connection. This incredible lower level features a second full kitchen and a dedicated bar, creating the ultimate setting for hosting lively holiday celebrations, Sunday football games, or intimate family gatherings. Whether you're whipping up a late-night snack or serving drinks to friends, this versatile space adds a whole new dimension of comfort and entertainment. Every corner of this residence speaks to possibility. The three inviting bedrooms provide a soft place to land at the end of the day, while the expansive backyard serves as your own private canvas for summer garden parties and morning coffee in the grass. This isn't just a house; it's a solid, enduring retreat offering the perfect balance of neighborly charm and your own private piece of Middletown.

68 Pleasant View Dr, Middletown

23 Brentwood Ct, Middletown
$515,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24177686 MLS
Just Listed in Middletown's Desirable The Hunt Club in Westfield Section! Welcome home to this lovely Dutch Colonial nestled on a level lot on a quiet cul-de-sac in one of Middletown's most sought-after neighborhoods. A true gardener's delight, this exceptional home is surrounded by professionally landscaped grounds featuring winding pathways, a tranquil koi water pond w/a waterfall & thoughtfully designed outdoor spaces that create your own private retreat. A Pergola Covered 21 x 11 stamped concrete patio w/Retractable Awning creates the perfect setting for outdoor dining, entertaining or simply enjoying the peaceful surroundings. Step inside to find a freshly painted & remodeled interior w/gleaming floors, abundant natural light & an inviting floor plan designed for comfortable living. Front to back livingroom with gas fireplace. A formal Diningroom w/crown molding & a beautiful light & bright updated kitchen with Granite counters & stainless steel appliances. Offering 3 BRs, 1.5 baths, a 2 car garage & a split mini split Central Air system on each floor for added comfort, this home blends charm, functionality & pride of ownership throughout. Additional highlights include a remodeled full bath w/tile, New Roof 2025, New Windows 2025, 2 year old hot water heater, full basement offering potential for future expansion & a 14x10 storage shed for all your gardening & outdoor needs. From the picturesque grounds to the inviting interior, this home is one you won't want to miss

23 Brentwood Ct, Middletown

87 Meech Rd, Middletown
$510,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 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

279 Congdon St, Middletown
$510,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24194846 MLS
*Multiple offers received - Seller is requesting all offers to be submitted by Tuesday 8/4 @ 2:00pm.* Welcome to this beautifully maintained, original-owner Colonial, perfectly nestled on a quiet cul-de-sac in Middletown's highly sought-after Westfield neighborhood! From the moment you step inside, you'll be welcomed by an abundance of natural light, gleaming hardwood floors, and a bright, open floor plan designed for both comfortable everyday living and effortless entertaining. The main level offers spacious gathering areas, convenient first-floor laundry, a half bath, and a flexible room that can easily serve as a home office, playroom, den, or additional living space to fit your lifestyle. Upstairs, you'll find three generously sized bedrooms and two full bathrooms, including an exceptional primary suite featuring an oversized bedroom, an expansive walk-in closet, and a private en-suite bath-your own peaceful retreat at the end of the day. Step outside and enjoy the beautiful deck beneath the gazebo while overlooking the large, level yard-perfect for entertaining, gardening, pets, or creating lasting memories with family and friends. The full unfinished basement offers approximately 1,000sq.ft of potential, giving you the opportunity to create a home gym, media room, recreation space, or whatever you've been dreaming of. Lovingly cared for by its original owners, this home offers the perfect combination of pride of ownership, timeless charm, and endless possibiliti

279 Congdon St, Middletown

24 Meadowood Dr, Middletown
$505,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24168515 MLS
WOW! Do not miss out on this spectacular 4 bedroom home located in the Westfield section of Middletown. This beautiful abode sits on a gorgeous level landscaped lot on a quiet cul-de-sac street. The exterior boasts a front porch with brick front accent, a manicured picturesque yard with double patios, large deck, above ground pool and beautiful plantings and flowers. Amazing space to enjoy spring, summer and fall. The interior boasts a large front to back living room with a stunning fireplace with wood stove insert for those winter months. Oversized dining room with French doors, recently remodeled kitchen, gorgeous hardwood floors throughout. The upstairs offers a large primary suite and 3 additional bedrooms and 1 and 1/2 baths. One will enjoy the large finished rec room in the lower level for additional space or game room. Some of the updates include 5 1/2 year old roof, wired for generator and so much more. This home truly will not last! Don't miss out! Minutes away from downtown Middletown. This thriving New England downtown offers local venues to include many shops and boutiques and an array of restaurants from pizza to fine dining. Hop on Rte 9 and you're only 25 - 30 minutes from some of CT's most beautiful beaches and shoreline.

24 Meadowood Dr, Middletown

58 Morning Glory Dr, Middletown
$505,000
4 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24161658 MLS
WOW this Riverbend beauty is absolutely a show stopper! Nestled on a beautiful home site with stunning views of the CT River Valley hills and amazing sunsets from every window of the back of this abode. The exterior affords plenty of color with seasonal flowers throughout the year. The interior of this abode is equally as impressive with a kitchen that will blow your socks off that opens up to a large dining area and family room with wood burning fireplace and built ins all taking advantage of that incredible view. Beautiful high end flooring throughout. Newer high end windows throughout. The 2nd floor boasts an oversized primary bedroom with ensuite and 3 large additional bedrooms. If more space is what you are looking for the above grade full walkout basement with sliders and full size windows is waiting for your personal finishing touches. Do not miss out on this amazing home. Minutes away from downtown Middletown. This thriving New England downtown offers local venues to include many shops and boutiques and an array of restaurants from pizza to fine dining. Hop on Rte 9 and you're only 25 - 30 minutes from some of CT's most beautiful beaches and shoreline towns. Highest and best by 3/30/26 @ 9am. No escalation clauses.

58 Morning Glory Dr, Middletown

38 Sylvan Dr, Middletown
$500,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24186798 MLS
Welcome to 38 Sylvan Drive, a beautifully maintained raised ranch nestled on a quiet cul-de-sac in the highly sought-after Sylvan Run neighborhood. Rarely available, this exceptional home offers the perfect combination of comfort, curb appeal, and an unbeatable location. Featuring 3 bedrooms, 3 full bathrooms, and beautiful hardwood floors, this home has been meticulously cared for and is ready for its next owner. The timeless brick exterior, professionally landscaped grounds, and inviting curb appeal make a lasting first impression. Step outside to enjoy the expansive deck and charming gazebo-perfect for entertaining, summer barbecues, or simply relaxing while overlooking the beautifully maintained private yard. A roof that's only 6 years old provides added peace of mind. Residents of Sylvan Run also enjoy two beautifully maintained common areas, creating a picturesque neighborhood setting. The annual Unit Owners Association HOA fee is only $265, and the Westfield Fire Tax of approximately $570 per year. Conveniently located near shopping, restaurants, parks, golf courses, major highways, and everything Middletown has to offer, this is a rare opportunity to own a home in one of the area's most desirable neighborhoods. Don't miss your chance to make 38 Sylvan Drive your next home!

38 Sylvan Dr, Middletown

153 Country Club Rd, Middletown
$495,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24159528 MLS
Well maintained colonial home with charm & curb appeal! Great commuter location close to highways, shopping & Middletown's vibrant restaurant scene. The backyard at this property is a relaxing sanctuary with a $25,000 swim spa/hot tub, a koi pond, bluestone patio, stone fireplace, large deck, outdoor lighting & mature trees & plantings! The front entryway welcomes you with a covered wraparound front porch. First floor has a living room, open to the dining room, a large eat-in kitchen, half bath, and a first floor office/bedroom. Kitchen sliders open up to the deck & patio area. The pantry/utility room has a stand up shower & could be made into a laundry room. Upstairs are 3 additional bedrooms, a full bath & a lovely open foyer/sitting area. The walk-up attic is fully insulated & a great storage area & is currently set up as a recreation room. Recent updates include a new boiler & indirect water heater, 2 A/C split units, central air system for 2nd floor, updated 200 AMP electrical panel that is wired for a generator. Roof is less than 2 years old & has newer solar panels! City water & sewer! Detached 2 car garage plus a garden shed adds plenty of additional storage. This home is loaded with charm & character!! Don't miss this one!

153 Country Club Rd, Middletown

35 Sisk St, Middletown
$475,000
3 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24193293 MLS
*Best and final offers by Monday 8/10 3pm. * Offered for the first time in more than four decades, this Dutch Colonial home has been lovingly maintained by only its second owner for over 40 years.35 Sisk Street features solid construction, hardwood floors,Harvey windows,a newer roof (2017),central air,a fireplace, and nearly a half-acre of property in Middletown's desirable Westfield neighborhood. While today's trends may inspire your own cosmetic touches, the hard work has already been done. It's time for the next generation to move in and make it their own. The home features a generously sized kitchen that flows seamlessly into two living areas, offering flexibility for both everyday living and entertaining. A fireplace anchors one of the living rooms, which opens to your patio with low-to-no maintenance composite decking and a private backyard with mature landscaping. Need extra shade? The patio comes equipped with an electric awning, creating the perfect space for relaxing or entertaining family and friends. Upstairs, you'll find three generously sized bedrooms along with a full bath. The closet and storage space in this home are unmatched among homes of similar size. The desirable Westfield neighborhood offers easy access to Route 9 and I-91, while Middletown's growing downtown, riverfront, shopping, and dining are just minutes away. Homes cared for this long don't come to market often.Over 40 years of pride in ownership, sold as is.

35 Sisk St, Middletown

25 Pleasant View Dr, Middletown
$468,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24170759 MLS
Welcome to 25 Pleasant View Drive in the highly desirable Westfield section of Middletown. A completely updated home nestled on a quiet cul-de-sac, offering the perfect blend of comfort, style and functionality. This inviting property features large, sun filled rooms and beautiful hardwood floors throughout the main living areas, adding warmth and appeal. The spacious living room is highlighted by a cozy fireplace, creating the perfect setting for relaxing evenings at home. The updated kitchen offers modern finishes, plenty of cabinetry, and a layout ideal for both everyday living and entertaining. Downstairs, the fully finished basement expands your living space and includes a custom bar perfect for hosting gatherings, game nights, or creating your own private retreat. Step outside to enjoy the large yard, offering plenty of space for outdoor entertaining, gardening, or simply unwinding in your own private setting. A 2 car garage with ample storage. A truly move in ready home not to be missed. AGENT RELATED TO SELLER

25 Pleasant View Dr, Middletown

168 Hendley St, Middletown
$402,500
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24178507 MLS
Welcome to 168 Hendley Street, a well-maintained and thoughtfully updated two-family home located in the desirable Westfield section of Middletown. Perfect for both investors and owner-occupants, this property offers strong income potential, timeless character, and an unbeatable location close to many of the area's top amenities. The vacant first-floor unit features a renovated bathroom, refreshed kitchen with butcher block countertops, hardwood floors, and charming original details including a stained glass window and original craftsman-style door. The second-floor unit offers an updated kitchen and bath, abundant natural light, and a spacious living room with high ceilings. Both units include 2 bedrooms and 1 full bathroom. Conveniently located just minutes from downtown Middletown's vibrant restaurant scene, shopping, and entertainment, as well as Wesleyan University, Snow Elementary, major highways including Route 9 and I-91, and nearby Wadsworth Falls State Park for hiking and outdoor recreation, adding to the property's long-term appeal. Whether you're looking to offset your mortgage with rental income or expand your investment portfolio in a strong rental market, 168 Hendley Street offers flexibility, location, and character all in one.

168 Hendley St, Middletown

177 Barbara Rd, Middletown
$401,500
2 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24197262 MLS
Welcome to 177 Barbara Road, where classic Cape Cod charm meets comfortable, inviting living. From the moment you step inside, you will appreciate the character throughout this 2-bedroom, 2.5-bath home, featuring beautiful hardwood floors, a cozy living room with a wood-burning fireplace, and an arched doorway leading into the dining room with a timeless built-in hutch. The kitchen has been refreshed with a brand-new backsplash, granite countertops & a new dishwasher, and just off the kitchen, the sunroom offers a bright and relaxing space to unwind. A convenient half bath completes the main level. Upstairs, you'll find two good-sized bedrooms, both with hardwood floors and ceiling fans, along with a full bath. The partially finished lower level adds even more flexibility, offering space for a family room, home office, hobby area, or whatever suits your lifestyle. The basement also includes a laundry room with a full bathroom for added convenience. Step outside to a backyard made for relaxing and entertaining, complete with a deck, patio, beautiful pergola, and fencing added in 2022. Whether enjoying your morning coffee, hosting a summer cookout, or simply unwinding at the end of the day, there's plenty of space to enjoy. Valuable updates include a newer roof (2020), water heater (2024), central air (2024), and oil tank (2025). Conveniently located near schools, shopping, restaurants, parks, and major highways, come see all that 177 Barbara Road has to offer!

177 Barbara Rd, Middletown

171 Smith St, Middletown
$401,000
4 Beds ⋅ 1 Baths ⋅ CLOSED Status ⋅ 24198560 MLS
Back on Market, and meant to be for You!! This adorable Cape boasts 4 bedrooms, an Open Layout, Fully Finished Basement, and an Enchanting private, flat fenced yard with a pool, Magnificent Weeping Willow tree, Firepit, and Gazebo. The Main level welcomes a friendly open layout connecting the open kitchen to the living room with cozy wood burning fireplace, Primary bedroom, Full bathroom, and another bedroom which can be used as an office if a 4th is not needed, as well as a laundry area quietly tucked away. Enter the Breezeway with dramatic wood vaulted ceiling, and french doors looking out to the patio and pool, which is currently being used as a Romantic Dining Room. Upstairs you will find two ample sized bedrooms. The Fully Finished basement offers more room for an In-Law possibility complete with kitchen and full bath. The oversized Tandem garage will hold 3 compact cars, or two large trucks and motorcycles, or hobbies. The roof is 5 years old, and the solar panels are owned and convey with the home at no additional cost to save you money on your electric bill. Located in a convenient location for commuting close to 91, route 9, close to shopping, restaurants, golf courses and more. Must Come see!!

171 Smith St, Middletown

85 Ten Acre Rd, Middletown
$400,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24192475 MLS
HIGHEST AND BEST by 5pm Friday July24th. Seller reserves the right to accept an offer at any time prior to the deadline. Nestled near the end of a quiet dead-end road, this beautifully maintained 3-bedroom ranch offers peaceful country living with picturesque pasture views. Stunning perennial gardens, designed by a master gardener, provide exceptional curb appeal and seasonal color. Hardwood floors run through the bedrooms, hallway, and formal dining room. The inviting living room features a wood-burning fireplace and bay window overlooking the front gardens, while the dining room's picture window captures the scenic farmland beyond. The primary suite includes a private full bath. A spacious family room with sliders opens to a bright sunroom and deck, creating the perfect space to relax or entertain while enjoying the tranquil backyard. First-floor laundry, an attached two-car garage, solar panels, and a whole-house generator add comfort and convenience. The walk-out lower level features a second fireplace with a wood stove, dry bar, workshop, pool table, secure safe, abundant storage, and unfinished space for future expansion. A wonderful opportunity to enjoy one-level living in a beautiful country setting.

85 Ten Acre Rd, Middletown

390 Ballfall Rd, Middletown
$400,000
3 Beds ⋅ 3 Baths ⋅ CLOSED Status ⋅ 24183231 MLS
Beautifully Maintained Home with Finished Lower Level & Private Backyard Retreat. Come discover this exceptionally well-maintained home featuring an inviting open floor plan and a spacious lot in a convenient location. Hardwood flooring flows through the living room and all three bedrooms, creating warmth and timeless appeal throughout. The home offers three generously sized bedrooms, including a primary suite with its own private full bath, plus an additional 11/2 baths for family and guests. The finished lower level provides valuable extra living space and includes a versatile office/flex room, ideal for remote work, a home gym, playroom, or hobby space. A standout feature is the enclosed three-season room, added in 2010, providing approximately 180 square feet of additional living space. Overlooking the private backyard, it's the perfect place to relax, entertain, or enjoy the changing seasons. Additional highlights include vinyl siding, thermopane windows, economical oil-fired hot water heat, central air conditioning, and a layout designed for comfortable everyday living. Conveniently located near shopping, downtown Middletown, medical facilities, public recreation areas, and numerous local amenities, this move-in-ready home offers the perfect combination of comfort, space, and convenience.

390 Ballfall Rd, Middletown

123 Smith St, Middletown
$380,000
4 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24170761 MLS
Welcome home to this well-maintained and inviting 4bedroom property, ready for your personal design touches. Updated windows, a refreshed kitchen, and modernized bathrooms complement the recently repainted interior, creating a bright and welcoming atmosphere. The kitchen opens seamlessly into the living room, offering an easy flow for everyday living and effortless conversation while preparing meals. A pellet stove insert adds warmth and ambiance during the colder months. Step outside to the westerly facing deck and enjoy stunning sunsets over dinner or gather with friends around the patio's fire feature. The walkout basement provides an unfinished space ideal for the home craftsman, hobbyist, or future expansion. Conveniently located, you're just a short walk to the Red Fox Restaurant, a quick 5minute ride to Miner Hills Golf Course, and only minutes from dining in Downtown Middletown or shopping in Cromwell.

123 Smith St, Middletown

108 Cambridge Commons Unit 108, Middletown
$365,000
2 Beds ⋅ 2 Baths ⋅ CLOSED Status ⋅ 24181826 MLS ⋅ Cambridge Commons BLDG.
MOVE IN READY!! Outstanding, well maintained townhouse style, spacious 1753 Sq. Ft. Heated including lower level full walk out, end unit. This property has so much to offer (MUST SEE!) The main level has stunning hardwood floors throughout, a beautifully updated Kitchen with a breakfast bar, a large window offering plenty of daylight with visibility to dining area and elegant living room including a wood fireplace with a french door on either side leading to a large deck overlooking the refreshing in-ground pool/ well maintained open areas. As well as a 1/2 bath for convenience. The 2nd floor includes the primary bedroom, amazing full bath and an additional lg. bedroom. Don't forget the full walk out Lower Level with Lg. family room/ office wired for surround sound speakers (Enjoy Movie night!!!) Also, Ample Storage, utility area and Laundry room. Walking out onto stone area accessing open areas and in-ground pool. Location, you got it: easy access to Rt.9, 91, Rt.3, Rt.15, close to Middlesex Hospital, Wesleyan University, easy commute to Hartford & New Haven. This is a Very Desirable end unit, you will love it! See you soon (Don't Hesitate)

108 Cambridge Commons Unit 108, 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.

How much is your home worth?

Get instant property value now!