Winchester, MA Real Estate | Winchester, MA Homes between $1,000,000 and $1,500,000 for Sale

Excellent development opportunity in Winchester! This 22,403 sq. ft. lot at 67-69 Hemingway Street is approved for the construction of two townhomes, with architectural plans included in the sale. The proposed design features two spacious residences, each offering 4 bedrooms, 2.5 baths, open-concept living and dining areas, mudroom, walk in pantry, a private primary suite, outdoor living space, an attached garage, and the option to finish the basement for additional living space. Zoned RG, the property will be delivered as a vacant lot, with public water, public sewer, and natural gas available, providing an excellent opportunity for builders and developers to bring this project to life. The location offers an appealing combination of neighborhood living, outdoor recreation, and commuter convenience. Just minutes from the newly constructed Lynch Elementary School, Horn Pond's scenic walking trails, and the Tri-Community Bike Path, the property provides easy access to some of Winchester's favorite outdoor destinations. Downtown Winchester offers a vibrant mix of local shops, restaurants, cafés, and community amenities, along with commuter rail service to Boston. Convenient access to Routes 93 and 95 adds to the property's appeal. Winchester continues to be a highly desirable community with a strong buyer pool seeking quality new construction. With approvals in place, architectural plans included, and a location that appeals to today's homebuyers, this is an attractive opportunity to develop two new residences in one of the area's most sought-after markets.

67-69 Hemingway St, Winchester

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

$1,049,000

4 Beds ⋅ 2 Baths ⋅ 73594513 MLS

Welcome to 16-18 Russell Road, a classic two-family home tucked along a tranquil one-way street just a short walk from downtown Winchester. The bright upper level features 3 bedrooms and 1 bath, while the flexible lower level offers a 1-bedroom, 1-bath layout with the potential to expand to two bedrooms, providing added versatility for investors, multigenerational living, or owner-occupants looking to offset their mortgage with rental income. Hardwood floors run throughout much of the home, while ductless mini-split systems provide efficient heating and cooling, complemented by a gas forced-air system in the basement*. Vinyl siding and an asphalt roof help keep exterior maintenance manageable, while ample off-street parking and a yard add everyday convenience. Located within the district for the newly built Lynch Elementary School, the home is also just a short walk to the commuter rail, a new neighborhood coffee shop, restaurants, and amenities of Winchester's vibrant town center.

16-18 Russell Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$1,299,000

6 Beds ⋅ 2 Baths ⋅ 73592723 MLS

An exceptional turnkey opportunity in Winchester, 419–421 Washington Street presents a beautifully refreshed two-family residence featuring significant mechanical upgrades and refined finishes throughout. Major improvements include a brand-new roof, newly paved driveway with parking for 4–5 vehicles, separate central heating and air conditioning systems, separate utilities, fresh interior and exterior paint, and beautifully refinished hardwood floors. Ideally situated near vibrant Winchester Center, enjoy convenient access to local dining, boutique shopping and commuter rail service to Boston. Proximity to Winchester Hospital, I-93, Route 128/I-95, Middlesex Fells Reservation and Winchester's highly regarded schools further enhances the appeal. Move-in ready with extensive recent improvements, this exceptional property offers an ideal opportunity for owner-occupants and investors seeking lasting value in one of Greater Boston's most desirable communities.

419-421 Washington St, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.

$1,125,000

3 Beds ⋅ 2 Baths ⋅ 73591400 MLS

Welcome to this charming center-entrance Colonial, ideally situated on a lovely side street just moments from Winchester Center! Offering 3 bedrooms and 1.5 baths, this sun-filled home is ready for its next owners to make it their own. Timeless features include hardwood floors, a cozy fireplace, a sunroom, a full basement, a detached garage, and a wonderful yard with patio—perfect for relaxing or entertaining. The spacious eat-in kitchen offers plenty of room for gathering with family and friends. The primary bedroom has a generously sized walk-in closet and views of breathtaking sunsets. Lovingly maintained and cherished for many years, this special home is ready to welcome its next chapter and create lasting memories for years to come.

8 Stone Ave, Winchester

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.

$1,399,000

3 Beds ⋅ 3 Baths ⋅ 73590311 MLS

Situated on a quiet cul-de-sac in a desirable Winchester neighborhood surrounded by substantial homes, this well-maintained 3-bedroom, 2.5-bath Split-Level offers comfortable living and plenty of potential on a generous 19,998 sq. ft. lot. Built in 1976, the home features hardwood floors throughout and central air conditioning. The main level includes a spacious living room, formal dining room, and eat-in kitchen with access to a screened porch overlooking the backyard. Three bedrooms, including a primary suite with private bath and a renovated family bathroom, complete this floor. The lower level provides additional living space with a family room featuring a fireplace, laundry area, half bath, and direct access to the attached two-car garage. Lovingly cared for over the years, this home is ready to enjoy as is, with room to make it your own over time. Conveniently located near Vinson-Owen School, Wright-Locke Farm, and the Winchester Swim & Tennis Club, it's a great opportunity to settle into one of Winchester's sought-after neighborhoods.

6 Aricia Ln, Winchester

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

$1,399,000

5 Beds ⋅ 2 Baths ⋅ 73588977 MLS

Welcome to 15 Lloyd Street, ideally situated in one of Winchester’s most desirable downtown neighborhoods! This charming, recently updated colonial welcomes you with a newly constructed farmers porch & features 4- 5 bedrooms, 1.5 baths, and a flexible layout with plenty of space for everyday living, working from home, and entertaining. The inviting sun-drenched living room features high ceilings and opens to the dining room which has slider access to a large deck, along with an eat in kitchen, 1/2 bath and spacious entry foyer blending together to create a warm and welcoming home to enjoy. The second floor features 4 bedrooms including a spacious primary along with a full hall bath. An additional bedroom or recreation space and office add great bonus space on the third floor. Some recent 2024 updates include new roof, heating system/HVAC, new front porch, updated electrical, all new hardwood floors, new window and baseboard trim in LR/FR & more! Walk out lower level offers laundry area & provides potential for future expansion/ family, game room. Additional highlights include a detached garage, off-street parking, and lovely yard to enjoy. Conveniently located in the heart of downtown Winchester close to parks, public transportation, and all that Winchester has to offer. This is a wonderful opportunity to enjoy the charm and convenience of this great home located in one of the town’s most sought-after neighborhoods! **Open houses Saturday & Sunday please stop by!**

15 Lloyd Street, Winchester

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

$1,299,000

3 Beds ⋅ 2 Baths ⋅ 73588863 MLS

Welcome to this beautifully updated and meticulously maintained 3-4 bedroom, 2 full bath home, perfectly blending timeless charm with modern amenities. An inviting farmer’s porch sets the tone for this wonderful property, situated on an expansive, level lot offering exceptional space for outdoor enjoyment. The main level features a spacious family room with a gas fireplace, custom built-ins, and a convenient desk area. French doors lead to an elegant dining room with classic chair rail detailing. The stunning, newly renovated modern kitchen features stylish finishes, stainless steel appliances, and thoughtfully designed space for everyday living. A beautifully updated full bath and versatile room office/bedroom with a new walk-in closet complete the first floor. Upstairs offers three bedrooms with hardwood floors, an updated full bath, and a charming office nook. Additional improvements new mini-split systems throughout, and an EV charger. Enjoy the oversized screened-in porch overlooking the expansive, level backyard, perfect for relaxing or entertaining. A detached oversized garage provides additional storage, while the lower level offers excellent potential for future use and duplex potential.Ideally located in Winchester's desirable Muraco Elementary School district, this move-in-ready home offers an exceptional combination of charm, comfort, and modern convenience!

39 Forest St, Winchester

Listing courtesy of Listing Agent: Danielle Storella from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,325,000

4 Beds ⋅ 2 Baths ⋅ 73579538 MLS

1st OPEN HOUSE! SUNDAY, OCTOBER 4th, 11:30am-1:00pm! Timeless New England charm meets prime Winchester living at 9 Priscilla Lane. Tucked along a quiet, tree-lined neighborhood on Winchester’s East side, this inviting 4-bedroom home offers the perfect balance of suburban tranquility, outdoor adventure, and seamless connectivity.Inside, the sun-drenched home features rich hardwood floors, a gorgeous kitchen, wood burning fireplace, flexible living areas, and an intuitive layout designed for both daily relaxation and effortless entertaining. Step outside to an expansive, private backyard—a sunlit haven perfect for weekend barbecues, garden projects, or crisp New England evenings.Outdoor enthusiasts will love living moments away from the endless hiking, trail running, and scenic escapes of the Middlesex Fells Reservation. For commuters, rapid access to I-93 and Route 128/I-95, combined with nearby Commuter Rail stations, makes reaching Boston, Cambridge, or local tech hubs exceptionally fast and direct. Complete with proximity to top-rated Winchester public schools and vibrant downtown dining and shops, this property delivers the quintessential North Shore lifestyle in an unmatched location. MAKE 9 PRISCILLA LANE YOUR HOME TODAY!

9 Priscilla Ln, Winchester

Listing courtesy of Listing Agent: Robert Del Greco from Listing Office: Compass.

$1,250,000

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.

465 Washington Street Unit 465, Winchester

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 73574929 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 Unit 465, Winchester

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

$1,049,000

4 Beds ⋅ 3 Baths ⋅ 73571480 MLS

Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace adds warmth in the family room off the kitchen, which has a slider out to a generous sized deck overlooking the serene back yard. Fresh paint throughout means there is nothing to do but move in. The same addition brought two bedrooms (primary with en suite bath), a walk-in closet, and updated kitchen cabinetry. Out back, a wood deck steps down to a spacious fenced yard with a built-in tree house, a garden area, storage shed, and in-ground sprinkler system. Central air conditioning, gas heat, town water and sewer, a one-year-old hot water tank, a partially finished, heated basement, a walk-up attic, and a four-car driveway. The location is the real headline: walk to the commuter rail, the bus, and Winchester Center's shops and restaurants, with the park, bikeway, and conservation trails minutes away. Newly renovated Lynch Elementary, McCall Middle and Winchester High School.

24 Richardson St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$1,050,000

5 Beds ⋅ 3 Baths ⋅ 73571418 MLS

Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

257 Cross Street, Winchester

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

$1,098,000

3 Beds ⋅ 2 Baths ⋅ 73566405 MLS

Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.AI-generated virtual staging. Furniture and decor are digitally added for illustration purposes only.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..

$1,289,000

3 Beds ⋅ 3 Baths ⋅ 73562273 MLS

Key upgrades include 200-amp electrical service, a 2021 Brute natural gas boiler and replacement windows. The updated kitchen features stone counters, stainless appliances and a double oven. On Winchester's West Side, this 3-bedroom, 2.5-bath home offers 2,459 sq. ft., including a finished lower level. Enjoy hardwood floors, two fireplaces, central air and a year-round sunroom.The 0.46-acre property includes a patio, in-ground pool and two-car garage. Nearby are Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. Some photos are virtually staged.

110 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Mark Kiklis from Listing Office: Kiklis Real Estate, LLC.

$1,025,000

3 Beds ⋅ 3 Baths ⋅ 73519082 MLS

GREAT OPPORTUNITY TO BUILD EQUITY!! LOW PRICE!!! Charming Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

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

$1,110,000

5 Beds ⋅ 3 Baths ⋅ 73515601 MLS

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside.

63-65 Harvard Street, Winchester

Listing courtesy of Listing Agent: Beth Sager Group from Listing Office: Keller Williams Realty Boston Northwest.

Winchester, MA Homes between $1,000,000 and $1,500,000 for Sale

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