Homes for Sale near Highland School

The spectacular awaits in Cheshire - welcome to 25 Surrey Drive! This one-of-a-kind bespoke architectural masterpiece perfectly blends cosmopolitan design with a tranquil brook-side setting, creating a truly livable work of art. Inside, the dramatic, sculptural staircase immediately commands your attention, spanning 3 levels of striking proportions & walls of glass. The main level features

Tommy Connors Redfin Corporation

Build your dream Carriage Home from the ground up at The Reserve at Stonebridge Crossing-Cheshire's premier low-maintenance community by EG Home. This spacious 2,450 sq ft floor plan offers the perfect blend of comfort, flexibility, and energy efficiency, with the opportunity to personalize every detail. Create your ideal kitchen by selecting from EG Home's curated layouts, including our Pro

Michael Helmuth EG Group Realty LLC

Pride of ownership shines in this beautifully maintained Colonial. A spacious foyer with hardwood floors welcomes you into a thoughtfully designed eat-in kitchen featuring a cherry wood island with leathered granite, abundant cabinetry, stainless steel appliances, and under-cabinet lighting. The sun-filled family room offers vaulted ceilings and a brick wood-burning fireplace with a rustic barn

Daniela Volo Calcagni Real Estate

Unique Multi-Home Property on Over 3 Private Acres! A rare opportunity to own two homes on one beautiful property in a peaceful, private setting. Property Highlights: Over 3 acres of land R-40 zoning - ideal for farming, gardening, horses, or hobby farm potential Quiet country setting surrounded by nature Endless possibilities for multi-generational living, rental income, or guest house Main

Nancy Newman LPT Realty

Nestled in the desirable Castle Glenn community, this beautifully maintained detached home offers the ease of community living with the privacy of a single-family residence. Built in 1989, this home features 2,840 sq ft plus an additional 900 sq ft in the finished lower level. A standout feature is the first-floor primary suite, complete with walk-in closet and en-suite bath with jetted tub,

The Sally Bowman Team Berkshire Hathaway NE Prop.

Discover this beautifully expanded Cape, perched high above the street on a private, nearly one-acre lot - minutes from the heart of Cheshire. Offering 2,755 sq ft, this home boasts hardwood floors throughout and a flexible open floor plan for one-level living while providing three finished levels to suit your lifestyle. The sun-filled living room with a wood-burning fireplace flows into a

Frank Santino MidState Realty, LLC

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

Set on a quiet cul-de sac on almost 2.5 acres, this spacious 4 bedroom, 2.5 bath colonial with lower level finished area and walk out, offers an exceptional opportunity to create something truly special in a highly desirable location. The setting- adorned with mature trees and flowering plants on a large parcel is just lovely, yet is close to all the everyday conveniences. This home features a

Donna Myjak CRS,SRES,SRS Berkshire Hathaway NE Prop.

200 Chipman Drive is the home that Cheshire buyers wait for! A move-in ready gem, it offers the ease of one-floor living without sacrificing space or style. With over 3,100 square feet of usable space, a warrantied basement, solar efficiency, updated windows, and set on a one acre lot nestled at the end of a quiet, sought-after prime cul-de-sac location; it is a property that truly has it all.

Kathleen DeRossi William Pitt Sotheby's Int'l

Welcome to 568 Wiese Rd in the heart of Cheshire, a beautifully maintained home set in one of the town's most desirable areas. From the moment you arrive, you'll notice the thoughtfully designed landscaping that creates incredible curb appeal and a true sense of privacy. Step into the backyard and discover your own private sanctuary. Lush greenery, mature plantings, and carefully curated outdoor

Arthur King Hall YellowBrick Real Estate LLC

Perfectly maintained and beautifully appointed Colonial set at the end of a cul-de-sac in one of Cheshire's most desirable neighborhoods. Surrounded by higher-end homes on 1.86 private, park-like acres, this property is ideal for both everyday living and entertaining. The eat-in kitchen features granite countertops, center island, stainless steel appliances, double wall ovens, cooktop, built-in

Stacey Deangelis Calcagni Real Estate

This is the one you've been waiting for-fully remodeled, absolutely move-in ready, and not a detail overlooked. Homes like this in Cheshire rarely come to market, combining timeless charm with today's most sought-after updates. Renovated top-to-bottom between 2020-2022, this home offers true peace of mind-there is nothing left to do but move in and enjoy. The show-stopping kitchen is the heart of

Sarah Andrea Coldwell Banker Realty

Hillside Village, age restricted community 62+. One level living, 1 bedroom with an additional living space that could be used as a 2nd bedroom (no closet). Slider to patio and yard area, stackable washer/dryer. Condo fees include heat and hot water. Close to restaurants, shopping, public library, and highways. Sold in as is condition, needs work and updating.

Phil Giampietro Coldwell Banker Realty