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$1,500,000
3 Beds ⋅ 3 Baths ⋅ 73379267 MLS ⋅ ['The Elmwood'] BLDG.
Welcome to Elmwood condos with over 2,100 SF of stunning single-level luxury living in vibrant downtown Winchester! This sparkling, modern condo offers a beautifully open floor plan designed for today's discerning buyer with the kitchen, dining & living areas seamlessly integrated for both comfort and style. Enjoy high end/ top-of-the-line, rich finishes throughout, including gleaming hardwood floors, high ceilings, crown molding, and designer light fixtures. The chef’s kitchen is a standout, featuring gorgeous inset custom cabinetry, rare quartzite countertops & Thermador appliances w/ large center island, perfect for entertaining. This spacious home includes 2 oversized bedrooms, each with its own en-suite marble bathroom, plus an additional bedroom or home office for flexible living. Every detail has been thoughtfully crafted to provide the perfect blend of sophistication & functionality. 2 Deeded parking spaces included ~ enjoy easy living/ near commuter rail & easy access to 93/95

23 Elmwood Avenue Unit C, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 73373421 MLS
Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu dance parties. A renovated kitchen with a center island offers the ideal chef space and opens onto a large dining area and sweet family room. The primary, with large windows and beautiful hardwood floors, offers a surprisingly large double walk-in closet...no fighting for space here! Downstairs, a sprawling basement is exactly what is needed with room for a gym, media room, home office and storage. Outside, the ever-coveted flat yard awaits, with almost a half acre of manicured lawn and mature plantings. Meticulously maintained and brimming with character, this gem is ready to impress.

1 Saint Augustine Ct, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.
$3,600
2 Beds ⋅ 3 Baths ⋅ 73370607 MLS
Sunny and Bright Townhouse in a Desirable Location! This well-maintained townhouse offers comfortable living across two spacious levels. First Floor: Granite kitchen countertops and stainless-steel appliances, Dining area and half bath. Spacious living room with skylight, leading to a private patio. Second Floor features two large bedrooms, two full bathrooms. Washer and dryer conveniently located on this floor. Additional features include central AC, access to a swimming pool, tennis court, and clubhouse. Available: July 1st

171 Swaton St Unit 16, Winchester

Listing courtesy of Listing Agent: Wei Wang from Listing Office: WW Real Estate LLC.
$3,000
3 Beds ⋅ 2 Baths ⋅ 73369229 MLS
Bright & Sunny 3 bedroom, 1.5 bathroom, hardwood floor throughout townhome with 3 level living. it features living room, eat-in kitchen and half bath on the 1st floor, 3 bedroom with a full bath on the 2nd floor, recently finished basement that could be family room, office, or playroom, washer/dryer located in this level. Spacious backyard outdoor space for private use. It's great friendly and quiet neighborhood. Rent includes water, landscaping, trash removal. Newly built tri-town bike-way connecting Winchester, Woburn and Stoneham nearby. Convenient to shops and restaurants. Easy access to major highways to Boston and more..

11 Bradford Unit 11, Winchester

Listing courtesy of Listing Agent: Wei Wang from Listing Office: WW Real Estate LLC.
$1,877,000
3 Beds ⋅ 2 Baths ⋅ 73363882 MLS
Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious family room features a gas fireplace and doors leading to an oversized deck—perfect for summer gatherings or peaceful morning coffee.Enjoy the ease of first-floor laundry & a handy mudroom area, making everyday living a breeze.Second floor features 3 b/r, a quiet nook & potential for 4th b/r. Set on approx 13,000 sq ft of beautifully landscaped land, there's plenty of room to relax,play & entertain. A spacious 2-car garage adds even more convenience & storage.The finished lower level offers flexible bonus space for a playroom, home gym or media room—tailored to your lifestyle.Come fall in love!

20 Seneca Road, Winchester

Listing courtesy of Listing Agent: Stephanie Mcgowan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 73357768 MLS
Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A big family room is open to the kitchen, with high ceilings and loads of room to host a crowd. There is an enormous deck accessed by sliding doors. The oversized primary suite offers a luxurious retreat with plenty of room to unwind. Highlighted by a gas fireplace, the hardwood floors and big windows add an element of comfort. Huge spa-like bathroom and two walk-in closets. There is a second en-suite bedroom on this floor. Downstairs, wow! At grade, so there is tons of natural light and sliders that open to the yard Bright, airy vibe and unbeatable space.

7 Wainwright Rd Unit 117, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.
$1,250,000
4 Beds ⋅ 2 Baths ⋅ 73357438 MLS
Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom. Downstairs, you’ll find a large family room/play area, a bonus kitchen, and an additional 4th bedroom, offering plenty of options. Ample storage throughout enhances convenience. Set in a conveniently located neighborhood near schools, parks, and shopping, the town boasts two commuter rail stops just minutes from Boston. Enjoy the perfect blend of comfort and style in this charming residence. The backyard features a firepit and space for gardening and storage. Don’t miss this opportunity—envision making this house your new home!

80 Harvard Street, Winchester

Listing courtesy of Listing Agent: Robert Ellington from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,359,000
4 Beds ⋅ 4 Baths ⋅ 73355738 MLS
Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! Step into a light-filled, open-concept 1st floor, where a soaring beamed ceiling enhances the inviting ambiance. The living room boasts built-in shelves, while the kitchen impresses w/timeless white cabinetry, soapstone counters, SS appliances, large island, & pantry. The dining area, warmed by a cozy wood-burning stove, overlooks the expansive deck & beautifully landscaped yard. Upstairs, the primary suite offers a spa-like bath w/radiant heat floors, double vanity, a zero-entry shower, & luxurious soaking tub. Generously sized bedrooms & a bonus sitting room complete this level. Lower level offers endless possibilities w/2 flexible rooms, wet bar area, & a full bath. Additional highlights: a mudroom w/custom built ins, 2-car garage, C/A. Ideally located near top-rated schools, vibrant Winchester Center, the commuter rail, and scenic Fells Reservation, this home is a special find!

57 Jefferson Rd, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,260,000
3 Beds ⋅ 3 Baths ⋅ 73342253 MLS ⋅ ['Graystone At Winchester Condominiums'] BLDG.
Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms, including a master suite with a walk-in plus 2 additional closets & full bath. The finished 3rd floor adds versatility, offering the perfect space for an office, playroom, or additional living area. The large, unfinished basement with high ceilings presents endless possibilities for customization or additional living space. Enjoy the convenience of a 2-car tandem garage, providing plenty of parking and storage space. Relax and unwind on the patio, or take a stroll through the nearby walking trails. Enjoy the convenience of condo living in a unit that lives like a single family home!

261 Cambridge St Unit 261, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,330,000
3 Beds ⋅ 2 Baths ⋅ 73374660 MLS
Nestled on a quiet, tree-lined street near Winchester’s vibrant town center, this delightful storybook colonial offers charm, character, and exceptional potential. Beautifully sited on a 10,000+ sq ft wooded lot, this three-bedroom, two-bath home invites your vision to blend timeless architectural details with thoughtful updates. A fireplaced front-to-back living room flows seamlessly into a sun-drenched sunroom featuring a wood-burning stove and sliders to a spacious deck and patio—perfect for relaxing or entertaining. The main level also includes a formal dining room with built-in, a full bath, and a kitchen ready for transformation. Upstairs, find three generously sized bedrooms, a second full bath, and access to unfinished attic space ideal for storage or expansion. Additional highlights include gleaming hardwood floors, newer windows, an attached garage, and a full basement. A rare opportunity to reimagine a classic home in one of Winchester’s most sought-after neighborhoods.

17 Mason St, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,100,000
4 Beds ⋅ 3 Baths ⋅ 73371836 MLS
Back Bay meets Winchester in this victorian style attached residence in a premier Flats/ downtown location. This lovingly modernized home offers central air, first floor laundry, gas heating & cooking & tremendous closet space. The kitchen seamlessly transitions to the deck & huge manicured fenced in yard perfect for kids, pets & all outdoor fun. First floor is adorned with a dining room with butlers pantry & French doors leading to the large living room complete with wood burning marble fireplace & a beautiful entry way with regal staircase. This sundrenched home is dripping with superb detail such as high ceilings on all 4 floors & oversized windows. 2nd floor has 3 spacious bedrooms & full bath with soaking tub & skylight. Top floor has dynamite bedroom suite with den or home office & nursery. Partially finished basement is ideal for gym. A very special opportunity to live a short walk from the train, schools & all that the center of town has to offer. This is an urban oasis!

63 Church Street Unit 63, Winchester

Listing courtesy of Listing Agent: Nancy Ciampa McLaughlin from Listing Office: Redfin Corp..
$715,000
2 Beds ⋅ 3 Baths ⋅ 73371092 MLS ⋅ ['The Willows'] BLDG.
Welcome to this beautifully updated corner unit townhouse-style condo, offering ample-sized rooms, abundant natural light, & hardwood floors throughout! The layout includes 5 well proportioned rooms. Kitchen, living room w/gas fireplace w/marble surround, dining room & 2.5 bathrooms, creating a comfortable & functional living space. Both bedrooms are en-suite, providing privacy & convenience, w/one featuring a private deck, perfect for unwinding outdoors. The unit also includes an in-unit washer & dryer hookup, generous storage throughout, & was thoughtfully upgraded in 2023 w/brand-new hardwood flooring, fresh paint, & a new central A/C & heating system. This unit also has a "Garage and an additional parking spot"! Enjoy worry free living in this highly desirable community, featuring professional landscaping, snow removal, extra storage, an in-ground pool, & a welcoming clubhouse. This is the perfect blend of style, comfort, & convenience. Don't miss the opportunity to call it home!

7 Conant Rd Unit 37, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$299,000
1 Beds ⋅ 1 Baths ⋅ 73370454 MLS
Immaculate, recently renovated Jumbo Studio Condominium with a private/direct-entry terrace level. This unit is spacious and bright, featuring a slider that leads to a private patio overlooking scenic duck ponds and lush landscaping. The large eat-in kitchen features white cabinets, with a white tiled backsplash and granite countertops. The bathroom was recently updated with new fixtures, vanity, mirror, flooring, and lighting. The Condominium amenities include: an in-ground swimming pool, barbecue area, large parking area with plenty of overnight guest parking, on-site laundry rooms, on-site management, and private storage units. The low condo fee includes: heat, hot water, electricity, and air conditioning. Winchester is a quaint little town with a charming New England feel, only 8 miles north of Boston. This A-1 location is only two blocks from Winchester Center, shops, restaurants, parks, and the commuter rail. Don’t miss the exceptional opportunity!

200 Swanton St Unit T4, Winchester

Listing courtesy of Listing Agent: Michael Masci from Listing Office: North Atlantic Realty Group.
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 73366788 MLS
Available for the first time in over four decades and nestled just footsteps from Winchester Center, welcome to 117 Mount Vernon Street! As you enter, you are greeted by tall ceilings adorned with beautiful molding and a flood of natural light that fills the space with warmth and tranquility. The home offers three spacious bedrooms, including a flexible primary suite that boasts an adjoining space perfect for a home office or nursery and access to a private bath. The home's unique design includes both front and rear staircases, adding to its functional flow and classic allure. The fireplaced living room offers a cozy yet elegant setting. Step outside to discover a stunning, fenced-in yard. With multiple patios, mature landscaping, and beautiful gardens, it's an idyllic setting for gatherings or serene morning coffee moments surrounded by nature's beauty. The proximity to Winchester's shops, restaurants, schools, and commuter rail ensures a lifestyle of convenience and connectivity!

117 Mount Vernon Street, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$7,500
3 Beds ⋅ 3 Baths ⋅ 73354401 MLS
Top of the Line! Stunning newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2 1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim and white culinary grade kitchen equipped with Sub Zero refrigerator and top of the line Blue Star chef's gas range. 23' x 16' Living room overlooks 30' x 13' Privacy Veranda with marine quality mahogany flooring, cedar millwork, gas fireplace, amazing outdoor kitchen, with gas industrial grill. Unlike any executive, luxury rental in town. Short distance to Town Center, shoppes, village cafes, restaurants, and Commuter line Train. First class construction with no expense spared, in a modern & incredibly equipped luxury space.

846 Main Street Unit 4, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
$2,899,000
6 Beds ⋅ 8 Baths ⋅ 73334317 MLS
Welcome to a rare opportunity to select the final finishes in your dream home right within Winchester’s most coveted neighborhoods. 5 Clearwater presents a luxurious canvas for your vision, offering 6 bedrooms, 7.5 baths, and 5,658 sq. ft. of meticulously planned living space. The spectacular floor plan seamlessly combines modern sophistication with timeless elegance, offering the perfect foundation to personalize every detail and create a home that reflects your unique style and vision.The location is unbeatable—just minutes from Winchester Center's shops, dining, and commuter rail, with the serene trails of Middlesex Fells Reservation nearby. With top-rated schools, a welcoming community, and easy access to major routes, Winchester offers the ideal setting for your family's next chapter. This is more than a home—it's your chance to create a legacy. Don't miss this rare opportunity to make 5 Clearwater your forever home!

5 Clearwater Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$4,200,000
6 Beds ⋅ 6 Baths ⋅ 73334088 MLS
Nearing completion! Welcome to this exquisite 6-bedroom, 5-1/2 bath residence nestled in one of Winchesters most prestigious neighborhoods. This completely rebuilt, expanded & tastefully renovated home is one of a kind, offering a perfect blend of elegance & modern sophistication for a lifestyle of luxury & comfort. Step inside to discover a beautifully designed interior that exudes charm & style at every turn. The stunning chef's kitchen features a dining area, pantry, top-of-the-line appliances, custom cabinetry & a spacious 10' island w adjacent family room. The expansive, beautiful living spaces have great flow & are bathed in natural light. The primary bedroom features a dramatic vaulted ceiling, large walk In closet & a spa-like marble bath. 5 add'l beds offer space for all. Lower level w/ fabulous gym/golf simulator space, steam shower, media room & wet bar. Fabulous porch & large yard w/ built in grill area perfect for family enjoyment. All new systems, 2 car garage to be built

3 Foxcroft Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73333668 MLS
Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle

2 Chestnut St, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Advisors Living - Winchester.
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 73375278 MLS
Nestled on a picturesque lot with lush landscaping and mature trees, 9 Thornberry Road offers a perfect blend of natural beauty and refined living. Sunlight pours into this thoughtfully designed home, featuring an open-concept layout ideal for comfortable living and entertaining. The main level includes a welcoming fireplace, hardwood floors, large living room, dining area, and an updated kitchen with granite counters, stainless steel appliances, a skylight, and tranquil backyard views. With 4 bedrooms and 3 full baths, including a serene main-level primary suite, this home also features a spacious walk-out lower-level family room, separate laundry room, and abundant storage. Enjoy an attached 2-car garage, plus parking for 4+ additional vehicles. Newer exterior stairs and stone wall. Located in close proximity to Vinson Owen Elementary school, this property offers a rare blend of privacy, space, and convenience. Welcome home!

9 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Louise Coakley from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,650
1 Baths ⋅ 73365251 MLS
This rental is SHORT TERM and comes fully furnished. Sparkling, recently renovated studio with amazing views of a beautifully landscaped garden and pond. White cabinet kitchen features stainless steel appliances, tiled backsplash and a marble top peninsula with seating.The main area has hardwood floors and glass sliders out to a good sized balcony, letting in plenty of natural light. In the hall leading to the bath is a double closet. The bathroom was recently refreshed with a new vanity, mirror, shower, tiled floor and lighting. The rent covers heat, hot water, and electricity. Professionally management on-site. Convenient to town shops, restaurants and commuter rail. Explore the nearby Tri-Community Greenway with 10.6 miles for biking and walking. A "just right" place to land for a sabbatical or transition to a new home.

200 Swanton St Unit 502, Winchester

Listing courtesy of Listing Agent: Susan Murie from Listing Office: Aikenhead Real Estate, Inc..
$2,450,000
4 Beds ⋅ 4 Baths ⋅ 73351001 MLS
Welcome to this gracious Colonial, seamlessly blending traditional charm with modern amenities, perfect for today’s lifestyle. Located in one of Winchester’s most desirable neighborhoods, you’ll enjoy easy access to top-rated schools, the commuter rail, and downtown. This home showcases deep moldings along w/ a stunning kitchen that naturally flows into the living/dining area & family room, complete w/ a cozy fireplace. The first-floor study offers built-ins, perfect for a home office. Retreat to the primary bedroom, featuring an extraordinary spa-like bath. 3 additional bedrooms, 2 full bathrooms & a laundry room completes the 2nd floor. The 3rd floor boasts a spacious entertainment room, ideal for gatherings. Professionally landscaped grounds include a great backyard & a deck off the kitchen, perfect for outdoor dining & relaxation. With a 2-car garage & ample off-street parking, this home truly has it all. Timeless elegance and a prime location await you here!

31 Lawson Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$904,000
2 Beds ⋅ 1 Baths ⋅ 73375144 MLS
Delightful ranch, well maintained and located conveniently near the major routes. The kitchen is spacious and opens to the comfortable dining area with large built in hutch. It has been updated and features a tile backsplash, stainless steel appliances and recessed lighting. The living room is fireplaced and is nicely appointed with hardwood floors. Easy one level living with two first floor bedrooms both with refinished hardwood flooring. The lower level is spacious offers great expansion and provides easy access to the lovely 15,612 back yard area, ample off street parking and the covered and rear patios. Great opportunity to enter the highly competitive Winchester market and enjoy all the town has to offer. Don't miss this one!

703 Washington St, Winchester

Listing courtesy of Listing Agent: Michael Barrett from Listing Office: Barrett, Chris. J., REALTORS®.
$650,000
2 Beds ⋅ 2 Baths ⋅ 73373673 MLS
Attention investors, contractors, and handy owner occupants looking to build sweat equity! This single family home is in need of major renovation and is the perfect opportunity for a contractor to make a profitable investment or an owner occupant to unlock instant sweat equity. Dream location just around the corner to Winchester Center's shops and restaurants, less than 0.3 miles to the top rated Winchester High School, and minutes to the Winchester Center commuter rail station. Conveniently located less than half a mile to the Fells Reservation trails for the outdoor enthusiasts along with easy access to highways. Property features aluminum siding, hardwood floors, and a newer forced hot air heating system. This is an estate sale and the owner has no information about the home. Buyers to perform all due diligence. Private appointments begin immediately. Open House both Sat and Sun 11 am -- 1 pm!

27 Elm St, Winchester

Listing courtesy of Listing Agent: Paul Shao from Listing Office: RE/MAX Executive Realty.
$1,890,000
4 Beds ⋅ 5 Baths ⋅ 73368474 MLS
Explore this pristine newer construction, freshly updated home just outside the center!! Situated on a gorgeous level lot with slider to patio & expansive rear yard, this captivating home has an absolutely beautiful setting w/natural stone walls, raised planting beds w/flowering trees, perennials & a spectacular rose garden! Enjoy the lovely farmers porch & desirable layout w/sun-drenched kitchen showcasing an abundance of windows overlooking the rear yard - featuring a Viking range, breakfast bar, dining area open to lovely family room w/ gas fireplace! Side door entry offers mudroom w/ office, laundry, walk in pantry & 1/2 bath. Formal living room & dining room complete this floor. The second floor has 4 bedrooms & 2 baths including a stunning master suite w/ walk in closet, spa like bathroom w/ vaulted ceilings, skylights, soaking tub & oversized shower. Lower level game room, media & exercise space~ Garage w/ a great work room offering space for tools, painting, projects & more!

15 Kendall Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,950,000
5 Beds ⋅ 5 Baths ⋅ 73346386 MLS
Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly desired streets in town. A stunning fire-placed foyer welcomes you into the home, enhanced by a new chefs kitchen w/ 10' island, custom cabinetry, & adjacent family room overlooking yard. With four floors of beautifully finished spaces, there's room for every lifestyle need. Enjoy entertaining in the large dining room, relax in the inviting living room w/ fplc, the sunroom is perfect for home office. The primary boasts a newly constructed/ tastefully renovated suite w/designer bath & large closet. The other bedrooms are generous in size & offer ample closet space. Enjoy Movie nights & workouts in the renovated lower level. The private level yard w/ patio is perfect for kids to play, BBQs, gardening, or simply enjoying the serenity of your surroundings. 2 car garage & more! This home truly offers a unique opportunity to live in a sought-after location w/ all the modern updates

51 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$4,950
5 Beds ⋅ 2 Baths ⋅ 73364380 MLS
Available 5/1/25! Set in one of Greater Boston’s most sought-after communities, this oversized 5-bed, 2-bath Cape offers the perfect blend of comfort, character, and location. Enjoy light-filled, spacious rooms, gleaming hardwood floors, and insulated windows throughout. The detached 2-bay garage and expansive yard provide exceptional outdoor living, while the screened-in porch is perfect for warm summer evenings. Oil heat and propane cooking add efficiency and practicality. Located minutes from Winchester’s vibrant town center, top-rated schools, scenic parks, and the Minuteman Bikeway. Tenant responsible for yard maintenance, utilities, and water/sewer. A rare rental in a beloved town—don’t miss out!

137 Ridge St, Winchester

Listing courtesy of Listing Agent: The Elle Group from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$930,000
4 Beds ⋅ 3 Baths ⋅ 73357199 MLS
Welcome to this well loved 4-bedroom expanded Cape, on quiet cul-de-sac, cared for by the original owners for nearly 65 years! Located in the brand new Lynch Elementary School district, just steps from Winchester HS, Skillings Field, less than a mile from the Commuter Rail and downtown Winchester. Great for commuters. First floor features mudroom with laundry, front-to-back fire-placed living room, formal dining room,eat-in kitchen, full bath, 2 bedrooms, and vaulted sunroom with slider to back deck. Upstairs 2 large bedrooms, walk-in storage room, and full bath. Partially finished basement includes fire-placed flex space, full bath, and workshop + storage room. Situated on a flat, private 9,121 sq ft lot, the outdoor potential is endless. An incredible opportunity in the competitive Winchester market. Don't miss out!

48 Tremont Street, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,187,000
3 Beds ⋅ 2 Baths ⋅ 73363618 MLS
This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living room with gas fireplace, a well proportioned dining room with views into the back yard, updated kitchen, a half bath and a sunny family room/ home office. The 2nd floor offers 3 spacious bedrooms and 1 bath; the primary offers a walk in closet that has potential to be a 2nd bath. The recently remodeled basement is perfect for a playroom, home gym, movie nights or a bit of everything. Plenty of additional storage in the basement with direct yard access. This property has ben lovingly maintained & is equipped with updated systems including central A/C! Don't miss the opportunity to own this gem

44 Forest Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,000
2 Beds ⋅ 1 Baths ⋅ 73388103 MLS
This top-floor beautiful home features a spacious living room and dining room with hardwood floors throughout. The kitchen features stainless steel appliances, gas stove, and an abundance of cabinet space. The two bedrooms provide ample closet space and an adjacent full bath. A bonus room can be an office or a guest room. Two baconies, one open, one closed. Access to the shared garage from the basement. Separate basement storage and laundry areas. Located close to the Winchester Town Center, Schools, and Middlesex Fells. Easy access to major routes (Rte. 2 & Rte. 3, Rte. 93 & Rte. 95), there’s always something to see or do! The listing agent has an ownership interest in this property. Looking for tenants with good credit score and reliable income.

359 Washington St Unit 359, Winchester

Listing courtesy of Listing Agent: Zuqian Jin from Listing Office: Hestia.
$3,300
3 Beds ⋅ 2 Baths ⋅ 73386187 MLS
This sizable home is great for entertaining as well as raising kids on a quiet street. There is a large basement with Laundry and lots of storage. New heating and water heater. The first floor has a huge open floor plan living room/dining room opening up to a lovely private back deck. Modern kitchen with all stainless steel appliances. The 3 Bedrooms are upstairs with a full bath. No ACs. There is ample parking 4+ cars.Tenant responsible for: Snow removal on sidewalk and driveway; Cut grass on front and back yard; Garbage removal to town transfer station. Tenants pay utilities including water.

71-73 George Rd Unit 71, Winchester

Listing courtesy of Listing Agent: Cheng Charles Fu from Listing Office: Baymaxx Realty, LLC.

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