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$3,600
3 Beds 2 Baths 73575968 MLS
Welcome to this charming Winchester home! Nestled amidst lush greenery, it exudes classic ranch style and is located in the sought-after Muraco School District, near Horn Pond and Middlesex Fells Reservation. Just a 20-minute drive to downtown Boston, this location offers both convenience and tranquility. Renovated in 2022, it consists of modern upgrades including stainless steel appliances, an updated AC system, and a new gas water heating system. Step into the beautiful garden leading to the spacious kitchen with new quartz countertops and Imitation wood grain tiles. The open-concept living room features gleaming hardwood floors. Two bright bedrooms and an office/den provide cozy spaces, while the expansive basement offers endless possibilities. Outside, stone pathways lead to the well-maintained backyard with a swing and picnic area, perfect for outdoor gatherings. Don't miss the chance to make this dream home yours!

235 Forest St, Winchester

Listing courtesy of Listing Agent: Lin Wu from Listing Office: JW Real Estate Services, LLC.

$3,800
3 Beds 3 Baths 73575703 MLS
This beautifully maintained residence offers a unique opportunity to lease a comfortable and stylish home.This residential property, built in 1997, offers 1367 square feet of inviting, move-in ready space, presenting an open floor plan living room, dining area and kitchen with hardwood floors and lots of windows with natural sunlight. Modern kitchen white cabinets, quartz counters, range, dishwasher, refrigerator, microwave and disposal. First floor half bath with tiled floor, linen closet and washer and dryer hook ups. Second floor with 2 bedrooms, double closets, hard wood floors and full bath with tiled tub and shower and tiled floor. Third floored en-suite bedroom, double closets and bathroom with walk-in shower and tiled floor, and hardwood floors. Full unfinished basement for exercise and storage. Enjoy 4 car parking and grassy area for relaxing. Convenient to Shopping, Winchester Center, Schools, Horn Pond, Restaurants and Major Highway access. Tenant is responsible to purchase trash permit at Winchester Transfer Station. The cost is 330.00 for year and is located at 15 McKay Ave, Winchester, MA 01890

52 Sheridan Circle Unit 52, Winchester

Listing courtesy of Listing Agent: Robin Griffiths from Listing Office: J. Mulkerin Realty.

$775,000
3 Beds 2 Baths 73575116 MLS
Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester

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

$1,679,900
3 Beds 2 Baths 73572791 MLS
Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

5 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.

$1,699,000
3 Beds 2 Baths 73572661 MLS
Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

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

$3,000
3 Beds 1 Baths 73572192 MLS
Welcome to 341 Washington St, Winchester, MA! This spacious 3-bedroom, 1-bath apartment offers a comfortable and convenient layout in a desirable Winchester location.The unit features laundry, parking for 2 cars, and access to a backyard, providing extra space to relax and enjoy the outdoors.Conveniently located near local shops, restaurants, schools, public transportation, and major routes, making commuting and everyday errands easy.Property Features: 3 Bedrooms 1 Full Bathroom Laundry 2-Car Parking BackyardMove in cost: 1st Month & Security due at signing contract. A great opportunity to enjoy comfortable living in Winchester. Schedule your showing today!Lease 12 monthsTenants pay for gas & Electricity and Trash disposalOwner pays water & sewer

341 Washington St Unit 2, Winchester

Listing courtesy of Listing Agent: Claudia Morais from Listing Office: P&Co Real Estate.

$619,000
3 Beds 4 Baths 73571573 MLS
Great opportunity to live on a quiet side street conveniently located near the town center and Elizabeth C. McDonald Field, featuring tennis courts, ball fields, basketball courts, and a playground. This well-maintained 3-bedroom, 3.5-bath townhouse offers 1,225 sq. ft. of comfortable living space. The charming home features high ceilings and a functional multi-level layout with a bright living area, spacious kitchen, two generously sized bedrooms, and a large office. Numerous updates were completed in 2023, including hardwood flooring, a finished attic, five ductless mini-split AC units, and renovated bathrooms. A new roof was installed in 2024. Additional updates include a high-efficiency gas boiler and hot water system installed in 2019. Conveniently located within walking distance to the newly built Lynch Elementary School and Winchester High School, with easy access to local shops, restaurants, and major routes. A wonderful opportunity to enjoy comfortable living in highly desirable Winchester!

23 Shepard Ct Unit 23, Winchester

Listing courtesy of Listing Agent: Ning Sun from Listing Office: United Real Estate, LLC.

$1,098,000
3 Beds 2 Baths 73566405 MLS
Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..

$4,400
3 Beds 2 Baths 73564765 MLS
Rare opportunity to rent an exceptionally spacious home on historic Church Street in the heart of Winchester! Offering over 2000 sq. ft. of living space, this charming Victorian features 3 generous bedrooms, 1.5 baths, a grand foyer, spacious living and dining rooms, and an eat-in kitchen with granite countertops and gas cooking. High ceilings, hardwood floors, original architectural details and a decorative fireplace add to the home's character. Enjoy a private wraparound farmer's porch, in-unit washer/dryer, ample closet space and two off-street driveway parking spaces. Pet friendly. Ideally located less than half a mile from Winchester Center and approximately 0.3 mile from the commuter rail, with shops, restaurants and cafés nearby. A beautiful combination of space, character and convenience!

79 Church St Unit 1, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.

$3,500
3 Beds 1 Baths 73563669 MLS
**Flexible lease terms** Prime location close to town! Spacious and beautifully maintained 3-bedroom first floor unit in the heart of Winchester, with a full driveway! This great home offers a blend of classic character and thoughtful updates. This unit has always been owner occupied and is in meticulous condition .. featuring generously sized rooms with high ceilings, oversized windows, hardwood floors, beautiful original woodwork, crown molding, and timeless architectural details. The layout includes a welcoming living room with a wood-burning fireplace, dining room with wainscoting, sunroom, updated kitchen with upgraded cabinets and countertops, and an updated full bath. The kitchen includes a range, dishwasher, refrigerator, and freezer, with washer and dryer also available. Additional features include pantry and storage space, an enclosed porch/patio & a great back yard. Ideally located near downtown Winchester, with convenient access to shops, restaurants, parks, walking and biking trails, schools, public transportation, and the commuter rail. A spacious home combining historic charm, modern updates, and a convenient Winchester location.

303 Washington Street Unit 1, Winchester

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

$6,000
3 Beds 3 Baths 73559660 MLS
This beautifully renovated home offers over 2,400 sq ft 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 baths, 3 generous bedrooms, and multiple living areas, there's plenty of room to spread out. The home also offers a two-car garage and ample storage. Set on almost half an acre 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: McCaul & Mounsif Real Estate Group LLC.

$5,500
3 Beds 3 Baths 73557783 MLS
Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite countertops, ample workspace, and a cozy breakfast nook with convenient access to the side yard. A separate home office and full bathroom on the first floor provide additional flexibility for working from home, guests, or everyday living.Upstairs, the spacious primary bedroom includes a walk-in closet and en-suite bathroom, along with an additional adjoining room that can serve as a nursery, private office, dressing room, or guest space. Two additional generously sized bedrooms, a full family bathroom, and a spacious landing with additional closet storage complete the second floor.The lower level offers an unheated bonus/family room with a decorative fireplace, laundry area, additional storage, and direct access to the two-car garage.Outside, enjoy a beautiful, spacious fenced backyard, perfect for relaxing, entertaining, and outdoor activities.Conveniently located near Middlesex Fells Reservation and all that Winchester has to offer, this home combines space, character, privacy, and convenience in a highly desirable residential setting.

111 Highland Ave, Winchester

Listing courtesy of Listing Agent: Michelle Li from Listing Office: Zhensight Realty LLC.

$1,549,000
3 Beds 3 Baths 73556633 MLS
Completely remodeled with exceptional custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!

50 Holland Street, Winchester

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

$1,749,000
3 Beds 4 Baths 73555777 MLS
Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

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

$849,000
3 Beds 2 Baths 73555218 MLS
Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.

$849,000
3 Beds 2 Baths 73553626 MLS
Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and effortless entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or a dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester Center commuter rail, and major routes, this home embodies the very best of Winchester living. No HOA fee.

15 Clark St Unit 15, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.

$4,200
3 Beds 2 Baths 73550305 MLS
Beautifully renovated single-family home on a quiet cul-de-sac in desirable Winchester. Situated on a spacious 9,500± sq. ft. lot, this move-in-ready home features newly finished hardwood floors throughout, an open-concept living and dining area, an updated kitchen with gas cooking, a cozy family room with a wood-burning fireplace, and a full bath on the main level. Upstairs offers three spacious bedrooms and a newly renovated full bath. Conveniently located near schools, parks, shopping, and major commuter routes. Tenant is responsible for all utilities, snow removal, and lawn maintenance. First month’s rent, one month’s security deposit, credit/background check, proof of income, and photo ID required.

22 Baldwin St, Winchester

Listing courtesy of Listing Agent: Qian Han from Listing Office: JW Real Estate Services, LLC.

$950,000
3 Beds 2 Baths 73549935 MLS
Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.

$650,000
3 Beds 3 Baths 73549877 MLS ['Winchester Green'] BLDG.
Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

247 Washington St Unit 11, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Coldwell Banker Realty - Lexington.

$1,075,000
3 Beds 3 Baths 73519082 MLS
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

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

$4,800
3 Beds 2 Baths 73507654 MLS
Move in date: Now. Tenant pays all utilities (gas, heat, electricity, cold/hot water and trash disposal). Lead Paint: Certified Treated. 2 off street parking. Central AC ,Pets negotiable. Laundry in the unit. 12-month lease minimum Move-in costs: First month's rent, one month's rent as a security deposit, Last month rent Welcome to 17 Russell Road, a well-maintained single-family home tucked away on a quiet one-way street in one of Winchester’s desirable family neighborhoods. Enter through a welcoming mudroom with radiant floor heat and bead board walls, leading into a bright main level featuring hardwood floors, a sun-filled living room with cozy bow window seating, and a functional kitchen with ample cabinet and counter space. Dining room sliders open to a private deck overlooking a fully fenced, tree-lined backyard — ideal for entertaining or outdoor play.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..

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