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$1,607,000
4 Beds ⋅ 3 Baths ⋅ 73505351 MLS
Location, location, location! Enjoy one-level living in this charming Ranch-style home, beautifully situated on a cul-de-sac, within walking distance to the vibrant Town Center. This exceptional property, lovingly maintained by the same owners for 50+ years, offers a large fireplaced living room with ample natural light, gracious dining room with built-in cabinets, tasteful new kitchen with quartz countertops and stainless appliances (2025), spacious primary bedroom with en-suite bath and cedar closet, 3 additional good-sized bedrooms, beautiful hardwood floors, central airconditioning, sunroom overlooking private backyard, mudroom, abundant storage space, and more. Bring your creative ideas for the large space in the lower level to personalize for your needs. The 2-car garage, motion-sensor lights, and the landscaped yard complete the picture. Welcome to Winchester with its highly rated schools, two commuter rail stations, Mystic Lakes, and the much-treasured Fells Reservation.

6 Oakland Circle, Winchester

Listing courtesy of Listing Agent: Seeme Moreira from Listing Office: Coldwell Banker Realty - Lexington.
$1,440,150
6 Beds ⋅ 3 Baths ⋅ 73498871 MLS
Exceptional opportunity in a highly desirable Winchester neighborhood! This spacious 6-bedroom home offers incredible flexibility for today's lifestyle, perfect for multi-generational living, work-from-home setups, or growing households. The sun-filled main level 3-bedrooms feature hardwood floors and a seamless flow, ideal for both everyday living and entertaining. The updated second floor includes a full bath, private laundry, and generously sized 3 bedrooms with abundant natural light. A standout feature is the expansive 1,337 sq ft lower level - ideal for a playroom, gym, media room, or future customization. Enjoy a level, private backyard perfect for outdoor gatherings, gardening, and recreation. Conveniently located near top-rated schools, commuter rail, and Winchester center. Incredible value and space in one of Winchester's most sought-after communities!! The seller will gift the new buyer a pool and a ping-pong table for the playroom.

65 High Street, Winchester

Listing courtesy of Listing Agent: Anna Jung from Listing Office: K Stadium Realty INC.
$3,100,000
6 Beds ⋅ 5 Baths ⋅ 73496654 MLS
Welcome home to this stunning colonial on one of Winchester's most beloved streets. Featuring 6 bedrooms and 4.5 baths, this has been extensively renovated, creating space to spread out and truly live. Rich hardwood floors, 3 fireplaces, and a gracious flow make every room feel warm and inviting. The gourmet kitchen- complete with granite countertops, a large island, butlers pantry, wine chiller, double dishwashers and stainless appliances- is the heart of the home. The primary suite is a true retreat with a fireplace, walk-in closets, and spa bath with soaking tub. A sun room, custom mud room, finished basement, and 3rd-floor bedrooms offer room for everyone and everything. Outside, a bluestone patio, wood burning fireplace, covered deck, enclosed porch, professional landscaping and irrigation system create a beautiful and private setting, while a 2-car detached garage and 6-car paved driveway provide exceptional storage and parking. Surely a highlight of Winchester's spring market!

12 Salisbury Street, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$3,300
2 Beds ⋅ 3 Baths ⋅ 73457225 MLS
Condo community with use of wonderful exercise facility, outdoor heated pool and community center. In-unit laundry, no lead paint, Central AC. Beautiful 2 bed 2.5 bath townhouse with a 2 car parking at the sought-after Willows in Winchester. Elevator building to second floor then the unit is a spacious townhouse 2nd and 3rd floors. No one above you. Open floor plan from kitchen to living room with plenty of natural sunlight in this southwest facing unit. Gas fireplace. Two very large bedrooms are located on the top level both with full baths and large closets. In-unit full size washer and dryer just outside the bedrooms. 2 private balconies. Newer windows and new window blinds / sliding door blinds. Large 10’ by 5’ with 7’ height storage in the basement. Plenty of guest parking. Water included. Gas heat. Mostly owners and in this well-maintained / beautiful condominium complex.

7 Conant Road Unit 67, Winchester

Listing courtesy of Listing Agent: David W. Ledwig from Listing Office: Coldwell Banker Realty - Lexington.
$1,250,000
4 Beds ⋅ 2 Baths ⋅ 73500869 MLS
Beautifully renovated 4BR home situated across from McDonald field & playground offering a desirable floor plan ideal for entertaining & easy living. Enter into a lovely sun porch/ mudroom leading to the main level featuring a bright and airy open floor plan w/gorgeous wide plank hickory flooring, many windows, high ceilings & stunning renovated kitchen showcasing high-end appliances & a spacious center island. The versatile 1st floor also offers a large bedroom suite w/ full bath providing the perfect option for a primary suite, guest suite or family room. Upstairs includes 3 additional bedrooms & full renovated hall bath. Tucked away on the third floor, a peaceful retreat/ ideal home office space. An oversized yard w/ new trex deck is ideal for play, bbq's and offers potential space for an ADU! Enjoy a vibrant cheerful neighborhood & a turnkey property w/ many recent thoughtful updates. Close to town & train to Boston! Don't miss this great home in the NEW Lynch Elementary district!

87 Wendell Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,200,000
4 Beds ⋅ 2 Baths ⋅ 73499525 MLS
Charming, beautifully updated town home in prime downtown Winchester neighborhood! This 4 bed 2 bath home offers living space across 3 levels, blending classic character w/ everyday functionality. The layout features a welcoming main level with high ceilings, oversized windows & a nice open flow between the living room, dining room, family room & kitchen, creating an ideal setup for both daily living and entertaining. Upstairs, you’ll find 4 large bedrooms w/ flexibility for guest space or home offices. Generous room sizes, hardwood flooring, and great natural light carry throughout the home, enhancing its warm and inviting feel. Timeless architectural details add to this great home. Enjoy private spaces with room to spread out, all while being conveniently located close to Winchester center, commuter rail, top-rated schools, and local shops and restaurants. A great opportunity for both commuters and those looking to enjoy all the town has to offer.

31 Mystic Ave Unit 31, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$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.
$2,649,000
4 Beds ⋅ 4 Baths ⋅ 73485423 MLS
Under construction / Beautifully crafted 4 bedroom home offering thoughtful design, quality finishes & an ideal layout. The open-concept 1st floor is both spacious & welcoming, perfect for entertaining & everyday living. The chef’s kitchen features quartz countertops, stainless appliances, large center island w/seating & pantry. The kitchen flows seamlessly into the generous family room w/ gas fireplace & sliders leading to a large deck w/ private yard. The main level also includes a formal dining room w/ wainscoting, & a tray ceiling, a functional mudroom w/ bench seating, & a stylish half bath. Upstairs, the expansive primary suite offers 2 walk-in closets a luxurious bath with double vanities, soaking tub, & oversized shower. 3 additional bedrooms, a full hall bath, & convenient laundry room complete the 2nd floor. The finished LL provides a versatile media room,a full bath, & abundant storage. Two-car garage w/ direct entry. Convenient location close to town, train & Boston!

2 Priscilla Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,100,000
5 Beds ⋅ 8 Baths ⋅ 73474290 MLS
This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builders commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, wine fridge, coffee bar, charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite & full third floor w/ hardwood floors & bath. The expansive lower level offers a family room, movie theatre, game room, gym plus private entry separate living quarters w/full in-law/au-pair suite w/ kitchen, 2nd laundry,BR & bath

54 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 73502604 MLS
Charming 3-bedroom Colonial nestled on a lovely street in desirable Macdonald playground neighborhood! This well-maintained single-family home on a large lot offers a thoughtful floor plan w/hardwood flooring throughout. The main level features a spacious living room and an open-concept kitchen and dining area, perfect for everyday living and entertaining. The updated cherry kitchen is equipped with stainless steel appliances, granite countertops, and a slider that opens to a large, sun-filled backyard, with patio ideal for gatherings or simply enjoying beautiful sunrise and sunset views. Upstairs, you’ll find three bright and generously sized bedrooms along with an updated full bath. The basement offers additional playroom space, w/ laundry & excellent storage The expansive backyard w/shed is great for outdoor entertaining, play, or gardening. Enjoy all that Winchester has to offer, including top-rated schools, and convenient access to Boston.

104 Wendell Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,150,000
5 Beds ⋅ 7 Baths ⋅ 73499287 MLS
OPEN HOUSE CANCELLED 4/12 **OFFER ACCEPTED** Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or everyday living & entertaining. Must see this fabulous home~

257 High Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,330,000
3 Beds ⋅ 2 Baths ⋅ 73498431 MLS
Oh, how beautiful life can be when lifestyle & location align! Imagine living just over a mile from the shops & restaurants in the Center, while also being able to stroll down the block to enjoy Leonard Field & the bike path? Stylish & chic, this quaint yet elevated gem was thoughtfully designed to preserve its original, nostalgic charm. Surprisingly spacious, the main level features a sunny front-to-back living room, dining room, & a truly beautiful sunroom/office. The updated kitchen w/marble island & built-in breakfast nook connects beautifully to the outdoor space including the bluestone patio & fenced yard. Upstairs, appealing angles & peaks frame a front-to-back primary w/customized closets & private deck, a fully tiled bath, + 2 additional bedrooms. Dreaming of more space? The finished lower level is perfect for occasional guests or playroom, + offers laundry & a pristine utility/mudroom! All in a neighborhood known for its friendly vibe, near the train, ask agent for updates!

1 Orient Street, Winchester

Listing courtesy of Listing Agent: Julie Gibson from Listing Office: Gibson Sotheby's International Realty.
$1,060,000
3 Beds ⋅ 2 Baths ⋅ 73493684 MLS
Move in ready & nicely remodeled ranch on a fabulous 10K fenced lot! This 3-4bedroom, 2 full bath home w/full lower level including office, family room/bedroom & full bath offers a sunny, functional layout w/ tasteful updates throughout.The main living spaces flow seamlessly, highlighted by a newer eat-in kitchen w/ access to deck & great yard; perfect for indoor/outdoor living & entertaining. Spacious living room offers a fireplace, bay window & opens to dining area. Generously sized bedrooms & updated full bath complete the 1st floor. You will love the large lower level w/ high ceilings, a nice family room/ bedroom/office and full bath. The fenced yard w/ lush grass & large deck offer a private outdoor retreat. This home is ideally situated in a central location, just moments to town, Whole Foods & Horn Pond, w/ easy access to major highways for an easy commute. Enjoy all that Winchester has to offer, including its highly rated schools, the train to Boston & the vibrant town center!

15 East Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$2,575,000
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.
$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.
$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.
$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.
$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.

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