Middletown, CT Homes for Sale under $400,000

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

52 Cimarron Road, a lovely raised ranch offering three bedrooms and one and a half bathrooms. Hardwood floors flow through the living spaces, and a fireplace is the heart of the living room. The kitchen is fully equipped and flows nicely to the dining and living areas, making everyday routines and gatherings comfortable. The lower level adds additional living space, a laundry room, and storage.

Heidi Matusik Lamacchia 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

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.

Welcome Home, Fall in love and move in for the holidays. Stunning 3 bedroom~2 full bath Cape Cod completely remodeled from exterior to interior. This is what you have been searching for. A beautiful custom home with great curb appeal on .17 acre yard, with a stunning stone patio, front walkway and a new privacy fencing. Located close to schools, shopping & major highways it is priced right for

Jackie Williams Sterling REALTORS

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

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

Fall in love with this charming, well-maintained Cape home with attached garage located at 237 Boston Road in Middletown! Step inside to a spacious and welcoming living room featuring beautiful hardwood floors, a cozy fireplace, and an efficient pellet stove - perfect for New England seasons. The main level continues into a bright dining area and kitchen equipped with solid-wood cabinetry,

Giulia Terese Hagel & Assoc. Real Estate

Calling all investors! Duplex located in residential neighborhood with tenants already in place! Two side by side units, both townhouse style. Detached garage and ample yard space makes this a unique and appealing piece of property. Many recent updates in both units, including new flooring & partial roof repair completed in 2025. Both units have enclosed porches in the front and back of house.

Karen Kesten William Raveis Real Estate

Beautiful Spacious Custom Built ONE Owner Home in Desirable Neighborhood. Unigue Cobblestone Exterior. When entering from the front door you're met with a beautiful staircase and a large living room with wood burning fireplace. Many windows provide tons of natural light. To your right is a formal dining room that has held large crowds for the holiday feasts. Main level has a full updated bath as

Robin Rios Berkshire Hathaway NE Prop.

Step into timeless New England charm with this beautifully updated historic colonial farmhouse that perfectly blends classic character with modern comfort. Every corner of this home reflects care and craftsmanship, with thoughtful improvements that make it both beautiful and reliable for years to come. The property features a freshly updated exterior, structural enhancements, a newer roof (2024

Emily Braman Berkshire Hathaway NE Prop.

Welcome to this inviting 3-bedroom, 1.5-bathroom home, offering 1,438 sq. ft. of living space on a 0.16-acre lot. Nestled in a desirable neighborhood of Middletown, this property combines comfort, convenience, and character. Key Features: 3 Spacious Bedrooms - Plenty of natural light and versatile space for family, guests, or a home office. 1.5 Bathrooms - A full bath plus a convenient half bath

Thomas Mele Dorrance Realty

Welcome home to this beautifully maintained Raised Ranch offering the perfect blend of comfort, style, and functionality. The main level features a sun-filled, open-concept living and dining area with gleaming hardwood floors throughout. Host your gatherings in the well-appointed dining room accented with classic chair rail and shadow box trim. The working kitchen offers refreshed lower cabinets,

Kristin Daly-Murphy Calcagni Real Estate

This charming brick ranch offers so much potential! The spacious, sun-filled living room features hardwood floors and a cozy fireplace. The open kitchen and dining area provide an ideal layout for everyday living and entertaining. Just off the kitchen is a small bonus room-perfect for a future walk-in pantry or mudroom. Upstairs, you'll find three comfortable bedrooms and a full bath. The lower

Lisa Sader-Goede Aspen Realty Group

This beautifully updated Ranch offers the ease of single-level living and wonderful privacy at the end of a quiet cul-de-sac, bordered by 275 acres of protected wooded land. The peaceful setting creates an immediate sense of calm. Inside, the main level feels bright and inviting with an open layout and hardwood floors flowing through the living and dining areas-ideal for everyday living or

Angela Smeriglio William Raveis Real Estate