Refine Search
Map
Sort by
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 73427429 MLS
Welcome to this charming Cape on a spacious corner lot in Winchester. The main level offers hardwood floors, a front-to-back living room with fireplace and built-ins, a dining room with corner hutch, and a half bath. The kitchen features granite counters, stainless steel appliances, abundant cabinetry, and a breakfast island that opens to the cathedral-ceiling family room. A side entry with mudroom keeps things organized, and a sun-filled three-season porch adds flexible living space. Upstairs you’ll find three bedrooms with hardwood floors, including a primary with walk-in closet, plus a full bath. The finished lower level provides extra living area with a full bath and direct walk-out access to the fenced backyard. Conveniently located near Lincoln School, a 7 minute walk to Winchester Center, and the Wedgemere commuter rail station.

89 Main St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$665,000
2 Beds ⋅ 2 Baths ⋅ 73339113 MLS ⋅ ['Willows At Winchester'] BLDG.
Rarely available and beautifully renovated first-floor unit at The Willows designed with everyday functionality in mind. This one-story unit offers stair-free access and living, along with easy accessibility from the adjacent one-car garage with an attic and a tandem parking spot. Upon entry, you’ll find an inviting open concept living and dining area with freshly installed hardwood flooring, a cozy gas fireplace and access to the enclosed private patio. The updated kitchen offers an ideal blend of openness and convenience and is outfitted with brand new granite countertops and appliances. The spacious primary bedroom features a refreshed en-suite bath and full walk-in closet. A second bedroom, updated full bath, central A/C, and in-unit laundry complete this gem. Upscale amenities such as the pool, fitness center, clubhouse with full kitchen, professional landscaping and snow removal optimize convenience. Come check it out!

7 Conant Rd Unit 20, Winchester

Listing courtesy of Listing Agent: Brian Woods from Listing Office: Woods Properties Inc..
$2,050
1 Beds ⋅ 1 Baths ⋅ 73442666 MLS
This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The well-maintained, gated community includes a pool, picnic area, cabana, on-site laundry, and ample parking. Just minutes to downtown Winchester, the commuter rail to Boston, and highly rated Winchester public schools. Also near local healthcare, dining, shops, parks, and walking trails. Rent includes heat, AC, electricity, hot water, water, sewer, swimming pool, and landscaping. With its unbeatable location and move-in-ready condition, this is one you won't want to miss! Moving-in fee: first month and security deposit. Looking for tenant with reliable income and good credit.

200 Swanton Unit 432, Winchester

Listing courtesy of Listing Agent: team_hestia from Listing Office: Hestia.
$1,610,000
5 Beds ⋅ 5 Baths ⋅ 73429273 MLS
The buyer got cold feet. Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A formal dining room, family/playroom, and half bath complete the first level.The second floor includes a spacious primary suite with ensuite bath, two additional bedrooms, full bath, laundry, generous closet space, and sunset views. The third floor offers two additional bedrooms and a full bath-ideal for guests, offices, or extended family.The finished lower level includes a yoga room, large recreation room, and direct exterior access to a fenced backyard with patio and hot tub.New heating and water heater. Close to downtown Winchester, schools and transportation.

166 Forest St, Winchester

Listing courtesy of Listing Agent: Ning Sun from Listing Office: United Real Estate, LLC.
$1,600,000
8 Beds ⋅ 3 Baths ⋅ 73433062 MLS
Rare Opportunity: Spacious Side-by-Side Two-Family Home Less Than 1 Mile from Town Center. This charming two-family home offers classic period details, including fireplaced living rooms, formal dining rooms with built-in china cabinets located directly off the kitchen. Each unit features two large bedrooms with hardwood floors and a full bath on the second floor, plus two additional bedrooms and storage on the third floor. Both units have separate, spacious basements with tall ceilings and separate utilities. Great yard space, two-car garage and driveway located off Glen Rd. Located less than 3/4 mile from the town center, this property is ideal for both investors and owner-occupants. Don’t miss this exceptional opportunity! Open House Saturday 9/20, 12-1:30pm & Sunday 9/21, 1:30-3pm

112 Church St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$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.
$4,700
3 Beds ⋅ 3 Baths ⋅ 73450052 MLS
Experience luxury living in this beautifully renovated 2-level townhome in the coveted Willows at Winchester community. This rare 3 bed, 2.5 bath residence offers an open layout with gleaming hardwood floors, a chef’s kitchen, dining area, and a spacious living room with gas fireplace and access to a private deck — perfect for entertaining. Upstairs features all bedrooms, including a luxurious primary suite with spa-like bath and walk-in closet, plus 2 additional bedrooms, renovated full bath, and in-unit laundry. Enjoy private storage, 2 parking spaces, and unbeatable access to Winchester Center, commuter rail, and Rt-93. Community amenities include a fitness room, club room, and heated pool, offering the ideal blend of comfort, convenience, and resort-style living.

7 Conant Rd. Unit 16, Winchester

Listing courtesy of Listing Agent: William Natoli from Listing Office: Compass.
$1,950
1 Beds ⋅ 1 Baths ⋅ 73437640 MLS
The sought after Parkview Condominium! Prime Winchester Location ! All newly PAINTED ! Living room with glass sliders to balcony overlooking a calming and picturesque landscaped wildlife garden and pond with ducks & swans. Rent includes ALL utilities - heat, cold & hot water, electricity and 1 gated parking space! Amenities: swimming pool and on-site laundry facilities! Brand new Vent Hood. No pets. No smoking of any substance. Professionally management on-site. Close to town shops, restaurants, and commuter rail to Boston. Explore the nearby Tri-Community Greenway! Come Home! Sweet Home!

200 Swanton St Unit L25, Winchester

Listing courtesy of Listing Agent: Ai Cheng Goh from Listing Office: Z. Realty.
$1,890
1 Beds ⋅ 1 Baths ⋅ 73445421 MLS
Sunny top-level studio apartment available now at desirable Parkview Condominiums in Winchester! This bright and open studio features a spacious layout with sliders to a balcony overlooking the beautifully landscaped grounds and pond. Enjoy a well-maintained kitchen and bath, ample closet space, and one assigned parking spot (extra spot can be rented). The community offers a pool, picnic area, laundry facilities, and on-site management. Heat, hot water, and electricity included! Conveniently located near Winchester Center, Horn Pond, and major routes.

200 Swanton St Unit 708, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: Gibson Sotheby's International Realty.
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 73438722 MLS
OFFER ACCEPTED OH SUNDAY CANCELLED Taken down to the studs, this renovated and reimagined center entrance Colonial offers timeless elegance and modern comfort in one of Winchester’s most desirable neighborhoods. The gracious foyer gives way to a front-to-back living room anchored by a wood-burning fireplace with custom mantle. An adjacent sun-filled, south-facing room provides the perfect space for an office, den, or playroom. Nestled between the dining room and charming covered back porch, the expanded kitchen features a large island, white cabinetry, under-cabinet lighting, quartz countertops and SS appliances. A stylish powder room with beadboard and designer wallpaper completes the first floor. Upstairs the bright and spacious primary suite features a full bath and walk-in closet. Three additional bedrooms, a second full bath, and walk-up attic access complete this level. The lower level offers versatile living space, dedicated laundry room, and mudroom with direct exterior access

15 Westland Ave, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.
$1,550,000
5 Beds ⋅ 3 Baths ⋅ 73428890 MLS
Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the tone for what awaits inside. Oak floors run throughout, while tiled kitchens and baths add sophistication. Heated bathroom floors and five heating zones ensure year-round comfort, with flexible living spaces ideal for entertaining or everyday living. The chef’s kitchen opens seamlessly to dining and living areas, while upstairs, spacious bedrooms including a serene primary suite—offer peaceful retreats. Outdoors, a beautifully landscaped yard with an eight-zone irrigation system frames the in-ground pool, which can be propane-heated. Just minutes to top-rated schools, shops, and Boston.

205 Ridge St, Winchester

Listing courtesy of Listing Agent: Debby Valdes from Listing Office: eXp Realty.
$1,656,000
4 Beds ⋅ 5 Baths ⋅ 73397190 MLS
Rare 5-car garage on a quiet, tree-lined cul-de-sac in one of Winchester’s most exclusive enclaves! Offering both serene privacy and seamless connectivity, 4 Aricia is perfectly positioned within walking distance to a coveted elementary school and Wright-Locke Farm, and minutes from the commuter rail and Routes 128 & 93. Set on nearly .5 acres of manicured grounds, the home’s exterior is framed by mature plantings, sculpted gardens, and a sweeping lawn that creates a resort-like sense of arrival. Inside, contemporary touches meet everyday comfort with soaring vaulted ceilings, skylights, and floor-to-ceiling windows that fill the home with natural light, while hardwood floors and a central fireplace anchor the open-concept living and dining spaces. A built-in wet bar makes entertaining effortless, and the spacious kitchen with breakfast nook, pantry, laundry room, and direct access to a sprawling deck and stone patio connect indoor comfort with outdoor beauty.

4 Aricia Ln, Winchester

Listing courtesy of Listing Agent: The McLaren Team from Listing Office: Compass.
$6,900
3 Beds ⋅ 3 Baths ⋅ 73444871 MLS
No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking 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 33' x 13.5 ' Enormous private outdoor veranda with marine grade mahogany flooring, cedar millwork, gas fireplace, ceiling fans, amazing outdoor kitchen with gas commercial grill tied in to domestic gas line. Unlike any executive, luxury rental in town. Short distance to Town Center, shops, village cafes, restaurants, and Commuter line Train stations. First class construction with no expense spared, in a modern & wonderfully finished residence.

846 Main Street Unit 4, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
$6,000
3 Beds ⋅ 3 Baths ⋅ 73427180 MLS
No broker fee. Pets Negotiable. This beautifully renovated home offers over 2,400 square feet of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today’s lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high-end Spanish panels, dovetail drawers, and Blum hardware. Additional upgrades include Harvey windows and doors, sleek Kuzco modern lighting, and Italian tile finishes that bring a touch of elegance to every room. With 3 full bathrooms, 3 generous bedrooms, and multiple living areas, there’s plenty of room to spread out. The home also offers a two-car garage, ample storage, and the option to include some furniture if desired. Set on a large 22,000 sq ft lot, this home is close to shopping, schools, medical facilities, public transportation, and highway access. Convenience and style!

25 Berkshire Dr, Winchester

Listing courtesy of Listing Agent: McCaul & Mounsif Real Estate Group from Listing Office: Coldwell Banker Realty - Cambridge.
$2,895,000
5 Beds ⋅ 5 Baths ⋅ 73424449 MLS
Here's a rare opportunity to own a spectacular new construction home by a premier local builder on a BRAND-NEW road. This property stands prominently on its lot, overlooking a lush wooded area with close proximity to “The Fells”. The first floor is designed for both entertaining and everyday living, featuring formal dining, a designer kitchen with a butler's pantry, and a fireplaced family room that exudes warmth and comfort. Each of the bedrooms are found on the second floor, including a versatile space that could seamlessly integrate into the primary. The primary bath is a sanctuary of luxury, accompanied by an opulent dressing room. The lower level offers a walk-out rec room and a dedicated home gym. The HUGE garage is perfect for car enthusiasts who might wish to install a lift, or for sports enthusiasts aiming to create an indoor basketball/golf simulator area! Seize your chance to acquire this exceptional property, where construction and finishes of such caliber are seldom found.

6 Abby Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$3,800
4 Beds ⋅ 2 Baths ⋅ 73433939 MLS
Spacious 4-bedroom, 1.5-bathroom townhouse - duplex unit - located close to Winchester Center, with a park across the street and Wright Pond and Park nearby. Enjoy top rated Winchester schools nearby. Open-concept kitchen with granite countertops, island, pantry, and space for your table, plus hardwood floors, central gas heating, in-unit washer and dryer, and modern/new appliances. Close to Stop and Shop, Dunkin Donuts, Burger King and many other shops and restaurants.

848 Main St. Unit 1, Winchester

Listing courtesy of Listing Agent: The Abundant Group from Listing Office: Real Broker MA, LLC.
$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.
$2,750,000
5 Beds ⋅ 6 Baths ⋅ 73419844 MLS
Open house canceled! Offer accepted! Luxury, location, and lifestyle come together in this beautiful new 5-bed, 5.5-bath home in Winchester’s sought-after Westside. Just steps to Ambrose School, one block from the Alewife bus stop, a short stroll to the commuter rail, and right down the street from the Winchester Boat Club, this home offers unmatched convenience and charm. Inside, enjoy over 4,600 sq. ft. of thoughtfully designed space with white oak floors, imported tile, a chef’s kitchen with Viking appliances and custom cabinetry, and a cozy living room with a natural stone gas fireplace. Dual primary suites—on both the first and second floors—feature spa-like en-suite baths. The finished lower level includes a gym, family room, full bath, and mudroom with direct access to an oversized double-bay garage. This turnkey home is the perfect blend of elegance and everyday ease. A rare opportunity in an exceptional location!

11 Taft, Winchester

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
$3,900,000
5 Beds ⋅ 5 Baths ⋅ 73439119 MLS
A rare Winchester offering set on an acre in a wooded enclave of luxury homes near town center. Custom-built, this 5-bedroom, 4.5-bath residence combines timeless design with balanced proportions across four levels. The primary suite includes a private deck, spa-like bath with soaking tub, and gas fireplace. The chef’s kitchen features quarter-sawn oak cabinetry, high-end appliances, large island, pantry, and wet bar, opening to casual and formal spaces. A four-season sunroom leads to an outdoor oasis with extensive landscaping, stonework, patio, outdoor kitchen, built-in fireplace, and private tennis court. High ceilings, crown molding, custom quarter-sawn oak built-ins, and classic finishes are found throughout, thoughtful choices using healthy home materials. Additional highlights include a large mudroom, laundry room, and a finished lower level with family room, bath, exercise area, and ample storage. Truly unique close to town center, top-ranked schools, and easy access to Boston.

12 Ledgewood Road, Winchester

Listing courtesy of Listing Agent: Leigh Ventura from Listing Office: Compass.
$4,450,000
5 Beds ⋅ 7 Baths ⋅ 73431361 MLS
A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over ½ acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for relaxed family living or refined gatherings. Highlights include eat-in chef’s kitchen w/ island & timeless finishes, butler’s pantry, stately dining rm, large living & family rms & private study. Upstairs offers a luxurious primary suite w/ marble bath & dressing rm, plus 4 add’l BRs, 3 en suite. Lower level features versatile family/game rms & wine cellar. Carriage house (2007) w/ 4 garage bays, cabana bath & studio/gym offers endless possibilities & ADU potential. Moments to town center, top rated schools & train, this iconic home is where elegance & livability come together in perfect balance.

20 Foxcroft Road, Winchester

Listing courtesy of Listing Agent: Carolyn Walsh from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$800,000
2 Beds ⋅ 2 Baths ⋅ 73423434 MLS ⋅ ['Wedgewood Place Condominium'] BLDG.
Bright & Airy Cottage at Desirable Wedgewood Place in the heart of Winchester! This charming 2-level, 2-bed, 2-bath “cottage” style condo offers convenience of condo living w/ the feel of a single-family home. Sun-filled layout features a wood-burning fireplace w/ brick hearth, built-ins, hardwood floors, and an updated kitchen with new lighting, flooring, stainless fridge, dishwasher, cooktop & vent hood. Upstairs, primary suite includes an updated bath w/ double vanity, walk-in closet & sliding doors to large private deck. Lower level offers a spacious bedroom, full bath, laundry, shelving & direct access to landscaped common area w/ pool & patio. Additional features include central air, abundant storage, private deck & parking just outside your door! Steps to Winchester Center shops, cafes, parks, new commuter rail just 20 mins to Boston. Walker's Paradise Walk Score of 92! Meticulously maintained & pro managed, it is the perfect balance of small-town charm & modern convenience!

62 Vine Street Unit 62, Winchester

Listing courtesy of Listing Agent: The Shorey Realty Group from Listing Office: Real Broker MA, LLC.
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 73423932 MLS ⋅ ['Allegro'] BLDG.
Welcome to this stunning 2-bedroom, 2-bathroom condo, built in 2021 and being offered by its original owner. Perfectly situated in the center of Winchester, this home is designed for effortless one-level living and offers the best of modern convenience and timeless style with an open and airy floor plan with oversized windows which fill the space with natural light. The gourmet kitchen flows seamlessly into the living and dining areas, which opens directly to a private outdoor balcony. Both bedrooms are generously sized, each with its own full bathroom, including a spacious primary suite for comfort and privacy. For added convenience, the condo includes in-unit laundry, extra storage in the garage area, an underground parking space, and elevator access within the building. Step outside and enjoy being just moments away from Winchester's charming shops, restaurants, and newly renovated commuter rail, making this the perfect blend of convenience and luxury.

36 Elmwood Ave Unit 4, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$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.
$900,000
3 Beds ⋅ 3 Baths ⋅ 73430034 MLS ⋅ ['The Village In Winchester'] BLDG.
Charming townhouse located at The Village, one of Winchester’s most sought-after and impeccably maintained communities, offers 1,843sf of living space. Featuring 3 generously sized bedrooms with full-height ceilings, and 2.5 updated bathrooms, it is one of the largest homes in the community. The home is flooded with natural light thanks to its end-unit position, windows on three sides, and a skylight in the dining area. The freshly painted interior is complemented by refinished hardwood parquet floors, new carpeting in two of the bedrooms, and wood flooring in the third bedroom. The expansive living room is anchored by a wood-burning fireplace, while the open-concept kitchen and dining area offer an ideal layout for modern living. Additional highlights include a private patio and dedicated parking (1 garage and 2 exterior spaces). Residents enjoy exceptional community amenities including a swimming pool with pool house, a tennis court, picturesque grounds, and professional management.

171 Swanton St Unit 5, Winchester

Listing courtesy of Listing Agent: Jonathan Radford from Listing Office: Coldwell Banker Realty - Boston.
$1,651,000
3 Beds ⋅ 2 Baths ⋅ 73426639 MLS
Welcome to 4 Oakland Circle, a spacious home tucked away on a desirable cul-de-sac in Winchester. Thoughtfully designed with oversized rooms and a versatile layout, this residence provides comfort and flexibility for a variety of lifestyles. The main level features expansive living and dining areas along with a 1st floor primary bedroom option that opens onto a private deck, plus a dedicated home office perfectly suited for remote work. Upstairs, the private primary bedroom offers a generous retreat, accompanied by a well-sized third bedroom. Large windows bring in abundant natural light, creating a warm and inviting atmosphere throughout. Step outside to enjoy the beautiful backyard, an ideal space for entertaining, gardening, or simply relaxing in a peaceful setting. With its generous floor plan, tranquil location, and close proximity to Winchester’s vibrant center, schools, this home presents an exceptional opportunity to enjoy both space and convenience.

4 Oakland Cir, Winchester

Listing courtesy of Listing Agent: Surabhi Rathi from Listing Office: Redfin Corp..
$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.
$3,242,250
5 Beds ⋅ 5 Baths ⋅ 73397101 MLS
Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor office/flex space. A separate but attached ADU—perfect for extended family or guests—boasts soaring 13’6” ceilings, a grand entertaining area with chandeliers, a full kitchen, and a private guest primary suite. With every imaginable bell and whistle, this home is truly one of a kind.

4 Norwood St, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Gibson Sotheby's International Realty.
$1,700,000
5 Beds ⋅ 4 Baths ⋅ 73428068 MLS
This isn’t just a house — it’s a front-row seat to the good life, where you can walk to shops, schools, cafés, restaurants, and everything the town has to offer! This 5-bedroom, 3.5-bath Victorian sits proudly in the heart of Winchester Center, in the highly coveted Lincoln School district. Original hardwood floors, soaring ceilings, and stunning architectural details give this home its timeless character, while the updated kitchen and spacious rooms bring modern comfort to everyday living. With its gorgeous design and generous layout, it’s perfect for hosting friends or enjoying quiet evenings at home. And the best part? The backyard offers a quiet space with a dining patio, garden and pergola....it's like a secret garden in the heart of the action. A full basement with good ceiling height offers plenty of expansion possibilities. An ample primary suite, excellent closets and big bedrooms combine with young systems/roof and ample parking!

77 Washington St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
$2,500
2 Beds ⋅ 1 Baths ⋅ 73438723 MLS
Welcome to this meticulously maintained 2 bedroom with a full bath. This apartment has a large kitchen, spacious living room along with large bonus room. Plenty of storage in the basement along with in-unit washer and dryer, along with two off-street parking spaces. All this just steps away from Mamadou's Bakery, Muraco School, Leonard Field and the Fellsway Reservation.

69 Irving Street Unit 69, Winchester

Listing courtesy of Listing Agent: The Serrano Team from Listing Office: Leading Edge Real Estate.
$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.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.