Middletown CT Just Listed Real Estate, Homes, Condos for Sale

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

$1,350,000

3 Beds ⋅ 4 Baths ⋅ 24196036 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

$309,000

3 Beds ⋅ 2 Baths ⋅ 24194943 MLS

Move right in! 34 Franklin Street is a well-cared-for Middletown split-level offering 3 bedrooms, 1 fully renovated bath, and 966 sq ft of comfortable living. Highlights include hardwood flooring, an eat-in kitchen with sliders to a huge covered deck, and a spa-style bathroom with a walk-in shower, built-in seat, and skylight. Outside, enjoy a private, fenced 0.16-acre yard with mature trees and a storage shed - plenty of room to garden, play, or entertain. Forced-air heat, central air, and durable vinyl siding keep maintenance simple. Zoned for Farm Hill Elementary (0.5 mi) and Woodrow Wilson Middle School, with quick access to downtown Middletown and major routes. Priced to move and ready for its next owner - schedule a showing today.

34 Franklin St, 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

$289,900

2 Beds ⋅ 2 Baths ⋅ 24194866 MLS ⋅ Laurel Ridge BLDG.

Rarely available and meticulously maintained, this move-in ready Laurel Ridge townhome features modern updates, spacious living areas, and prime location. The main level offers a bright living room centered around a cozy fireplace, seamlessly transitioning to a private rear deck. Recent updates include a freshly remodeled kitchen with new SS appliances, and an updated half bath. Upstairs, are two oversized bedrooms with generous closets and a full bath. A second floor laundry h/u offers future flexibility. The full unfinished lower level includes the laundry area, abundant storage, with excellent potential for additional flex space. Updates to the home include; a new heat pump and new patio doors. A detached garage just steps from your front door add daily convenience. Enjoy beautifully landscaped grounds with perennial gardens and serene walking paths, all within the desirable Laurel Ridge community. Conveniently located near major highways, shopping, dining, and Wesleyan University, this thoughtfully updated home is truly move-in ready. Make it yours today!

2 Canterbury Ct Unit 2, Middletown

$352,500

4 Beds ⋅ 2 Baths ⋅ 24194795 MLS

Turnkey investment opportunity! Well-maintained two-family with both units fully rented, providing immediate rental income. Each unit offers 2 bedrooms, separate utilities, natural gas heat, and spacious layouts. Level lot with ample off-street parking in a highly convenient location near Middlesex Hospital, Wesleyan University, downtown Middletown's restaurants and shopping, and major highways including Routes 9, 17, and I-91. A great addition to any investment portfolio!

20 Cooley Ave, Middletown

$244,900

2 Beds ⋅ 2 Baths ⋅ 24194219 MLS ⋅ Carriage Crossing BLDG.

Fabulous first floor offering in the desirable Carriage Crossing community. This 950 sqft condo contains 2 bedrooms and 2 full baths (updated with granite countertops). The living room's sky high windows make this large unit feel even larger. The updated kitchen has stainless appliances and granite countertops. This property also boasts in-unit laundry, an actual wood-burning fireplace, and an exterior storage room. Sliding door off dining area leads to private/fenced exterior patio/sitting area. The Carriage Crossing complex offers a fitness center, tennis, spa, racquetball and sizeable in-ground pool. The well maintained grounds and nearby walking/biking trails provide residents with plentiful options for exercising pets and getting fresh air. HVAC system new in 2022/Water heater new in 2024.

84 Carriage Crossing Ln Unit 84, 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

$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

$385,000

3 Beds ⋅ 2 Baths ⋅ 24193289 MLS

Welcome home to this beautifully remodeled 3 bedroom, 2 full bath home that's truly move in ready! Enjoy relaxing on the inviting front porch or entertaining in the fenced backyard. The updated kitchen features stainless steel appliances, plenty of cabinet and counter space, and room for meal preparation. The spacious living room offers a cozy fireplace and new flooring, creating a warm and inviting atmosphere. The finished lower level provides additional living space with two finished rooms, a full tiled bathroom, and a laundry area with washer and dryer. Perfect for a family room, home office, gym, playroom, or guest space. Recent updates include central air, windows, flooring, fenced backyard, along with many additional improvements. This home is conveniently located near shopping, restaurants and parks and offers the perfect combination of comfort, style, and convenience. Don't miss your opportunity to make this beautiful home yours!

49 George 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

$199,900

2 Beds ⋅ 2 Baths ⋅ 24195105 MLS ⋅ Hamlin Court BLDG.

Welcome to Hamilton Court! This beautifully remodeled 2 bedroom, 1.5 bath townhouse offers stylish updates, low-maintenance living, and an unbeatable location just one block from Wesleyan University. Renovated within the last year, this move-in-ready home features a remodeled kitchen with updated appliances, renovated bathrooms, new flooring, brand-new carpeting, freshly painted walls and trim, and modern finishes throughout. The bright and inviting main level offers an open layout with a spacious living room flowing into the dining area and kitchen, creating the perfect space for everyday living and entertaining. A convenient half bath and private front terrace add to the home's appeal. Upstairs, you'll find two generously sized bedrooms, including a primary suite with a walk-in closet and en-suite bathroom. An in-unit washer and dryer provide added convenience. Enjoy one assigned parking space and a prime location within walking distance to downtown Middletown, Middlesex Hospital, restaurants, shopping, parks, and entertainment, with easy access to major commuter routes. Whether you're looking for a primary residence or an investment opportunity near Wesleyan University, this turnkey townhouse is one you won't want to miss. Property is being sold AS IS, WHERE IS.

201 College St Unit 22, Middletown

$245,000

2 Beds ⋅ 2 Baths ⋅ 24191054 MLS ⋅ Trolley Crossing BLDG.

Welcome to this beautifully maintained 2-bedroom, 1.5-bath townhouse-style condominium offering the perfect blend of comfort, convenience, and low-maintenance living. Featuring 1,206 square feet of inviting living space, this well-cared-for condo offers central air, natural gas heat, and an attached 2-car garage. The kitchen was updated approximately 3 years ago with cabinets, countertops, flooring, and appliances. Enjoy added peace of mind with a central air system approximately 3 years old, a hot water heater approximately 5 years old, a brand-new architectural shingle roof installed in 2025, and a special assessment that has been paid in full. Relax and unwind at the community's in-ground pool, or enjoy the convenience of being just minutes from shopping, restaurants, schools, parks, major highways, and nearby walking, biking, and hiking trails. Move right in and enjoy the comfort, convenience, and lifestyle this exceptional condominium has to offer. Schedule your private showing today!

79 Trolley Crossing Ln Unit 79, Middletown

$334,500

3 Beds ⋅ 1 Baths ⋅ 24194926 MLS

Welcome to 67 Butternut, a charming home that offers comfort, character, and convenience. The main level features a bright, open kitchen with stainless steel appliances that flows seamlessly into the inviting living room, creating the perfect space for everyday living and entertaining. Beautiful hardwood floors extend throughout the home, adding warmth and timeless appeal. Upstairs, you'll find the comfortable bedrooms and a full bathroom. Ideally located just minutes from grocery stores, parks, shopping, dining, and major conveniences, this home combines charm with an unbeatable location.

67 Butternut St, Middletown

$489,000

5 Beds ⋅ 3 Baths ⋅ 24194393 MLS

PROFESSIONAL PHOTOS COMING SOON! 98 S Front Street, Middletown Welcome home to this lovingly maintained and meticulously cared-for Cape, ideally situated on a quiet and welcoming neighborhood. Offering a wonderful blend of comfort, functionality, and quality updates, this move-in-ready home has been thoughtfully maintained both inside and out. The inviting floor plan features a bright eat-in kitchen that flows seamlessly into the cozy family room with a fireplace, creating the perfect gathering space for everyday living and entertaining. Just beyond, a sun-filled four-season room provides additional year-round living space with easy access to the deck and private backyard. A dedicated first-floor laundry room adds everyday convenience. The flexible layout includes a spacious primary en suite on the main level, along with an additional bedroom and a convenient half bath. Upstairs, you'll find two generously sized bedrooms and a third smaller room, ideal as a home office, nursery, or hobby space. Every bedroom offers excellent closet space, providing abundant storage throughout the home. The walk-out lower level offers exceptional storage and workshop space, with the potential to be finished for additional living area.

98 S Front St, Middletown

$449,900

3 Beds ⋅ 3 Baths ⋅ 24194846 MLS

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 possibilities. Schedule your private showing today and experience everything this exceptional home has to offer!

279 Congdon St, Middletown

$264,900

2 Beds ⋅ 2 Baths ⋅ 24192644 MLS ⋅ Newfield Commons BLDG.

Lovely 2-bed townhouse in a quiet complex near shopping, coffee, restaurants and the high school. You'll enjoy a peaceful spot to sip your coffee on the upgraded trex deck & with a view of the woods. Heat pump is under 10yrs, CAIR, Low HOA cost includes trash and snow removal. Finish the basement for even more space. This is the perfect place to start out. Some upgrades will make this home shine, but well-loved for years. Stair chairs will be removed, some furniture can stay. Visitor parking is a plus too!

675 Newfield St Unit 9, Middletown

$180,000

3 Beds ⋅ 2 Baths ⋅ 24194531 MLS ⋅ Beacon Hill Towne Homes BLDG.

Investment Opportunity! This spacious condo is being sold as-is and offers excellent potential for investors or buyers looking to build sweat equity. The unit features gleaming hardwood floors throughout, a partially finished basement offering additional living or storage space, and a finished attic that adds even more usable square footage. A convenient 1.5 bath layout rounds out the floor plan. Enjoy community amenities including access to a sparkling in-ground pool. Conveniently located near I-91 and Route 9, offering easy access for commuters. With its combination of extra finished space, low-maintenance hardwood flooring, and community amenities, this unit presents a strong opportunity for value-add renovation or rental income. Sold as-is.

106 Rising Trail Dr Unit 106, 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

$539,999

3 Beds ⋅ 3 Baths ⋅ 24191099 MLS

Welcome to this beautifully updated 3-bedroom Contemporary retreat, perfectly situated on a lush, private lot. A charming wraparound covered front porch welcomes you home and offers the perfect space to relax, unwind, or gather with family and friends. Inside, you'll find freshly painted 1,600 plus sqft of above grade thoughtfully designed living space featuring soaring vaulted ceilings, abundant natural light, NEW beautiful (LVT) flooring, 2 1/2 bathrooms, and a spacious primary suite with an updated en-suite bathroom complete with a relaxing Jacuzzi tub. More than $60K in renovations have been completed within the past year, including new rear siding, new balcony, a freshly stained deck, and numerous additional updates, making this home truly move-in ready. The finished lower level expands your living space with a cozy family room centered around a fireplace. Adjacent to the family room is a space already equipped with plumbing, offering a true blank canvas for your vision. Whether you dream of a future kitchenette, home office, guest suite, multigenerational living space, or a potential in-law setup, the possibilities are endless.Step outside to your own backyard oasis. Surrounded by mature trees & lush greenery, the expansive deck, brand-new above-ground pool, and newly built balcony create a private, resort-like setting that's perfect for morning coffee, summer pool parties,or relaxing evenings under the stars.

1512 Country Club Rd, Middletown

$239,900

2 Beds ⋅ 2 Baths ⋅ 24193840 MLS ⋅ Cedar Ridge BLDG.

This lovely move in ready unit, is set within a peaceful and quiet complex. On the main level you with find a large living room, dining room combination, 1/2 bath, pretty kitchen with plenty of cabinets, and a brand new refrigerator and oven hood. Also, the door off the kitchen will lead you right out onto your pretty deck for some relaxation time and grilling. Upstairs you will find the primary and 2nd bedrooms, along with a spacious full bath. There are pull down stairs, as well as an attic fan. The basement is large and ready for your special touches to create a workout room, office, or whatever may be suitable for you. Located close to highway access, both route 17 as well as Routh 9, Middlesex Community College, plenty of restaurants, shopping, banking, and just about anything else that you may need. C'mon and make your appointment today, as this very clean unit will surely not last long. Lucky will be the new owner for this truly great unit!

10 Countryside Ln Unit 5, Middletown

$450,000

24028033 MLS

Are you seeking boundless opportunities? Whether it's a serene retreat, a haven for animals, a solar venture, or a hunting plot, this property is a canvas for your dreams. Nestled upon Chestnut Mountain, this property is located in the South Fire District of Middletown. Breath-taking views and stunning sunsets are just a bonus! This property offers a two-stall barn with a tack room that stands ready to accommodate equestrian pursuits. Additionally, there are two elevated hunting blinds and a rudimentary 100 yard rifle range. Roughed in roadways and dirt bike trails make navigating this property a breeze. The potential here is limitless...come experience it for yourself!

East Mount Road, Middletown

$688,000

4 Beds ⋅ 3 Baths ⋅ 24193869 MLS

Welcome home to this beautifully maintained 5-bedroom, 2.5-bath Colonial, ideally located in the heart of vibrant Middletown. Enjoy easy access to Middletown's many wonderful restaurants and downtown charm, with Middlesex Health, Wesleyan University, and the scenic CT River all just minutes away. Freshly painted throughout, this turn-key home is ready for you to move right in! The main level offers a wonderful flow for both everyday living and entertaining. The spacious eat-in kitchen features a center island and a sunlit breakfast nook with a skylight, creating the perfect spot to enjoy your morning coffee or casual meals. The kitchen opens seamlessly into the inviting great room, complete with a cozy fireplace and a built-in sound system, creating the ideal setting for gatherings, movie nights, or relaxing at home. A separate living room and formal dining room provide additional space for hosting family and friends. A standout feature of this home is the impressive 500-square-foot first-floor fifth bedroom, traditionally designed as a media room. Complete with surround sound and a projector, this exceptional space is perfect for movie nights and entertaining. Its generous size also makes it an ideal primary or guest bedroom, home office, playroom, or recreation room-offering incredible flexibility. Upstairs, you'll find four generously sized bedrooms and well-appointed bathrooms, providing plenty of room for family, guests, or additional workspace.

166 Mccormick Ln, Middletown

$209,000

2 Beds ⋅ 2 Baths ⋅ 24193843 MLS ⋅ Hamlin Court BLDG.

This freshly painted townhouse-style condo offers 2 bedrooms, 1.5 bathrooms, newer windows, updated appliances, newer flooring throughout, and an open-concept layout. The main level features a spacious living room that flows into the dining area and kitchen, along with access to a private terrace. The kitchen includes tile flooring, a mosaic tile backsplash, and appliances replaced within the past three years. Upstairs are two bedrooms with spacious closets, a full bathroom, and convenient in-unit laundry with a new washer and dryer. Previously rented for $1,900 per month, this investor-friendly unit offers strong income potential. Additional features include a dedicated storage unit, one assigned parking space, and visitor parking. Ideally located within walking distance of Downtown Middletown, Wesleyan University, and Middlesex Hospital, with easy access to restaurants, shopping, and major commuter routes.

201 College St Unit 20, Middletown

$85,000

24192347 MLS

Approved 0.42-acre building lot offering the opportunity to build your custom single family or two family home. Public water, public sewer, and natural gas are available at the street. Ideally located just minutes from downtown Middletown, shopping, restaurants, parks, and major highways, this property offers the perfect combination of convenience and potential. Don't miss this opportunity to bring your vision to life!

672 E Main St, Middletown

$365,000

2 Beds ⋅ 2 Baths ⋅ 24191334 MLS

***Highest and Best by Monday July 27th at 50pm***Turnkey two-family investment opportunity on a quiet residential street in Middletown. Built in 1900 and offering 1,654 sq. ft. across two self-contained units, this property brings in reliable rental income with minimal upkeep thanks to durable vinyl siding and an architectural shingle roof. Combined the units offer 2 bedrooms and 2 full baths, plus additional flex space in each unit ideal for a home office or storage. The upstairs unit's primary bedroom includes its own walk-in closet, and each unit has private laundry hookups - a major draw for tenants. Recent updates include new luxury vinyl plank flooring and a modern kitchen island in one unit, while the other retains warm hardwood floors and classic charm. Large double-hung windows keep every room bright. Each unit enjoys its own private deck, and parking accommodates up to 4-6 vehicles across two parking areas. The 0.19-acre lot also includes a shared, fenced backyard.

200 E Ridge Rd, Middletown

$425,000

3 Beds ⋅ 3 Baths ⋅ 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

$229,900

3 Beds ⋅ 1 Baths ⋅ 24192281 MLS

Welcome to 21 Inverness Ln. Make this spacious 3 bedroom your new home. This home is nestled in the sought-after Highland Lake Community. The home features an open floor plan with generous sized rooms. Upon entering, you'll be met with an updated kitchen and a comfortable dining area. The adjacent family room features laminate flooring and sliders to a private fenced in patio complete with a pergola to shield you from the sun on scorching hot summer days. The upstairs features 3 spacious bedrooms, updated full bathroom, laundry nook and an area for den, office or media play. The 2-car garage also has an additional storage area off the back. You can enjoy single family home living without the extensive yard work. This home is waiting for your next summer party. Highest and best Sunday, 7/26 by 5:00 PM.

21 Inverness Ln, Middletown

$370,000

3 Beds ⋅ 2 Baths ⋅ 24190857 MLS

Beautifully maintained ranch offering the perfect blend of comfort, style, and functionality! This move-in-ready home features 3 spacious bedrooms and 2 full bathrooms, including a generous primary suite with a private en-suite bath. The bright and inviting living spaces are ideal for both everyday living and entertaining. A true highlight of the home is the stunning full-glass sunroom overlooking the expansive backyard, creating the perfect space to enjoy your morning coffee, unwind after a long day, or host family and friends year-round. An attached one-car garage and enclosed patio provide additional flexible space for entertaining, hobbies, or relaxing in every season. Conveniently located with central air conditioning and a thoughtfully designed layout, this home offers comfort, versatility, and pride of ownership throughout. Whether you're a first-time homebuyer, looking to downsize, or searching for your next home, this exceptional property is ready to welcome its new owners. Don't miss this incredible opportunity-schedule your private showing today!

417 Mile Ln, Middletown

$245,000

3 Beds ⋅ 2 Baths ⋅ 24192257 MLS ⋅ Beacon Hill Towne Homes BLDG.

Just renovated. Kitchen has just been remodeled with new counters, white cabinets, white backsplash and stainless steel appliances. 1st floor is tile floor and there is a pellet stove in corner of livingroom. 1/2 bath on main level has new toilet and vanity. 2nd level offers 2 bedrooms with walk in closets and laundry in hall. Floor's just refinished. 3rd level offers 3rd bedroom and a finished room that could be study, playroom or storage. Town records lists this as a 2 bedroom but incorrect. Carport in driveway and room for another car. Diagonally located across from pool.

45 Rising Trail Dr Unit 45, Middletown

$269,000

3 Beds ⋅ 2 Baths ⋅ 24191998 MLS

Investors are you looking for a charming 2/3 bedroom, 1.5 bath Colonial that is located on a quiet street in a desirable neighborhood, offering convenient location just minutes from the shops, restaurants, Wesleyan University, hospitals, and major healthcare centers? This is an excellent choice for anyone seeking an easy commute and access to everyday amenities. Filled with warmth and character, this inviting home is ready for its next chapter. Whether you're a first-time homebuyer, looking to make it your forever home, or searching for a great investment opportunity, this property offers endless potential. Add your personal touch and some love to make this charming Colonial truly your own while creating lasting memories for years to come. City water and city sewer. Don't miss the opportunity to own a home in a convenient and quiet location. Schedule your showing today and discover all that 153 Eastern Drive has to offer!

153 Eastern Dr, Middletown

$365,000

3 Beds ⋅ 2 Baths ⋅ 24187059 MLS

Tucked at the quiet end of a cul-de-sac on a level half-acre, this move-in ready split level delivers the one thing that's hard to find: it's already done. Extensively remodeled in 2018, the home blends timeless finishes with the kind of major updates buyers hope for but rarely get. A bright kitchen with granite counters and stainless appliances opens to warm, refined living space, where hardwood floors carry through and the baths have been tastefully reworked. The improvements extend well beyond the cosmetic, reaching the roof, siding, and windows along with the doors, garage, and central air. Three comfortable bedrooms rest upstairs, while a flexible finished lower level offers space for a variety of uses, and mud room space with easy walk-out access to the attached garage. Out back, the porch and hot tub wait for slower evenings. Nothing left here but to move in and enjoy.

24 Annette Pl, Middletown

$245,000

2 Beds ⋅ 2 Baths ⋅ 24191144 MLS ⋅ Cedar Ridge BLDG.

Welcome home to Cedar Ridge! This beautifully maintained 2-bedroom, 1.5-bathroom end-unit townhouse offers 1,319 square feet of bright, thoughtfully designed living space across three finished levels.The main level welcomes you with an expansive living room that flows effortlessly into an open-concept dining area and kitchen-complete with a spacious pantry and seamless access to your private Trex deck, perfect for morning coffee or evening relaxation. A tastefully updated half bath rounds out the main floor. Upstairs, you will find two generously sized bedrooms with excellent closet space, including a primary bedroom featuring direct "Jack and Jill" access to the full bathroom with its expansive double-sink vanity. The value continues in the fully finished, heated lower level! This versatile space features a dedicated laundry room and exterior walk-out access, making it the perfect setup for a home office, family media room, or fitness studio. Enjoy stress-free condo living with low maintenance, an assigned parking space right at your doorstep, and an ideal Middletown location just minutes from shopping, dining, and major commuter routes. Schedule your tour today and see everything this turn-key gem has to offer!

10 Countryside Ln Unit 1, 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

$175,000

1 Beds ⋅ 1 Baths ⋅ 24190931 MLS ⋅ Carriage Crossing BLDG.

Middletown's Best Buy! Excellent opportunity to own third floor one bedroom condo in desirable Carriage Crossing, a community known for it's distinct contemporary architectural features like vaulted ceilings and oversized windows. This unit features open floor plan with newer flooring through out and private balcony. The Carriage Crossing complex offers in ground pool, tennis court, fitness center and racquetball court. Conventionally located close restaurants, shopping and major highways (I91, 691, 5/15 and Route 9). Schedule your showing today and come see everything that 222 Carriage Crossing has to offer!

222 Carriage Crossing Ln Unit 222, Middletown

$399,900

3 Beds ⋅ 3 Baths ⋅ 24190665 MLS

Classic Colonial on a picture-perfect lot with sweeping pastoral views in one of Middletown's most scenic settings! This home offers solid bones, generous room sizes, and loads of potential for anyone ready to add their own touches. The sun-filled living room offers oversized windows and flows easily into the dining area, while the beamed family room delivers warmth and character with wood paneling and a brick fireplace. The eat-in kitchen features ample counter space, stainless appliances, and a picture window overlooking the private backyard. A main-level laundry room and half bath add everyday convenience. Upstairs you'll find three comfortable bedrooms, including a spacious primary suite with its own private bath and double closets, plus a second full bath off the hall. The finished lower level adds fantastic flexible space with a large recreation room and dry bar - perfect for movie nights, a home office, or gym. Step outside and this property truly shines: an expansive deck with covered gazebo overlooks a sprawling, level backyard bordered by mature trees and open field views - a wonderful setting for entertaining or simply unwinding at the end of the day. Additional highlights include a two-car garage, mini-split systems for efficient heating and cooling, and a peaceful country feel just minutes from shopping, schools, and Route 9. Opportunities to own this view, space, and charm don't come along often. Bring your vision and make it home!

9 Round Hill Rd, Middletown

$359,000

3 Beds ⋅ 2 Baths ⋅ 24190638 MLS

Welcome to 116 Schuyler Ave! This home is conveniently located on a dead end close to Middletown's shopping and restaurant district, highways, parks and more. This 3 bedroom home was built in 1890 and carries a lot of colonial charm like the incredible hardwood floors throughout, a fully finished attic, and built-in cabinets. The Main level has a full bathroom with a walk-in shower, living room, formal dining room, an eat-in kitchen, sunroom featuring 180 degree windows and French doors, and a mudroom located on the back of the home. The Upper Level has three bedrooms, and a full bath. The master bedroom has been opened up into a fourth bedroom to create a versatile primary space. Access to the third floor is a pull-down ladder in bedroom #2 and includes two finished rooms, floor to ceiling wood paneling, and built-in storage. The basement is fitted with a French drain, a new electric hot water heater, and storage space. *Primary bedroom not pictured

116 Schuyler Ave, Middletown

$349,900

4 Beds ⋅ 2 Baths ⋅ 24189620 MLS

Bring your growing family to this spacious colonial! 4 bedrooms with two on first floor. 2 full baths. Eat in kitchen. Living room with fireplace. Spacious room at top of staircase can potentially be 5th bedroom! Hardwood floors thru-out. Walk out basement to level yard. Deck. Whether you are a car enthusiast or need a lot of storage space, you will love the oversized detached 2 car heated garage with steel beam and loft area. Solar panels...see attachment

125 Stevens Ln, Middletown

$465,000

3 Beds ⋅ 3 Baths ⋅ 24140266 MLS

*Multiple offers received! Please submit offers by Thursday, July 15th at noon.* Move right into this light-filled, spacious high ranch nestled on a quiet, low-traffic street in the highly sought-after Riverbend neighborhood. A dramatic two-story foyer welcomes you into an open-concept main level designed for comfortable everyday living and effortless entertaining. The sun-drenched living room features soaring cathedral ceilings, a cozy fireplace, and flows seamlessly into the dining area with sliding doors leading to a spacious deck-perfect for indoor-outdoor living. Bamboo flooring extends through the dining area and updated kitchen, which boasts granite countertops, ample cabinetry, and all appliances included. The main level offers three generously sized bedrooms, including a private primary suite with en-suite bath and walk-in closet. A full hall bath serves the additional bedrooms. The finished walk-out lower level provides exceptional flexible living space with a large family room, a dedicated office or flex area, a full bathroom, -ideal for guests, working from home, or multi-generational living. Additional highlights include LVP flooring, central air conditioning, a two-car garage, a high-efficiency natural gas tankless wall-hung boiler providing both heat and hot water, roof (2018), and first-floor laundry with washer and dryer included.

15 Mulberry Ln, Middletown

$199,900

1 Beds ⋅ 1 Baths ⋅ 24190471 MLS ⋅ Carriage Crossing BLDG.

Welcome to the highly sought-after Carriage Crossing community! This beautifully renovated condo is completely move-in ready and offers the perfect combination of style, comfort, and convenience. The stunning new kitchen features modern cabinetry, updated countertops, and stainless steel appliances, while the fully renovated interior showcases fresh finishes throughout. Enjoy year-round comfort with central air conditioning and a bright, inviting layout designed for easy living. A spacious loft overlooking the main living area provides the perfect space for a home office, guest area, workout room, or additional living space, adding both character and versatility to the home. Carriage Crossing is one of Middletown's most desirable condominium communities, offering resort-style amenities including a clubhouse, fitness center, swimming pool, tennis courts, sauna, hot tub, racquetball court, and beautifully maintained grounds. Conveniently located just minutes from shopping, restaurants, downtown Middletown, Wesleyan University, and major highways, this turnkey home is perfect for owner-occupants or those looking for low-maintenance living. Come view it and make it yours!

198 Carriage Crossing Ln Unit 198, Middletown

$419,000

9 Beds ⋅ 5 Baths ⋅ 24190092 MLS

Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

71 E Main St, Middletown

$480,000

3 Beds ⋅ 3 Baths ⋅ 24188018 MLS

Nestled in the highly desirable South Farms neighborhood, this well-maintained home is filled with quality features and timeless appeal. Car enthusiasts and hobbyists will appreciate the impressive 4-car garage, offering exceptional space for vehicles, storage, or the perfect workshop. The spacious eat-in kitchen features granite countertops, abundant cabinetry, and generous workspace for cooking and entertaining. Throughout the home, you'll find an abundance of closet space in each of the 3 bedrooms. Hardwood floors lie beneath the carpeting, offering the opportunity to restore their original beauty. The expansive finished basement, complete with a full bath, additional laundry room, and cozy gas fireplace, provides the perfect setting for entertaining, relaxing, or creating the ultimate recreation space. The sunroom off the kitchen can also be used for a home office. A second gas fireplace in the living room adds warmth and charm, making this home inviting in every season. Step outside to enjoy the deck, complete with a retractable awning for shade on sunny days. Additional highlights include a full-house generator, walk-up attic, central A/C, laundry on the main floor and exceptional storage space throughout the home. Take advantage of all that Middletown has to offer with its many restaurants, cultural centers, and shopping. Close to I-91 and Rt 9. This home presents an exceptional opportunity for its next owner. Don't miss your chance to make it yours!

779 Ridge Rd, Middletown

$220,000

24188906 MLS

An exceptional opportunity to acquire a well-established restaurant that has successfully served the Middletown community for 26 years. This turnkey operation is strategically positioned in a high-traffic corridor surrounded by schools, office parks, medical facilities, and densely populated residential neighborhoods, generating consistent customer traffic and strong year-round demand. The business benefits from an efficient operating model, a loyal repeat customer base, and a fully trained, long-tenured staff already in place. With decades of successful operation, the restaurant has earned a strong reputation within the community and offers a proven foundation for continued growth and profitability. Recent renovations and upgraded kitchen equipment enhance the property's appeal and operational efficiency. The business is designed for smooth day-to-day management with minimal owner oversight, making it an ideal opportunity for an owner-operator or an experienced restaurant group seeking to expand its portfolio. To ensure a seamless transition, the current owner will provide comprehensive training and support at no additional cost.

280 Main St, Middletown

$499,999

4 Beds ⋅ 3 Baths ⋅ 24183267 MLS

****Highest and Best by Monday July 13 at 5:00pm.**** This beautifully maintained Colonial, tucked away on a quiet cul-de-sac, in the highly sought after Riverbend development is a must-see! Filled with natural light and abundant storage, this home also features two spacious decks for relaxing and entertaining. The sun-filled eat-in kitchen boasts soaring ceilings that extend to the second floor, creating an open and airy feel. Large windows flood the space with light, while direct access to the upper deck and adjoining family room make it ideal for everyday living and gatherings. The main level also offers a spacious living room with oversized windows that flows seamlessly into the formal dining room. Upstairs, the primary suite features a walk-in closet and a private full bath. Two additional bedrooms each include walk-in closets and share a full bath, while a fourth bedroom is currently being used as a home office. A conveniently located second-floor laundry room adds to the home's functionality. The finished lower level offers a generous recreation room with walkout access to the lower deck, along with entry to a third garage bay that provides exceptional space for storage, a workshop, or hobby area. With abundant storage throughout, versatile living spaces, and a desirable cul-de-sac location, this home is ready to impress. It's only minutes away from I-91 and Route 9 so commuting is no problem. HOA includes grounds maintenance and snow removal of common areas only.

175 Rolling Grn, Middletown

$319,900

2 Beds ⋅ 3 Baths ⋅ 24189364 MLS

Welcome to 824 Randolph Rd, Middletown! You'll fall in love with this beautiful ranch offering the convenience of one-floor living, a two-car garage, and an inviting in-ground pool with patio that's perfect for relaxing or entertaining. Step inside to find a bright, spacious living room with a beautiful fireplace, an eat-in kitchen with stainless steel appliances, and a dining room featuring a cozy wood stove. Most of the interior has been freshly painted, giving the home a fresh, welcoming feel throughout. The home offers two full bathrooms, plus a convenient half bath located just off the primary suite and with easy access to the pool-perfect for guests while entertaining. The expansive basement offers endless possibilities for a home gym, office, media room, or additional living space. Complete with energy-efficient solar panels, this home truly has something for everyone!

824 Randolph Rd, Middletown

$180,000

4 Beds ⋅ 2 Baths ⋅ 24189537 MLS

This contemporary 4-bedroom home offers a functional layout, great living space, and an excellent opportunity to add your personal touch! The first floor features a bright, open-concept kitchen with a stainless steel refrigerator and oven, seamlessly flowing into the dining area. The spacious living room has sliding glass doors that lead to a private deck with a storage shed. A convenient half bathroom is also located on the main level. Upstairs, you'll find four generously sized bedrooms, a full bathroom, and the convenience of a second-floor laundry area. An attached two-car garage provides plenty of parking and storage, while the fenced front yard offers added privacy and outdoor space. While the home could benefit from some cosmetic updates, including fresh paint and some new flooring on the second level, it presents an excellent opportunity to build instant equity. Conveniently located close to major highways, shopping, restaurants, and everyday amenities, this home offers both comfort and accessibility. Whether you're a first-time buyer, investor, or looking for your next project, this property is full of possibilities!

63 Braeburn Ln, Middletown

$1,299,000

24189275 MLS

Exceptional commercial opportunity in one of Middletown's busiest retail corridors. Situated on approximately 0.47 acres, this 5,115 SF commercial building offers outstanding visibility with average daily traffic counts of approximately 20,000 vehicles. Currently operating as an auto repair facility with five vehicle lifts, the property is well-suited for continued automotive use or redevelopment. Located in the desirable B-2 General Commercial Zone, this site offers tremendous flexibility for a variety of commercial uses, making it an excellent investment or development opportunity. Surrounded by established national and local businesses, the property benefits from strong exposure, convenient access to major roadways, and a thriving commercial environment. Whether you're looking to expand your existing business, invest in an income-producing property, or redevelop a prime commercial site, this is a rare opportunity to secure a highly visible location in one of Middletown's most sought-after business districts.

516 Washington St Unit 1, Middletown

$475,000

3 Beds ⋅ 2 Baths ⋅ 24188822 MLS

Some homes are built to impress. Others are built to be lived in. This extraordinary farmhouse does both. A charming covered front porch, framed by mature perennial gardens that bloom with the seasons, welcomes you home. It's the kind of place where evenings are best spent watching breathtaking sunsets as the sounds of nature replace the noise of the day. Inside, rustic charm blends seamlessly with modern design. Exposed beams, leathered granite countertops, and a stunning tile backsplash create a kitchen that is as beautiful as it is functional. Tucked behind the home, a detached viewing deck overlooks the neighboring tree farm, offering a peaceful retreat immersed in nature. Whether you're enjoying your morning coffee while listening to birdsong or simply taking in the ever-changing landscape, this setting provides a sense of tranquility that's hard to find. As evening falls, gather beneath the pergola around the fire pit, where laughter lingers and every night feels like a getaway. The primary bedroom offers its own private sanctuary with fireplace and private balcony overlooking the peaceful surroundings. This is more than a beautifully designed farmhouse-it's a home that celebrates simple pleasures, timeless craftsmanship, and a connection to nature. **HIGHEST AND BEST DUE 07/13 7PM**

364 Coleman Rd, Middletown

$284,500

2 Beds ⋅ 1 Baths ⋅ 24189063 MLS

Welcome home to this well-maintained 2-bedroom, 1-bath ranch offering easy one-level living and the perfect condo alternative. The inviting floor plan features a spacious living room, formal dining room, and an updated kitchen complete with stainless steel appliances. Beautiful hardwood flooring flows throughout much of the home, while recent updates, including a newer furnace, new hot water heater, and newer roof, provide added peace of mind. Relax with your morning coffee or unwind in the three-season porch overlooking the level, private backyard-ideal for gardening, entertaining, or simply enjoying the outdoors. Additional features include a one-car detached garage and a sought-after South Farms location close to shopping, dining, parks, and major commuter routes. Don't miss this wonderful opportunity to own a move-in-ready home in a desirable neighborhood!

4 Crown St, Middletown

$449,900

3 Beds ⋅ 2 Baths ⋅ 24188979 MLS

Lovingly cared for home set in a beautiful yard with mature plantings and natural rock outcroppings. Lots of space in this charming home including a sunroom surrounded by windows that opens to a deck. The eat-in kitchen with Corian counters and tile backsplash leads to the formal living and dining rooms. Three bedrooms, including the primary that is connected to a full bath, complete the main level. The lower level offers a cozy family room with wood stove, another room that can used as a guest room or office, and another full bath with shower stall and laundry. Other features and updates include a new central a/c system, new oil tank, and a two-car garage. Beautiful yard with perennial plantings and convenient location close to Rt 9 and less than 10 minutes to fabulous downtown Middletown with lots of dining and shopping. Welcome Home!

1258 Saybrook Rd, Middletown

Browse All Middletown CT Just Listed Properties for Sale

Middletown Just Listed Real Estate