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3 Chesterford Terrace, Winchester
$1,325,000
3 Beds ⋅ 2 Baths ⋅ 73545054 MLS
Nestled at the end of a coveted cul-de-sac, 3 Chesterford Terrace presents a rare opportunity to own a timeless Winchester home on a picture-perfect 12,972 SQ FT flat lot. Designed by renowned Winchester architect Jerome Bailey Foster, this charming 3+ bed, 1.5-bath residence blends classic architectural character with an exceptional setting. Surrounded by mature landscaping & set on one of Winchester's most desirable streets, the home offers endless potential for today's buyer. Enjoy the convenience of being a short stroll to Lynch Elementary School & moments from Winchester's scenic Three Ponds area, where walking trails & outdoor recreation await. Whether you're looking to restore & enhance an architectural gem or create your dream home in an unbeatable location, this property offers a truly special combination of charm & opportunity. Rarely does a home with \setting & potential become available in Winchester. Estate Sale. Sold in as-is condition. Offers due @ noon on 7/14.

3 Chesterford Terrace, Winchester

Listing courtesy of Listing Agent: The Fenway Group from Listing Office: Compass.
6 Marchant Road, Winchester
$1,325,000
3 Beds ⋅ 3 Baths ⋅ 73473803 MLS
Updated / move in ready 3 bed, 2.5 bath home *Set on a generous 11K lot* in a fantastic Winchester location/ Lincoln Elementary close to town, schools, train & Boston. The first floor offers an ideal layout w gleaming hardwood floors, updated kitchen w/stainless steel appliances & island seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc & dining room. A 3 season sunroom in the rear provides bonus living space w/direct access to large back & side yards, perfect for outdoor enjoyment. The second floor features three spacious bedrooms, 2 new baths incl. a primary suite w/ bath. The partially finished basement offers flexible space for a playroom, office, gym, or media area. With a wonderful yard and convenient location, this home presents an excellent opportunity in a highly desirable neighborhood. Enjoy the cul-de-sac location & 1 car garage! Don't miss this move in ready home with plenty of room on the lot for expansion down the road!

6 Marchant Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
12 Hancock St, Winchester
$1,310,000
3 Beds ⋅ 2 Baths ⋅ 73508959 MLS
This beautifully maintained home blends timeless craftsmanship with thoughtful modern updates. Architectural details, including stunning stained-glass windows, add warmth and personality throughout, and pair beautifully with the updated kitchen and baths. Spacious rooms, oversized windows, 9-foot ceilings, and a desirable layout create an airy, expansive feeling that lives larger than the square footage. The primary bedroom features a soaring cathedral ceiling, skylights, and a cozy window seat. Two additional spacious bedrooms and a home office offer flexible space for today’s lifestyle, with the possibility to add a 2nd full bath. Step outside from the fireplaced family room to a level, fenced backyard and patio, ideal for relaxing & entertaining. Just 0.6 miles or less to Winchester’s top-rated schools, the train to Boston, the Fells’ trails & forests, and vibrant shops and cafés, this home delivers classic character paired with exceptional amenities and convenience.

12 Hancock St, Winchester

Listing courtesy of Listing Agent: Elena Langlois from Listing Office: Compass.
2 Eaton Ct, Winchester
$1,280,000
3 Beds ⋅ 2 Baths ⋅ 73522338 MLS
Classic Winchester Gambrel offering charm, space, and an ideal location close to town and the commuter rail. Tucked away on a quaint court shared with just one other home, this 3-bedroom, 2-bath property blends character with comfortable everyday living. The main level features an inviting fireplace living room, large dining room, full bath, beautiful kitchen with eating bar, and spacious family room with excellent potential for a playroom, media room, or au pair setup. The second level includes three bedrooms, an additional office/bonus room, and a second full bath. Additional highlights include basement laundry, 3-car parking, and garage storage. this property offers ample outdoor space for leisure and entertaining. This residence represents a unique opportunity to acquire a home of significance within a desirable Winchester location. A wonderful opportunity to enjoy Winchester living close to shops, restaurants, and commuting routes.

2 Eaton Ct, Winchester

Listing courtesy of Listing Agent: Robert Ellington from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
6 Alden Lane, Winchester
$1,275,000
3 Beds ⋅ 2 Baths ⋅ 73520993 MLS
Set in one of the area’s most beloved neighborhoods, this charming 3 bedroom home blends warmth, comfort, and opportunity on a gorgeous corner lot surrounded by mature landscaping. Inside, an easy flowing layout is filled with abundant natural light, creating bright and inviting living spaces perfect for both everyday living and entertaining. Hard to find first floor bedroom could work as a home office as well. Hardwood floors add timeless character throughout, while the beautiful sun room offers a peaceful retreat to relax and unwind. Step outside to a large deck overlooking the yard, an ideal setting for summer dining, morning coffee, or gathering with friends. Additional highlights include a one car garage, new roof, irrigation well and a full basement ready for your future ideas, whether it’s a playroom, gym, office, or expanded living space. A lovingly maintained home in a quiet, tree-lined neighborhood.

6 Alden Lane, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
11 Ridge Street, Winchester
$1,270,000
3 Beds ⋅ 2 Baths ⋅ 73498537 MLS
Discover this beautifully updated 3-bedroom, 2-bath single-story ranch offering 1,888 sf of stylish, comfortable living – perfect for first-time buyers or those looking to downsize! Primary bedroom includes an en-suite bathroom and spacious closet. Wood floors, vaulted ceilings, recessed lighting, and abundant natural light throughout. Updated kitchen boasts modern appliances, a pantry, and generous counter space. Custom built-ins include a full-wall bookcase and gas fireplace in the living room creating a stunning and warm living space and a dining room hutch. Newer roof and furnace. Fenced backyard provides a secure and private outdoor area. Sunny professionally landscaped yard features an expansive wrap-around deck and gazebo, a spacious storage shed and an additional shaded rear deck, offering peaceful outdoor living and entertaining spaces. Two driveways on either side offer ample off-street parking. Convenient location to shops and only steps to Wright-Locke Farm and Whipple Hill

11 Ridge Street, Winchester

Listing courtesy of Listing Agent: Yvonne Logan from Listing Office: Coldwell Banker Realty - Lexington.
87 Wendell Street, Winchester
$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.
12 Thornberry Road, Winchester
$1,240,000
3 Beds ⋅ 2 Baths ⋅ 73479658 MLS
Lovingly maintained and tastefully renovated, this spacious three bedroom, two bath ranch with 3 car garage will impress! This remodeled open concept home is set on an oversized 16k lot and features a beautiful kitchen with custom cabinetry & dining island ideal for both every day living and entertaining. The main level also offers an inviting living room with bay window & fireplace, dining room & access to three season porch and deck.This home includes three spacious bedrooms and an updated full bath on the main level. The finished lower level provides additional living space featuring a large family room w/fireplace & walls of windows overlooking yard, a home office, a full bathroom and a dedicated workshop. The expansive lot is stunning, offering peace and tranquility just moments from the town center. Enjoy the convenience of an attached garage plus a second oversized 2 car garage, a rare find in Winchester! Don't miss this gem close to Boston & all major routes, move right in!

12 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
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.
8-10 Oak St, Winchester
$1,200,000
5 Beds ⋅ 3 Baths ⋅ 73555245 MLS
Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

8-10 Oak St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
52 Middlesex Street Unit 52, Winchester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 73546076 MLS ⋅ ['50-52 Middlesex St Townhomes'] BLDG.
Newly renovated 4-bedroom, 3-bath townhome offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy new white oak hardwood floors, a stunning chef's kitchen with quartz countertops and full-height quartz backsplash, Bosch stainless steel appliances, and beautifully designed bathrooms with custom tile and premium Kohler fixtures. Additional upgrades include a new roof, new central A/C and heat, recessed lighting, and all-new systems throughout. Winchester is renowned for its award-winning schools, charming New England downtown filled with shops, restaurants, and cafés, easy commuter rail access to Boston, and convenient proximity to major highways—offering the perfect blend of suburban tranquility and city convenience.

52 Middlesex Street Unit 52, Winchester

Listing courtesy of Listing Agent: The North Star Group from Listing Office: Keller Williams Realty Evolution.
31 Mystic Ave Unit 31, Winchester
$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.
6 Hancock St, Winchester
$1,170,000
5 Beds ⋅ 2 Baths ⋅ 73510153 MLS
Classic turn-of-the-century Victorian filled with charm and character, ready for its next owner. 5 total bedrooms; 4 on the second floor and 1 on the 3rd floor, plus 3rd floor office. 1.5 baths, this well-maintained home awaits your finishing touches and features hardwood floors throughout, showcasing its timeless architectural details. Enjoy warm summer evenings on the inviting screened front porch. Recent exterior paint, roof and updated high-efficiency gas heating system ensures modern comfort.The large, fenced backyard is perfect for entertaining, play, or gardening, complemented by a detached oversized garage. Ideally located just a short distance to the 2,600-acre Middlesex Fells Reservation perfect for hiking, jogging and dog walking. Close to Winchester Center’s vibrant shops and restaurants, top-rated schools, and commuter rail to Boston. With easy access to Rt. 93, downtown Boston is just minutes away. A rare opportunity to own a classic Victorian in an exceptional location.

6 Hancock St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
52 Salem Street Unit 52, Winchester
$1,160,000
3 Beds ⋅ 3 Baths ⋅ 73549484 MLS
Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its own full bath. Second floor features 2 ample sized bedrooms, full bath and laundry. Step outside through the sliding glass doors to a newly installed stone patio and backyard—perfect for relaxing, entertaining, or outdoor dining. Additional highlights include two off-street parking spaces and thoughtful updates throughout. Ideally located just moments from the Winchester Center commuter rail station, vibrant downtown shops and restaurants, Winchester High School, and the brand-new Lynch Elementary School, this move-in ready home offers the perfect combination of style, space, and convenience.

52 Salem Street Unit 52, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
70 Grove St, Winchester
$1,160,000
3 Beds ⋅ 2 Baths ⋅ 73537575 MLS
Well-maintained brick Cape offering 1996 sq. ft. of comfortable living space and a flexible floor plan. The sought-after first-floor primary bedroom and full bath provide convenient one-level living, complemented by hardwood floors, a fireplaced living room, dining room, sunroom, and an inviting kitchen with exterior access to the deck. A vaulted family room adds valuable living space, while additional bedrooms upstairs accommodate family, guests, or home office needs. Situated on a beautiful level .30-acre lot with a paved driveway and attached garage, this home has been lovingly cared for over the years. Enjoy easy access to Winchester Center's shops, restaurants, parks, trails, and commuter rail. Just minutes from Boston and major routes, the location is ideal for commuters. Winchester is renowned for its top-rated schools, vibrant town center, and exceptional quality of life.

70 Grove St, Winchester

Listing courtesy of Listing Agent: Maija Sawyer from Listing Office: William Raveis R.E. & Home Services.
38 Robinhood Rd, Winchester
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 73537786 MLS
Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open dining area with direct access to the oversized screened porch—perfect for relaxing or entertaining. The eat-in kitchen provides access to the patio and backyard, ideal for summer cookouts. The top floor also features three bedrooms with hardwood floors, a full bath, and a half bath. Conveniently located with easy access to all that Winchester has to offer, this cherished home is not to be missed.

38 Robinhood Rd, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
104 Wendell Street, Winchester
$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.
38 Pickering St Unit A, Winchester
$1,082,000
3 Beds ⋅ 3 Baths ⋅ 73488929 MLS
Step into this beautifully maintained 2004 townhouse that has the feel of a single-family home, perfectly blending comfort, convenience, and modern living. The house features high ceilings, crown molding, hardwood floors and a spacious kitchen. Master bedroom includes a walk-in closet and en-suite bathroom with double vanity and jacuzzi. Finished basement provides a flex space for a cozy family/game room with a built-in home theater, perfect for creating memories. Additional highlights include freshly painted interior, 3-car parking, large fenced backyard and a whole house water filtration system. The home is within walking distance to the brand-new Lynch Elementary school, MBTA bus stop, daycares and is located within minutes to Winchester downtown making commuting and daily routines effortless. Enjoy peaceful mornings or evening walks just steps away at Horn Pond, offering scenic trails and a wonderful outdoor lifestyle. This is more than just a house—it’s a place to feel at home.

38 Pickering St Unit A, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
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.
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.
15 East Street, Winchester
$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.
62 Richardson St, Winchester
$1,060,000
5 Beds ⋅ 3 Baths ⋅ 73117876 MLS
Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/ shower stall. Finished family room in basement w/ beamed ceiling, carpet, & w/d hookups. Unit 2 located consists of two living levels. Complete w/ a sunny living room, 3 beds, & full bath w/ shower/tub. Spacious kitchen w/ dining area & electric range. W/d hookups & 1/2 bath in basement. Fantastic backyard complete w/ a patio & heated in-ground pool! 3 driveways & a 2-car garage! You'll love all that Winchester has to offer: award-winning schools, shopping and dining in Winchester Center, Middlesex Fells Reservation, Farmer's Market, Tri-Community Greenway, and easy access to downtown Boston.

62 Richardson St, Winchester

Listing courtesy of Listing Agent: Frank Ventresca from Listing Office: Strategy Street.
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.
46 Clark St, Winchester
$1,035,000
4 Beds ⋅ 2 Baths ⋅ 73547513 MLS
Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as well as a mudroom and a full bath. The fenced backyard is perfect for entertaining. Upstairs, four bedrooms each offer generous closet space. The lower level--with new half bath, new carpet, laundry and storage--is ideal for a media space or playroom. Newer roof, tankless water heater, and a new 200-amp electrical panel provide peace of mind. Close proximity to Horn Pond Reservation, trails, and parks, and easy access to Boston via rail and bus. A rare chance to own a fully updated home in a truly special neighborhood.

46 Clark St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
149 Horn Pond Brook Road, Winchester
$1,020,000
5 Beds ⋅ 2 Baths ⋅ 73478668 MLS
Picture-perfect Cape Cod single family home on a corner lot across the street from the brand new Lynch Elementary School. This special residence is much larger than it looks & has 4–5 spacious bedrooms across two levels & two full baths on each floor. Such space offers versatility with 2 beds on main level & 3 bedrooms on the upper floor. The sun-filled living room flows nicely to a charming eat-in kitchen. The partially finished lower level adds valuable bonus space for a home office, gym or family room & has direct access to yard. Great basement storage & whole house generator powered by propane. Minutes from Winchester Center & Horn Pond. Commuter friendly location, close to the Winchester Center train Station.

149 Horn Pond Brook Road, Winchester

Listing courtesy of Listing Agent: Nancy Ciampa McLaughlin from Listing Office: Redfin Corp..
150 Cambridge Street, Winchester
$990,000
3 Beds ⋅ 2 Baths ⋅ 73530959 MLS
Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for den, home office or playroom area. First floor half bath. Upstairs features 3 well proportioned bedrooms and a full bath, hardwood floors throughout, partially finished basement with bonus room, 2 car garage and ample driveway parking, sunny back yard. Freshly painted exterior

150 Cambridge Street, Winchester

Listing courtesy of Listing Agent: Diane Plunkett from Listing Office: Plunkett Properties.
339-341 Washington Street, Winchester
$980,000
5 Beds ⋅ 2 Baths ⋅ 73534223 MLS
Exceptional opportunity for investors, owner-occupants, or multigenerational living in this two-family home conveniently located near Winchester Center, restaurants, shopping, commuter rail, and major routes. The first floor has 2 bedrooms plus an office, while the second floor includes a third bedroom. Both units are filled with natural light and share nearly identical layouts with enclosed front porches, spacious front-to-back living and dining rooms, original built-in china cabinets, high ceilings, and timeless character throughout. The kitchens offer granite countertops, stainless steel appliances, dedicated pantries, and access to rear porches, while renovated bathrooms and freshly painted interiors add modern appeal. Additional highlights include a 2-car garage, 4 off-street parking spaces, hardwood floors throughout, basement storage, laundry, and an expansive private backyard.

339-341 Washington Street, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
9 Governors Avenue Unit 2, Winchester
$888,000
3 Beds ⋅ 2 Baths ⋅ 73509305 MLS
Perfectly positioned just moments from the charm and vibrancy of the town center, this inviting 3-bedroom, 1.5-bath condo offers a lifestyle as appealing as its location. Step inside to discover a bright, thoughtfully designed layout filled with generous living spaces and abundant natural light. Three bedrooms provide the versatility you need—whether for family, guests, or a home office. Enjoy everyday ease with in-unit laundry and private basement storage, while the enclosed front porch opens the door to endless possibilities—imagine a cozy reading nook, sun-drenched lounge, or your own personal retreat. Outside, a driveway with two off-street parking spaces adds convenience, and the shared backyard with patio sets the stage for relaxing afternoons or effortless entertaining. All this, just minutes from Winchester Center, top-rated schools, local shops, dining, and the commuter rail!

9 Governors Avenue Unit 2, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
63 Dunster Lane, Winchester
$825,000
2 Beds ⋅ 1 Baths ⋅ 73532111 MLS
Bring your vision and your tool box to 63 Dunster Lane! This 1910 bungalow is a 1208 square foot fixer-upper that sits on a 8300 square foot lot. If you're a savvy investor or a contractor/builder this is a great opportunity to completely renovate/rebuild in a highly desirable Winchester neighborhood.

63 Dunster Lane, Winchester

Listing courtesy of Listing Agent: John Ferolito from Listing Office: Keller Williams Realty.
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.

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