Winchester Highlands Real Estate

Winchester Highlands Real Estate

Welcome to Winchester Highlands, a hidden gem nestled in the heart of Massachusetts’ Middlesex County. This charming neighborhood in the picturesque town of Winchester offers a perfect blend of suburban tranquility and vibrant community life, making it an ideal place for families, professionals, and retirees alike.

Winchester Highlands is renowned for its stunning landscapes, featuring tree-lined streets and beautifully maintained parks that invite outdoor activities year-round. The area is rich in history, with a quaint downtown that boasts a delightful mix of boutique shops, cozy cafes, and essential services. Residents enjoy the convenience of local amenities while being just a short drive or train ride away from the bustling city of Boston, making it easy to experience urban excitement without sacrificing the peace of suburban living.

Education is a cornerstone of the Winchester Highlands community, with top-rated schools serving students from kindergarten through high school. Families here take pride in their strong sense of community, often coming together for local events, farmers’ markets, and seasonal festivities that celebrate the unique character of the area.

For nature lovers, the nearby Middlesex Fells Reservation offers miles of hiking trails, scenic views, and opportunities for outdoor recreation, ensuring that residents can enjoy the beauty of nature right at their doorstep. Whether you’re looking to settle down in a charming single-family home or a modern condo, Winchester Highlands provides a welcoming atmosphere that feels like home.

Discover the warmth and charm of Winchester Highlands, where community spirit and natural beauty come together to create a truly exceptional living experience.

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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