Middletown, CT Homes for Sale

Welcome to 23 Hotchkiss Street, where historic charm meets modern convenience in the heart of downtown Middletown. This classic brick Colonial, built in 1900, has been thoughtfully updated while retaining its timeless character. Inside, you'll find bright living spaces, a well-appointed kitchen with updated appliances, and flexible rooms that adapt to your lifestyle-whether for entertaining,

Jonathan Zuromski Real Broker CT, LLC

Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "MARTIN II," available for occupancy in 2026! Located in the highly sought-after Westfield section of Middletown, this beautiful 1,430 sq. ft. home has the convenience of single-floor living with top-of-the-line features and Elegant Design: Enjoy the sophistication of wood cabinetry with

Phyllis Bysiewicz Berkshire Hathaway NE Prop.

A functional layout in an ideal setting! This is a TO BE BUILT 2,006 sq ft home on a nice sized 2.12 acre lot. A traditional style house plan featuring an open concept Kitchen and Family Room space with hardwood flooring throughout the first floor. The Dining Room will have decorative picture frame molding creating a timeless feel. Relax and recharge in the large Primary Bedroom suite. Three

Dori Degennaro William Raveis Real Estate

Welcome to 14 Rising Trail Dr in Middletown! This beautifully updated townhouse is truly move-in ready, featuring fresh paint throughout, brand-new flooring, and a stylishly updated bathroom. The bright and open layout offers comfortable living spaces, perfect for both everyday living and entertaining. Located in a convenient area close to shopping, dining, parks, and major commuter routes, this

Timothy Faucher eXp Realty

Renovated in 2023, this charming 3-bedroom, 1.5-bath home combines modern updates with timeless character. A large, bright screened-in 3-season front porch welcomes you. Step inside to an open floor plan featuring a quartz kitchen with stainless steel appliances, a spacious dining island, and two convenient access points - one from the front porch and another through a bright mudroom leading to

Mike Sangapore eXp Realty

Welcome to 565 High St, Middletown, CT. This unique commercial building is located in the heart of a residential neighborhood. It has operated as a karate dojo since 1998. The space is perfect for a hall, dance studio or open space. With dormered ceilings and a spacious basement this building is a perfect creative space. It has potential for renovations and to be converted for multiple uses. The

David Tobin William Raveis Real Estate

Property to be sold in "as is" condition Contingent upon probate approval. This is home is located convenient to Shopping center and and route 9. First floor main bedroom with full bath Addition three bedrooms on the upper level and a full bath. Builtin hutch in the dinning area. Living room with fireplace. (never used) Hardwood floors under carpeting. Ramp A detached two car garage.

Ramona B Gonzalez Berkshire Hathaway NE Prop.

This is NOT A DRIVE-BY!!! What you see from the front is not what you will see inside!! As you enter through the side door, you will love the mudroom, for everyones shoes, coats, bag, etc. Then walk in to your large kitchen with vaulted ceilings! The front dining room with fireplace is off the kitchen perfect for gatherings. The sunken family room will WOW you with how much room there is! The

Brittany O'Hara William Raveis Real Estate

Timeless Colonial rich with historic charm, minutes from downtown Middletown, Wesleyan University & Middlesex Hospital, this home offers the perfect blend of convenience & character. Featuring 4 nice sized bedrooms, high ceilings, original woodwork & a warm inviting layout. The detached garage adds extra storage or workshop potential & the walk-up attic offers endless possibilities for expansion

Michelle Mazzotta eXp Realty

Classic charm meets everyday comfort in this beautifully maintained 3-bedroom, 2 full bathroom Colonial located in Middletown. Step inside to find sun-filled living spaces with warm hardwood floors, timeless built-ins & inviting details throughout. The living room offers a cozy yet elegant setting, perfect for relaxing or entertaining, while the thoughtfully styled kitchen blends character with

Michelle Mazzotta eXp Realty

Experience Carefree Living at Founders' Ridge - the Premier 55+ Award-Winning Community! Introducing our newest Model Home -the "KIRBY II", now available for early 2026 occupancy! Nestled in the highly desirable Westfield section of Middletown, this thoughtfully designed 1,555 sq. ft. single-level home offers both luxury and ease in one perfect package. Elegant Interior Features include stunning

Phyllis Bysiewicz Berkshire Hathaway NE Prop.

Located on the edge of downtown Middletown, Spring Street is a quiet one-way street with a dedicated bike lane. Positioned on the corner of Spring Street and Rome Avenue, 32-34 Spring Street is a classic brick duplex with symmetrical front porches and timeless curb appeal. Each unit features a private front entrance that leads into a spacious living room, accented by an elegant central staircase.

Richard Tabor Berkshire Hathaway NE Prop.

Fantastic investment opportunity in Middletown! This unique single-family home with a fully permitted ADU offers exceptional versatility and strong rental income. The property features three fully rented units-a spacious upper-level unit, a ground-level unit, and a private ADU attached off the back. Together, these units currently generate $3,400/month, and all existing tenants will convey with

Thomas Mele Dorrance Realty

Welcome to 56 Burgundy Hill Lane, Middletown! This totally renovated 2-bedroom ranch-style condo was beautifully remodeled in 2023 with updates in every room. The new kitchen showcases granite countertops, stainless steel appliances, white cabinetry, and modern finishes, while the spacious living/dining area opens through sliding doors to a private covered deck. Two generous bedrooms, a

Giulia Terese Hagel & Assoc. Real Estate

To be Built - The Nathan Hale Estates offer an exceptionally private and secluded setting, making it the perfect place for you and your family. Experience modern luxury in this stunning new construction colonial offering 3 bedrooms, 2.5 baths boasting 1,761 sq. ft. of beautifully designed living space. Ushering you from the covered front porch, the first floor features a gourmet chef's kitchen

Jenna Talbot Coldwell Banker Realty

To be Built - The Nathan Hale Estates offer an exceptionally private and secluded setting, making it the perfect place for you and your family. Experience modern luxury in this stunning new construction colonial offering 3 bedrooms, 2.5 baths boasting 1,761 sq. ft. of beautifully designed living space. Ushering you from the covered front porch, the first floor features a gourmet chef's kitchen

Jenna Talbot Coldwell Banker Realty

This 1,500 sq ft ranch-style home, built by Silvin Homes, offers thoughtfully designed one-level living with an open-concept layout ideal for everyday living and entertaining. The spacious living area flows seamlessly into the kitchen with a center island and ample cabinetry, creating a welcoming gathering space. The private primary suite features a custom full bath and walk-in closet and is set

Jenna Talbot Coldwell Banker Realty

To be Built - The Nathan Hale Estates offer an exceptionally private and secluded setting, making it the perfect place for you and your family. Experience modern luxury in this stunning new construction colonial offering 3 bedrooms, 2.5 baths boasting 1,761 sq. ft. of beautifully designed living space. Ushering you from the covered front porch, the first floor features a gourmet chef's kitchen

Jenna Talbot Coldwell Banker Realty

Discover comfortable and convenient living in this well-kept 2-bedroom, 1-bath condo offering a functional layout across 930 sq ft. Perfect for entertaining family and friends-or simply enjoying peaceful days at home-this inviting space provides versatility for any lifestyle. Located just 10 minutes from Cromwell's shopping and dining and only 5 minutes from vibrant downtown Middletown, you'll

LeAndra Trotman William Raveis Real Estate

There's something immediately comforting about a home that gives you room to breathe-and this spacious condo does exactly that. With a thoughtfully designed floor plan and generous living spaces, it feels welcoming from the moment you step inside. The living room is warm and inviting, centered around a gas fireplace that sets the tone for quiet evenings, movie nights, or gathering with friends.

Debbie Huscher Real Broker CT, LLC

Wesleyan University area Ranch on a cul-de-sac. A nice sized living room with inviting atmosphere featuring a hearth fireplace, creating a warm, welcoming space as soon as you enter. Three cozy bedrooms, perfect for family or guests, gleaming hardwood floors, full bath with tub and an eat-in kitchen perfect for casual meals and gatherings round out the first floor. Abundant sunlight fills the

Jackie Williams Sterling REALTORS

This charming, well cared for colonial is the perfect place to create memories. A rare find, home is built in 2006 and it only had 1 person living there. This home boasts 4 bedrooms, master has an ensuite, 2.5 baths, laundry upstairs, full dining room and front to back living room for all your gatherings. A full basement and a 2 car garage provide ample storage and room to grow. This home is move

Joseph Ercolani William Raveis Real Estate

To be Built - The Nathan Hale Estates offer an exceptionally private and secluded setting, making it the perfect place for you and your family. Experience modern luxury in this stunning new construction colonial offering 3 bedrooms, 2.5 baths boasting 1,761 sq. ft. of beautifully designed living space. Ushering you from the covered front porch, the first floor features a gourmet chef's kitchen

Jenna Talbot Coldwell Banker Realty

REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 2000, this two story home offers approximately 1934 finished square feet, three bedrooms and two full baths, fireplace, covered front porch, fully finished basement and attached one car garage. This home sits on an approximate 11326 sqft lot. "As is" cash only sale with no

Sherry Price Realhome Services & Solutions

BACK ON THE MARKET DUE TO BUYER'S MORTGAGE DENIAL!! Don't miss this incredible opportunity! This lovingly cared-for, one-owner ranch home offers the perfect canvas to add your own style and vision. Featuring hardwood floors throughout and a timeless layout, the main level provides easy, comfortable living with three generous bedrooms and a bright full bath. But the true gem of this property is

Joseph Harvey Best Real Estate Brokerage LLC

Highly sought after residential condo complex, Carriage Crossing unit - 2 bedrooms, 2 full baths, 866 sqft of space to make yours! Complex amenities include pool, tennis courts, fitness center, sauna and so much more! Unit has storage area right around corner from its entrance, as shown in the last photo.

Jennifer Hussey Century 21 Clemens Group

Welcome to this updated, energy-efficient home, located just minutes from Wesleyan University, downtown Middletown, restaurants, shopping, and the riverfront. With solar panels, a newer kitchen, and a surprisingly deep backyard, this property blends convenience, modern comfort, and value. The first floor offers a bright living room with hardwood floors, a large eat-in kitchen with white

Abby Breau New England Prestige Realty

In the heart of Middletown and within walking distance to countless amenities, 54 Washington Street offers both location and opportunity. Once home to the Italian American Club, the building carries a unique history and is now ready for a new vision. This spectacular building has received zoning approval to convert this once community/event space to residential units. Take advantage of the

Ariel Tortora William Raveis Real Estate

Discover comfort, space, and flexibility in this beautifully maintained 4-bedroom, 2-bathroom home offering nearly 3,000 sq ft of living space in peaceful Higganum. Set on a serene lot, this property blends classic charm with modern convenience and provides an ideal layout for multi-generational living. Step inside to find bright, generously sized rooms, including a large living room, formal

Victor Santana Santana Realty Group LLC