Winchester Highlands Homes under $2 million

Welcome to Winchester Highlands, a charming neighborhood nestled in the heart of Winchester, Massachusetts. This picturesque community, part of Middlesex County, offers a perfect blend of suburban tranquility and urban convenience. With its tree-lined streets, historic architecture, and vibrant local culture, Winchester Highlands is an ideal place for families, professionals, and anyone looking to enjoy a high quality of life.

One of the standout features of Winchester Highlands is its accessibility to Boston and surrounding areas. The neighborhood is well-connected by public transportation, making it easy for commuters to reach the city while returning home to a peaceful environment. The area boasts top-rated schools, lush parks, and a strong sense of community, providing residents with a welcoming atmosphere that feels like home.

For those in search of their dream home, Winchester Highlands offers a diverse array of properties, with many charming options available under $2 million. Whether you’re looking for a cozy single-family home with modern amenities or a spacious residence with a beautiful yard, this neighborhood has something to suit every taste and budget. The real estate market here is thriving, with homes that often feature stunning architectural details and are situated on generous lots.

In addition to its beautiful homes, Winchester Highlands is also close to local shops, restaurants, and recreational facilities, ensuring that residents have everything they need within reach. Come explore the enchanting Winchester Highlands, where your dream home awaits amidst a community that feels just right.

Newest Winchester Highlands Homes under $2 million

$1,195,000

3 Beds ⋅ 2 Baths ⋅ 73582171 MLS

Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious front foyer opens into the living room with a wood burning fireplace. The formal dining room leads out to a serene private rear deck, overlooking a fully fenced yard with native plantings. The sizable kitchen highlights electric cooking, a built in microwave, and peninsula providing additional seating. A side addition added a large front to back family room with abundant natural light, providing even more livable space on the first floor. A private home office with classic French door completes this level. Upstairs, you’ll find a 2021 renovated full bathroom, three sizable bedrooms, and extensive storage space including 25FT attic closet. The walk out basement offers W/D, an above grade, finished room perfect for a home gym or office, and unfinished storage space. A one car garage, off street parking for 3 additional cars and cost efficient solar panels add everyday practicality. Just minutes from vibrant Winchester Center, this home offers access to local shops, cafés, highly rated restaurants, two MBTA commuter rail stations and Winchester’s acclaimed public school system, along with easy access to I-93, Route 128 and Route 3.

4 Stone Ave, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.

$1,080,000

3 Beds ⋅ 1 Baths ⋅ 73578621 MLS

Opportunities and possibilities for builders or handyman!! At 6 Reservoir Street, Winchester, a distinguished single-family residence on an expansive 10818 square foot lot. This property represents a unique opportunity for refined living within a desirable community. The residence encompasses three well-proportioned bedrooms plus walk-up to a generously sized attic and one full bathroom. Traditional wrap-around porch in front, and large deck at the rear accessed from the driveway which enters from the street behind. Great location close by to the reservoir and Fells Reservation with easy highway access as well. Sell by owner and AS IS conditions.

6 Reservoir Street, Winchester

Listing courtesy of Listing Agent: Dongjun Lou from Listing Office: HMW Real Estate, LLC.

$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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