Winchester Highlands Real Estate

Winchester Highlands Real Estate

Welcome to Winchester Highlands, a picturesque neighborhood nestled in the heart of Winchester, Massachusetts. Located in Middlesex County, Winchester is a charming town known for its beautiful homes, top-rated schools, and vibrant community.

Winchester Highlands offers residents the perfect blend of suburban tranquility and urban convenience. With tree-lined streets, well-manicured lawns, and a strong sense of community, this neighborhood provides an idyllic setting for families, professionals, and retirees alike.

Residents of Winchester Highlands enjoy easy access to a range of amenities, including boutique shops, cozy cafes, and delicious restaurants in downtown Winchester. Outdoor enthusiasts will appreciate the nearby Middlesex Fells Reservation, where they can explore miles of hiking and biking trails.

Families are drawn to Winchester Highlands for its excellent schools, including the Winchester Public Schools district, known for its academic excellence and dedicated teachers. The neighborhood is also just a short drive away from Boston, making it a convenient option for commuters looking to escape the hustle and bustle of the city.

Whether you're looking for a peaceful place to raise a family or a close-knit community to call home, Winchester Highlands has something for everyone. Come discover the beauty and charm of this lovely neighborhood in Winchester, Massachusetts.

Newest Listings in Winchester Highlands

258 Cross St, Winchester
$974,900
3 Beds ⋅ 3 Baths ⋅ 73575764 MLS
Are rates making you feel like home buying is out of reach? The sellers are now offering A TWENTY THOUSAND DOLLAR ($20,000) CREDIT, PERFECT to put towards closing costs or a 2/1 rate buy down. Enjoy over a ONE THOUSAND ($1000) DOLLAR PER MONTH savings year one and over a FIVE HUNDRED ($500) DOLLAR PER MONTH savings year two. A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

258 Cross St, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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