Winchester Homes under $1 million

Welcome to Winchester, Massachusetts—a charming town that beautifully blends suburban tranquility with vibrant community life. Nestled in Middlesex County, Winchester is known for its picturesque landscapes, top-rated schools, and a strong sense of community. With its rich history and an array of outdoor activities, Winchester is the perfect place for families, young professionals, and retirees alike.

The town boasts an impressive array of parks, walking trails, and recreational facilities, making it an ideal environment for those who appreciate the great outdoors. Residents enjoy easy access to the scenic Middlesex Fells Reservation, perfect for hiking, biking, and enjoying nature. Winchester’s downtown area is a delightful mix of quaint shops, cozy cafes, and diverse dining options, ensuring that there’s always something new to explore.

For those looking to settle down in this idyllic town without breaking the bank, Winchester offers a selection of charming homes under $1 million. These properties range from classic New England-style houses to modern family homes, each brimming with character and potential. With its welcoming neighborhoods and a strong sense of community, you’ll find that Winchester is not just a place to live, but a place to thrive.

Whether you’re drawn to the rich history, the excellent schools, or the friendly atmosphere, Winchester is a town that truly has it all. Discover your dream home in this vibrant community, where comfort meets convenience, and every day feels like a breath of fresh air. Come explore Winchester today—your perfect home awaits!

Newest Winchester Homes under $1 million

$899,000

3 Beds ⋅ 1 Baths ⋅ 73585414 MLS

Charming ranch offering 1,313 square feet of main living area plus an additional 260 square feet of flexible basement space ready for finishing. Built in 1955 and set on a generous 15,800-square-foot lot, this home seamlessly blends comfortable interior living with exceptional outdoor space. Key updates include a new roof installed in 2020 and an updated electrical panel in 2023. The inviting layout features a bright living room centered around a classic fireplace, which flows effortlessly into the formal dining room and functional kitchen. Step right outside to a large deck overlooking an expansive, lush backyard—providing a wonderful setting for outdoor dining and gatherings. The sun-filled primary suite serves as a quiet retreat, complemented by two additional versatile bedrooms.

39 Henry Street, Winchester

Listing courtesy of Listing Agent: Kelly Batti from Listing Office: Coldwell Banker Realty - Belmont.

$1,000,000

3 Beds ⋅ 1 Baths ⋅ 73581744 MLS

Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

23 Stone Ave., Winchester

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

$700,000

2 Beds ⋅ 2 Baths ⋅ 73581469 MLS ⋅ ['Wedgewood Place'] BLDG.

Easy one-floor living in Winchester Center with garage parking for one car! Fabulous location near town center, TRAIN, shopping, restaurants, schools and library. Enjoy the open layout with extra wall of beautiful kitchen cabinets, large peninsula/eating bar, fireplace, balcony and a nook for a desk or whatever you wish. Large primary bedroom has two windows, large walk-in closet and full bath. Second bedroom is across hall from laundry and bath with shower. Air handler and condenser replaced in 2022. Central air throughout. Hot water heater and water shutoff installed - 2018. The additional storage unit is off the main lobby for easy access. Amenities include 2 elevators, inviting POOL and onsite rubbish pickup. Perfect home for first time buyers, downsizers, anyone commuting to Boston or in search of a vibrant town center lifestyle.

666 Main Street Unit 217, Winchester

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

$319,000

1 Beds ⋅ 1 Baths ⋅ 73580409 MLS ⋅ ['Parkview'] BLDG.

Best Price 1 Bedroom at The Parkview in Winchester! An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient open-concept layout where the kitchen features a functional peninsula and brand-new, never-used stainless steel appliances. All inclusive monthly HOA fee. Perfect for budget-conscious buyers, investors, or downsizers, completely covers your major monthly utility expenses: heat, hot water, electricity, water/sewer, and central air conditioning. In an era of rising utility costs, this structure provides total peace of mind and simplified monthly budgeting. Residents also enjoy access to the community pool, outdoor picnic grounds, and ample open parking. The location provides premium convenience, situated just minutes from vibrant Winchester Center with its local shops, cafes, highly rated restaurants, and two MBTA commuter rail stations for a straightforward commute. Enjoy everything Winchester has to offer, from the acclaimed public school system to the nearby trails of the Middlesex Fells Reservation, alongside quick access to Route 3 and I-93. If you have been searching for a smart entry into a high-demand market or a turn-key rental property with highly predictable expenses, this unit delivers outstanding utility and location for the price. ~DIRECTIONS TO OPEN HOUSE~ park in lot to the right and walk to the rear of the building (the part with the duck ponds) it is a terrace level with its own door unit T-14 Open House Saturday 10/03 11:00AM-12:30PM.

200 Swanton St Unit T14, Winchester

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

$399,000

1 Beds ⋅ 1 Baths ⋅ 73579389 MLS ⋅ ['Parkview Condominiums'] BLDG.

Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and electricity, as well as access to the in-ground swimming pool. A private basement storage unit is also included for added convenience. With its comfortable layout, private balcony, pond and garden views, included utilities, and convenient location, this move-in-ready condo is a great opportunity you won’t want to miss!

200 Swanton St Unit 727, Winchester

Listing courtesy of Listing Agent: Alice Zheng from Listing Office: Shore Real Estate LLC.

$495,000

2 Beds ⋅ 1 Baths ⋅ 73578112 MLS ⋅ ['Parkview'] BLDG.

Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both generously sized bedrooms offer excellent closet space and flexible living options. The living area overlooks a scenic duck pond and professionally maintained grounds, creating a peaceful setting year-round. The secure card-entry building offers ample resident parking, guest parking off Swanton Street, and access to an in-ground pool. HOA includes heat, hot water, electricity, and AC for exceptional convenience and value. One basement storage unit is included.

200 Swanton St Unit 303, Winchester

Listing courtesy of Listing Agent: Joseph Pollack from Listing Office: Redfin Corp..

$974,900

3 Beds ⋅ 3 Baths ⋅ 73575764 MLS

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.

$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.

$660,000

2 Beds ⋅ 2 Baths ⋅ 73572854 MLS

Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all off, you have a private outdoor patio with water views! One deeded parking space included with an additional second space available for $40 per month. Prime location - walk to downtown restaurants, commuter rail, schools, supermarket, beach, and much more. Updates include kitchen (2020) downstairs bathroom (2023) new windows (2026) heating (2020)

60 Lake St Unit E, Winchester

Listing courtesy of Listing Agent: Shaundize Moosavizadeh from Listing Office: Coldwell Banker Realty - Boston.

$919,999

4 Beds ⋅ 2 Baths ⋅ 73561829 MLS

Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens effortlessly into a bright eat-in kitchen — an inviting space for both everyday living and entertaining. Two well-sized bedrooms with ample closet space and a full bath complete the main level, kept comfortable year-round by central air-conditioning.The lower level offers exceptional flexibility with its own private in-law suite, featuring a warm, fireplaced living room, two bedrooms with plush wall-to-wall carpeting, and a full bath — ideal for extended family, guests, or additional living space.Outside, enjoy a level, easy-to-maintain backyard, convenient off-street parking, and a one-car garage. Ideally located just minutes from Skillings Field and McDonald Field, this home offers wonderful access to local recreation, with Lynch Elementary only 0.8 miles away and the scenic Horn Pond Recreation Area close at hand. Enjoy the convenience of nearby Winchester Hospital, easy access to Route 3, and commuter rail service for a smooth trip into Boston. A home that blends comfort, versatility, and an unbeatable location — a must-see that won't last long. Showings begin 8/22 @ Open House 1:30-3PM

96 Loring Ave, Winchester

Listing courtesy of Listing Agent: Jeremy Smith from Listing Office: StartPoint Realty.

$799,000

3 Beds ⋅ 2 Baths ⋅ 73555218 MLS

Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.

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