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171 Swanton Street Unit 39, Winchester
$805,000
2 Beds ⋅ 3 Baths ⋅ 73496879 MLS ⋅ ['The Village In Winchester'] BLDG.
Welcome to this sun-filled end unit townhome, featuring 2 bedrooms, 2.5 bathrooms, sparkling hardwood floors, central air & a sought-after bonus family room on the main level. Upon entering you’ll find an airy dining area, kitchen w/ granite countertops & stainless steel appliances, & large living room w/ fireplace & skylight, which flows seamlessly into a family room/office/den w/ oversized windows & built-in window seats. Don’t miss access to a private patio overlooking the pool & grassy courtyard, plus a half bath on this level. Upstairs, the primary suite offers hardwood floors, generous closets & stylish marble bathroom. This level also includes a second bedroom w/ hardwood floors, ample closets, a full family bath, & laundry. Unit 39 includes a covered carport parking space w/ second tandem space & a private storage room. Enjoy lifestyle amenities including an in-ground pool, clubhouse & tennis court. All of this just moments to Winchester’s vibrant town center, schools & train.

171 Swanton Street Unit 39, Winchester

Listing courtesy of Listing Agent: Carolyn Walsh from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
7 Wainwright Road Unit 107, Winchester
$1,515,000
3 Beds ⋅ 3 Baths ⋅ 73500873 MLS ⋅ ['The Ledges'] BLDG.
Move right into this spacious, light-filled townhouse at The Ledges! This upscale condominium community right outside Winchester center offers the ease of low maintenance living with the feel of a single family home & with the added bonus of a private club w/swimming pool and tennis court! This sought after layout offers a grand FIRST FLOOR PRIMARY bedroom & bath suite. Easy access main floor w/ direct entry from garage features a flowing, casual layout w/ beautiful family room w/ fireplace & vaulted ceilings leading to deck, a spacious dining area, great kitchen with sunny breakfast area, laundry & half bath. Second floor offers a spacious bedroom, loft/office, sitting/ tv room/ or guest room & full bath. The finished walk out lower level includes a generously sized family/ game room, space for additional bedroom, bath & storage! Conveniently located w/ easy access to Winchester center, Whole foods market, major highways & many great restaurants and shops. Only 7 miles from Boston!

7 Wainwright Road Unit 107, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
200 Swanton Street Unit L12, Winchester
$2,200
1 Beds ⋅ 1 Baths ⋅ 73495648 MLS
Recently renovated one bedroom, one bath condominium available in downtown Winchester. Bright and sunny unit with an open floor plan and amazing park & water views from private balcony. Rent includes all utilities - heat/hot water, air conditioning, electricity, and parking for 1 car. Incredible location walkable to shops, town center, and train to Boston. *Pets not allowed.*

200 Swanton Street Unit L12, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.
205 Washington St., Winchester
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 73503540 MLS
This charming home abounds in style and character. It is Steps to downtown Winchester, where you can enjoy a variety of fine restaurants, easy commute to Boston & be able to walk to all the public schools & St. Mary's .Beautiful natural wood trim & hdwd floors throughout, grace this home. A spacious & sunny kitchen w/ center island, great for entertaining w/ a built-in desk. Large pantry for storage. Lots of cabinets, and stainless steel appliances. The dining room showcases a built-in display china cabinet. Formal living room with a gas f.p. and french doors leading to an informal family room. A wrap around screened- in porch which will expand your lifestyle in the summer, overlooking a front yard with beautiful perennials. Upstairs: 3 bedrooms plus a small office space w/built-ins. Spacious tile bathroom with soaking tub, shower and double sinks. Parking for 3-4 cars. 4th B/R on 3rd floor. EV charger, .Full basement w/sink.

205 Washington St., Winchester

Listing courtesy of Listing Agent: Jayne Zeamer from Listing Office: Coldwell Banker Realty - Boston.
9 Mount Vernon Street Unit A, Winchester
$3,800
3 Beds ⋅ 2 Baths ⋅ 73500245 MLS
Beautiful, modern 3-bedroom, 2-bathroom unit located in the town's center! Steps to the commuter rail, shops and restaurants nearby. The unit ison the second floor, featuring an open floor plan with the kitchen (full stainless steel appliances) overseeing the dining area and living room, highceilings, large windows- great natural lighting, gleaming hardwood floors throughout, two full bathrooms, spacious bedrooms, generous closets,private in-unit laundry and central air and heat. The parking is availablein the municipal lot nearby. Non-aggressive pets will be considered.

9 Mount Vernon Street Unit A, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.
198 Pond St, Winchester
$1,070,000
4 Beds ⋅ 2 Baths ⋅ 73499450 MLS
Welcome to this classic Cape, ideally situated in a coveted location near Horn Pond and the brand-new Lynch Elementary School. Blending timeless charm with exciting potential, this recently refreshed home features newly painted interior and refinished hardwood floors, creating a warm and inviting atmosphere throughout. A sun-drenched family room addition with radiant heat offers a truly special retreat. With walls of glass framing views of the scenic yard, this space is perfect for both relaxed living and entertaining. The flexible layout includes four bedrooms, thoughtfully distributed with two on each floor, offering versatility for today’s lifestyle. The full basement presents additional opportunity for customization and future living space. Ready to be cherished by its next owners, this home is brimming with character and potential.

198 Pond St, Winchester

Listing courtesy of Listing Agent: from Listing Office: William Raveis R.E. & Home Services.
40 Englewood Rd, Winchester
$1,218,000
4 Beds ⋅ 2 Baths ⋅ 73497917 MLS
Nestled on a quiet, tree-lined street near the Fells, this charming Cape with classic dormers blends timeless character with thoughtful updates. The sun-filled kitchen features granite countertops and overlooks a peaceful backyard, while the breezeway between the one-car garage and kitchen offers an ideal mudroom or expansion potential. A beautifully updated first-floor bath includes radiant heated floors and a spacious glass-enclosed shower. A flexible first-floor bedroom or office adds versatility, and the fireplaced living and dining rooms provide inviting spaces for everyday living and entertaining. Custom built-ins enhance both charm and function. Upstairs are two generously sized front-to-back bedrooms and a full bath with radiant heat. The lower level offers a finished fourth bedroom with separate entrance, laundry, and a bonus room ideal for a gym, playroom, or office. Convenient to the Fells, the Muraco School, shops, restaurants, and major commuter routes.

40 Englewood Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
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.
65 Church Street, Winchester
$7,500
5 Beds ⋅ 4 Baths ⋅ 73506709 MLS
One of Winchester's premiere rentals! This gorgeous farmhouse style home just outside the town center has been beautifully renovated w/ designer finishes and offers 9 rooms, 4/5 bedrooms & 3.5 baths with plenty of space for a home office! An inviting farmers porch welcomes you into this great home, w/ double foyer, 10' ceilings, gorgeous millwork, completely updated with all new windows, new systems including high efficiency heating by gas & central A/C!! Spacious, sunny eat in kitchen with hardwood floors, stainless appliances, quartz counters & gas stove. Formal dining room w/ wainscoting, stunning living room w/bow front windows, fireplace, gleaming hardwood floors. Second floor features huge 30' family/ TV room, Primary BR w/ gorgeous new tiled bath, glass encl. tile shower & double closet; 4 rooms on second w/ 2 baths, third offers two add'l beds & full bath; and to top it off a location that can't be beat! Close Proximity to all Winchester has to offer and the TRAIN to BOSTON!

65 Church Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
15 Edward Drive Unit 15, Winchester
$1,055,000
3 Beds ⋅ 3 Baths ⋅ 73492749 MLS ⋅ ['Pepper Hill Estates'] BLDG.
Welcome to the highly sought-after Pepper Hill Estates, ideally situated on a quiet street near Vinson-Owen Elementary School and within walking distance to Wright-Locke Farm and McClennen Park. This Colonial-style home offers a highly desirable and functional layout. The first floor features an open-concept design with a spacious living room, dining area, and a custom-built kitchen by Schrock Cabinetry, along with a versatile bedroom/home office. The second floor showcases a beautiful primary suite with stunning hardwood flooring, an walk-in closet, and a well-appointed en-suite bath complete with a Jacuzzi tub and separate shower. A well-sized secondary bedroom with its own full bath completes this level. The lower level includes a laundry room and provides direct access to the one-car garage. Enjoy the exclusive-use fenced backyard with a charming patio—great for outdoor entertaining. A fantastic opportunity to move into charming Winchester and enjoy all the town has to offer.

15 Edward Drive Unit 15, Winchester

Listing courtesy of Listing Agent: Alina Wang Team from Listing Office: Coldwell Banker Realty - Lexington.
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.
200 Swanton St Unit T28, Winchester
$355,000
1 Beds ⋅ 1 Baths ⋅ 73450853 MLS
1 bedroom condo in Winchester. This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with access to the community pool and well-kept grounds, all within a short distance of Winchester Center, shops, and public transportation.

200 Swanton St Unit T28, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: RE/MAX Andrew Realty Services.
2 Abby Rd, Winchester
$2,575,000
4 Beds ⋅ 5 Baths ⋅ 73492061 MLS
Tucked on a quiet cul-de-sac within an exclusive enclave of homes, this newer residence offers a harmony of refined living and natural beauty. Just moments from the trails and vistas of the Middlesex Fells Reservation, this home is ideally positioned for those who value serenity and effortless access to the outdoors. Thoughtfully designed, it unfolds with an airy, open-concept where a sunlit kitchen, dining area, and family room create an inviting backdrop for everyday living and elegant entertaining. The family room exudes warmth and sophistication, while the chef’s kitchen impresses with an expansive center island and a suite of premium Thermador appliances. A first-floor office or den, paired with a full bath, offers versatility. Upstairs, the primary suite is a true retreat, with soaring ceilings, a spa-inspired bath, and a generous walk-in closet. 3 other roomy bedrooms complete this floor. A full finished basement is a true bonus, with direct walk-out access to the back.

2 Abby Rd, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
6 Holland Street Unit 6R, Winchester
$2,150
1 Beds ⋅ 1 Baths ⋅ 73508446 MLS
RENOVATED 1st floor apartment where no detail was spared. Level consists of XL bedroom, gorgeous kitchen, living room and full bath. Impressive open concept layout. Brand new kitchen with plenty of cabinets/storage, stainless appliances, recessed lights and quartz countertops. Kitchen opens to living room with gleaming hardwood floors. Tiled bath with tub. In unit washer and dryer. One off-street designated parking space. Quick access to Rte 93, 2,16 and 60. Walk to parks, restaurants and shops that Winchester offers. Good credit, minimum gross income and exceptional references. No pets. No smoking.

6 Holland Street Unit 6R, Winchester

Listing courtesy of Listing Agent: Marina Tramontozzi from Listing Office: True North Realty.
26 Lebanon Unit 26, Winchester
$2,550
2 Beds ⋅ 1 Baths ⋅ 73495776 MLS
This great second floor 2 bedroom is bright and spacious. The office leads to a three-season room. The entry hall leads to living room, dining room, and office. The full bath is flanked by 2 bedrooms. Eat in kitchen with pantry is spacious enough to have a dining table. Available immediately to qualified tenant.

26 Lebanon Unit 26, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
39 Town Way, Winchester
$3,200,000
6 Beds ⋅ 7 Baths ⋅ 73442521 MLS
Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to life! First floor offers a mudroom, half bath, office/living room, bedroom w/ full bath & a stunning high-end kitchen open to the dining room & spacious family room w/ fireplace, leading to a deck & large yard! The second floor features four generous bedrooms & three full baths, including a luxurious primary suite w/ a spa-like bath & walk-in closet, plus a convenient laundry room. The third floor includes an additional bedroom w/ rec/lounge area & oversized full bath! The walk out finished lower level provides a large recreation room, gym & full bath..perfect for family fun or entertaining. Reach out today for a site visit and a tour of this fabulous home to be completed by early spring 2026!

39 Town Way, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
76 Woodside Road, Winchester
$1,080,000
4 Beds ⋅ 2 Baths ⋅ 73492483 MLS
Welcome to this charming 4-bedroom, 2-bath home in desirable Winchester. Ideally located in one of the town’s most sought-after neighborhoods, this well-maintained residence offers the perfect blend of classic character and everyday comfort. The home features a bright and inviting layout with generous living spaces, hardwood floors, bookshelves and windows seats. The kitchen flows seamlessly into the dining and living areas, making it ideal for both daily living and entertaining. Four well-proportioned bedrooms provide flexibility for family, guests, or home office needs, while two full baths add convenience and functionality. Outside, enjoy a private yard perfect for relaxing, gardening, or outdoor gatherings with tons of sunlight. Additional highlights include ample storage, garage with plenty of off-street parking, and a location that truly can’t be beat—just minutes to Winchester Center, commuter rail, parks, and top-rated schools. Open Houses 3/28 & 3/29 .

76 Woodside Road, Winchester

Listing courtesy of Listing Agent: Michael Pierce from Listing Office: Mystic Properties Real Estate.
15 Englewood Road, Winchester
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 73480343 MLS
Cleverly reimagined for modern living, this energy-efficient Craftsman bungalow is ideally located in Winchester with close proximity to the natural beauty of the Middlesex Fells and the shops, dining and commuter rail of the town center. Thoughtfully expanded and renovated, the home features newer systems, windows and roof, among too many other updates to list. A functional mudroom with custom storage welcomes you inside, where the living room flows seamlessly into an exquisite chef’s kitchen with premium appliances, dual sinks and a dining room overlooking the landscaped, fully fenced yard. A spacious bedroom and full bath complete this level. Upstairs offers three additional bedrooms, two full baths and laundry, highlighted by a generous primary suite with walk-in closet and spa-like bath, complete with soaking tub and extra large shower. Owned solar panels, EV charging, a one-car garage, and a versatile lower level with bonus room complete this exceptional offering.

15 Englewood Road, Winchester

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

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.

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