Middletown, CT Homes for Sale under $800,000

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

Carissa Mastriano GRL & Realtors, LLC

Discover Carefree Living at Founders' Ridge - the Award-Winning 55+ Adult Community! Come experience the "MARTIN II," Under CONSTRUCTION! Now with many new UPGRADES - available for occupancy in early 2027 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:

Phyllis Bysiewicz Berkshire Hathaway NE Prop.

Beautifully updated Saltbox Colonial in Middletown's Westfield neighborhood! This 3-bedroom, 2.5-bath home offers a spacious, open floor plan with the perfect balance of classic charm and modern updates. The updated kitchen featuring granite countertops, stainless steel appliances, and a bright eat-in dining area with cathedral ceilings and a slider leading to the expansive deck-ideal for indoor

LaurieAnn Hansen Coldwell Banker Realty

Experience Carefree Living at Founders' Ridge - the Premier 55+ Award-Winning Community! Introducing our newest Model Home -our sought after "KIRBY II", now available for early 2027 occupancy! This is the last Kirby at this price point! 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

Phyllis Bysiewicz Berkshire Hathaway NE Prop.

Historic 1868 South Farms area of Middletown Home with Exceptional Outbuildings Step back in time while enjoying the comfort of modern updates in this distinctive 1868 home, set on a property filled with character, history, and functionality. The home features three bedrooms, 1 1/2 baths, an upstairs office, and a completely remodeled kitchen area. The full-height basement has a granite

Pam Rizy Berkshire Hathaway NE Prop.

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

Sharon Linder Berkshire Hathaway NE Prop.

Exceptional 3-Unit Mixed-Use Investment Opportunity A rare opportunity to own a well-maintained three-unit property offering townhouse-style living, private garages, excellent parking, and strong income-producing potential in the heart of Middletown. 227 East Main Street is an attractive investment opportunity for both seasoned investors and owner-occupants looking to build equity while

Tanya Reyes William Raveis Real Estate

Welcome to this beautifully maintained 4+-bedroom, 2.5-bath Colonial conveniently located in the heart of Middletown. Freshly painted and move-in ready, this home offers the rare combination of generous living space, flexible room options, entertaining areas, and valuable recent updates-including a new roof in 2025. The spacious eat-in kitchen features a center island and bright breakfast nook

Heather Kilbourn Cavanaugh & Company LLC

Welcome to 220 Randolph Rd - This spacious 4-bedroom, 2.5-bath Colonial offers the rare opportunity to enjoy 2.53 acres of privacy in the heart of Middletown. The first floor features a welcoming living room with a propane fireplace, an open-concept eat-in kitchen, and a convenient primary suite complete with a walk-in closet and a large en-suite bathroom featuring both a shower and jetted tub. A

Alyssa Gambell William Raveis Real Estate

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

Joe Koontz eXp Realty

The tax record may say 1935, but this is far from your typical 1935 home. The original footprint represents just a small portion of the home you see today, thoughtfully renovated and expanded over the decades by its builder-owner to create a home designed for the way we live now. The spacious kitchen features a center island, abundant cabinetry, pantry and breakfast area, flowing easily into the

Debbie Huscher Real Broker CT, LLC