Homes for Sale near Highland School

Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor

Amy LaMaster The Bella Group, LLC

Classic Colonial * 0.92-acre private lot * 4 BR, 2.1 BA * 1,696 sf * Quartz kitchen * Hardwood floors throughout * Fireplace family room * French doors to patio * Roof 2022 * Thermopane windows * Electric baseboard heat * Split system * 2-car garage Set on a peaceful 0.92-acre setting in the Town of Cheshire, 346 Village Drive offers classic New England style with thoughtful updates. The

The Sally Bowman Team Berkshire Hathaway NE Prop.

Welcome to Old Towne Condos, a highly desirable center-of-town community offering convenience & walkability. This spacious 1,536 sq. ft., 2-bedroom, 2-1/2 bath Townhouse unit features a welcoming eat-in kitchen at the front of the home, a formal dining room, and a sunken living room complete with a wood-burning fireplace and French doors leading to a covered sun porch. The porch overlooks a very

The Sally Bowman Team Berkshire Hathaway NE Prop.

Welcome to this exceptional estate set deep off the road on 3.3 private, beautifully wooded acres in Cheshire, Connecticut. The main residence offers over 4,000 sq. ft. of living space, combining comfort, elegance, and versatility for today's lifestyle. Inside, you'll find five generous bedrooms, multiple living and entertaining areas, and a warm, inviting fireplace on the main level. The fully

Nancy Newman LPT Realty

Welcome to this stunning 2-year-young townhouse offering modern design and exceptional comfort. The open-concept main level is ideal for both everyday living and entertaining, featuring a beautiful kitchen with sleek quartz countertops, ample cabinetry, and a seamless flow into the living and dining areas. Rich hardwood flooring spans the entire first floor and continues through the upper-level

Tracey Fiasconaro Berkshire Hathaway NE Prop.

Move right into this nicely maintained Raised Ranch in a desirable neighborhood in Cheshire. This home has 3 bedrooms on the main level and a 4th bedroom/office on the lower level. Welcoming foyer, large living room/dining room with sliders to the deck. Newly updated kitchen with stainless steel appliances, vinyl flooring and a pass-through window between kitchen and living room, a primary

Sali Barolli Fercodini Properties, Inc.

Come enjoy nearly new construction at The Reserve at Stonebridge. Built in 2024, this home offers modern features with a comfortable, welcoming feel. It sits on a desirable Phase 1 lot with natural gas and includes several high end upgrades throughout. The open living layout features a well designed kitchen with ample storage, a coffee bar, beverage fridge, and gas range, making it ideal for both

Craig McCabe Century 21 AllPoints Realty

Brand-new construction completed on 12/12/2025 and currently receiving final finishing touches by the owner. This beautiful home offers 4 spacious bedrooms, 3 full bathrooms, and a 2-car garage with an additional 506 square feet of garage space. The Town has issued the Certificate of Occupancy (CO). Thoughtfully designed layout with modern finishes throughout. A rare opportunity to own a newly

Carlos Ventura Ventura Group Realty LLC

Welcome to 30 Kensington Court - refined, move-in ready living on a quiet cul-de-sac in desirable Cheshire. This beautifully updated 3-bedroom, 2.5-bath ranch offers effortless one-level living paired with thoughtful upgrades throughout. The open-concept layout is anchored by a striking stone fireplace and gleaming hardwood floors, creating a warm yet sophisticated atmosphere. The completely

Kelly Hill-Mihalyak Coldwell Banker Realty

Inquire about special builder incentives available until June 30th! Welcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot presents a rare opportunity to build your dream home with a respected local builder known for quality craftsmanship, meticulous attention to detail, and energy-efficient design. The Magnolia model showcases 9' ceilings, hardwood flooring in

Abby Breau New England Prestige Realty