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$2,750,000
5 Beds 6 Baths 73455886 MLS
Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive kitchen and dining area form the heart of the home—perfectly suited for lively entertaining, relaxed gatherings, and everyday living. Upstairs, the primary suite offers a luxurious retreat, while the spacious third-floor teen suite provides comfort, privacy, and versatility. The finished lower level—with its full bath—adds tremendous bonus space for play, guests, or hobbies. Blending modern craftsmanship with timeless appeal, this home delivers exceptional living just a stone’s throw from the Middlesex Fells Reservation, where nature’s beauty is right at your doorstep.

19 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,530,000
4 Beds 4 Baths 73480199 MLS
Step into timeless charm in this STUNNING, impeccably maintained Dutch Colonial Revival home, where historic character meets modern living! Thoughtfully updated with 4 bedrooms and 4 baths, including TWO ENSUITE RETREATS—one private and perfect as a 4th bedroom, au pair suite, studio, or office. Endless flexibility! The updated kitchen shines with abundant cabinetry, center island, granite countertops, gas range, and stainless-steel appliances. First-floor laundry! Soaring ceilings and sun-filled rooms with ALL DAY NATURAL LIGHT deliver effortless comfort. Original balusters and custom built-ins preserve the home’s classic soul. Outside, enjoy a FENCED YARD, lush, curated landscaping, and raised garden beds with rich soil. An aluminum one-car garage and off-street parking add ease. Set in a coveted Winchester location just 0.4 miles to the vibrant town center, farmers market, and train—this is a rare blend of space, charm, walkability, and convenience. Get ready to fall in love!

259 Washington Street, Winchester

Listing courtesy of Listing Agent: Laurie Cappuccio from Listing Office: Classified Realty Group.

$1,025,000
6 Beds 2 Baths 73470713 MLS
Investor alert! About one mile from an array of shops, restaurants, & the commuter rail to Boston, this Winchester multi-family is a rare opportunity waiting to be redesigned! Held by the same family for many years, the property offers substantial square footage & endless potential for those ready to roll up their sleeves. While it requires significant renovation, the reward will be well worth the effort. The classic wood exterior provides timeless character while an addition off the upper level offers valuable extra living space. Each apartment includes fully applianced kitchens & in-unit laundry. Explore the possibilities: convert to a single-family home, pursue a condo conversion, or live in one unit while generating rental income from the other. The main-level unit may be shown at open house only; the upper unit is available for private showings. An exceptional chance to invest in Winchester, known for its top-rated schools, charming neighborhoods, and unbeatable lifestyle!

353-355 Washington Street, Winchester

Listing courtesy of Listing Agent: Julie Gibson from Listing Office: Gibson Sotheby's International Realty.

$560,000
5 Beds 3 Baths 73477596 MLS
Welcome to your move-in-ready sanctuary—where modern updates meet peaceful nature, with a tranquil brook alongside the property for privacy and charm. Enjoy major peace-of-mind upgrades including a BRAND NEW ROOF, NEW 2,500-gallon SEPTIC system, fresh paint, and stylish laminate flooring throughout. The updated kitchen features NEW APPLIANCES and finishes, while the main-level bath feels like a spa with a jetted soaking tub. Versatility shines with an oversized high-ceiling garage and a fully finished walk-out basement complete with its own kitchen, living space, and private entrance—ideal for an IN-LAW SUITE or multigenerational living. Outside, a detached, fully powered and heated “hobby house” offers the perfect workshop, studio, or home office. A rare blend of space, function, and natural beauty—ready to enjoy from day one.

583 Burt Hill, Winchester

Listing courtesy of Listing Agent: Munise Ulker from Listing Office: Homesmart Success Realty.

$6,995
4 Beds 3 Baths 73477507 MLS
Available July 1, 2026 or later. 3000+ sq ft,4-story townhouse in a side-by-side 2-family lives like a single. Like-new quality on a cul-de-sac that ends at Muraco Elementary. Features 4 beds, 2½ ba, 2-zone central AC and gas heat. Soaring ceilings and lots of light. Delightful open-plan kitchen w/stainless Bosch appliances, quartz countertops, gas cooking, walk-in pantry, bookshelves. Huge family room with built-in bar. Big closets. 2-car garage (tandem) w/opener and electric car charger. Energy efficient windows w/interior shutters throughout. Restoration Hardware lighting. Expansive back deck and fenced yard with flat lawn. 2 basement storage rooms make great home gyms. 2nd floor laundry with front loading washer and electric dryer. 3rd floor bonus room plus potential study/office space could make a great au pair or in-law suite. ~1 mi to Winchester station. 1st mo+1mo security due at signing.

11 Tufts Unit 11, Winchester

Listing courtesy of Listing Agent: Robyn Bonnett from Listing Office: Coldwell Banker Realty - Lexington.

$452,500
3 Beds 1 Baths 73468681 MLS
Welcome to Winchester! Ideally located within walking distance of WHS and Winchester Center, this home offers exceptional value in one of the area’s most desirable communities. The main level features a newly renovated kitchen with adjacent living and dining areas, creating a functional and inviting open layout ideal for everyday living and entertaining. The second floor includes three bedrooms and a full bath, with hardwood flooring throughout. A finished basement provides flexible additional space, perfect for a home office, workout area, or bonus room. Off-street driveway parking and a storage shed add everyday convenience. With close proximity to shops, restaurants, parks, and commuter rail access, this property presents a fantastic single-family alternative and an affordable opportunity to enjoy all that Winchester has to offer. Deed-restricted affordable housing sale.

22 Oak St Unit 22, Winchester

Listing courtesy of Listing Agent: Rameel Rana from Listing Office: Advise Realty.

$1,574,500
4 Beds 4 Baths 73461480 MLS
Great new price, below assessed value!!! Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home office, sun room, central AC (8 mini-splits), Lochinvar heating sys (2025), hardwood floors, 3 fireplaces, and more. The stunning kitchen combines function, design, and quality showcasing custom cabinets, granite countertops, stainless appliances, and tasteful lighting. The lower level, with an outside entrance and a half bath, is well suited for an in-law suite, or au pair accommodations. The lovely backyard with its Zen Garden includes many thoughtfully organized plantings and flowering trees. COME SEE THE RECENTLY RENOVATED 3RD FLOOR!

263 Highland Ave, Winchester

Listing courtesy of Listing Agent: Seeme Moreira from Listing Office: Coldwell Banker Realty - Lexington.

$5,000
4 Beds 2 Baths 73454988 MLS
Ideally located near Winchester Center, this beautifully updated home combines modern design with classic New England charm. 113 Cambridge Street features a fully renovated kitchen with custom cabinetry, quartz counters, and premium appliances, opening to bright, inviting living spaces. The newly finished basement adds incredible versatility, ideal for a playroom, gym, or guest suite. With four bedrooms, two full baths, and thoughtful updates throughout, this turnkey home offers comfort and flexibility for today’s lifestyle. Enjoy a spacious, level yard and easy access to top-rated schools, town center, commuter rail, and major routes. Don't miss out on this true Winchester gem.

113 Cambridge, Winchester

Listing courtesy of Listing Agent: Ryan Clunan from Listing Office: Campion & Company Fine Homes Real Estate.

$1,850,000
5 Beds 4 Baths 73455673 MLS
From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a sitting area complete this level. The third floor provides space for additional bedrooms or an office. The finished lower level includes a family room, wine cellar, sauna, gym, and full bath. Enjoy a tree-lined backyard with deck and hot tub, perfect for entertaining. The home office opens to the yard and attached two-car garage with Level 2 EV charger. Central A/C and a Tesla solar roof with 27 KW battery storage complete this stunning home.

20 Grove Pl, Winchester

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

$681,888
3 Beds 2 Baths 73478441 MLS
Nicely renovated & GREAT price!! This unique 3 bed, 1.5 bath townhouse offers a spacious layout and has a private level large back yard, and 2 car parking! This home offers a spacious open living/ dining room with hardwood floors and plenty of natural light. The second floor offers 3 spacious bedrooms with large closets and a full bath. The updated interior makes this home move in ready. Gleaming hardwood floors run throughout, and ductless mini splits provide AC and heat. The basement offers excellent potential to be finished, creating the perfect space for a family room, home office, or gym. Numerous windows create a bright and inviting feel. Low condo fee and close to everything Winchester has to offer. Located in the Lynch School district, brand new as of the 2025 school year. Easy commuter rail access into Boston with convenient access to Routes 93 and 95. Just minutes from Winchester Center and only 7 miles from Boston.

9 Charles Road Unit 9, Winchester

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

$1,470,000
3 Beds 3 Baths 73475677 MLS
Classic New England charm defines this pristine 3-bedroom, 2.5-bath Colonial set on a generous, level corner lot with a beautiful stone wall in a sought-after neighborhood. Lovingly maintained by the same owners for over 50 years, the home is neat as a pin and filled with warmth and character. Hardwood floors, a traditional Colonial layout, and a fireplaced living room create comfortable living spaces, while a lovely sunroom brings in abundant natural light. Spacious bedrooms offer comfort, and the partially finished basement provides bonus space for work or play. An attached two-car garage adds everyday convenience. Ideally located just about .5 mile to the MBTA Wedgemere commuter rail station for easy Boston access, with quick connections to I-93 and nearby outdoor recreation at the Middlesex Fells Reservation. Move right in and enjoy, with the option to make thoughtful updates over time in a home that truly reflects pride of ownership.

2 Canterbury Rd, Winchester

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

$3,300
2 Beds 2 Baths 73482077 MLS
The Village ! Spacious 5 room townhouse with a cozy fireplaced living room, sunny bump out nook with skylight perfect for a desk area with serene wooded view. Living room opens out to private patio outdoor space; galley kitchen with plenty of cabinets; newer stainless appliances and countertop; bright dining area and half bath on 1st fl; upstairs hosts 2 generous size bedrooms and a full bath; primary bdrm has a walk in closet plus another full closet with access to the full bath from both the bdrm and hallway, laundry room has washer & dryer included and a storage room. A carport plus 2nd space tandem; pool; tennis and close to downtown, train to Boston Winchester center with all it has to offer.

171 Swanton Unit 70, Winchester

Listing courtesy of Listing Agent: Sheri O'Connor from Listing Office: Plunkett Properties.

$1,015,000
3 Beds 2 Baths 73476114 MLS
Classic Victorian charm in a convenient Winchester location close to shops, the commuter rail, library, Farmers’ Market, and the Middlesex Fells. An inviting entry opens to a bright living room with a built-in window seat offering hidden storage. The main level flows into the dining room with an attached office alcove and half bath, providing flexible work-from-home space. The renovated eat-in kitchen features granite counters, a custom peninsula, and built-in pantry, with a mudroom just off the back entry. Upstairs are three bedrooms with generous closet space, including a custom walk-in in the primary bedroom. A finished walk-up attic offers bonus space for a playroom, office, or guest area. Hardwood floors throughout, fenced yard for outdoor enjoyment, and owned solar panels for added efficiency and long-term savings. A home that blends character, comfort, and everyday convenience.

320 Washington St, Winchester

Listing courtesy of Listing Agent: John D. Conroy from Listing Office: East Coast Realty, Inc..

$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..

$2,250
1 Beds 1 Baths 73479574 MLS
Updated 1-bedroom apartment for rent near Winchester Center, MA available May 1 with all utilities included. This bright, freshly painted unit features scenic pond views, a sun-filled living room, and an updated kitchen with dishwasher. Heat, hot water, electricity, and A/C are included for convenient, worry-free living. Community amenities include an onsite swimming pool, pool house, and included parking, with additional parking available. Ideally located near Winchester Center shops, restaurants, banks, hospitals, and commuter routes, with easy access to Boston and public transportation. Enjoy comfortable living in a well-maintained community offering convenience, natural views, and great location

200 Swanton St Unit 619, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: RE/MAX Andrew Realty Services.

$3,470,000
5 Beds 6 Baths 73472359 MLS
Exceptional Colonial Revival in one of Winchester’s most sought-after Sheffield neighborhoods, known for its tree-lined streets and a shared community green. Timeless architecture meets modern livability across four finished levels. The chef’s kitchen features a large island, walk-in pantry, wet bar, and custom cabinetry, opening to a spacious family room with gas fireplace. Formal living and dining rooms offer hardwood floors, crown molding, and abundant natural light. The primary suite includes walk-in closets and a spa-like bath, with additional generously sized bedrooms and baths. The 3rd floor provides flexible living with bedroom, study, bonus room, and full bath, while the finished lower level adds recreation space. Recent improvements include exterior paint (2024), perimeter fencing with gated driveway, ornamental landscaping, enclosed mudroom storage, and a custom Dutch door. Detached 2-car garage and private yard. Close proximity to Winchester Center and Wedgemere Stations.

10 Sheffield West, Winchester

Listing courtesy of Listing Agent: Jay Noble from Listing Office: Lamacchia Realty, Inc..

$1,750
1 Baths 73477190 MLS
Bright and sunny studio overlooking a quaint duck pond with private balcony for morning coffee or evening relaxation. ALL utilities included—heat, hot water, electricity, and air conditioning covered in rent. Community perks include guaranteed parking spot for 1 car, on-site laundry, and seasonal swimming pool access. Minutes from Winchester town center and commuter rail with easy connections to Boston. Shopping, dining, and major highways all nearby. Well-maintained condo community provides no-fuss rental living with the small pleasure of peaceful pond views. Perfect for anyone seeking a practical home base with convenient amenities in an established neighborhood. Price is $1750 through June and then will increase to $1850/month.

200 Swanton St Unit 306, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.

$680,000
2 Beds 2 Baths 73467438 MLS ['The Willows'] BLDG.
Rarely available ground-floor townhouse at The Willows with easy access to a private garage. This bright and sunny 2-bedroom, 2-bath condo offers the convenience and comfort today’s buyers are seeking. Open concept kitchen with a breakfast bar, and an adjacent dining area—perfect for everyday living or entertaining. The expansive living room is highlighted by a gas fireplace and slider that opens to a private patio area.The generous primary suite includes a walk-in closet and an ensuite bath with double vanity. A large second bedroom also offers a walk-in closet, while the hallway bath features a tub and shower, there is an in-unit laundry and extra basement storage. Amenities include a clubhouse with community room, fitness center, restrooms, and a heated outdoor saltwater pool. Enjoy all that Winchester has to offer, the 2,600 acre Middlesex Fells, vibrant downtown, restaurants, shops, library, farmers market and commuter rail service to Boston.

7 Conant Rd Unit 33, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$815,000
3 Beds 2 Baths 73468847 MLS
Fantastic opportunity to own in Winchester! This inviting home is move-in ready and offers a flexible layout. The bright living room with picture window opens to the dining area, with a kitchen and a convenient half bath with laundry just beyond. Upstairs features a comfortable primary bedroom, sunny home office, additional bedroom, and a full bath. The third-floor bedroom spans the length of the home with windows at both ends, ideal for a playroom, lounge, or guest suite. The lower level presents useful space for storage, a workshop, or playroom with direct access to the backyard. Located near Winchester High School and less than half a mile to Winchester Center with shops, dining, commuter rail, conservation trails, and only 8 miles to Boston.

49 Spruce St, Winchester

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

$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.

$1,350,000
4 Beds 4 Baths 73459193 MLS
Beautiful newer-construction home in a wonderful Muraco school location! This meticulous 4-bed, 3.5-bath property offers modern living with an inviting open-concept layout & high ceilings spanning across 4 finished levels with attached garage! The stunning chef’s kitchen features high-end appliances, large island & abundant storage, flowing seamlessly into the dining area & living room with a gas fireplace, perfect for everyday living and entertaining. A slider leads out to the expansive fenced yard w/ patio for outdoor enjoyment. The second level offers 3 spacious BR’s& 2 BA including the primary suite w/ spa-like bath & great closet space. The finished 3rd floor.provides a fantastic bonus/media room, home office, fitness space, or guest suite w/ a full bath!.. the finished LL adds more family space! Central air & thoughtful finishes throughout make this home truly turn-key.Enjoy easy access to schools, town center & commuter rail all nearby!—don’t miss this exceptional opportunity

95 Irving Street Unit 95, Winchester

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

$3,700
3 Beds 3 Baths 73477585 MLS
Winchester Center at your doorstep. You’ll love being able to stroll to your morning coffee, grab dinner with friends, browse the local shops, or catch the commuter rail without ever needing your car. Inside, this home offers three levels of comfortable living space plus a finished basement that works beautifully as a quiet office, a cozy hangout spot, or simply extra storage. The main floor features beautiful wood floors and an easy, open layout that makes everyday living feel effortless. The kitchen includes double ovens, granite counters, and a wine fridge, and opens directly to a private deck — perfect for warm evenings or enjoying your morning coffee outdoors. Upstairs, the primary bedroom offers a generous walk-in closet and in-unit laundry. The third floor holds two additional bedrooms filled with natural light and flexible enough to adapt to your lifestyle. One off-street parking space is included. Available January 1st.

11 Elmwood Avenue Unit 11, Winchester

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

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