Winchester Real Estate

Welcome to Winchester, Massachusetts, a charming town nestled in Middlesex County, just a stone's throw from the bustling city of Boston. Known for its picturesque landscapes and rich history, Winchester offers a unique blend of suburban tranquility and urban accessibility, making it a coveted destination for families, professionals, and retirees alike.

One of the town's standout features is its vibrant community spirit. With a population that prides itself on involvement and engagement, Winchester boasts an array of local events, farmers' markets, and seasonal festivals that foster connections among residents. The town's historic downtown area is lined with delightful boutiques, cafes, and restaurants, offering a perfect setting for leisurely strolls or a cozy afternoon coffee.

Education is a cornerstone of Winchester, with its highly-rated public schools and a commitment to academic excellence. Families are drawn to the area for its exceptional educational opportunities, which are complemented by a strong sense of community support.

Nature enthusiasts will appreciate the town's abundance of parks and recreational spaces. The scenic Winchester Town Common, along with the nearby Mystic Lakes, provides ample opportunities for outdoor activities such as hiking, biking, and kayaking. The town also offers well-maintained trails and playgrounds, ensuring that residents of all ages can enjoy the great outdoors.

With its rich history, strong community ties, and convenient access to Boston via the commuter rail, Winchester is not just a place to live—it's a place to thrive. Whether you're looking for a serene suburban lifestyle or a vibrant community atmosphere, Winchester has it all. Come discover your new home in this enchanting town!

Newest Listings in Winchester

$1,899,000

4 Beds ⋅ 3 Baths ⋅ 73596915 MLS

Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High Street, Winchester

$1,699,000

4 Beds ⋅ 3 Baths ⋅ 73596720 MLS

Welcome to 3 Sunset Road, a beautifully updated 4 BR 2.5 bath colonial with rear addition featuring a 1st floor primary option, a fabulous great room w/vaulted ceilings, and a versatile floor plan! This beautiful home is situated on a generous 1/2 acre lot in one of Winchester’s most loved neighborhoods! The large renovated kitchen with custom cabinetry & high end appliances offers plenty of room for storage, cooking and gathering and opens to a lovely dining room w/ easy access to an expansive deck overlooking the gorgeous back yard, perfect for indoor and outdoor entertaining. A warm and inviting living room features a wood-burning fireplace, while the impressive family room with soaring vaulted ceilings provides an incredible space to gather. The luxurious primary suite offers a spacious bath with double vanities, a walk-in closet, and a private sunroom, ideal for a home office, gym, or quiet retreat. Three additional bedrooms and a full updated bath complete the second level. The finished lower-level playroom offers even more flexible living space. Outside, the expansive, private backyard is truly special, offering endless possibilities for kids play, gardening, entertaining, relaxing. A wonderful opportunity to move right in and enjoy spacious living in a fantastic Winchester location, convenient to schools, shops, restaurants, and all that Winchester has to offer!

3 Sunset Road, Winchester

$329,900

3 Beds ⋅ 1 Baths ⋅ 5116190 MLS

YOUR SCENIC LAKE-VIEW HOME AWAITS WITH EXPANDABLE VALUE! Wake up every day to beautiful water views! This 3-bedroom ranch sits just across the street from Forest Lake and perfectly blends effortless single-level living with an extraordinary equity-building opportunity. Step outside your front door to views of Forest Lake, or look inside to discover the home’s hidden gem: a sunlit 500 SF dry-walled garage boasting high vaulted ceilings and windows with lake views. While it functions beautifully as a clean oversized 1 car garage, this architectural canvas is a buyer’s dream, offering an established foundation and roof-line with the possibility of transforming into a massive heated family room or bonus space. Enjoy the quintessential New Hampshire lake lifestyle with low maintenance and easy proximity to the town beach. Whether you are looking to downsize, invest, or capture a beautiful scenic escape before winter, this property delivers immense lifestyle value. Come explore the possibilities this home offers, PLUS it's located just 15 minutes south of Keene. Showings begin at the open house Saturday 10/31 at 11-2p and Sunday 11/01 from 12-2p.

481 Forest Lake Rd, Winchester

$1,450,000

73595844 MLS

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

$699,000

5115957 MLS

Welcome to 37 Michigan Street, a meticulously cared-for, turnkey four-unit multi-family property offering incredible versatility, robust cash flow, and complete flexibility. The unit mix features a spacious four-bedroom open-concept layout that is ideal for an owner-occupant or high-yield rental income, complemented by one two-bedroom apartment and two one-bedroom apartments for a total of eight bedrooms across the entire building. High-quality infrastructure provides rare peace of mind, highlighted by a dependable Buderus furnace, durable metal roof, separate electric meters for each apartment, a coin-op laundry room, and a sprawling, private back yard. Situated on 8.9 wooded acres, the property boasts valuable standing timber and unlimited potential for future expansion or development with town approval. Nestled in charming Winchester, owners and tenants enjoy a vibrant Monadnock Region lifestyle with local craft tasting rooms, historic covered bridges, and peaceful paddling on the Ashuelot River. Outdoor enthusiasts will appreciate being just minutes from the 13,300-acre Pisgah State Park for hiking, mountain biking, and trail exploration, all while commuting with quick drives to Keene, Massachusetts, and Vermont. Whether you choose to house-hack by living virtually rent-free in the flagship four-bedroom home or expand your investment portfolio with an income-generating property, this presents a rare blend of charm, turnkey quality, and immediate upside.

37 Michigan St, Winchester

$499,900

4 Beds ⋅ 2 Baths ⋅ 5115929 MLS

Step back in time with this 1770 post-and-beam Antique Colonial. Poised in a picturesque setting, the property welcomes you with iconic stone walls and scenic views of surrounding pastures. Inside, rich wide-pine flooring tells a story of age-old craftsmanship, anchored by three stately brick fireplaces that serve as warm, distinguished focal points. Character-rich kitchen, complete with a built-in hutch, a cozy pellet stove, and a versatile loft space. Adding immense value is the attached 50-by-20-foot barn, offering an expansive, flexible footprint for a workshop, hobby space, or extra storage. A rare opportunity to own a piece of living history. Additional acreage available. Agent interest.

679 Warwick Rd, Winchester

$629,000

2 Beds ⋅ 2 Baths ⋅ 5115857 MLS

Discover a unique property offering comfortable living, excellent visibility, and exceptional versatility. This property features a 1,500 SF home/living space, providing an inviting residential space, along with additional buildings and income-producing opportunities. Conveniently located on Route 10, the property offers easy access and outstanding potential for a variety of residential and business uses. In addition to the living area, the property includes a 1,500 SF commercial space and a 3,345 SF garage featuring four bays, a paint booth, and office space. The garage is nearly turnkey and could be ideal for an automotive enthusiast, mechanic, motorcycle hobbyist, or anyone seeking space for a home-based business, subject to applicable approvals. The property also has town permission to display up to ten vehicles for sale and includes a leased food truck site. With the apartment and commercial space already leased, the property offers an opportunity to enjoy rental income while exploring its many possibilities. The garage is currently leased month-to-month at below-market rent, providing flexibility for a future owner to occupy the space or maximize its income potential. The previous garage tenant paid $2,700 per month, and projected net operating income for the property is approximately $45,795 annually once the garage is leased at market rates. Serviced by private well and septic, this distinctive property combines residential living with additional space, income potential, and versatility in a convenient Winchester location. Whether you're looking for a property with room for your hobbies, space for a business, or an opportunity to supplement your income, 581 Keene Road offers a compelling combination of possibilities.

581 Keene Rd, Winchester

$1,049,900

3 Beds ⋅ 2 Baths ⋅ 73595417 MLS

Welcome to 28 Olive Street, a renovated 3-bedroom, 2-bath ranch in Winchester with 1,783 square feet of finished living space and a top-to-bottom update that lets you move right in. The main level centers on an all-new, slightly expanded eat-in kitchen that opens to an adjacent living room. A wood-burning fireplace and shiplap accent wall anchor the living room. The main living level features refinished hardwood floors, all-new doors, trim, ceilings, and lighting, plus new central AC. Three bedrooms share a completely updated full bath. Downstairs, the finished lower level adds valuable flexible space. The spacious recreation room offers plenty of space for a media area, gym, or home office, plus a second full bathroom, recessed lighting, vinyl flooring, and its own mini-split for heating and cooling. A separate utility room keeps storage, laundry, and mechanicals out of sight. The big-ticket items are done: new roof, windows, siding, electrical service, and exterior doors. The 6,527-square-foot corner lot has a private driveway, new entry stairs, and a crisp new white vinyl fence surrounding the entire property. With the heavy lifting already complete, 28 Olive Street is a rare chance to own in Winchester without the projects. Offers, if any, will be reviewed Monday at Noon.

28 Olive St, Winchester

$269,900

3 Beds ⋅ 3 Baths ⋅ 5115622 MLS

Nestled in a picturesque setting directly across from the scenic Coombs Covered Bridge, this antique farmhouse offers a blend of rustic charm and practical living space. Situated on over two sloping acres, the property features two bedrooms and a country kitchen with a cozy fireplace perfect for gathering after a long day. Livingroom features wide wood flooring and small first-floor office with a half bath provides flexible functionality, making it ideal for a home office, studio space, or bedroom. BBHW heat with large supplemental wood stove in the basement. Though the home could use some updates, its layout and charm make it a fantastic choice for a personalized renovation and the Seller will also contribute $10000 towards Buyers allowable closing costs!!

976 Old Westport Rd, Winchester

$1,450,000

8 Beds ⋅ 6 Baths ⋅ 73594547 MLS

67-69 Hemingway St, Winchester

$2,999,000

5 Beds ⋅ 5 Baths ⋅ 73594545 MLS

New construction currently underway. Estimated completion in approximately Spring/Summer 2027. Set on an impressive 22,629 sq. ft. lot, this beautifully crafted new construction offers exceptional space, thoughtful design, and a peaceful setting with easy access to the Middlesex Fells Reservation and I-93. Designed for today's lifestyle, the main level features a welcoming foyer, elegant living and dining rooms, a spacious family room with fireplace, and a stunning chef's kitchen with a walk-in pantry and adjoining mudroom and half bath. Upstairs, the luxurious primary suite is complemented by four additional bedrooms, 4 beautifully appointed baths, and a convenient second-floor laundry room. An attached two-car garage, generous backyard, and exceptional craftsmanship throughout complete this rare opportunity to own a stunning new home on a charming side street.

5 Forest Cir, Winchester

$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

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Winchester Real Estate

Newest Listings in Winchester

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