Middlesex, CT Homes

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  $634,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  604 Higby Rd, Middletown, CT 06457

  The Ranch. One floor living at its best offering old world charm with all the modern conveniences. Approximately 8'x8' front covered porch leads you to the dramatic entry of this abode. The large primary suite will impress with large walk in closet, spacious en suite offering an oversized walk in tile shower and vanity with double sinks. The great room is amazing with large kitchen and island

  Mark Toledo Berkshire Hathaway NE Prop.

  604 Higby Rd, Middletown, CT 06457
• 

  $692,000 Sold Jun 20, 2025

  • 4,382 Sq Ft
  • $158/SF
  • 91 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2000

  34 Watch Hill Dr, Middletown, CT 06457

  Set high on Watch Hill, this stunning 3-4 bedroom, 2.5-bath Colonial offers breathtaking views and over 4,382 SqFt of living space on a 1.04-acre lot. The main level features gorgeous hardwood floors, a formal dining room, and a spacious living room with a cozy wood-burning fireplace. The chef's kitchen is a dream, with granite countertops, stainless steel appliances, a wall oven, a glass

  Joe Cafasso mygoodagent

  34 Watch Hill Dr, Middletown, CT 06457
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  Est $134,849 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 704 Sq Ft

  1251 Washington St Unit 5, Middletown, CT 06457

  1251 Washington St Unit 5, Middletown, CT 06457
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  $619,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  603 Higby Rd, Middletown, CT 06457

  This beautiful Cape with 1st floor primary offers it all. You will enjoy the classic historic Cape look on the exterior, framed by a center chimney with a brick-look style. The inside is wow! You walk into an oversized entry boasting an open staircase offering vaulted ceilings in entry and 2 story front/flex room. You will make your way to the back of the home which is one entire great room

  Mark Toledo Berkshire Hathaway NE Prop.

  603 Higby Rd, Middletown, CT 06457
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  $350,000 Sold Jun 20, 2025

  • 1,959 Sq Ft
  • $179/SF
  • 149 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  233 Barbara Rd, Middletown, CT 06457

  Tudor-Style Home simply oozing with charm in Middletown, CT! Step into timeless elegance with this vintage 1930 built home that offers an abundance of charm, space, and unique features. Nestled in a cute Middletown neighborhood, this residence is the perfect blend of classic details and modern conveniences. Key Features: Expansive Family Room with soaring cathedral ceilings and wood floors create

  Lisa McCarthy Coldwell Banker Realty

  233 Barbara Rd, Middletown, CT 06457
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  Est $374,570 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,822 Sq Ft

  122 Sisk St, Middletown, CT 06457

  122 Sisk St, Middletown, CT 06457
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  $632,400 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  602 Higby Rd, Middletown, CT 06457

  Expanded Colonial I - this stately home offers a spacious and dramatic first floor with two story entry and double sided balcony overlook. The large kitchen is open to eating area and large great room. One will enjoy a mudroom, first floor office and fantastic sized dining room. This amazing abode offers plenty of large windows throughout letting the outside in. The upstairs offers an oversized

  Mark Toledo Berkshire Hathaway NE Prop.

  602 Higby Rd, Middletown, CT 06457
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  $255,000 Sold Jun 17, 2025

  • 1,260 Sq Ft
  • $202/SF
  • 22 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1977

  92 Cynthia Ln Unit B6, Middletown, CT 06457

  Welcome to this beautifully maintained 3-bedroom, 1.5-bathroom end unit condo offering 1,260 square feet of comfortable living space. Freshly painted throughout, this bright and airy home is move-in ready! The spacious living and dining areas are perfect for entertaining or relaxing, with plenty of natural light flowing through large windows. The kitchen offers ample cabinet space and a

  EMILY Milano Kings of the House LLC

  92 Cynthia Ln Unit B6, Middletown, CT 06457
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  Est $178,318 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  274 Carriage Crossing Ln, Middletown, CT 06457

  274 Carriage Crossing Ln, Middletown, CT 06457
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  /3

  $609,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,214 Sq Ft

  601 Higby Rd, Middletown, CT 06457

  The Greek Revival offers a classic 1700's look with a grand open modern floor plan. 2 story entry, first floor office, mud room, open great room and upstairs laundry. Some possible options include front porch and extended dining room. The large upstairs primary bedroom offers an incredible walk in closet and an en suite with soaking tub and walk in tile shower. Some additional standard features

  Mark Toledo Berkshire Hathaway NE Prop.

  601 Higby Rd, Middletown, CT 06457
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  $130,000 Sold Jun 17, 2025

  • 706 Sq Ft
  • $184/SF
  • 62 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1987

  206 Burgundy Hill Ln Unit 206, Middletown, CT 06457

  BACK ON THE MARKET. BUYER'S FINANCING FELL THROUGH. Welcome to your personal sanctuary! First floor living at its best! Step into this renovated 2-bedroom ranch-style condo nestled in a beautiful complex. The kitchen features new granite countertops, a refreshed bathroom, and a spacious living room/dining area that opens onto your private deck through sliding doors. Whether you're seeking an

  Katrina Pratt Rainbow Realty

  206 Burgundy Hill Ln Unit 206, Middletown, CT 06457
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  Est $678,476 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,178 Sq Ft

  40 Annello Way, Middletown, CT 06457

  40 Annello Way, Middletown, CT 06457
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  /3

  $499,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft

  600 Higby Rd, Middletown, CT 06457

  Stunning Contemporary Raised Ranch with multiple gables and large picture window in 2-story entry. Open great room, dining room and kitchen with center island. With standard 9' ceilings - vaulted ceilings optional. 2-story entry with open railing. Gas fireplace, deck, hardwood throughout including bedrooms on main level. All bathrooms tiled. Granite countertops throughout. Large base molding

  Mark Toledo Berkshire Hathaway NE Prop.

  600 Higby Rd, Middletown, CT 06457
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  $400,000 Sold Jun 16, 2025

  • 1,290 Sq Ft
  • $310/SF
  • 45 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1961

  570 Atkins St, Middletown, CT 06457

  Must see updated ranch located in desirable Westfield section of Middletown. The town lists house as having 3 bedrooms but has a possible 4th bedroom/office in the finished walkout basement along with a spacious family room with view and access to patio and your private back yard. The kitchen opens to living room creating a very functional great room. Laundry is located on the main floor. The

  Francine McKiernan Clermont Real Estate

  570 Atkins St, Middletown, CT 06457
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  Est $293,678 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,368 Sq Ft

  24 Spencer Dr, Middletown, CT 06457

  24 Spencer Dr, Middletown, CT 06457
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  /5

  $719,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  462 Higby Rd, Middletown, CT 06457

  Price Reduced! 4 bedroom home in a country setting near elementary school. Close to highway. Propane fired hydro-air heating and cooling. On floor plan. Gas fireplace, oak flooring, walk-in closet, tile shower in master suite, main bath. lot size is a flat acre and half with city water. Under construction.

  David White OwnerEntry.com

  462 Higby Rd, Middletown, CT 06457
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  $500,000 Sold Jun 16, 2025

  • 1,964 Sq Ft
  • $255/SF
  • 96 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1900

  24 Burr Ave, Middletown, CT 06457

  Welcome to this Beautifully Renovated 3 Family Home. Nestled in the heart of Middletown. This property is perfect for investors or Owner-Occupant. Looking for a turnkey property look no further! Conveniently situated near downtown Middletown, Middlesex Hospital and Wesleyan University.This property offers, easy access to shopping, dining, and entertainment.Newer siding and windows in 2010,Roof

  Shari Jones Coldwell Banker Realty

  24 Burr Ave, Middletown, CT 06457
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  Est $349,440 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,121 Sq Ft

  158 Russell St, Middletown, CT 06457

  158 Russell St, Middletown, CT 06457
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  $669,995 New Construction

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  123 Webster Ln, Middletown, CT 06457

  Founders' Ridge Award-Winning 55+ Adult Community! Introducing our model home, the "STOW IV," at 123 Webster Lane has 1,555 square feet of one-level living in the highly sought-after Westfield section of Middletown. This home features many high-end upgrades, including 9-foot ceilings, white wood cabinets with quartz countertops, hardwood floors in the living areas and bedrooms, and tile in the

  Phyllis Bysiewicz Berkshire Hathaway NE Prop.

  123 Webster Ln, Middletown, CT 06457
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  $217,740 Sold Jun 13, 2025

  • 2,292 Sq Ft
  • $95/SF
  • 6 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1887

  14 Walnut St, Middletown, CT 06457

  Excellent opportunity to own this duplex style home featuring a total of four bedrooms and two full bathrooms, with an overall living area of 2,292 square feet. Each unit consists of two bedrooms and one full bathroom, with the first unit located on the ground floor and the second unit situated on the upper floor. Upon entering, you will be welcomed by elegant hardwood floors and an abundance of

  John Oliveri Property Works New England

  14 Walnut St, Middletown, CT 06457
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  Est $283,597 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,212 Sq Ft

  187 Spencer Dr, Middletown, CT 06457

  187 Spencer Dr, Middletown, CT 06457
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  $593,900 New Construction

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  145 Webster Ln Unit 2-41, Middletown, CT 06457

  Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "KIRBY II," available for occupancy in late 2025! Located in the highly sought-after Westfield section of Middletown, this beautiful 1,555 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design: Enjoy the sophistication of white cabinetry with

  Phyllis Bysiewicz Berkshire Hathaway NE Prop.

  145 Webster Ln Unit 2-41, Middletown, CT 06457
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  $180,000 Sold Jun 13, 2025

  • 845 Sq Ft
  • $213/SF
  • 24 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1985

  1221 Washington St Unit 8, Middletown, CT 06457

  Run - do not walk to see this spectacular 2 bedroom loft home at Woodgate. Complex has been completely remodeled on the exterior, including new roof, new windows, new decks, new siding, new doors - the community looks brand new! This 2-level home offers large open vaulted living room, oversized galley kitchen, 1st floor laundry, full bath and guest bedroom. The upstairs offers an oversized 2nd

  Mark Toledo Berkshire Hathaway NE Prop.

  1221 Washington St Unit 8, Middletown, CT 06457
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  Est $301,633 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,651 Sq Ft

  603 High St, Middletown, CT 06457

  603 High St, Middletown, CT 06457
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  /18

  $227,000 Pending

  • 1 Bed
  • 1.5 Baths
  • 1,121 Sq Ft

  234 S Main St Unit 103, Middletown, CT 06457

  Welcome to Unit 103 at the Parker House - where historic charm meets modern convenience in the heart of Middletown! This turnkey first-floor condo features high ceilings, large windows, and a bright, open layout. The remodeled kitchen includes custom soft-close cabinets, stainless steel appliances, quartz countertops and designer lighting. Additional updates: new flooring, fresh paint, and an

  Derek Greene Derek Greene

  234 S Main St Unit 103, Middletown, CT 06457
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  $415,000 Sold Jun 13, 2025

  • 1,422 Sq Ft
  • $292/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  85 Margarite Road Extension, Middletown, CT 06457

  Welcome to 85 Margarite Road Extension, a thoughtfully updated 3-bedroom, 2-bathroom ranch-style residence that seamlessly combines comfort, style, and functionality. Nestled on a spacious lot with a beautifully expansive yard, this home offers refined living in a serene setting. Inside, the open-concept layout creates a sense of flow and light. This is anchored by a designer kitchen fully

  Rob Squeglia Sky Realty Group

  85 Margarite Road Extension, Middletown, CT 06457
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  Est $333,624 Not Listed For Sale

  • 6 Beds
  • 2.5 Baths
  • 2,408 Sq Ft

  71 Spring St, Middletown, CT 06457

  71 Spring St, Middletown, CT 06457
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  /40

  $379,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,038 Sq Ft

  64 Andrew St, Middletown, CT 06457

  Your Dream Home is Finally Here! You can see the tremendous pride & meticulous attention to detail from the outstanding curb appeal with the gorgeous front walkway & landscaping to the Energy Efficient Windows (2025), 3 Split Hyper Heat/AC Units (2025), Baseboard covers (2025), Roof (2016), Chimney Liner (2024), Hot Water Heater (2022), Fence (2024), Vinyl Floors, Freshly Painted, OVER 2,000 sq

  Kathy Dell'Aquila Coldwell Banker Realty

  64 Andrew St, Middletown, CT 06457
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  $230,000 Sold Jun 13, 2025

  • 1,344 Sq Ft
  • $171/SF
  • 65 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  9 Burr Ave, Middletown, CT 06457

  Welcome to 9 Burr Avenue, a cozy 3-bedroom, 1-bathroom home located in a quiet and welcoming Middletown neighborhood. This charming property offers comfortable living with plenty of potential, including a spacious attic currently used as an additional bedroom. The attic could easily be transformed into extra storage or a future expansion project. Ideally located, this home is within walking

  Wayne Stapleton eXp Realty

  9 Burr Ave, Middletown, CT 06457
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  Est $226,022 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft

  211 Carriage Crossing Ln, Middletown, CT 06457

  211 Carriage Crossing Ln, Middletown, CT 06457
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  /37

  $375,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,406 Sq Ft

  96 Mcdowell Rd, Middletown, CT 06457

  Here's your chance to build equity in a highly desirable, quiet side street location-minutes from all the conveniences Middletown has to offer. This home is full of potential & ready for your personal touches. Step onto the property & be greeted by a half-circle driveway that provides great curb appeal, complemented by a 2nd driveway leading to an attached 2-car garage. There's also an additional

  Lauren Freedman Coldwell Banker Realty

  96 Mcdowell Rd, Middletown, CT 06457
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  $230,000 Sold Jun 12, 2025

  • 1,485 Sq Ft
  • $155/SF
  • 11 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1942

  232 Cross St, Middletown, CT 06457

  Discover the timeless charm and boundless potential of 232 Cross St., Middletown, CT! This Colonial-style gem, built in 1942, offers 6 inviting rooms waiting for you to transform into your dream home. Relax by the cozy fireplace in the living room or enjoy memorable meals in the dining room featuring a classic built-in corner cabinet and French doors that open to a wood deck. The kitchen,

  Todd Bakoledis Coldwell Banker Realty

  232 Cross St, Middletown, CT 06457
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  Est $312,150 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 992 Sq Ft

  388 Fowler Ave, Middletown, CT 06457

  388 Fowler Ave, Middletown, CT 06457
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  /13

  $399,900 Pending

  • 10 Beds
  • 4 Baths
  • 5,039 Sq Ft

  84 High St, Middletown, CT 06457

  Captivating original woodwork throughout this home! Dining room with built-ins, great wood floors and room after room! There are 13 rooms in unit #1! Currently used as a rental property, this home could continue as a solid investment! The lication is ideal for anyone! Walk to downtown Middletown and enjoy everything the City has to offer without parking concerns, minutes to the Wesleyan

  Dawn Satagaj William Raveis Real Estate

  84 High St, Middletown, CT 06457
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  $258,000 Sold Jun 12, 2025

  • 1,279 Sq Ft
  • $202/SF
  • 4 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1954

  56 Jefferson Ave, Middletown, CT 06457

  Minutes from the college, this Cape Cod style home features a large living room with hardwood floors, eat-in kitchen, dining room, full bath, office and enclosed porch on the first floor. Upper level has three bedrooms and half bath. Large unfinished basement for additional storage. One car detached garage. Great for owner occupied or investor.

  Maryann Stanley Century 21 AllPoints Realty

  56 Jefferson Ave, Middletown, CT 06457
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  Est $470,848 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 2,639 Sq Ft

  665 Ridgewood Rd, Middletown, CT 06457

  665 Ridgewood Rd, Middletown, CT 06457
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  /27

  $329,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,404 Sq Ft

  60 Old Mill Rd, Middletown, CT 06457

  Move-in ready Colonial located on a charming residential street and surrounded by other well-maintained homes. This home features a bright and open layout with beautiful hardwood floors and a living room with a fireplace. The large eat-in kitchen offers granite countertops and plenty of space for cooking and gathering. With 3 bedrooms, 1.5 baths, and plenty of storage throughout, there's room to

  Laura Frisch Coldwell Banker Realty

  60 Old Mill Rd, Middletown, CT 06457
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  $327,000 Sold Jun 10, 2025

  • 2,048 Sq Ft
  • $160/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1969

  22 In Town Terrace Unit 22, Middletown, CT 06457

  Welcome to The Pines at Indian Woods, unit 22-a beautifully appointed, contemporary 3 bedroom, 2.5 bathroom residence nestled in the vibrant heart of Middletown, CT. This meticulously maintained home spans approximately 1388 square feet and effortlessly blends modern elegance with everyday comfort. As you step inside, you'll be greeted by a bright, airy interior with plenty of natural light. The

  Agota Perry-Hill William Raveis Real Estate

  22 In Town Terrace Unit 22, Middletown, CT 06457
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  Est $220,700 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,136 Sq Ft

  123 Trolley Crossing Ln, Middletown, CT 06457

  123 Trolley Crossing Ln, Middletown, CT 06457
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  $369,900 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,285 Sq Ft

  60 Hemlock Place, Middletown, CT 06457

  Don't miss this beautifully updated 4-bedroom, 1.5-bath Cape in a quiet Middletown neighborhood! Step inside to find refinished hardwood floors throughout, a stunning new kitchen with stainless steel appliances, updated bathrooms, and fresh paint throughout. Enjoy outdoor living on the oversized 14' x 19' deck overlooking a large, fully fenced backyard-perfect for relaxing or entertaining. Stay

  Richard Santana Santana Realty Group LLC

  60 Hemlock Place, Middletown, CT 06457

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