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7 Wainwright Rd. Unit 13, Winchester
$2,155,000
3 Beds ⋅ 5 Baths ⋅ 73443550 MLS ⋅ ['The Ledges'] BLDG.
Stunning townhouse with 3 bedrooms and 4.5 bathrooms, meticulously renovated with high-end, designer finishes. The sun-drenched living room features 13 ft. ceilings, 5-in. oak floors, custom built-in book shelves, and a double-sided marble-surround fireplace that flows seamlessly to the brand-new gourmet chef’s kitchen. The kitchen is a showpiece with a Sub-Zero fridge, Thermador range, Acadia quarts counter top, handmade Moroccan tile backsplash, custom cabinetry, and a bar area with a wine fridge. The luxurious first- floor primary suite offers vaulted ceilings, an attached sitting room, and a spa-like ensuite bath featuring marble and porcelain finishes, double vanities, large soaking tub, and a glass-enclosed shower. Two additional spacious guest bedrooms each include beautifully reimagined ensuite bathrooms with designer tile and fixtures. The partially finished basement has another private room, plus over 1000 sq. ft. of bonus space. *Professional photos coming soon*

7 Wainwright Rd. Unit 13, Winchester

Listing courtesy of Listing Agent: Isabella Bruno from Listing Office: William Raveis R.E. & Home Services.
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.
7 Appalachian Rd, Winchester
$2,150,000
4 Beds ⋅ 5 Baths ⋅ 73463596 MLS
Sophisticated updates and a bright, open layout define this beautifully appointed Winchester Fells home. Generous living spaces and thoughtful design enhance both everyday comfort and entertaining. The gourmet kitchen flows seamlessly into inviting gathering areas, while French doors and multiple outdoor access points create an effortless indoor–outdoor connection. Two dedicated home offices offer outstanding flexibility, and four full baths provide ease and convenience throughout. The front-to-back primary suite serves as a serene retreat with spacious closets and a private ensuite bath. Surrounded by mature landscaping that ensures beauty and privacy, this home combines timeless charm with a versatile floor plan—an exceptional blend of space, style, and location next to the scenic trails and lakes of the Fells.

7 Appalachian Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
7 Wainwright Rd Unit 72, Winchester
$2,150,000
4 Beds ⋅ 5 Baths ⋅ 73427753 MLS ⋅ ['The Ledges'] BLDG.
Extensively renovated and move-in ready, this stunning F-unit townhouse offers 4 bedrooms and 4.5 baths with impeccable detail and modern appeal throughout. The many windows, high ceilings, gleaming hardwood floors, and open design create a warm sun-filled home. You will enjoy the large kitchen and the ability to retreat to the dazzling first-floor primary suite, which provides single floor living in a separate bedroom wing. The living areas feature a dramatic two-sided gas fireplace with floor-to-ceiling stone tile. Enjoy outdoor living on the two expansive decks. The finished walkout lower level includes a sitting room, additional bedroom, and full bath—ideal for guests or a private retreat. Amenities include a pool, tennis/pickleball courts, and a clubhouse for gatherings. With too many upgrades to list, this home combines style, comfort, and convenience in a premier location. A rare chance to own an updated luxury townhouse in one of the area’s most sought-after communities.

7 Wainwright Rd Unit 72, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
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.
10 Hawthorne Rd, Winchester
$2,100,000
5 Beds ⋅ 6 Baths ⋅ 73474032 MLS
Spectacular 5 bedroom home set on an impressive fenced lot in a picturesque neighborhood setting! The interior underwent a major renovation in 2016, including a new dormer, updated systems, + upgraded finishes throughout. The bright, updated kitchen features honed countertops, a tiered island, separate refrigerator + freezer units, recessed lighting, and an open flow to the dining area. Additional features incl. oak floors, crown molding, custom built-ins around the fireplace, and smart storage. The flexible lower level includes a den, sun filled family room with abundant windows and rear walkout, + a mudroom with custom built-ins. The upper levels offer 5 generous bedrooms including a spacious primary suite w/walk-in closet, luxurious private bath, + convenient upper level laundry. This home also offers exceptional indoor/outdoor living with a stunning farmer’s porch, expansive deck, patio w/fire pit, + storage shed. Attached 2 car garage with direct entry. See feature sheet for more

10 Hawthorne Rd, Winchester

Listing courtesy of Listing Agent: from Listing Office: Fiv Realty Co..
5 Bacon St, Winchester
$2,090,000
6 Beds ⋅ 4 Baths ⋅ 73411839 MLS
This stunning Victorian home, in the style of Painted Ladies w/ soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & Boston. The house lives as a harmonious single family with a second kitchen on the 1st floor (multigenerational living potential). It has 6 beds & 4 baths, over 4,385 SF of living area on 3 flrs. Features include 2 covered porches, renovated garage, butler’s pantries, built-in cabinetry, new interior & exterior paint, & ample outdoor space. Upgrades include high-velocity A/C throughout, 2 new gas water heaters, restored chimney, a gas F/P, oversized custom walk-in closet, & fenced-in side yard. Professionally landscaped, mature fruit trees, flower & vegetable gardens & 2 extra cobblestone parking spots complete the outdoor space. Full, unfinished walkout basement with a high ceiling has endless possibilities. Don't miss this rare opportunity in Winchester!

5 Bacon St, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
64 Westland Ave, Winchester
$2,050,000
4 Beds ⋅ 5 Baths ⋅ 73428326 MLS
Open Houses Cancelled. Elegant 1930s Colonial boasts charming architectural features, 4 bedrooms, a recent addition & gorgeous top-of-the-line designer kitchen! The heart of the home is the open concept kitchen, which boasts Wolf & Sub-Zero appliances. The front foyer welcomes you to a grand living room with a fireplace, plus a pair of French doors opening to the most charming screen porch. The thoughtful addition includes a rear entry with a well designed mudroom & laundry room. The floor plan flows w/ ease. Handsome staircase leads to primary BR and BR-2 & 3 then turns to the third floor for BR 4 & a full bath. The sun-filled staircase also leads to the freshly designed lower-level family room w/ built-ins and cozy fireplace. This 20,000 sq ft lot offers a private oversized bluestone patio, stonewalls, & blooming perennials along with a lush lawn. There are 2 driveways for easy parking and a 2-car garage under. Enjoy Winchester schools and convenient train to Boston!

64 Westland Ave, Winchester

Listing courtesy of Listing Agent: The Murphy Group Lexington from Listing Office: William Raveis R.E. & Home Services.
58 Bacon St, Winchester
$2,030,000
6 Beds ⋅ 6 Baths ⋅ 73442841 MLS
Welcome to 58 Bacon Street—a perfect blend of classic charm and modern comforts. The main level features a front-to-back fireplaced living room, sunroom, formal dining room, and a stunning 2024 kitchen renovation with custom cabinetry, quartz island, and high-end stainless appliances, opening to a bright family room. Upstairs offers flexible space with dual primary suite options (one with elevator access & attached sitting room), plus an additional bedroom and office. The third floor includes two bedrooms, a bath, and a bonus room; the finished basement adds a playroom, full bath, ample storage and a mud area. Enjoy two outdoor living areas and a fully fenced yard. Elevator access from the attached, heated garage, plus a detached two car garage. Ideally located near Wedgemere Station with quick access to Boston, Winchester Center, Mystic Lakes, and the Fells, this expansive home is perfect for multigenerational living or those seeking accessibility and space.

58 Bacon St, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
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.
5 Wood Lane, Winchester
$2,000,000
3 Beds ⋅ 3 Baths ⋅ 73449729 MLS
Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite millwork, and a beautiful stained-glass door create a sense of warmth and refinement. The inviting eat-in kitchen opens to a charming screened porch, perfect for quiet mornings or evening gatherings overlooking the lush rose gardens. Three spacious bedrooms w/ a large primary suite on the first floor with 2.5 baths. Completing this exceptional property is a distinctive garden gazebo, an architectural complement to the main home. The possibilities are endless...a rare opportunity to own a piece of the towns heritage, blending historic craftsmanship in a top country club location!

5 Wood Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
1 Fox Hunt Lane, Winchester
$2,000,000
5 Beds ⋅ 5 Baths ⋅ 73426371 MLS
Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office. Sun-filled dining and family areas flow to a well-appointed kitchen and a large family room with fireplace. Sliders from the dining area open to an expansive deck and private, level backyard—perfect for entertaining. The second floor offers two additional bedrooms and a full bath. The finished lower level provides excellent in-law or au pair potential, with a kitchenette, bonus room, bedroom and walk-out access. Three levels of living offer exceptional flexibility for today’s lifestyle. close to shopping, commuter routes—just minutes from Charming Winchester Center and close to Boston.

1 Fox Hunt Lane, Winchester

Listing courtesy of Listing Agent: Leigh Ventura from Listing Office: Compass.
5 Azalea Road, Winchester
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73442291 MLS
NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and French doors opening to a new composite deck and tranquil backyard. Gather in the elegant dining room and sunken living room with fireplace, or retreat to the serene primary suite with sitting area and spa-inspired bath. A flexible fifth bedroom or office with private entrance is perfect for guests or in-laws. The finished lower level offers a game room, gym, wine storage, cedar closet, and more. Spectacular & unbeatable location and neighborhood awaits you! Move-in ready, moments to Winchester Center, top schools, and commuter access—where timeless style meets effortless living.

5 Azalea Road, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
6 Samoset Rd, Winchester
$1,987,000
4 Beds ⋅ 4 Baths ⋅ 73416647 MLS
Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up private office offers a private & inspiring space for the at-home professional. The separate dining room is ideal for entertaining, while the eat-in kitchen provides a casual space for daily meals. Upstairs, a vaulted-ceilinged primary bath impresses with dramatic windows and a serene ensuite bath. All 4 bedrooms are spacious with plenty of natural light. The finished lower level is a dream—complete with a bonus room, game room, exercise room, and full bath—versatile enough to suit any lifestyle. Outside, the private backyard features a stunning stone patio, professional landscaping, & a hot tub.

6 Samoset Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
46 Church St, Winchester
$1,965,000
4 Beds ⋅ 4 Baths ⋅ 73458603 MLS
Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features four bedrooms, three and a half bathrooms, two dedicated home offices, and a generously sized bonus room that can be adapted to serve a variety of purposes – including conversion to an additional primary suite. An additional guest suite on the lower level provides even more versatility. This property also includes an attached two-car garage, owned solar panels that can help lower electric costs, and an inviting outdoor space with a private backyard and patio. With its thoughtful layout and extensive living area, this home can accommodate a wide range of lifestyle needs. Don’t miss this opportunity to enjoy downtown living!

46 Church St, Winchester

Listing courtesy of Listing Agent: Joan Francis Sullivan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
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.
8 Felsdale Close, Winchester
$1,930,000
4 Beds ⋅ 3 Baths ⋅ 73452706 MLS
Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M. Ramsay, this home blends timeless Tudor charm with modern updates. Features include 4 bedrooms, 2.5 baths, renovated kitchen, cozy family area, & a spacious living room with a striking fireplace. The finished third floor adds extra living space, along with the finished lower level, currently set up as a home gym. Built in 1929, the home boasts exceptional craftsmanship, with steel I-beams & wire lath plaster walls. A detached two-car garage & peaceful yard complete the property, making this a once-in-a-lifetime chance to own a historic home in one of Winchester's most sought-after neighborhoods.

8 Felsdale Close, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
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.
2 Lagrange Street, Winchester
$1,900,000
7 Beds ⋅ 3 Baths ⋅ 73411626 MLS
EXQUISITE 12 ROOM, 7 BEDROOMS, 2 STUNNING FIREPLACES, 2.5 BATH QUEEN ANNE VICTORIAN! Easy Stroll to Center of Town. Hear the Church Bells Strike the Hour. Delightfully Quiet Street with a Family Orientated Community. Beautiful Morning and Evening Sun. During the Day the Huge Sun Deck off the Kitchen with a SPACIOUS AWNING is both Shady and Warm. Multi Outdoor Opportunities for Living including a Stone Built Bar and Grill Area, a Walled Patio with Fireplace, a Veranda with Turret and Dining Area. Step into this Charming Victorian and you will Fall in Love!

2 Lagrange Street, Winchester

Listing courtesy of Listing Agent: Alison Lules Cuccio from Listing Office: Don Baker Real Estate.
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.
5 Squire Rd, Winchester
$1,875,000
6 Beds ⋅ 4 Baths ⋅ 73471882 MLS
Designed for modern living and effortless entertaining, this home’s exceptional open-concept main level sets it apart from the moment you enter. Anchored by a chef’s kitchen with stone countertops, an oversized island, and premium Viking appliances, the space flows seamlessly into the family room with a striking shiplap fireplace and direct access to a spacious composite deck. Set in a desirable neighborhood, this fabulous 6-bedroom, 3.5 bath home offers luxury finishes at an exceptional value. The primary suite provides a private escape with a walk-in closet and dual vanity, complemented by three additional second-floor bedrooms—two with walk-in closets—a shared bath, and laundry. A large unfinished attic offers future expansion potential, while the finished lower level adds flexibility with full-size windows, a sixth bedroom, full bath, recreation space, and a mudroom with direct garage entry. Enjoy a landscaped, fenced yard with irrigation, close to top-rated schools.

5 Squire Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
1 Copley Street, Winchester
$1,865,000
7 Beds ⋅ 3 Baths ⋅ 73457068 MLS
Gracious Center Entrance colonial situated in top Flats location on a desirable corner lot. This home has all the charm of yesteryear and has many custom features including a beautiful front staircase with window seats, hardwood floors and sunny rooms. Attractive cherry cabinet kitchen with granite island. Large front to back living room has fireplace and is situated next to enclosed porch. Elegant dining room has attractive gumwood paneling..Second floor has four bedrooms including primary suite with full bath. Third floor has three additional bedrooms or use space as artist loft.or office space.Desirable location close to town and trains.While this house requires some updating and is being sold as is, it is well worth the investment for size ,location and potential.

1 Copley Street, Winchester

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

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