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$1,750,000
5 Beds 3 Baths 73374060 MLS
OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart inside and out. The primary ensuite has cathedral ceiling and walk-in closet. 4 additional rooms and a shared bath complete the second floor. First floor has a beautiful flow - formal living room, dining room adjacent to the gorgeously renovated kitchen which opens to the family room. From there, a french door leads to a beautiful private patio and fenced yard space perfect for outdoor dining or perhaps a firepit. Lower level offers finished space with an exercise room that walks out to the driveway and garage; laundry and 1/4 bath. Close to Middlesex Fells!

18 Englewood Road, Winchester

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

$3,200
2 Beds 3 Baths 73380725 MLS
Available 9/1/2025! Highly Desirable The Willows Condominiums.... Sunny 2 bedrooms and 2.5 bathrooms second floor unit... Openlayout living room, dining room, kitchen & sliding door leads to private deck.... In-unit laundry, Stainless Steel Appliances, Gasfireplace, Hardwood floors... Gas heating with Central AC... Spacious master bedroom with large walk-in closet and bathroomin suite... Generous second bedroom and family bathroom... The Condominiums has spacious Clubhouse with gym exercisefacilities, inground outdoor pool, large entertainment space complete with kitchen... Easy access to Rt 93, Rt 95 & Boston… NoSmoke, No Pets. First, last, plus security deposit prior of move in.

7 Conant Rd Unit 11, Winchester

Listing courtesy of Listing Agent: Yongcheng Wang from Listing Office: Phoenix Real Estate Partners, LLC.

$2,350,000
6 Beds 4 Baths 73360850 MLS
Welcome to the Flats, where elegance and charm abound, the neighborhood is the one everyone aspires to. A gorgeous foyer welcomes you and flows easily into the living room and dining room, both impressively lit with natural light. A fireplace and custom built-ins add warmth and charm, beckoning for dinner parties and entertaining. A huge kitchen offers ample counter space, a sweet banquet, custom Kidder Blaisdell cherry cabinets & easy flow to the attached family room. There is an impressively large mudroom with cabinets, laundry, and plenty of room for sports gear. Upstairs, a large primary site offers a quiet retreat, with double closets, hardwood floors, and a spa-like bath. There are 4 other large bedrooms with high ceilings plus two home offices. The lower level offers an expansive playroom, home gym, storage room, and plenty of closets. A wonderful front porch, fenced yard, and two-car garage complete this pretty picture, all on one of the Flats most desirable street

19 Yale St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.

$2,550
2 Beds 2 Baths 73379241 MLS
Wonderful, bright two bedroom townhome in Winchester at an affordable price. Move right in, the previous owner updated the kitchen with granite countertops and stainless steel appliances. Along with newer windows, increased insulation has been added for lower heating bills.The hot water heater has also been updated. The walls are neutral and the floors are gleaming hardwood. The unit has a flowing layout with a large master bedroom and its own bath. Both bedrooms have expansive closet space. Part of the basement can be used as storage room. There are two assigned parking spots, a great patio in the backyard for summer fun. All of this plus great schools, easy commutes and a cute downtown to explore. Hurry over before this one is gone too.

279 Cross St Unit 279, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Blue Ocean Realty, LLC.

$749,900
2 Beds 2 Baths 73362463 MLS ['The Willows'] BLDG.
Rarely available at The Willows, you enter this unit with ease through your private, attached one car garage or the step-free front entrance—an ideal setup for everyday convenience. This beautifully maintained first-floor unit offers the perfect blend of comfort, style, and accessibility. Inside, you'll find two generously sized bedrooms, including a spacious en-suite with direct access to one of your own private patios. The open-concept living and dining areas are anchored by a cozy gas fireplace and rich hardwood floors, while the modern kitchen flows seamlessly to a second private patio—perfect for morning coffee or evening unwinding. With tasteful finishes throughout, this move-in ready home is a true retreat. In unit laundry and plenty of storage complete this perfect space. Enjoy worry-free living with professional landscaping, snow removal, extra storage, an in-ground pool, and a welcoming clubhouse—all part of this highly desirable community. Come see it before offers are due.

7 Conant Rd Unit 34, Winchester

Listing courtesy of Listing Agent: Melanie Lentini from Listing Office: Leading Edge Real Estate.

$3,025,000
6 Beds 5 Baths 73350559 MLS
Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one of the town’s most picturesque streets. The stunning state of art chef’s kitchen was just completed & seamlessly connects to a butler’s pantry w/ wet bar & wine chiller, leading to an elegant dining room w/ fireplace. The oversized family room is bathed in natural light w/walls of striking arched windows & a screen porch leading to a deck & custom stone patio overlooking a large level yard. The second floor showcases 4 spacious bedrooms, 2 baths including a generously sized primary/currently using BR 4 for walk in closet. The 3rd floor offers 2 additional bedrooms, office & full bath. The finished walk-out lower level offers great space for movie nights, a gym & storage w/direct entry 2 car+ garage & mudroom. Close to the town center, train to Boston, Mystic Lakes beach, playgrounds & scenic trails, this exceptional home offers both charm & convenience in a top neighborhood!

21 Sheffield West, Winchester

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

$1,535,000
4 Beds 3 Baths 73375531 MLS
Beautifully updated 4-bed, 2.5-bath ranch on a landscaped half-acre lot with attached 2-car garage. Enjoy single-level living with an open floor plan, cathedral-ceiling kitchen with granite counters, island seating, and stainless appliances. Living and dining areas flow seamlessly; cozy family room with fireplace. Sunroom with wall of windows overlooks the expansive backyard. Primary suite features cathedral ceiling, 2 custom walk-in closets, and renovated private bath. Four-zone gas heat, central air, Pella windows, sprinkler system, and full insulation in basement, attic, and walls. Ample basement storage. Outdoor living includes 3 decks, a circular stone patio, stone walls, and fire pit. Move-in ready!

65 Thornberry Rd, Winchester

Listing courtesy of Listing Agent: Jun Zhang from Listing Office: HMW Real Estate, LLC.

$1,510,000
3 Beds 2 Baths 73362193 MLS
A great opportunity to reimagine this custom built spacious cape in a sought-after Winchester neighborhood! Set on a generous lot, this unique home has been lovingly maintained and is full of potential; ready for updates & your personal touch! The floor plan provides a flexible layout that’s ideal for easy living with a spacious first-floor bedroom, full bath, an oversized home office or add'l bedroom, large living room w/ fplc & bay window, dining room & eat-in kitchen. Step out from the kitchen onto a large deck that overlooks the expansive lush back yard, finished LL w/ fplc, & bath plumbing. Two-car garage provides direct access into a charming sunroom, offering additional space or a potential mudroom. Upstairs, you’ll find two generously sized bedrooms & walk-in storage areas offering room to expand. Renovate/ add on or rebuild on this great West side oversized lot! The options are endless...Close to Lexington/Arlington/Winchester center/ major highways and 15 minutes to Boston!

7 Hutchinson Rd, Winchester

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

$1,182,000
3 Beds 2 Baths 73356684 MLS
Located in a very desirable East Hill neighborhood, this one owner Circa 1929 Dutch Colonial offers a wonderful opportunity for the next owners to bring their ideas and make this home their own. The interior features many generous sized rooms, hardwood floors, crown molding, built in China cabinet, French doors, a brick fireplace and many more original details. This home is traditional with the kitchen, dining room, living room and an ideal home office/den and a half bath on the first floor and 3 bedrooms and a full bath on the second floor. Beautiful natural sun light shines throughout. Outside, there is a detached one car garage and a lovely yard perfect for relaxing, gardening and entertaining. Within a short distance to Winchester Center, schools, commuter rail and major routes, don't miss this charming antique home with lots of potential!

10 Allen Rd, Winchester

Listing courtesy of Listing Agent: Sally Baldwin from Listing Office: Coldwell Banker Realty - Lexington.

$2,850,000
4 Beds 4 Baths 73352827 MLS
Sprawling expanded cape set on stunning private 1/2 acre lot in coveted Brooks neighborhood! The curb appeal alone will draw you in to this spacious 4300+ sf 4BD 4 BA home offering a classic exterior with a stunning "must see" interior; featuring formal spaces great for entertaining blended w/casual living areas both inside & out w/ walls of floor to ceiling windows capturing the elements of nature, visually blending the serene setting w/ the chic contemporary interior. The gorgeous new kitchen w/ 48" gas range is the heart of this home w/ stunning family room wall of sliders to deck & fabulous patio/yard recently completed by top landscape architect. The first floor also features a guest suite w/ adj. bath, laundry, plus a home office or playroom, mud room & 2 car garage. The second floor features a glorious primary suite w/ full bath / steam shower & walk in closet; plus two additional large bedrooms & full hall bath. Newly finished LL w/ full bath / guest suite & Family/Media room!

45 Brooks Street, Winchester

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

$690,000
2 Beds 3 Baths 73368504 MLS ['The Willows At Winchester'] BLDG.
OPEN HOUSE Sunday, May 18: 1-3:30PM. Welcome to the highly coveted condominium living in Winchester: the Willows. This unit has over 1,600 sq. ft., with two stories/duplex style condo, 2 beds, and 2.5 baths, making it one of the larger units in the complex. It features many modern amenities such as hardwood floors in the living area, three balconies, in-unit washer/dryer, gas fireplace, and Central A/C & heating with Nest thermostat. Additional amenities include 2 parking spots (one garage and one exterior space), deeded storage area in the basement, an in-ground Swimming Pool, exercise room, and clubhouse. It is located within a highly rated school system in Massachusetts and within two miles drive to Downtown Winchester and MBTA Commuter Rail.

7 Conant Road Unit 60, Winchester

Listing courtesy of Listing Agent: Irene Novia Loka from Listing Office: Matahari Real Estate LLC.

$1,650,000
4 Beds 4 Baths 73367726 MLS
A chance to update and create your personal design that is located in Winchester's sought after Vinson Owen School district. Set on a impressive massive manicured corner lot that has been maintained since it has been custom built by its original owners. Scenic backyard with a patio off the kitchen that spills on a large private backyard that has an inground pool. Set the stage with a large foyer that is adjacent to a large living and dining room. Eat in kitchen with a cooktop and double wall ovens that steps out to the private patio or the massive family room that has seen lots of gatherings. Second floor has four bedrooms and two bathrooms. The lower level walk out is finished with ceramic floors, kitchen cabinets and potential for a additional bedroom. With a full bathroom it is waiting to be a accessory suite or perfect for a au pair suite.

34 Coolidge Rd, Winchester

Listing courtesy of Listing Agent: Pauline Marino from Listing Office: Coldwell Banker Realty - Lexington.

$1,475,000
4 Beds 3 Baths 73365328 MLS
Lovely brick home just up the road from EVERYTHING!!! Commuter Rail, Library, Schools, Shopping, Restaurants, Town Hall. Less than 9 miles to Boston! So close to the Middlesex Fells and the Tri-Community Greenway. Location, location, location - CHECK! Now the structure...classic brick home built to stand the test of time with BIG IMPROVEMENTS. Grand front to back living room with fireplace leads to sunroom. Dining room and kitchen lead to mudroom with half bath at the back. Upstairs 4 bedrooms, a large bathroom off a lovely landing. Partially finished basement evokes years gone by awaiting your vision for the future. PELLA windows, new sewer pipe, newer roof, COPPER GUTTERS and downspouts on house and garage, landscaping improvements including new front brick wall and new driveway, 5 new mini-split units for cooling, leased solar panels to reduce your electric costs. Sellers would love a longer or flexible closing with possibility of U&O - make your offer and we will figure it out!

195 Mystic Valley Parkway, Winchester

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

$2,111,000
5 Beds 4 Baths 73358449 MLS
Located just outside the town center near Brooks neighborhood & the train to Boston! This spacious home has it all! Situated on a lovely level lot w/ 2 car garage & private yard, this updated move in ready home boasts an abundance of space w/ideal layout & large sun drenched eat in kitchen with skylights & bay window, adjacent family room, living room w/ fplc, formal dining, office, laundry & 2 1/2 baths all on the first floor. Upstairs, you will find 4 spacious beds, 2 baths including a large primary suite w/ beautiful updated bath w/ soaking tub plus home office #2. The finished third floor offers additional living space with 2 rooms incl. BR #5 & playroom/ family space. A large game room/ gym in basement presents endless possibilities for further customization to suit your needs. Enjoy outdoor living in the charming yard w french doors out to deck & patio perfect for gatherings or quiet afternoons. Experience comfort, space & location~ add your personal touch & its your dream home!

14 Grove Street, Winchester

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

$1,269,000
3 Beds 4 Baths 73363316 MLS
Welcome to 158 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel appliances, a spacious island, and an adjacent mudroom with a half bath. The second floor offers two bedrooms and a full bath, while the third floor is a private primary suite with a spa-like en-suite. The finished lower level provides a versatile space—ideal as a great room, office, or gym—with its own full bathroom. This home includes two off-street parking spaces with an EV charger. Conveniently located near Winchester’s shops, dining, parks, & commuter rail. Home designed for today's lifestyle with guidance from Louis Ashman.

158 Swanton Street Unit 158, Winchester

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

$1,084,000
3 Beds 4 Baths 73350237 MLS ['158-162 Swanton'] BLDG.
Welcome to 160 Swanton Street—a stunning Ron Roy new construction townhome blending modern design with unparalleled craftsmanship and attention to detail in the heart of Winchester. The first floor features an open-concept living, dining, and kitchen area with gleaming hardwood floors and a cozy fireplace, creating a warm and inviting ambiance. The chef-inspired kitchen boasts stainless steel appliances, a spacious island, and an adjacent mudroom with a half bath. The second floor offers two bedrooms and a full bath, while the third floor is a private primary suite with a spa-like en-suite. The finished lower level provides a versatile space—ideal as a great room, office, or gym—with its own full bathroom. This home includes two off-street parking spaces with an EV charger. Conveniently located near Winchester’s shops, dining, parks, & commuter rail. Home designed for today's lifestyle with guidance from Louis Ashman.

160 Swanton Street Unit 160, Winchester

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

$2,950
2 Beds 1 Baths 73372811 MLS
Stunning recently removated unit in the heart of Winchester with easy access to Boston and the surroundings. Conveniently located near commuter rail, library, resturants and shopping.The unit has an Open floor plan with high ceilings.The unit welcomes you with plenty of natural light with oversized windows. Completely updated kitchen with granite counter tops and upgraded cabinets. Also gather around the kitchen island for your morning coffee or for any meal for that matter. A great convenience is the washer and dryer in the unit. Over all it's just a wonderful unit in a great school district. It also has close proximity to Leahy Clinic and a great location for medical professionals

115 Washington Street Unit 2B, Winchester

Listing courtesy of Listing Agent: Vijoy Abraham from Listing Office: Abraham Realty.

$1,140,000
3 Beds 2 Baths 73356058 MLS
This inviting ranch house is cheerful and functional. Sunlight floods the open living and dining rooms, while custom plantation shutters offer privacy. Hardwood floors, a gas fireplace, and arched doorways add character and warmth to the space. The well-equipped kitchen features granite countertops, glass-front cabinetry and access to a side deck for al fresco dining. Three bright bedrooms and a full bath complete the 1st floor. The third bedroom, highlighted by wainscoting, is currently used as a den. The downstairs family room, complete with a wood-burning fireplace, a built-in bar and updated full bathroom, is perfect for recreation. The basement also offers ample storage, making it easy to keep your home organized. The even backyard is ready to host outdoor activities or quiet relaxation. Located in a highly sought after neighborhood, this home is 2 blocks from Ambrose Elementary School and just over a mile from the train station and Winchester's lively downtown. Welcome home!

7 Indian Hill Road, Winchester

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

$2,000,000
4 Beds 4 Baths 73360401 MLS
Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly into the spacious living and family rooms—ideal for everyday living & entertaining. The main level offers three generously sized bedrooms and two full baths, including a peaceful primary suite with panoramic views, a walk-in closet, and beautifully renovated bath with two individual vanities. The lower level adds fantastic flexibility with a media room, additional bedroom, full bath, and flexible multipurpose space. Step outside to enjoy a wraparound deck and lower-level patio with direct access to the pond—perfect for kayaking, fishing, and ice skating. This is a rare and special opportunity!

11 Chesterford Rd E, Winchester

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

$1,350,000
3 Beds 4 Baths 73352886 MLS
Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming front porch greets you, setting the tone for the warmth and charm inside. The first-floor primary suite provides convenience, while two fireplaces offer cozy spots for relaxation. The eat-in kitchen features radiant heat floors with an enclosed porch to the side complete with exposed beams and skylights, creating a serene space to unwind and enjoy the view of the natural surroundings. Upstairs, a versatile suite awaits, featuring a spacious bedroom, full bath, office space, and a cozy reading nook — ideal for guests, a home office, or a quiet retreat with a possibility of an expansion.

34 Fells Road, Winchester

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

$1,450,000
3 Beds 4 Baths 73350252 MLS ['The Ledges'] BLDG.
Welcome to The Ledges! This is a desirable end unit located in a fabulous cul de sac location. Freshly painted first level makes this unit ready to move in.This is a perfect floor plan with living room, dining room and family room with fireplace and bookcases opening up to expansive kitchen with pantry. Enjoy the serenity of a private deck off family room. Primary suite on first floor.with large updated bath.Second floor has a large loft office and full bath and bedroom. Finished lower level has third bedroom with updated bath and spacious media room with built in bookcases.There is plentiful storage areas in hall and cedar closet.Heating system has been updated.Put your finishing touches on the beautiful home with hardwood floors on first and second level. This is a rare opportunity to own this north facing property which receives consistent indirect light throughout the day with sunny south facing kitchen and family room overlooking private woods.

7 Wainwright Rd Unit 8, Winchester

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

$1,881,900
4 Beds 4 Baths 73337914 MLS
This stunning 4-bedroom, 4-bath modern home offers the perfect blend of luxury and tranquility. Featuring soaring vaulted ceilings, a floor-to-ceiling fireplace and an open-concept design, this spacious home is bathed in natural beauty. The gourmet kitchen is pristine and boasts high-end appliances, quartz countertops, a prep sink and secondary dishwasher, and a large island—ideal for entertaining.! Hardwood floors highlight the main living area and bedrooms, working as a perfect offset to all the natural light this home enjoys. There's a cozy den with a wet bar/entertainment area plus a huge family room in the lower level. The primary suite is a private retreat with a spa-like bath and walk-in closet. Step outside to a serene backyard oasis with a large deck, set against pristine conservation land for ultimate privacy. A rare find combining contemporary elegance with nature’s beauty!

4 Olde Lyme Rd, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.

$1,558,000
3 Beds 4 Baths 73352966 MLS
Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen boasts granite countertops and opens to a family room w/ a fireplace & slider to a spacious deck and backyard - perfect for entertaining. Host celebrations large & small in the charming living room & dining room. The 2nd floor welcoming primary suite boasts a walk-in closet and charming en suite bath. Two additional well-sized bedrooms share a full bath on this level. The finished lower level has a bonus room & also a great office/guest room & 4th bath. Brand new roof, freshly painted interior, HW floors & storage space galore are just some of the hallmarks of this great family home.

24 Eugene Drive, Winchester

Listing courtesy of Listing Agent: Andrea O'Reilly from Listing Office: Keller Williams Realty Evolution.

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