Winchester Highlands Homes for Sale

Winchester Highlands Homes for Sale

Welcome to Winchester Highlands, a picturesque gem nestled in the heart of Middlesex County, Massachusetts. This charming neighborhood, part of the vibrant town of Winchester, offers a delightful blend of suburban tranquility and urban convenience. Known for its lush landscapes and friendly community, Winchester Highlands is the perfect place for families, professionals, and retirees alike to call home.

The region boasts a rich history, with beautifully preserved architecture that reflects its New England roots. Residents enjoy access to top-rated schools, making it an ideal location for families seeking a nurturing environment for their children. The area is also known for its abundance of parks and recreational facilities, providing ample opportunities for outdoor activities, from hiking and biking to picnicking in the sun.

When it comes to homes for sale in Winchester Highlands, you’ll find a diverse array of properties that cater to various tastes and budgets. Whether you’re looking for a charming colonial home with classic features, a modern townhouse with contemporary amenities, or a spacious single-family residence, the options are plentiful. Many homes boast expansive yards, perfect for entertaining or enjoying a quiet evening under the stars.

With its close-knit community atmosphere, excellent schools, and convenient access to Boston via the nearby commuter rail, Winchester Highlands truly offers the best of both worlds. Discover your dream home in this enchanting neighborhood and experience the vibrant lifestyle that awaits you in Winchester, MA. Your perfect home is just a showing away!

Newest Winchester Highlands Homes for Sale

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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