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78 Bacon Street, Winchester
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73526460 MLS
Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR, mudroom, stylish 1/2 bath & home office/sunroom complete this floor. Upstairs you'll find five spacious bedrooms and two full baths including the most perfect primary suite w/gorgeous bath plus a sitting room. Many updates include new hardwood floors, new high end Pella windows, updated electrical, heating and cooling systems finished lower level offers excellent recreation Enjoy the great landscaped yard with patio, lawn and sports court! For sure a favorite gathering spot for family and friends.

78 Bacon Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
30 Rangeley Road, Winchester
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73526416 MLS
Welcome to this distinctive home set on a lush landscaped lot in Winchesters historic and highly sought after Rangeley Estates neighborhood. Just moments from the town Center, this hidden gem offers a rare opportunity to renovate, expand & create your dream home in one of the towns premier locations. Rich in character and timeless appeal the sun-filled home features, five bedrooms, 3.5 baths, gleaming hardwood floors, updated electrical, updated heating and a newer roof; beautiful perennial gardens and mature landscape surround the property~ the level backyard is stunning with flowering perennial gardens & specimen trees showcasing the ideal setting. The first floor offers high ceilings, spacious rooms & an oversized screen porch plus sunroom with walls of windows & 2 fireplaces. The second level offers 3 large bedrooms & 2 baths including the primary suite w/ full bath. The third floor offers 2 additional bedrooms & another full bath. Detached 2 car garage and oversized driveway.

30 Rangeley Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
53 Winford Way, Winchester
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73525195 MLS
OPEN HOUSE CANCELLED. Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home! Located within the Winchester School District

53 Winford Way, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
12 Yale St, Winchester
$2,300,000
4 Beds ⋅ 3 Baths ⋅ 73480345 MLS
Timeless architecture blends beautifully with curated updates designed for modern living in this classic Colonial. Sunlight pours into the newly renovated gourmet kitchen, where beautiful cabinetry, premium appliances, and thoughtful design create an inviting heart of the home for both everyday living and elegant entertaining. A gracious front-to-back living room offers exceptional scale and flow, anchored by a fireplace and an abundance of natural light. Attached, a charming three-season sunroom provides a tranquil retreat, seamlessly connecting indoor comfort with the beauty of the outdoors. 4 bedrooms and 2 baths complete the second floor. Bonus: extra 900 unfinished square feet in the attic just waiting for your ideas! The basement offers one of the best finished areas we've seen, with vintage hardwood floors and a fireplace. A thoughtfully landscaped yard feels like a private oasis, with room for play or private mornings. Impeccably maintained, in a prime Flats location.

12 Yale St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
2 York Road, Winchester
$2,255,000
4 Beds ⋅ 4 Baths ⋅ 73537657 MLS
Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized shower, soaking tub & double vanity. A second en-suite bedroom, two additional bedrooms & full bath complete the second floor. The partially finished lower level provides flexible bonus space. Outdoors, enjoy a private sports court & expansive fenced yard, ideal for recreation & entertaining. An attached 2-car garage, including one heated bay, adds convenience. Ideally located adjacent to Town Forest walking trails and just minutes from Wedgemere Station, downtown Winchester, schools, parks, and commuter routes. A rare opportunity to enjoy comfort, recreation & convenience in a sought-after location.

2 York Road, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
6 Davey Ln, Winchester
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 73554545 MLS
Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.
15 Cabot St, Winchester
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 73502658 MLS
Set in one of Winchester’s most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece—generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools.

15 Cabot St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
10 Edgehill Road, Winchester
$2,200,000
7 Beds ⋅ 4 Baths ⋅ 73490604 MLS
Offer Accepted. Open houses cancelled. This exceptional Colonial Revival home in a sought-after Winchester neighborhood blends craftsmanship, thoughtful updates and a design layout perfect for entertaining and modern day living. A welcoming front porch introduces a double entry foyer, high ceilings with crown molding and period detail that flow through the formal dining and living room with fireplace to the family room, kitchen and butler’s pantry. Oversized windows drench hardwood floors with sunshine. Keep the French doors open to access the patio and fenced-in back yard, perfect for play. This well-proportioned home includes 2 primary suites, 5 additional bedrooms plus a 2nd floor office with bead board. Enjoy the private, renovated 3rd floor as an owner sanctuary, work space, or kid zone! With abundant storage, partially finished lower level rec room and 2-car garage this home has it all; including, a location close to the town center, schools, and train, close to Boston/Cambridge.

10 Edgehill Road, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
89 Wildwood St, Winchester
$2,200,000
7 Beds ⋅ 6 Baths ⋅ 73455053 MLS
Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half bath complete the first level. Upstairs, find five bedrooms, three full bathrooms & a laundry room outfitted with custom cabinetry & sink. The front to back primary suite has double walk in closets & an ensuite with dual vanities. Finished lower level features an additional guest suite & playroom, hangout space or gym. Conveniently located close to town, 89 Wildwood offers the best of Winchester living. Showings begin at first Open House Saturday 11/15 12:30-2!

89 Wildwood St, Winchester

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
21 Willowdale Road, Winchester
$2,170,000
5 Beds ⋅ 4 Baths ⋅ 73534988 MLS
New construction 2019, this impressive 4-5-bedroom, 4.5-bath custom built East side colonial offers exceptional space and a highly sought-after floor plan. The chef's eat-in kitchen features a large center island, abundant cabinetry & sunny dining area that seamlessly blends w/ the spacious family room w built ins & fireplace. Sun-filled living and dining rooms are connected by a double-sided fireplace, creating ideal gathering spaces. The stunning oversized primary includes a beautiful bath w/ shower & soaking tub & large walk-in closet. 3 additional generously sized bedrooms and full bath complete the upper level. The finished lower level offers a media room with a 4th fireplace, a BR/Office, full bath & mudroom area. w/direct access to the garage.Enjoy the large yard and patio, perfect for outdoor entertaining. Conveniently located near Winchester center, parks, & commuter routes, this turn-key home combines modern construction, generous living space, and quality finishes throughout

21 Willowdale Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
22 Hollywood Rd, Winchester
$2,150,000
5 Beds ⋅ 4 Baths ⋅ 73527768 MLS
OFFER DEADLINE TUESDAY JUNE 9, 12PM. Beautifully appointed 5BR, 2 full/2 half bath home with 3,136 sq ft of thoughtfully designed living space on a flat, fully fenced .34 acre lot. Renovated kitchen with quartz countertops and luxury appliances. Expansive and bright living room with custom built-ins, window seating, and gas fireplace. The main living level also offers 3 spacious bedrooms and a serene primary suite with a walk-in closet and private en suite bath. Fully refreshed entry-level offers another bedroom, includes a custom mudroom off the 2-car attached garage, half bath, and laundry room. Completed with an oversized media room with walkout access. Generous, manicured yard with expanded patio--perfect for everyday living and entertaining outdoors. New systems, flexible layout, abundant natural light, and thoughtful updates throughout. Extra outdoor storage with included shed. Minutes from the Middlesex Fells Reservation, top-rated schools, and vibrant downtown Winchester.

22 Hollywood Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
42 Wildwood Street, Winchester
$2,142,000
7 Beds ⋅ 5 Baths ⋅ 73556122 MLS
Exceptional craftsmanship defines this majestic home in The Flats, where beautifully-preserved architectural details blend seamlessly w/ modern livability. A showstopping foyer welcomes you w/ a sweeping staircase, exquisite millwork, graceful arched openings & leaded glass windows. You’ll find quarter-sawn oak floors, rich woodwork, generously scaled windows & impressive ceiling height throughout. The expanded eat-in kitchen includes granite, SS appliances, island, office area & steps to a custom mudroom. The main level also includes elegant living, dining & family rooms, a butler's pantry, & ½ bath. The 2nd floor showcases a dramatic landing w/ continuously curved railing & has 4 large bedrooms & two full baths, including a spacious primary suite w/ full bathroom and walk-in closet. 3 bedrooms & a full bath complete the 3rd floor. The finished lower level w/ recreation room, mudroom w/ built-in lockers, and full bathroom offers endless possibilities. Recent updates include Pella windows throughout (2020), new & upgraded heating system (2024), and exterior siding, paint & shutters (2020). Set on a flat, oversized lot featuring a bluestone patio w/ seating wall. Located in a highly-coveted neighborhood and less than a mile from the newly built Lynch elementary school, town center & train.This magnificent home pairs timeless character with today’s amenities.

42 Wildwood Street, Winchester

Listing courtesy of Listing Agent: Carolyn Walsh from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
211 Forest St, Winchester
$2,125,000
5 Beds ⋅ 4 Baths ⋅ 73532996 MLS
Welcomed by a convenient horseshoe driveway surrounded by thoughtfully designed gardens, 211 Forest has undergone a completely reimagined renovation. This curated family residence shows refined attention to detail and a designer’s eye at every turn. From the custom kitchen with bespoke cabinetry and premium hardware, AGA cast-iron range and Liebherr refrigerator to the sunporch filled with natural light, every space reflects intentional design. The living room is anchored by a wood-fired fireplace, while highlights include a 1,000-bottle wine room, home gym, outdoor barrel sauna for daily wellness, whole-house water filtration system with reverse osmosis drinking water, and Sonos surround sound inside and outside. Located in one of Winchester’s most desirable neighborhoods, imagine stepping out your door for a peaceful walk to a trailhead at The Fells or easily biking with your kids to the highly regarded Muraco Elementary School every day.

211 Forest St, Winchester

Listing courtesy of Listing Agent: Michael Gilbert from Listing Office: Stuart St James, Inc..
61 Grove Street, Winchester
$2,125,000
5 Beds ⋅ 5 Baths ⋅ 73470986 MLS
Experience the perfect blend of luxury and effortless living in this stunning custom-built residence, thoughtfully rebuilt and expanded to offer a sophisticated, maintenance-free lifestyle. Bathed in natural light, the flexible floor plan begins with a magnificent first-floor primary suite featuring a marble-clad bath, soaking tub, and walk-in shower. The heart of the home is a chef’s kitchen anchored by a granite island and premium Bosch appliances. Entertaining is seamless, whether hosting formal dinners by the wood-burning fireplace or relaxing in the spacious family room with its sleek gas fireplace and glass doors to the yard. A bright four-season sunroom offers a peaceful retreat year-round. The second level provides four additional bedrooms, two full baths, and a convenient second laundry. Downstairs, a heated bonus room with a third fireplace full bath serves as a gym or media room. Sited on a flat lot steps from Wedgemere station, this is suburban living at its best.

61 Grove Street, Winchester

Listing courtesy of Listing Agent: Dorothea Feffer from Listing Office: Churchill Properties.
4 Leslie Road, Winchester
$2,120,000
5 Beds ⋅ 4 Baths ⋅ 73481986 MLS
Set on a lush, private lot, this Royal Barry Wills home blends timeless design with extraordinary gardens. A welcoming mudroom opens to a cathedral-ceiling kitchen with slider framing views of the yard and perennial plantings. The dining room and front-to-back living room with fireplace and custom built-ins each offer sliders that extend living space outdoors and invite natural light throughout the day. A main-level primary suite also features direct garden access, creating a peaceful retreat with verdant views. Hardwood floors and classic detailing enhance the home’s warmth and architectural integrity. The second floor offers three bedrooms and two full baths thoughtfully arranged for comfort and privacy. Outside, a brick patio crafted from century-old Cambridge sidewalk pavers creates a storied setting for entertaining, surrounded by mature perennial gardens and a magnificent Dawn Redwood from the Arnold Arboretum, anchoring the landscape with beauty, scale, and distinction.

4 Leslie Road, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
15 Wildwood Street, Winchester
$2,100,000
6 Beds ⋅ 3 Baths ⋅ 73488105 MLS
Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized windows, rich architectural details, 10’ft ceilings & original crown molding. The kitchen combines function & style with Sub-Zero fridge leading to the elegant dining room w/ fireplace, china pantry, original marble sink & more. Upstairs, 6 bedrooms await, featuring hardwood floors, large closets & beautiful natural light. The stunning walk out lower level also features extremely high ceilings w/teak parquet floors. This property also includes a 3 story, 2200 sf barn with parking for 7 cars and potential for ADU / living space /home office/ gym & more! Close to downtown Winchester!

15 Wildwood Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
36 Cambridge St, Winchester
$2,025,000
5 Beds ⋅ 5 Baths ⋅ 73544504 MLS
Welcome to 36 Cambridge Street—an exceptional 5-bed, 5-bathhome blending modern design with everyday comfort inWinchester’s sought-after Lincoln School District. The mainlevel features an open-concept great room, designer kitchenwith large island, walk-in pantry, and a convenient first-floorbedroom with full bath. A spacious mudroom completes theentry. Upstairs, the luxurious primary suite offers two walk-inclosets and a spa-inspired en-suite, along with two additionalbedrooms, full bath, and laundry room. Third floor features abedroom and full bathroom. The finished lower level providesversatile living with a full bath—ideal for media, play, or fitnessspace. Perfectly located near Winchester Center, commuter rail,and the Middlesex Fells, this home offers upscale living andunmatched convenience.

36 Cambridge St, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
9 Wilson St, Winchester
$1,950,000
4 Beds ⋅ 4 Baths ⋅ 73537143 MLS
Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a full bath, and laundry. The 3rd floor offers two more bedrooms and a full bath, providing flexibility for any household. The large screened porch extends living space through the warmer months, providing a quiet spot to read, dine, or relax. The flat backyard is peaceful and private, with perennial gardens and a bluestone patio perfect for al fresco dining. A mudroom and two-car garage add everyday practicality. Set on a quiet, dead-end street, minutes from the trails of the Middlesex Fells, and close to Muraco Elementary, downtown Winchester, the commuter rail, shops, cafes, and restaurants.

9 Wilson St, Winchester

Listing courtesy of Listing Agent: Elena Langlois from Listing Office: Compass.
2 Gershon Way Unit 2, Winchester
$1,936,000
3 Beds ⋅ 3 Baths ⋅ 73496895 MLS ⋅ ['Winning Farm'] BLDG.
Welcome to Winning Farm of Winchester —an award-winning 55+ community and one of Winchester’s most sought-after addresses for effortless, elevated living. This meticulously maintained and lightly lived-in 3-bedroom, 2.5-bath townhome offers 2,306 sq ft of thoughtfully designed living, showcasing fine craftsmanship & timeless finishes throughout. Sun-drenched interiors highlight gorgeous hardwood floors, soaring ceilings, & an open-concept first floor ideal for both everyday living & entertaining. The main-level primary suite provides convenience & privacy, creating a seamless single-level living option, while additional bedrooms and flexible spaces upstairs offer room for guests, a home office, or hobbies. The home’s inviting layout is complemented by abundant natural light and a warm, welcoming feel in every room. Set within a beautifully maintained community known for its charm and lifestyle, residents enjoy a peaceful setting with close proximity to shops, dining, and major routes.

2 Gershon Way Unit 2, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
15 Fieldstone Dr, Winchester
$1,900,000
4 Beds ⋅ 4 Baths ⋅ 73537676 MLS
Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless appliances, an island, and a sunny window seat. A main-level primary suite with deck access, two walk-in closets, and a spa-like bath provides a calm retreat. Additional bedrooms offer flexibility for rest, work, or guests, while the full walk-out unfinished lower level—with abundant windows and slider—adds exceptional potential for an ADU, future living area, studio, or recreation space. Updated efficient heat pump heating and cooling, an oversized attached garage, professional landscaping, stone walls, sprinklers, and a cul-de-sac setting complete this distinctive property.

15 Fieldstone Dr, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
105 Thornberry Rd, Winchester
$1,899,000
5 Beds ⋅ 3 Baths ⋅ 73523785 MLS
Perfectly situated on Winchester’s sought-after Westside, this beautifully updated Colonial offers 5 bedrooms, 2.5 baths, and exceptional indoor-outdoor living. A recent renovation transformed and expanded the first floor, featuring an updated kitchen with oversized mahogany topped center island, family room, dining room, mudroom, and half bath. The kitchen opens seamlessly to a spacious family room w/ fire place and a large deck overlooking the expansive backyard with private fire pit — ideal for entertaining. Flexible first-floor bedroom or home office. Upstairs includes a primary suite with walk-in closet and en-suite bath, plus three additional bedrooms and updated full bath. The walk-out finished lower level with fireplace offers space for a playroom, gym, media room, or office. 2-car attached garage. Abuts conservation land and the Winchester Swim & Tennis Club, close to Vinson-Owen Elementary, Whipple Hill trails, vibrant downtown Winchester, and major commuting routes.

105 Thornberry Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
2 Olde Lyme Road, Winchester
$1,857,000
3 Beds ⋅ 4 Baths ⋅ 73549106 MLS
Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full baths, including an en-suite, offer exceptional flexibility. The 2nd floor primary suite is a private retreat w/ a vaulted ceiling, oversized walk-in closet, spacious bath w/ double vanity. This level offers an additional storage closet & unfinished room w/expansion potential. En-suite bedrooms on both the 1st & 2nd floors provide a versatile floor plan. The bright walk-out lower level includes a large family room w/ access to an expansive deck, mudroom, laundry room, half bath, & bonus room ideal for overnight guests. Replacement windows & beautiful storage shed complete this move in ready home.

2 Olde Lyme Road, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
237 Swanton Street, Winchester
$1,850,000
5 Beds ⋅ 4 Baths ⋅ 73496811 MLS
**Unbelievable deal!! **NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas fireplace and plenty of windows.The first floor also includes a bedroom suite w/ full bath! Upstairs you'll find 3 spacious bedrooms, including the primary suite w/ walk-in closet & beautiful en-suite bath w/ large shower, tub & double vanity sinks. Additional BR5 & bath on the 3rd fl. The finished lower level offers a family room w/ bar & large media/playroom. A fenced in yard, deck/ patio & direct entry two-car garage complete this home. Enjoy all the area has to offer including McDonald field playground, restaurants, shops, schools, train to Boston- just 7 miles!

237 Swanton Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
58 Jefferson Road, Winchester
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 73488901 MLS
This well-maintained colonial is tucked at the end of a cul-de-sac in a very desirable neighborhood. Upon entering, the bright foyer with hardwood floors opens to a spacious front to back living room. The formal dining room leads to the eat in kitchen, perfect for entertaining and gatherings. Just off the kitchen the family room features a stone fireplace and sliding doors leading to the deck and backyard - perfect for relaxing and entertaining. A convenient half bath with laundry hookups completes the first floor. Upstairs are four generously sized bedrooms and two full baths, including a primary suite with access to an open loft overlooking the family room - ideal for a home office or bonus space. The home also offers a large, dry basement high ceilings and potential for additional living space. Many updates including newer roof, heating system, A/C, windows, siding and more! Close to the shops and restaurants of Winchester Center, commuter rail access, and the Fells Reservation.

58 Jefferson Road, Winchester

Listing courtesy of Listing Agent: Stephanie Macfarland from Listing Office: Wilson Wolfe Real Estate.
10 Graystone Cir Unit 10, Winchester
$1,825,000
2 Beds ⋅ 4 Baths ⋅ 73508182 MLS ⋅ ['Graystone At Winchester'] BLDG.
Tucked within the coveted enclave of Graystone, this exceptional townhouse offers a rare blend of scale, privacy, and refined living. Among the largest residences in the community, this impeccably maintained 2-bedroom, 3.5-bath home unfolds across more than 3,800 square feet of thoughtfully designed space. Sunlight pours through expansive windows, illuminating gracious living and entertaining areas that flow seamlessly from room to room. The interiors are polished yet inviting, with generous proportions that allow for both elegant gatherings and comfortable everyday living. The first floor primary suite is large and inviting; another full bedroom suite is on the second floor, along with an expansive office and a cozy den. A rare walk-out patio on the lower level opens directly to a serene, forested backdrop—an uncommon offering that creates a private retreat, perfect for morning coffee or evening relaxation surrounded by nature.

10 Graystone Cir Unit 10, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
16 Glenwood Ave, Winchester
$1,820,000
6 Beds ⋅ 5 Baths ⋅ 73507145 MLS
Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac in the Lynch School district

16 Glenwood Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
12 Wincrest Drive, Winchester
$1,810,000
6 Beds ⋅ 5 Baths ⋅ 73492714 MLS
West Side! Set on a beautiful, serene oversized 1/2 acre lot, this turn key 2006* 5–6 bedroom, 4.5 BA home offers the perfect blend of space, comfort, & style. This home was completely renovated & expanded in 2004 offering an open floor plan w/ kitchen & dining area that flow seamlessly into an oversized family room w/ walls of windows showcasing the gorgeous yard. The main floor also offers living/ dining plus 2 bedrooms & a full bath. The luxurious primary suite w/vaulted ceilings is a true retreat, boasting a spacious walk-in closet & spa-like bath with double vanity, soaking tub & shower. 2 additional 2nd fl bedrooms offer large rooms w/ fun loft spaces. Enjoy the sun filled lower level w/ a sunny family room w/ fireplace, office or BR & bath. 2 car attached garage, & central AC complete this home. Enjoy panoramic views of the tranquil yard from nearly every room. Ideally located near Whipple Hill Conservation trails, VO Elementary w easy access to major routes/ Boston & Cambridge

12 Wincrest Drive, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
18 Graystone Circle Unit 18, Winchester
$1,800,000
3 Beds ⋅ 3 Baths ⋅ 73551306 MLS ⋅ ['Graystone At Winchester'] BLDG.
OFFER ACCEPTED-OH CANCELLED!Discover luxury & convenience in this impeccably maintained 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a 1st floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas fireplace, gleaming hardwood floors & soaring cathedral ceilings w/ skylights, leading to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, the spacious second bedroom, full bath plus an oversized loft family room area w/ potential to wall off a portion for 3rd bedroom, & a cozy a den/ office The walkout LL has high ceilings & offers opportunity to finish 1440SF for gym/rec room, media room, storage or anything you desire!

18 Graystone Circle Unit 18, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
8 Hawthorne Road, Winchester
$1,775,000
5 Beds ⋅ 4 Baths ⋅ 73522773 MLS
Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees. The open-concept living and dining area provides a seamless flow, ideal for hosting gatherings or simply relaxing with guests. Family room w/window seat and built-ins, leads to a sunny deck. Next level, you enter an en-suite bedroom and two large additional Bdrms with an updated bath. Two more Bdrms on the upper level can be utilized for a guest or family member w/ultimate flexibility. Lower level, there are Power Rm, Laundry Rm, Dog Spa & Study. This residence provides the ideal blend of functionality and style. Close to Vinson Owen School. This dream home provides easy access to everything!

8 Hawthorne Road, Winchester

Listing courtesy of Listing Agent: H. Elaine Song from Listing Office: Coldwell Banker Realty - Lexington.
35 Hollywood Rd, Winchester
$1,755,000
4 Beds ⋅ 5 Baths ⋅ 73485418 MLS
Tucked at the end of a cul-de-sac and bordering the Fells, this classic brick-and-wood Colonial blends generous living spaces with comfortable, easy flow. The fireplaced living room and spacious dining room are filled with natural light and framed by peaceful woodland views. The kitchen features stone counters, stainless appliances, and a peninsula that connects to the dining area and opens to a vaulted, beamed family room with fireplace and French doors to the outdoors. A home office offers added flexibility. Upstairs, four inviting bedrooms include a tranquil primary suite with walk-in, cedar closet and private bath, and a second bedroom with its own ensuite bath. The walk-out lower level offers additional living space with a playroom, wet bar, and full bath. Porch, patio, and fenced yard create welcoming outdoor areas, complemented by central air and an attached 2 car garage. With its thoughtful layout and cul-de-sac setting near the Fells, this home offers enduring appeal.

35 Hollywood Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

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