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

2 Beds ⋅ 2 Baths ⋅ 24204426 MLS

*** BRAND NEW 2-BEDROOM, 2-BATH MOBILE HOME - Fresh, Modern & Ready for You! *** Welcome to 500 Washington Street #8 in Middletown Mobile Home Park! Be the first to call this brand-new 2-bedroom, 2-full-bath mobile home yours. Designed with modern comfort and easy living in mind, this beautiful home offers a fresh, stylish interior and the peace of mind that comes with owning brand new. At the heart of the home is a beautifully appointed kitchen featuring elegant Glacier Quartzite countertops and new stainless steel appliances, including refrigerator, dishwasher, microwave/hood vent, and upgraded smooth-top electric range. The desirable 2-bedroom, 2-bath layout provides added privacy and flexibility-perfect for a guest room, home office, or additional living needs. Additional features include 200-amp electrical service and an efficient, low-maintenance design. Mobile home scheduled to be delivered onsite October 9, 2026, with anticipated move-in availability October 30, 2026. Everything is new, and all that's missing is you! Don't miss your opportunity to be the very first owner-schedule your showing and make #8 your new home! ***Note: Home to be delivered and installed onsite. Sketch is a rendering of the New Mobile Home Model. Colors and Details may differ. New Mobile Home on Pad Site - Taxes to be determined. Purchaser to verify with local municipality. MMHP LLC - one of the parties to the LLC has an active real estate license ***

500 Washington St Unit #8, Middletown

$329,900

3 Beds ⋅ 2 Baths ⋅ 24201404 MLS ⋅ Arawana Estates BLDG.

Welcome to Arawana Estates, where historic charm meets modern comfort in a truly unique setting! Located within a beautifully converted mansion, this rarely available penthouse-style condo offers a spacious & distinctive layout filled with character & natural light. High ceilings, hardwood floors, recessed lighting, oversized windows & custom built-ins create a warm & inviting atmosphere throughout. The updated kitchen features crisp white cabinetry, leathered granite countertops with breakfast-bar seating, stainless steel appliances & a new Bosch dishwasher. Beautifully appointed baths offer granite finishes, subway tile & a relaxing soaking tub. The impressive primary bedroom is a standout, offering generous proportions, beautiful hardwood flooring, a fireplace & extensive custom built-in cabinetry & shelving. In-unit laundry & abundant storage add everyday convenience. Set within an intimate 6-unit community, Arawana Estates is surrounded by expansive lawns, mature trees, distinctive stonework & picturesque views, creating a peaceful & private setting just minutes from everything Middletown has to offer. Conveniently located near Wesleyan University, downtown Middletown, restaurants, shopping, parks, trails & public transportation. Veterans Memorial Park is also nearby, offering a community pool, splash pad & walking trails. A rare opportunity to own a one-of-a-kind residence combining historic architecture, modern updates, generous living space & beautiful surroundings.

122 Newfield St Unit 3A, Middletown

$329,000

3 Beds ⋅ 2 Baths ⋅ 24204544 MLS

***Seller is ready for the next chapter and welcomes reasonable offers*** Welcome home to this beautifully updated property tucked away on a quiet cul-de-sac offering privacy, ample parking, and a spacious backyard perfect for relaxing, entertaining, or enjoying the outdoors. Inside, you'll find an updated and upgraded kitchen and bathrooms, complemented by newer vinyl windows and a newer roof for added peace of mind. A large two-car garage provides plenty of room for vehicles along with valuable additional storage. Conveniently located near the Cromwell/Middletown line, this home is a commuter's delight with easy access to Route 9, Route 372, and I-91. Enjoy being just minutes from restaurants, shopping, supermarkets, Wesleyan University, Wadsworth Falls State Park, Powder Ridge Park and Resort and many other area amenities. Offering a great combination of privacy, convenience, updates, and accessibility, this home is ready for its next chapter. AS-IS sale. Inspection for buyers' information only. Some photos virtually staged for illustration purposes only.

17 E Lake Pl, Middletown

$749,900

4 Beds ⋅ 3 Baths ⋅ 24204169 MLS

NEW CONSTRUCTION MODERN COLONIAL Beautiful 4-bedroom, 21/2-bath Modern Colonial privately situated on 1.8 acres of rolling country hills. Currently under construction to be complete mid Nov. Exterior features include vinyl siding, Harvey windows, architectural shingles, Trex front porch with white railings, & paved driveway not yet complete. The lot will be professionally graded, topsoiled, and seeded. The approximately 2,232 sq. ft. home features 31/4" natural-finish white oak flooring, tile baths, square-edge flat trim, recessed lighting, & inset floor registers. The kitchen offers white shaker cabinets, quartz counters, navy-blue eat-at island, stainless farmhouse sink, built-in hood, propane stove, & an appliance allowance. The family room features a gas fireplace. The primary suite includes a coffered ceiling with crown molding, walk-in closet with custom shelving,& bath with double vanity, quartz counter, and walk-in rain-head shower. Four bedrooms include a flexible 4th bedroom/bonus room, plus second-floor laundry. Additional features include white bathroom vanities, quartz bath counters, hydro-air heating/cooling, Insta-hot combination boiler/hot water system, 200-amp service, well & septic, oversized 2-car garage with openers, unfinished basement, and Trex rear deck. Adjacent 2.8-acre lot also available, with plans for a home in the same Modern Colonial style. AI-enhanced photos of anticipated finished home/landscaping- actual appearances may vary

85 Freeman Rd, Middletown

$889,000

24203918 MLS

PERMIT IN HAND - READY TO BUILD! Located in the heart of Middletown and within walking distance of an abundance of downtown amenities, 54 Washington Street presents an exceptional redevelopment opportunity in a highly desirable location. Formerly home to the Italian American Club, this distinctive property offers both character and history while being fully positioned for its next chapter. The property has received zoning approval for conversion from a community/event space into 18 residential units, with additional space incorporated for a superintendent. A tremendous amount of the development work has already been completed. The property includes professionally engineered 18-unit build-out plans, along with stamped electrical and plumbing plans. With major building systems professionally designed, code-compliant, and permit-ready, a new owner can move directly toward the construction phase-eliminating much of the time, cost, and uncertainty typically associated with the planning and approval process. Adding even greater value, the Town has approved 18 parking spaces directly across the street, adjacent to the police station. For the savvy investor or developer seeking a residential conversion opportunity with approvals, plans, parking, and a prime downtown location already in place, 54 Washington Street offers a rare opportunity to step into a project that is truly ready to build.

54 Washington St, Middletown

$305,900

5 Beds ⋅ 2 Baths ⋅ 24203700 MLS

**Multiple Offers, Highest and Best Due EOD Wednesday, 9/9/26** Opportunity knocks in the heart of Middletown! This two-family home sits just minutes from Route 9, public transportation, and the Main Street corridor with its restaurants, shops, and year-round events. Live in one unit and have a tenant help pay your mortgage, or add a solid two-family to the portfolio - a great fit for owner-occupants and investors alike. Unit 1 has been freshly updated with new flooring, fresh paint, an updated kitchen and bath, and ceiling fans. Unit 2 offers a functional layout with an enclosed sun porch and its own private entry. Separate utilities, including two electrical panels and two heating systems, keep operating simple. Additional highlights include enclosed porches, new flooring and updates throughout, an open unfinished basement with plenty of storage, and off-street parking for multiple vehicles. Appliances will be provided with the right offer. Close to Wesleyan University, hospitals, parks, and commuter routes to Hartford and the shoreline. Easy to show - schedule today! Agent Owner

105 Spring St, Middletown

$435,000

3 Beds ⋅ 2 Baths ⋅ 24203125 MLS

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

147 Old Mill Rd, Middletown

277 Carriage Crossing Ln Unit 277, Middletown

$220,000

1 Beds ⋅ 1 Baths ⋅ 24202361 MLS ⋅ Carriage Crossing BLDG.

Welcome to 277 Carriage Crossing Lane, where soaring ceilings, a charming loft, and a beautiful fireplace create a home you'll love coming back to. The inviting layout offers a comfortable, open feel with a cozy kitchen and versatile loft space perfect for a home office, reading nook, creative space, or relaxing retreat. Curl up by the fireplace on a cool evening or step outside and enjoy the community pool and hot tub when it's time to unwind. Warm, welcoming, and full of character, this is a home that truly feels like your own. Come see it and imagine yourself here!

277 Carriage Crossing Ln Unit 277, Middletown

$399,900

3 Beds ⋅ 2 Baths ⋅ 24200766 MLS

Oversized Ranch with Incredible Outdoor Living! This 3 Bedroom, 2 full Bath home offers 1,236 sq. ft., a mighty 2-car attached garage, and a picture-perfect backyard oasis! The inviting foyer opens to an expansive Living Room/Dining Room combination featuring an attractive gas fireplace and sliders to an amazing deck, patio, and backyard. The bright, spacious eat-in Kitchen captures the morning sun and offers a generous breakfast nook and plenty of counter space. The laundry is conveniently located at the far end of the Kitchen. Down the hall are 3 good-sized bedrooms and a welcoming full bath. The Master Bedroom Suite features crown molding, a Master Bathroom with a walk-in shower, and a walk-in closet. Step outside to a sprawling 30' x 15' deck/patio plus an adjacent 12' x 9' patio, creating an exceptional retreat for relaxing or entertaining. The large, flat backyard gives you plenty of room to enjoy it all! The 30' long, cozy front porch is another perfect spot to relax and watch the sunrise. The basement is huge, completely open, ready for finish (Family Room, Game Room, Work Shop). Comfort and efficiency come from 2 split units for heating and A/C, plus a newer heat pump for efficient heating, cooling, and improved electric bills. There are also select baseboard units and radiant ceiling heat, with the split units providing the greatest efficiency. City water and sewer complete the package. The home you've been waiting for!

65 Murray St, Middletown

$85,000

3 Beds ⋅ 1 Baths ⋅ 24202339 MLS

Bring Your Vision to Life! This 3-bedroom single-family home offers approximately 1,300 square feet of living space and is situated on a quiet dead-end street. Featuring a cozy backyard and a layout with plenty of potential, this property is an excellent opportunity for buyers looking to renovate and create a home tailored to their style. With some updating and TLC, this home has the potential to truly shine. A great opportunity for a homeowner, investor, or renovator looking to add value and make it their own. Sold AS-IS

17 Miller St, Middletown

$365,000

4 Beds ⋅ 2 Baths ⋅ 24202551 MLS

Welcome to this beautifully remodeled two-family home ideally located within walking distance of vibrant downtown Middletown! This property offers the perfect blend of modern updates, spacious living, and unbeatable convenience. Both units have been fully remodeled with new appliances and updates throughout, making this an excellent opportunity for an owner-occupant, investor, or multi-generational living arrangement. Enjoy the added charm and versatility of enclosed back porches, perfect for relaxing, extra storage. A standout feature is the walk-up attic, offering approximately 650 additional square feet of living space-an incredible opportunity to create additional bedrooms, an office, recreation room, or whatever best suits your needs. Natural gas heat and hot water, separate utilities. Common laundry area in the basement with brand new washer and dryer. Step outside and enjoy everything Middletown has to offer, with parks, restaurants, shops, and downtown attractions all just a short walk away. Located in the heart of a lively and growing community, this home combines convenience, character, and future potential. Move-in ready, fully updated, and in a fantastic location-this is a two-family opportunity you won't want to miss!

74 Grove St, Middletown

$299,900

3 Beds ⋅ 2 Baths ⋅ 24201757 MLS ⋅ Ridgely Condo Ii BLDG.

Welcome to 774 Long Hill Road, a meticulously maintained 3-bedroom, 1.5-bath townhouse in the desirable Wesleyan Hills community. Lovingly cared for by the same owner for the past 20 years, this home offers durable, easy-care laminate flooring throughout and annually serviced mechanicals for added peace of mind. The spacious eat-in kitchen opens through sliding doors to a large private deck, perfect for outdoor dining and relaxation. A finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a new washer, thermal windows, low-maintenance vinyl siding, two parking spaces and a roof approximately 10 years old. Set across 288 scenic acres, Wesleyan Hills offers a truly special neighborhood setting with ponds, fields, wooded open spaces and approximately two miles of walking paths connected by charming footbridges and tunnels. The community is also home to the historic Barns at Wesleyan Hills, a picturesque event venue overlooking the water. Just moments away, the beautiful Wadsworth Mansion and surrounding parklands offer miles of additional trails, seasonal events and popular outdoor summer concerts. Enjoy peaceful surroundings and a wonderful sense of community, all just three miles from vibrant downtown Middletown.

774 Long Hill Rd Unit 774, Middletown

$1,200,000

3 Beds ⋅ 4 Baths ⋅ 24202531 MLS

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

145 Monarca Dr, Middletown

210 Carriage Crossing Ln Unit 210, Middletown

$249,900

2 Beds ⋅ 2 Baths ⋅ 24198658 MLS ⋅ Carriage Crossing BLDG.

Welcome to 210 Carriage Crossing Lane, a desirable end-unit condo offering comfort, convenience, and low-maintenance living in the popular Carriage Crossing community. This bright and inviting 2-bedroom, 2-bath home features an open floor plan with a vaulted ceiling and fireplace in the living room, creating a spacious and comfortable gathering area. The kitchen opens easily to the main living space, while in-unit laundry adds everyday convenience. Step outside to your private patio, perfect for relaxing or enjoying your morning coffee, with additional exterior storage for added functionality. Carriage Crossing offers an impressive selection of amenities, including a clubhouse, swimming pool, fitness center, and tennis/racquetball facilities. Conveniently located near shopping, restaurants, Route 9 and I-91, this end unit combines a great location with easy condo living. Whether you're looking for your first home, downsizing, or simply seeking a low-maintenance lifestyle, 210 Carriage Crossing is one you won't want to miss!

210 Carriage Crossing Ln Unit 210, Middletown

$89,900

2 Beds ⋅ 1 Baths ⋅ 24201126 MLS

*** Remodeled Home in Middletown Mobile Home Park *** Welcome to 500 Washington Street #4, a beautifully refurbished 1986 Peerless Supra offering fresh, move-in-ready living in a convenient Middletown location. This 14' x 60' home features 840 sq. ft., 2 bedrooms and 1 full bath, with extensive updates throughout. The brand-new kitchen shines with quartz countertops, new cabinetry, refrigerator, electric range, sink and faucet. Enjoy new flooring throughout, fresh interior paint, new closet doors and a new front door. The remodeled bath features a new tub/shower insert, vanity and toilet. Additional improvements include a brand-new central A/C system, new electrical line, added insulation, new skirting and stairs, plus new washer/dryer hookups. Thoughtfully refreshed from top to bottom, this inviting home combines modern finishes, comfort and low-maintenance living. Move right in and enjoy - Schedule your private showing today! (On new pad site - taxes to be determined. Purchaser to verify with local municipality.MMHP LLC - one of the parties to the LLC has an active real estate license.)

500 Washington St Unit #4, Middletown

$349,000

5 Beds ⋅ 2 Baths ⋅ 24201926 MLS

Welcome to this spacious 1952 Middletown Colonial, where classic charm meets low-maintenance living in a quiet neighborhood. Step inside a welcoming foyer with an entry closet that opens into a sun-drenched living area highlighted by a large bay window. The home features stunning hardwood floors throughout, flowing into a functional kitchen complete with natural wood cabinets, Corian countertops, a matching backsplash, and durable laminate flooring. Designed for effortless lifestyle flexibility, the main level hosts two bedrooms, including the primary bedroom, alongside a full bathroom with a tub/shower. Upstairs, you will find three additional bedrooms, perfect for a home office or private gym, and a second full bathroom with a tub/shower. The expansive basement is perfect for a hobbyist equipped with a dedicated tool workbench, storage shelving, and a laundry area with a washer and dryer. Outside, the home has low-maintenance vinyl siding and a cleared, level rear yard with mature landscaping and a handy tool shed. This prime location keeps you tranquil at home while placing you just minutes from Wesleyan University, downtown restaurants, nightlife, and scenic walks at Harborpark or Wadsworth Falls State Park. Commuting is a breeze with instant access to Route 9 and Route 66. This turn-key five-bedroom gem blends comfort, space, and ultimate Connecticut convenience.

130 Spencer Dr, Middletown

$369,900

3 Beds ⋅ 2 Baths ⋅ 24200173 MLS

Welcome to 46 Middlefield Street in Middletown! This beautifully remodeled home offers three bedrooms, two full bathrooms, and stylish updates throughout. The brand-new kitchen features sleek quartz countertops and modern finishes, creating an inviting space for cooking and entertaining. The refreshed interior combines contemporary style with comfortable, functional living spaces, making this home truly move-in ready. Conveniently located near shopping, dining, schools, and major routes, this property is an excellent opportunity for today's buyer. Schedule your private showing and see all this updated home has to offer!

46 Middlefield St, Middletown

$605,000

3 Beds ⋅ 3 Baths ⋅ 24201081 MLS

Welcome to 23 Brookview Lane, a spacious Colonial tucked into the desirable Westfield section of Middletown. Set in a beautiful residential community, this home offers a great combination of space, privacy, and a comfortable layout with plenty of room to grow. Inside, beautiful hardwood floors run through much of the main living area, while the fireplace creates a warm focal point and a perfect place to gather. The kitchen and dining areas offer plenty of room for everyday living and entertaining, with direct access to the rear deck overlooking the backyard. Upstairs, you'll find spacious bedrooms and a primary suite complete with its own private full bathroom and walk-in closet, giving the homeowners a comfortable space of their own. The additional bedrooms offer plenty of flexibility for family, guests, or a home office. Downstairs, the fully finished walk-out lower level adds another dimension to the home and can easily serve as a second family room, recreation space, office, gym, or playroom. One of the highlights of the property is the outdoor setting. Step out onto the deck and enjoy views of the private, lightly wooded backyard, creating a peaceful setting for morning coffee, summer gatherings, or simply relaxing at the end of the day. The attached two-car garage and sizable private driveway provide ample parking and additional convenience. Located just minutes from Spencer School, Middletown High School, shopping, restaurants, parks, and major commuter routes, Broo

23 Brookview Ln, Middletown

$349,800

3 Beds ⋅ 2 Baths ⋅ 24200848 MLS

Built in 2000 and located in the Westfield neighborhood , this single family home offers approximately 1934 finished square feet, three bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 11326 sqft lot. Seller WILL NOT ACTIVATE UTILITIES. View home, inspect and confirm all listing information prior to making offer. Seller will NOT allow water service to be turned on for any reason. Property sold "AS-IS" without contingencies. Please check with City/County/Zoning/Tax and other records to determine details to their satisfaction.

5 Lorraine Ter, Middletown

$779,000

6 Beds ⋅ 4 Baths ⋅ 24199581 MLS

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

44 Chamberlain Hill Rd, Middletown

$364,900

5 Beds ⋅ 3 Baths ⋅ 24199686 MLS

This well maintained colonial, located just steps from the bustling downtown of Middletown, is ready for its new owner! Three units, all on different floors, offer flexible plans for owner-occupants and investors alike! The first and second floor units are comfortably controlled with high efficiency Navien units, both with a 2 bed/1 bath layout. The third unit is also natural gas, and provides a generous sized 1 bed/1 bath unit. The units themselves are mostly updated, some with fresh paint and tile work tastefully done. A two car garage and off street parking provide ultimate convenience for owners and/or tenants. Lively flower beds decorate the front walkway, adding to the curb appeal. A back staircase seconds as small deck platforms overlooking the backyard. Whether living in one unit and renting the others for residual income, or adding this wonderful opportunity to your investment portfolio, this one is NOT to miss. Schedule your private showing today!

53 Spring St, Middletown

$449,900

3 Beds ⋅ 2 Baths ⋅ 24199578 MLS

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

147 Ridge Rd, Middletown

$555,000

4 Beds ⋅ 3 Baths ⋅ 24198723 MLS

Welcome Home! 85 Oakcliff is a beautifully updated 4-bedroom, 2.5 bath home in a desirable Middletown neighborhood, privately set back from the road. Featuring an updated kitchen, new windows throughout, remodeled baths and a finished walk-out basement with a full bathroom this home offers space, flexibility and privacy. The finished lower level provides potential for an in-law apartment or separate living space, subject to town approval, making it ideal for extended family, guests, a home office or recreation. The expansive deck overlooks a beautiful yard for entertaining, a game of catch or running with your favorite four legged pal. Close to major highways, 20 minutes from Downtown Hartford, 35 minutes to New Haven, 45 minutes to CT Casinos, a little over an hour to the Rhode Island line and minutes from Wesleyan University, great shopping and restaurants in downtown Middletown! Major updates include: Brand New Septic- 2019 Kitchen remodeled - 2024 All windows replaced - 2024 Basement remodeled - 2023 Garage doors replaced - 2023 Full bathroom remodeled - 2022 AC air handler & condenser - 2021 Electrical upgrades & generator hookup - 2021 Well pump - 2021 Front door - 2021 Paver walkway & gutter/fascia improvements - 2020 Chimney repair & cap - approx. 2019 Boiler -2014 With a private setting, extensive updates, 4 bedrooms, 2.5 baths and a versatile walk-out lower level, this Middletown Colonial is ready to welcome its next owner!

85 Oakcliff Rd, Middletown

$279,900

2 Beds ⋅ 2 Baths ⋅ 24199007 MLS ⋅ Luther Ridge At Middletown Condos BLDG.

Designed for convenient one-floor living, this well-maintained home features 2 bedrooms and 2 full bathrooms with a bright, open floor plan. The kitchen offers warm cherry cabinetry, a dishwasher, and plenty of functionality, while tile flooring throughout provides easy maintenance. Enjoy the comfort and efficiency of central air, natural gas heat, and natural gas hot water. This is a wonderful opportunity for those seeking a smaller community and low-maintenance lifestyle. One owner must be 60 years of age or older. Move right in and enjoy easy, single-level living!

606 Congdon St W Unit 6, Middletown

$245,000

3 Beds ⋅ 2 Baths ⋅ 24199236 MLS

Cute 3-bedroom Cape with loads of potential! The spacious living room features a cozy fireplace and sliders leading to a private backyard-perfect for relaxing or entertaining. An open kitchen flows into the dining room, creating a comfortable layout for everyday living. Conveniently located near major roads while tucked away in a quiet neighborhood. The home needs some TLC, but the possibilities are endless to make it your own and add your personal touches!

46 Meech Rd, Middletown

$429,000

3 Beds ⋅ 2 Baths ⋅ 24196637 MLS

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

76 George St, Middletown

$649,000

4 Beds ⋅ 3 Baths ⋅ 24197740 MLS

Nestled in the sought-after Chimney Hill neighborhood, this spacious Colonial offers over 4,200 square feet of thoughtfully designed living space on a beautifully landscaped lot. The home features 4 bedrooms, 2.5 bathrooms, a bright, open floor plan, generous living and dining areas, and a spacious kitchen perfect for everyday living and entertaining. The family room provides a warm gathering space, while the primary suite offers a private retreat with ample closet space and an en-suite bath. Additional highlights include a two-car attached garage, a large backyard ideal for outdoor entertaining, and a prime location just minutes from downtown Middletown, Wesleyan University, shopping, dining, parks, and major commuter routes. This is a rare opportunity to own a beautiful home in one of Middletown's most desirable neighborhoods.

20 Chimney Hill Rd, Middletown

$1,500,000

2 Baths ⋅ 24196708 MLS

942 Washington Street presents a prime commercial investment opportunity in the heart of Middletown's busiest retail corridor. Positioned on the heavily traveled Route 66, with an average daily traffic count of approximately 20,000 cars, this property offers exceptional visibility and exposure for investors and end users alike. Surrounded by national retailers including Wendy's, McDonald's, AutoZone, and Home Depot, the location benefits from strong neighboring businesses and consistent consumer traffic. This high-profile commercial property is ideal for retail, restaurant, or service uses, or for redevelopment, and represents a valuable addition to any investment portfolio. Washington Street remains one of Middletown's most active commercial corridors, offering convenient access, strong demographics, and long-term growth potential. Don't miss the chance to secure a property in one of the city's most sought-after business locations.

942 Washington St, Middletown

$415,000

4 Beds ⋅ 2 Baths ⋅ 24197069 MLS

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

104 Bell St, Middletown

$495,000

3 Beds ⋅ 2 Baths ⋅ 24194620 MLS

Turnkey and beautifully maintained, this inviting home is nestled in a well-kept Middletown subdivision. The open-concept main level features a bright kitchen with granite countertops, a dining area and a comfortable living room - all flowing seamlessly together. Step outside the French doors to a fenced in spacious patio surrounded by low-maintenance turf, creating a peaceful retreat with no grass to mow. A private pool offers the perfect place to cool off on hot summer days or unwind during quiet evenings. The main level also includes a family room, a full bathroom, and a flexible home office that can serve as a fourth bedroom. Upstairs, you will find the primary bedroom, two additional bedrooms, and a second full bathroom with granite finishes. Hardwood floors run throughout the home, complemented by tile in the kitchen and bathrooms. The home's mechanical systems have been carefully maintained and include a top-of-the-line Buderus system also a new installed Heat Flow water heater. Enjoy easy access to Middletown's vibrant downtown dining scene, as well as Routes 9 and 91 for easy commute travel to Hartford and New Haven.

17 Coles Rd, Middletown

$399,999

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

$257,000

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

Desirable Newfield Commons! Welcome to this sunny townhouse in a quiet complex near shopping 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. Super spacious primary suite and bath with double sinks. This is the perfect place to start out. Some upgrades will make this home shine, but well-loved for years. Visitor parking and a walk-out basement too!

675 Newfield St Unit 9, 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

$419,000

8 Beds ⋅ 4 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

$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

$1,000,000

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

$410,000

6 Beds ⋅ 2 Baths ⋅ 24188066 MLS

Turnkey multifamily for owner occupied or investment opportunity in a desirable Middletown location! This fully remodeled property offers strong income potential with updated units featuring modern kitchens, renovated bathrooms, new flooring, and contemporary finishes throughout. The building has been well maintained and provides an excellent opportunity for investors seeking a low-maintenance asset with immediate cash flow. Conveniently located near downtown Middletown, shopping, restaurants, schools, parks, and major highways, making it attractive to tenants and ensuring long-term rental demand. Whether you're expanding your portfolio or acquiring your first investment property, this move-in-ready multifamily is an opportunity you won't want to miss. Being SOLD AS-IS.

163 Pearl St, Middletown

$390,000

7 Beds ⋅ 2 Baths ⋅ 24188106 MLS

Owner occupied or investors! Fully renovated investment opportunity in the heart of Middletown! This well-maintained 7 bedrooms 2 bath, multifamily property has been completely remodeled and offers immediate cash flow with tenants already in place. Each unit is currently rented, providing strong and stable rental income from day one. Updates include modern kitchens, renovated bathrooms, updated flooring, fixtures, and mechanical improvements throughout. The property has been thoughtfully upgraded while maintaining its charm and functionality. Ideal for investors seeking a turnkey asset with reliable tenants and minimal deferred maintenance. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Don't miss this opportunity to add a fully occupied, income-producing property to your portfolio. Being SOLD AS-IS. OWNER/AGENT.

194 Liberty St, Middletown

$898,000

4 Beds ⋅ 5 Baths ⋅ 24187393 MLS

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

49 Partridge Ln, Middletown

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 24187574 MLS

Nestled on an extraordinary 39-acre estate with breathtaking panoramic views, this stunning custom log home offers the perfect blend of rustic elegance, modern comfort, and exceptional investment potential. Originally built in 2005 with an addition completed in 2014, the home features 4 bedrooms and 3 full bathrooms. The interior showcases soaring cathedral ceilings, beautiful tile flooring, ceiling fans throughout, and a dramatic two-sided fireplace that serves as a focal point for multiple living areas. German-engineered windows with roll shutters & premium German doors provide exceptional quality. Kitchen features new appliances & an open concept. 2 bedrooms with full bathrooms on the main level offer one-floor living options. The lower level includes 2 oversized garages providing abundant storage, workshop space, and room for recreational equipment. A wood/storage shed adds even more utility. This home is in pristine condition with brand new well, new water heater, and 2 central air units. The property consists of three separately deeded parcels presenting a rare opportunity for future investment, development, or resale. The land features rolling acreage, mature trees, open spaces, and a picturesque man-made pond. Whether you're seeking a private retreat, recreational haven, family compound, or property with investment upside, this one-of-a-kind estate delivers stunning natural beauty, exceptional craftsmanship, and limitless possibilities.

1409 Millbrook Rd, Middletown

$75,000

5 Beds ⋅ 3 Baths ⋅ 24182301 MLS

Opportunity awaits at this 2-family residential property in a convenient Middletown location. The existing structure has sustained fire damage and is being offered strictly as-is. Ideal for investors, contractors, or buyers seeking a renovation or redevelopment project. Situated on a level lot with access to public water and public sewer. Close to shopping, dining, parks, and commuter routes. A unique chance to restore, reimagine, or rebuild subject to municipal approvals.

18 Portland St, Middletown

$1,300,000

10 Baths ⋅ 24184246 MLS

Welcome to 480 Main Street, Middletown - a rare investment opportunity in the heart of Downtown Middletown! This stunning brick mixed-use building blends timeless character with strong income-producing potential. Featuring 8 spacious residential units, each offering 900+ square feet, soaring ceilings, beautiful hardwood flooring, functional built-ins, and oversized layouts that tenants love. Seven of the Eight residential units have been updated, and many feature newer hot water heaters, helping minimize future capital expenses. The property is anchored by two commercial storefronts, including a 3,100 SF space and a 1,100 SF (long-term tenant). Commercial tenants contribute approximately 40% of CAM expenses, creating additional value for ownership. Featuring classic brick construction, a well-maintained roof, and a prime downtown location, 480 Main Street offers a rare blend of character, stability, and investment potential. Located just steps from restaurants, shopping, and entertainment, this is an excellent opportunity to own a standout mixed-use asset in the heart of Middletown

480 Main St, Middletown

$1,300,000

8 Beds ⋅ 10 Baths ⋅ 24182655 MLS

Welcome to 480 Main Street, Middletown - a rare investment opportunity in the heart of Downtown Middletown! This stunning brick mixed-use building blends timeless character with strong income-producing potential. Featuring 8 spacious residential units, each offering 900+ square feet, soaring ceilings, beautiful hardwood flooring, functional built-ins, and oversized layouts that tenants love. Seven of the Eight residential units have been updated, and many feature newer hot water heaters, helping minimize future capital expenses. The property is anchored by two commercial storefronts, including a 3,100 SF space and a 1,100 SF (long-term tenant). Commercial tenants contribute approximately 40% of CAM expenses, creating additional value for ownership. Featuring classic brick construction, a well-maintained roof, and a prime downtown location, 480 Main Street offers a rare blend of character, stability, and investment potential. Located just steps from restaurants, shopping, and entertainment, this is an excellent opportunity to own a standout mixed-use asset in the heart of Middletown

480 Main St, Middletown

$649,900

4 Beds ⋅ 4 Baths ⋅ 24183475 MLS

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

76 Thimble Rock Rd, Middletown

$3,990,000

4 Baths ⋅ 24182009 MLS

Rare opportunity to acquire a prominent mixed-use commercial asset in the heart of downtown Middletown, one of Connecticut's most dynamic and rapidly growing commercial districts. Situated along the highly desirable Main Street corridor, this approximately 39,000-square-foot building offers exceptional visibility, strong foot traffic, and a strategic location surrounded by restaurants, retail destinations, entertainment venues, professional offices, and ongoing redevelopment projects. The property has benefited from significant capital improvements and renovations, creating an attractive blend of historic character and modern functionality. Its diverse tenant mix and flexible layout provide a wide range of opportunities for investors and owner-users alike. Downtown Middletown continues to attract substantial public and private investment, fueling economic growth and increasing demand throughout the area. Surrounded by a vibrant mix of businesses, restaurants, cultural attractions, and major employers, this property is ideally positioned to benefit from the continued revitalization of the downtown corridor. With convenient access to Route 9, Interstate 91, and the greater Hartford and New Haven markets, 423-425 Main Street offers a rare combination of scale, visibility, and location in one of Connecticut's most sought-after commercial districts.

423 Main St, Middletown

$1,300,000

12 Beds ⋅ 8 Baths ⋅ 24178851 MLS

Unique mixed-use opportunity in Middletown offering strong cash flow and flexible ownership potential. Property consists of a fully occupied 4-family, a fully occupied 2-family, and two 1,600 SF commercial garage/workshop spaces all situated on one lot with views of the Connecticut River and Arrigoni Bridge. One commercial space is leased, while the second vacant garage offers ideal owner-user potential for contractors, storage, workshop space, or additional rental income. Projected 8.2% cap at current occupancy, with stabilization potential of approximately 9.4-9.8% upon lease of the 2nd garage. Residential units feature a desirable mix of 1-, 2-, and 3-bedroom layouts with updates completed over time, including newer boilers and water heaters. Off-street parking, minutes to Route 9, downtown Middletown, and walking distance to Wesleyan University. Property conveyed as-is.

13-15 Portland St, Middletown

$849,900

5 Beds ⋅ 4 Baths ⋅ 24177933 MLS

Tucked away on a quiet, highly desirable cul-de-sac of only 7 homes in the sought-after South Farms district, this beautifully crafted 5-bedroom, 3.5-bathroom colonial features a stunning brick-front facade and exceptional curb appeal. Boasting a coveted 3-car attached garage, the home greets you with an abundance of natural light and gleaming hardwood floors flowing seamlessly throughout the main and upper living areas. The spacious, well-designed layout is perfect for both effortless entertaining and comfortable daily living, offering a generous floor plan with an ideal flow. The Ultimate Flexible Space: The true crown jewel of this property is the fully finished walk-out basement that adds an additional 1,070 sq/ft! Configured as a complete, self-contained in-law apartment, this private lower level includes its own separate entrance, full kitchen, living space, bedroom and bath-absolutely perfect for multi-generational living or long-term guests. Situated in a fantastic location, this home offers the generous space you need, the classic aesthetic you desire, and the unique floor plan flexibility that is so incredibly hard to find. Don't miss this versatile gem!

29 Copper Beech Dr, Middletown

$225,000

3 Beds ⋅ 2 Baths ⋅ 24176493 MLS ⋅ Ridgely Condo BLDG.

Nestled in the highly sought-after Wesleyan Hills community, this well-maintained and affordable 3-bedroom condo offers the perfect blend of comfort, convenience, and privacy. Featuring an open floor plan, the home boasts an updated kitchen that flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. A sliding glass door leads to your own private deck overlooking a peaceful, quiet setting. The finished walk-out lower level provides additional flexible living space ideal for a family room, home office, or gym. Conveniently located just minutes from downtown Middletown, Wesleyan University, Middlesex Hospital, shopping, restaurants, and major highways, this property offers easy access to everything while still enjoying a serene neighborhood atmosphere. Enjoy nearby parks, hiking trails, golf courses, and the Connecticut River waterfront. A wonderful opportunity to own in one of Middletown's most desirable communities

714 Long Hill Rd Unit 714, Middletown

$679,900

24175820 MLS

Exceptional opportunity to own a beautifully maintained commercial property in one of Middletown's most desirable and visible locations. Currently operating as a professional attorney's office, this versatile building offers endless potential for professional, medical, office, boutique, or mixed-use possibilities. Perfectly positioned across from the historic town green and hospital, and just moments from downtown restaurants, shops, and major commuter routes, the location offers outstanding convenience and exposure. Blending timeless historic charm with modern updates, the property features an inviting entrance, impressive grand staircase, and a tastefully updated interior that preserves elements of the home's original character while incorporating modern finishes and functionality. Dedicated off-street parking, with charging for your EV, provides added convenience for clients and staff. The upper level offers exceptional flexibility with an updated full kitchen featuring quartz countertops, a luxurious full bath with a full tile shower, and two bedrooms. Ideal for an owner-occupant or live/work setup, you can simply walk downstairs to work each day. The sellers have also obtained city approval for a future rooftop expansion, creating the opportunity for an upscale rooftop terrace or executive entertaining space overlooking the downtown setting. A rare landmark-style property combining character, convenience, and future potential in an unbeatable location.

27 Pleasant St, Middletown

$950,000

24174532 MLS

This property abuts 35 acres of mixed conservation land and offers views of the Connecticut River and two nearby state parks, ensuring the scenery will remain protected and undeveloped. The spectacular, lightly wooded parcel is the result of combining three approved lots within the River Park Subdivision to create one exceptional private homesite with breathtaking river views. Underground electrical is already in place-just bring your plans. The property is easily accessible via approved private roads maintained by an association, with a properly constructed 18-foot wide gravel Scovill Road.

Scovill Rd, Middletown

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