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360 Chauncey Rd, Middletown
$345,000
3 Beds ⋅ 2 Baths ⋅ 24216264 MLS
Do you love downtown Middletown, but want to live in a quieter area? 360 Chauncey Road is the answer you're looking for! Enjoy what Middletown has to offer while being tucked away in a quiet area. This property offers 3-4 bedrooms, two full bathrooms, hardwood floors, harvey windows and a yard to enjoy. Throughout the home you'll find pockets of character that make it unique; the wood paneling on the ceilings, the bathroom trim, or the covered porch paired with a charming blue door. The eat-in kitchen has plenty of counter and cabinet space, all your needed appliances, and access to the brand new deck. The main floor bedroom is accompanied with a full bath and another potential bedroom, study, rec room, or dining room. Upstairs are the two spacious bedrooms with another full bath and crawl space storage. In the basement you'll find a ton of storage and future expandable space. Enjoy dedicated laundry space & shelving with access to outside. Outside, the back deck overlooks the level yard with plenty of tree cover for the Summer months and offering beautiful views in the Fall. Come check out 360 Chauncey Road and then head downtown to enjoy some of the incredible restaurants and shops Middletown has to offer, or hit the nearby hiking trails at Millers Pond or Crystal Lake! Updates include Brand new 2026 deck, 2021 plastic septic tank, 2022 well pump, 2026 well tank & water softener, 2019 roof, and AO Smith 2021 water heater. Take advantage of this well maintained home!

360 Chauncey Rd, Middletown
150 Millbrook Rd, Middletown
$340,000
4 Beds ⋅ 1 Baths ⋅ 24203998 MLS
Set on approximately 5.2 acres in Middletown, this historic 4-bedroom home offers a unique opportunity to enjoy space, privacy, and the character of an older property. Built in 1760, the home offers approximately 1,680 square feet of living space and plenty of room to explore the possibilities. The expansive parcel provides a peaceful setting with ample outdoor space for gardening, recreation, entertaining, or simply enjoying the privacy of your own property. Inside, the home offers four bedrooms and one full bath, providing a flexible layout with plenty of potential to make the space your own. The generous acreage creates opportunities for those looking for more land while still being conveniently located in Middletown. Whether you're looking for a property with history, land, or the opportunity to bring your own vision to life, 150 Millbrook Road is worth a look. Come see the property and discover its potential for yourself.

150 Millbrook Rd, Middletown
346 Main St, Middletown
$339,900
2 Baths ⋅ 24209376 MLS
Location, Location, Location! Nice 1482sf retail building in the heart of Main St. Middletown. High traffic area, property currently being used as smoke shop, but can fit many other retail needs. Building is Zoned B-1.

346 Main St, Middletown
42 Saybrook Rd, Middletown
$339,900
4 Beds ⋅ 2 Baths ⋅ 24210969 MLS
This is home is located convenient to Shopping center and route 9. First floor main bedroom. Addition four bedrooms on the upper level and a full bath one of the bedroom does not have a closet. Builtin hutch in the dinning area. Living room with fireplace. (never used) Hardwood floors under carpeting. Handicap Ramp A detached two car garage. Property to be sold in "as is" condition, Contingent upon probate approval. Easy to show

42 Saybrook Rd, Middletown
122 Newfield St Unit 3A, 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
17 E Lake Pl, 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
106 S Front St, Middletown
$319,999
3 Beds ⋅ 2 Baths ⋅ 24215963 MLS
WELCOME HOME to 106 S. Front Street, Middletown! Conveniently located near town with easy access to Route 9, this inviting 3-bedroom, 2-bath home offers comfortable living, charming details, and move-in-ready appeal. Inside, beautiful hardwood floors and fresh paint create a bright, welcoming atmosphere. The cozy living room fireplace adds warmth and character, while the relaxing sun porch provides the perfect spot for morning coffee, quiet reading, or unwinding at the end of the day. Outside, the lovely backyard offers plenty of room to gather, entertain, and enjoy the crisp autumn air-with space to create your own fire pit area... With its comfortable layout, inviting outdoor space, and convenient location, this home is ready for its next chapter-and it may not be available for long. Convenient Location, close to shopping, downtown with wonderful restaurants and Route 9 and the hospital easy commute. Don't miss the opportunity to make 106 S. Front Street yours! Schedule your private viewing and start imagining life in your new home today!

106 S Front St, Middletown
9 Burr Ave, Middletown
$314,900
3 Beds ⋅ 1 Baths ⋅ 24216947 MLS
Open house November 2nd 5pm-6pm Welcome to 9 Burr Avenue! This charming Colonial offers 3 bedrooms, 1 full bathroom, and 1,344 square feet of living space per public records. The home features a recently remodeled kitchen, updated within the past year, along with a finished walk-up attic that provides versatile additional space, ideal for a home office, hobby room, or bonus area. Additional improvements include a newer hot water heater, approximately one year old. Outside, enjoy a fully fenced backyard offering privacy and plenty of room for entertaining, outdoor gathering, or simply relaxing. This home is ready for its new owners! Property is being sold AS-IS

9 Burr Ave, Middletown
9 Magnolia Ave, Middletown
$285,000
4 Beds ⋅ 1 Baths ⋅ 24217261 MLS
Welcome to 9 Magnolia Place, a charming and well-maintained Middletown home offering an impressive list of thoughtful updates inside and out. Tucked along a quiet dead end, this 4-bedroom home combines character, comfort and many of the major improvements buyers appreciate. Recent updates include new kitchen cabinetry, new quartz countertops, sink and faucet, a metal range hood, and fresh interior paint throughout nearly every room, both hallways and the upper staircase. Approximately a year and a half ago, the first 10 feet of the exterior sewer line were replaced, another valuable improvement to the property. Additional improvements over the years include newer vinyl siding with insulation, energy-efficient double-pane replacement windows, a designer front entry door and surrounding structure, added attic/crawl-space and ceiling insulation, and an updated large shower/bath with generous built-in shelving. The home is equipped with an oil-fired Crown heating system, an above-ground oil tank, a newer A.O. Smith water heater and solar panels. The roof features high-performance asphalt shingles, reported by the seller to carry a 50-year rating and designed for winds up to 130 mph, along with updated gutters. Outside, enjoy a partially fenced backyard, storage shed and a wonderful covered rear deck overlooking the yard-a comfortable spot for morning coffee, outdoor dining or simply relaxing. A full unfinished basement with hatchway access provides additional storage

9 Magnolia Ave, Middletown
606 Congdon St W Unit 6, 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
732 Long Hill Rd Unit 732, Middletown
$275,000
3 Beds ⋅ 2 Baths ⋅ 24209665 MLS ⋅ Ridgely Condo Iii BLDG.
A great opportunity to own an end-unit townhouse in Middletown's Wesleyan Hills community! This 3-bedroom home offers 1,360 square feet of living space and a layout that lends itself to a variety of possibilities. The living room serves as the heart of the home, with a wood-burning fireplace that adds warmth and character. The adjoining space offers flexibility for a dining area, while the eat-in kitchen provides plenty of room for meal preparation and casual dining around the center island or kitchen table. Upstairs, three bedrooms offer comfortable accommodations and the opportunity to create spaces tailored to your needs. The primary bedroom features direct access to the full bathroom. A full basement with laundry adds valuable storage and extra flex space that could host a home gym or additional living or storage space. Central air provides added comfort throughout the warmer months. Set in a convenient Middletown location, this home is close to Wesleyan University, downtown shops and restaurants, and major commuter routes. Whether you're looking for your first home, a place to downsize, or an opportunity to add your personal touch, this end-unit townhouse is full of potential and ready for its next owner!

732 Long Hill Rd Unit 732, Middletown
12 Woodlot Ln, Middletown
$275,000
3 Beds ⋅ 3 Baths ⋅ 24216918 MLS
Welcome home to this charming contemporary styled home featuring 3 bedrooms, 1 full and 2 half bathrooms, 2 car garage and 1196 square feet of living space! The main level features an updated kitchen with granite counters, tiled flooring and backsplash! The open concept is great for entertaining! On the upper level, you will find the laundry room, a full bathroom, 3 bedrooms and another half bathroom in the master! Newer roof and replacement windows! Schedule your showing today!

12 Woodlot Ln, Middletown
675 Newfield St Unit 9, 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
180 Washington St, Middletown
$250,000
24209958 MLS
Great opportunity for builders and investors! This 0.35-acre vacant lot is conveniently located near Wesleyan University and Downtown Middletown, with easy access to Main Street, restaurants, and shopping. The City of Middletown's Land Use Department has confirmed that recent zoning changes allow for the potential development of up to 9 residential units, subject to city requirements and approvals. Other uses may also be permitted. Please see Additional Documents for more information on zoning and development possibilities.

180 Washington St, Middletown
212 Carriage Crossing Ln Unit 212, Middletown
$248,500
2 Beds ⋅ 2 Baths ⋅ 24209475 MLS ⋅ Carriage Crossing BLDG.
Rear first floor 2 bed/2 full bath unit at Carriage Crossing. It features the complex's trademark vaulted ceilings and wall of windows, with comfortable open plan of living room with fireplace, kitchen, and dining area. Enjoy in-unit laundry, central heat and air, and two private outdoor spaces. An active lifestyle is easy with outdoor pool, spa and exercise facilities, and tennis court, in this walkable neighborhood. Pet friendly and investors welcome. Conveniently located near shopping, dining, and commuter routes.

212 Carriage Crossing Ln Unit 212, Middletown
52 Trolley Crossing Ln Unit 52, Middletown
$240,000
3 Beds ⋅ 2 Baths ⋅ 24204011 MLS ⋅ Trolley Crossing BLDG.
THIS CONDO BUILDING IS FHA APPROVED! SELLER WILLING TO OFFER $5000 CREDIT TO BUY DOWN THE RATE. Welcome to Trolley Crossing in Middletown! This well-maintained three-bedroom, one-and-a-half-bath townhouse offers a comfortable layout with generously sized bedrooms and a spacious living room. The first floor features a convenient laundry room, half bath, and a well-equipped kitchen with an updated microwave and oven, dishwasher, and refrigerator replaced approximately two years ago. Major improvements include a 2022 furnace, newer water heater, brand-new windows with a lifetime warranty, and a new roof. Step outside and enjoy the private deck, perfect for relaxing or entertaining. The association also includes water and sewer, adding even more convenience to this move-in-ready home.

52 Trolley Crossing Ln Unit 52, Middletown
111 Knowles Ave Unit 111, Middletown
$235,000
2 Beds ⋅ 2 Baths ⋅ 24215455 MLS ⋅ Indian Hill BLDG.
Tremendous opportunity for an end unit townhome in a small, well managed complex just steps from Wesleyan University campus. Light and bright with a generous sized kitchen open to the living space. Both bedrooms are on the upper level and share access to a Jack and Jill full bath. Laundry is on the upper level and there is a half bath on the main floor. Ground level has garage and basement with ample storage area. Enjoy low maintenance living with a reasonable HOA and easy access to all downtown Middletown has to offer.

111 Knowles Ave Unit 111, 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
280 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
296 Carriage Crossing Ln Unit 296, Middletown
$217,500
2 Beds ⋅ 2 Baths ⋅ 24209330 MLS ⋅ Carriage Crossing BLDG.
Welcome to the desirable Carriage Crossing community, offering comfortable, low-maintenance living. The open-concept living and dining area features vaulted ceilings, oversized windows that fill the space with natural light, and a wood burning fireplace creating the perfect setting for relaxing. The kitchen well-appointed with stainless steel appliances and a breakfast bar. This layout creates an easy flow into the main living area with hardwood floors perfect for entertaining! BRAND NEW HVAC MAY 2026! Enjoy your own outdoor space, perfect for morning coffee, fall and summer evenings, or relaxing at the end of the day. The two spacious bedrooms provide comfortable retreats with closet spaces and a full private bathroom in each. In-unit laundry off the kitchen and exterior storage add everyday convenience. Carriage Crossing offers an array of amenities, including a swimming pool, clubhouse, fitness facilities, tennis and racquetball courts, and additional recreational spaces. Conveniently located near shopping, restaurants, Route 9, I-91, and the Cromwell area, this home combines an easy lifestyle with excellent everyday accessibility.

296 Carriage Crossing Ln Unit 296, Middletown
201 College St Unit 10, Middletown
$199,000
2 Beds ⋅ 2 Baths ⋅ 24205649 MLS ⋅ Hamlin Court BLDG.
Welcome to a bright and updated townhouse-style condo offering a comfortable layout and several features that set it apart. The first floor has been refreshed with luxury vinyl plank flooring and includes a spacious living area, dining space, and modern-style kitchen. Upstairs, two bedrooms are accompanied by a versatile bonus room featuring a vaulted ceiling and skylight, offering an ideal spot for a home office, reading room, gym, or creative space. Newer windows installed in 2020. One of the best highlights is the private composite deck overlooking the courtyard, creating an enjoyable outdoor space without the maintenance of a traditional yard. The unit also includes in-unit laundry, dedicated enclosed basement storage, 1 parking spot in the private lot and some overflow parking. With the association currently having capacity for rentals, this condo offers flexibility for an owner occupant or investor. Conveniently located next to Wesleyan's art building, near Downtown Middletown, Wesleyan University, shopping, dining, and major commuter routes. Cash buyers only.

201 College St Unit 10, Middletown
38 Trolley Crossing Ln Unit 38, Middletown
$148,000
1 Beds ⋅ 1 Baths ⋅ 24217926 MLS ⋅ Trolley Crossing BLDG.
Welcome home to this beautifully updated, first-floor, one-bedroom condo offering the perfect blend of comfort, convenience, and privacy! Featuring a spacious, open feel and a newer kitchen, this move-in-ready home has been tastefully renovated throughout. Enjoy the ease of one-level living with no stairs to navigate. Step outside to your screened-in back porch, the perfect spot to relax and unwind while enjoying the peaceful, secluded surroundings. Additional highlights include natural gas heat and AC with access to the community pool, ideal for those warm summer days. Centrally located in Middletown, with convenient access to shopping, dining, highways, and everyday amenities, yet tucked away in a private, tranquil setting. A wonderful opportunity for easy, low-maintenance living in a great location. Don't miss this one!

38 Trolley Crossing Ln Unit 38, Middletown
270 Burgundy Hill Ln Unit 270, Middletown
$139,900
1 Beds ⋅ 1 Baths ⋅ 24217655 MLS ⋅ Peppermill Village BLDG.
Investment Opportunity: Updated and leased condo in a quiet end building, conveniently located near 91 and RT 9. This top floor unit has two floors, with 1 bedroom, living/dining, and kitchen on the main floor, plus a spiral staircase to a bonus loft space with tons of windows and natural light. Soaring cathedral ceiling in the living area, plus a sliding door to rear balcony make this an easy unit to keep leased! New LVP flooring throughout, freshly painted, with all new appliances.

270 Burgundy Hill Ln Unit 270, Middletown
500 Washington St Unit #9, Middletown
$119,000
1 Beds ⋅ 1 Baths ⋅ 24204389 MLS
*** BRAND NEW MOBILE HOME - Modern, Stylish & Ready for You! *** Be the first to call 500 Washington Street #9 home! Located in Middletown Mobile Home Park, this brand-new 1-bedroom, 1-full-bath mobile home offers fresh, modern living with everything new from the start. A welcoming 6' front porch adds charm and the perfect spot to relax outdoors. Inside, enjoy a bright, thoughtfully designed interior featuring a beautiful kitchen with new stainless steel appliances, including refrigerator, dishwasher, microwave/hood vent, and upgraded smooth-top electric range. With 200-amp electrical service and an efficient, easy-to-maintain layout, this home offers comfort, convenience, and the peace of mind that comes with owning brand new. The new mobile home is now onsite with anticipated move-in availability November 13th. Why renovate when you can start fresh? Don't miss this opportunity to be the very first owner - schedule your showing and make #9 yours! ***Note: 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 #9, Middletown
Bow Lane, Middletown
$95,000
24208129 MLS
5.5 ACRES | MIDDLETOWN, CT DEVELOPMENT & INVESTMENT OPPORTUNITY Bring your vision to this approximately 5.5-acre parcel of raw, unimproved land in Middletown. An opportunity for builders, developers, investors, or buyers interested in exploring the property's future potential. Property is being sold in its current unimproved condition. Public assessor records indicate the parcel as landlocked. Buyer and buyer's representatives are responsible for conducting their own due diligence regarding legal access and/or easements, road frontage , subdivision and buildability, zoning and permitted uses, wetlands, septic and well requirements, utilities, surveys, engineering, road improvements, and any municipal or governmental approvals required for their intended use. Approximately 5.5 acres offering an opportunity for the right buyer to investigate the possibilities and potential of this Middletown property.

Bow Lane, Middletown
500 Washington St Unit #4, 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
18 Portland St, 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
Bow Ln, Middletown
$67,000
24210034 MLS
This unique parcel of land sits some 500 feet above the City of Middletown. While it has served me well as a peaceful recreational spot for the last 13 years, it is now time to let it go to someone else who might enjoy it. It's surrounded by other similar vacant and wooded plots of land due to there being no paved road or other services for some 800 feet in from the top of Bow Lane. Think 4-wheeling and dirt bike fun on the weekends while the rest of the family picnics under the shade awaiting your return. Potential buyers will need to do their own due diligence before they consider this purchase. No claims of suitability for any particular purpose are being represented, here. There is an easement in the deed requiring the owner to provide access to Bow Lane to the 5.5 acre parcel that sits directly behind this one. NOTE: At this time that parcel is also currently listed for sale.

Bow Ln, Middletown

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