Winchester Real Estate

Winchester, located in Middlesex County, Massachusetts, is a picturesque town that perfectly blends small-town charm with modern convenience. Known for its top-rated schools, beautiful parks, and vibrant community, Winchester is a highly sought-after place to live.

With its tree-lined streets and historic architecture, Winchester offers a tranquil escape from the hustle and bustle of city life. Residents can enjoy a variety of outdoor activities, from hiking and biking in Middlesex Fells Reservation to picnicking in the scenic town common.

In addition to its natural beauty, Winchester boasts a thriving downtown area filled with boutique shops, cozy cafes, and gourmet restaurants. Whether you're looking for a quiet spot to enjoy a cup of coffee or a lively restaurant to dine with friends, Winchester has something for everyone.

The real estate market in Winchester is diverse, with a mix of historic homes, modern condos, and spacious estates. Whether you're a first-time homebuyer, a growing family, or an empty nester looking to downsize, you're sure to find the perfect property to call home in Winchester.

Experience the charm and convenience of Winchester living – come and discover all that this vibrant town has to offer!

Newest Listings in Winchester

$974,900

4 Beds ⋅ 3 Baths ⋅ 73575764 MLS

Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably under $1M. 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2.5 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

258 Cross St, Winchester

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

$769,000

2 Beds ⋅ 2 Baths ⋅ 73575558 MLS ⋅ ['Wedgewood Place Condominiums'] BLDG.

Don't miss this beautifully appointed 2-bedroom, 2 bath unit at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Magnificent new kitchen with custom cabinets, quartz counter tops and stainless-steel appliances that looks out at a bright and sunny, spacious open living and dining room and small home office area. Featuring a wood burning fireplace and a private balcony with exceptional views of the pool and garden, perfect for your morning coffee. Beautiful wide plank hardwood floors throughout. Custom vanities and quartz counter tops in both bathrooms. The generous Primary bedroom features custom walk-in closet and large en-suite with separate vanity area. Fresh paint and new light fixtures are among the many upgrades. New elevators and upgraded pool. One level living at its best. Enjoy the serene setting of Wedge Pond and park area right next door or take a short stroll to Winchester's amazing shops and restaurants. Public transportation outside your front door, short walk to train, 2 stops, 20 min and you are in Boston. Covered parking! Additional storage in garage.

666 Main St Unit 310, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.

$775,000

3 Beds ⋅ 2 Baths ⋅ 73575116 MLS

Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,599,000

5 Beds ⋅ 3 Baths ⋅ 73575069 MLS

Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases timeless architectural character, generously proportioned rooms, and an abundance of natural light. The inviting front to back living room features a fireplace and serves as a wonderful gathering space, along with formal dining room, eat in kitchen, 1/2 bath plus a sunroom/den and a home office! The upper floors offer 5 spacious bedrooms & provide exceptional flexibility for family, guests, office space, or future customization. Enjoy the rear deck and the vast lot with lush grass, gorgeous perennial gardens and flowering trees offering plenty of space for outdoor entertaining, gardening or expansion. With this home's beautiful brick exterior, classic charm, substantial lot, and premier location, it offers an exceptional opportunity to renovate, reimagine, and create your dream home!

143 Arlington Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$4,299,000

5 Beds ⋅ 6 Baths ⋅ 73574948 MLS

Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

4 Dartmouth, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,300,000

4 Beds ⋅ 3 Baths ⋅ 73574928 MLS

Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,300,000

4 Beds ⋅ 3 Baths ⋅ 73574929 MLS

465 Washington Street Unit 465, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,299,000

4 Beds ⋅ 2 Baths ⋅ 73574477 MLS

Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.

253 Pond St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$2,995,000

5 Beds ⋅ 6 Baths ⋅ 73574330 MLS

A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

8 Priscilla Lane, Winchester

Listing courtesy of Listing Agent: The Pezzano Group from Listing Office: Rise Signature Homes.

$3,149,000

7 Beds ⋅ 8 Baths ⋅ 73573670 MLS

Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

37 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$975,000

4 Beds ⋅ 3 Baths ⋅ 73573734 MLS

Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

199 Washington Street Unit 199, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,650,000

5 Beds ⋅ 4 Baths ⋅ 73573887 MLS

Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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