Refine Search
Map
Sort by
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.
36 Elmwood Ave Unit 2, Winchester
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 73452498 MLS ⋅ ['Allegro'] BLDG.
Welcome to unit # 2 at Allegro, an ELEVATOR building, built in 2021. Containing 11 units. This building is comfortable, quiet, and modern. Just set back far enough to be out of the traffic. Easy one-level living with an open concept, living room, dining room, and kitchen that all flow seamlessly together. The primary bedroom has its own ¾ bathroom with a full bathroom for the rest of the household/visitors. This unit is unique in that it comes with TWO PARKING SPACES in the heated garage and your own storage area. PLUS, this unit is one of only two units with the largest OUTDOOR brick PATIO with sliding glass door access from the living room. Comforting to be able to open your slider and be outside in a spacious, quiet area of your own. In unit laundry. Step out to the street and enjoy being minutes away from all that Winchester Center has to offer: restaurants, shops,a supermarket, even a hardware store,and the commuter rail to North Station. You will truly enjoy living at the Allegro

36 Elmwood Ave Unit 2, Winchester

Listing courtesy of Listing Agent: from Listing Office: Coldwell Banker Realty - Lexington.
415-417 Washington Street, Winchester
$1,200,000
5 Beds ⋅ 2 Baths ⋅ 73440354 MLS
This well-maintained two-family home offers desirable one-level living on each floor & is filled with/natural light throughout. Both units feature high ceilings, HW floors, replacement windows, & generous storage.The 1st floor unit includes 2 BR, an eat-in kitchen, full bath, & open-concept DR & LR w/ built-in china cabinet. The 2nd floor unit has been tastefully renovated, featuring a modern kitchen w/granite countertops, SS appliances, & peninsula w/seating.The updated bath & den add to the appeal, while the DR w/ built-in china cabinet opens to a spacious living room.This unit also offers 3 BR, a bonus office space, & the comfort of central AC. Additional updates include a newer roof, new siding, new gutters, & a new boiler for Unit 1. Enjoy a fenced-in yard w/a patio & side-by-side driveway parking conveniently located on a side street. Ideally located just 0.2 miles from the highly rated Muraco school, half mile from the Fells, & less than a mile from Winchester center.

415-417 Washington Street, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
162 Swanton Street Unit 162, Winchester
$1,199,000
3 Beds ⋅ 4 Baths ⋅ 73415198 MLS
NEW CONSTRUCTION!! Welcome to this meticulously crafted, modern townhouse END UNIT offering over 2,100 sq ft of thoughtfully designed living space. The open-concept main level features gorgeous mill work, gleaming hardwood floors, a cozy fireplace & sleek chef-inspired kitchen w/ stainless appliances, large center island & an adjacent mudroom w/ half bath perfect for today’s lifestyle. The 2nd floor includes 2 generous bedrooms & a stylish full bath, while the top level is dedicated to the luxurious primary suite w/ a spa-like en-suite bath & great custom closet space. The finished lower level provides flexible space ideal for a family room, home gym, or office, complete with a full bath. Enjoy the convenience of two off-street parking spaces with an EV charger & a location that’s a commuter’s dream just minutes to the train, I-93, Route 128, Logan Airport, & downtown Boston. This exceptional home is close to Winchester Center’s shops, schools, restaurants & all the town has to offer!

162 Swanton Street Unit 162, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
189 High Street, Winchester
$1,191,000
4 Beds ⋅ 3 Baths ⋅ 73451954 MLS
This classic Cape offers exceptional space, character, and room to make it your own. The first floor features a gracious front-to-back living room, formal dining room, and an inviting eat-in kitchen, all highlighted by hardwood floors, high ceilings, and a seamless circular layout ideal for everyday living. A charming breezeway connects directly to the one-car garage, adding easy functionality. Upstairs, you’ll find four comfortable bedrooms and a full bath. The finished lower level provides two additional rooms and a brand-new full bath - perfect for guests, a gym, or a home office. Situated on just under a half-acre lot, this home offers endless possibilities for future expansion. Ideally located 1/2 mile to one of Winchester's most sought after elementary school and minutes from the beloved Wright-Locke Farm. This is the perfect place to make your home!

189 High Street, Winchester

Listing courtesy of Listing Agent: from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
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.
59 Johnson Rd, Winchester
$1,165,000
3 Beds ⋅ 3 Baths ⋅ 73415423 MLS
Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and patio, ideal for entertaining. Stylish kitchen offers brand-new stainless steel appliances, white cabinetry, and tiled floors. Gleaming hardwoods flow throughout the main level with a serene primary suite, 2 generous bedrooms (one convertible to 2), and full bath. LL includes an office, cozy family room, half bath, and laundry. Features professionally landscaped grounds with irrigation, private backyard oasis, and central vac system. 9mi to Boston, enjoy the best of both worlds: close to town center, Fells, parks, dining, shopping, commuter rail, Wright-Locke Farm, and Winchester Swim &Tennis Club.

59 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Angela Y. Zhang from Listing Office: Greatland Real Estate LLC.
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.
136 Sylvester Ave, Winchester
$1,156,000
3 Beds ⋅ 2 Baths ⋅ 73472376 MLS
A quintessential New England Colonial offers timeless charm and a welcome presence, introduced by an inviting front porch that sets the tone for what lies within. The gracious foyer opens to a sunlit living room with warm wood floors and classic details, creating an inviting space for easy living. Pocket doors lead seamlessly into the dining room, where a fireplace and a beautifully curved bow window add architectural character and a sense of tradition. The kitchen connects effortlessly to cascading decks and a picturesque backyard that abuts conservation land with Horn Pond Brook, providing a peaceful and natural backdrop. Upstairs offers comfortable bedrooms and a full bath arranged for privacy and ease. The walk-up attic features a finished room and a separate foyer -awaiting heat for expansion potential. A walk-out basement offers additional flexibility for storage or future use. Outdoor living is enhanced by multiple decks and porch spaces designed for enjoying the serene setting

136 Sylvester Ave, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
50 Lincoln Street, Winchester
$1,150,000
4 Beds ⋅ 2 Baths ⋅ 73442848 MLS
This beautiful Victorian home, featuring an inviting front porch, stunning period detail including wainscoting, original tin ceilings, custom built-ins, and three fireplaces is not to be missed! Maple hardwood floors flow through an open-concept layout to a spacious eat-in kitchen with a lovely exposed brick wall. The second floor has three bedrooms and a full bath plus a sweet window seat and an additional built-in. The third floor offers a fourth bedroom and a versatile bonus—ideal for a family room, office or studio. Freshly painted throughout and updated baths, newer windows, and electrical system enhance modern comfort and complement the original charm. Outside, enjoy a large brick patio and a detached garage with upstairs storage. This is a highly desirable neighborhood, conveniently located near excellent schools, the quaint town center, and commuter rail to Boston. Scenic Middlesex Fells has acres of forested trails to explore. Also nearby aer Leonard Park and the TC bike path.

50 Lincoln Street, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
89 Main St, Winchester
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 73427429 MLS
Welcome to this charming Cape on a spacious corner lot in Winchester. The main level offers hardwood floors, a front-to-back living room with fireplace and built-ins, a dining room with corner hutch, and a half bath. The kitchen features granite counters, stainless steel appliances, abundant cabinetry, and a breakfast island that opens to the cathedral-ceiling family room. A side entry with mudroom keeps things organized, and a sun-filled three-season porch adds flexible living space. Upstairs you’ll find three bedrooms with hardwood floors, including a primary with walk-in closet, plus a full bath. The finished lower level provides extra living area with a full bath and direct walk-out access to the fenced backyard. Conveniently located near Lincoln School, a 7 minute walk to Winchester Center, and the Wedgemere commuter rail station.

89 Main St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
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.
16 Ridge Street, Winchester
$1,090,000
3 Beds ⋅ 3 Baths ⋅ 73442463 MLS
27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning fireplace, a dining area w/access to deck, three spacious bedrooms w 2 full baths including the primary. The lower level offers a spacious family room w fireplace plus office or potential 4th bedroom w/ full walk out/ slider to yard plus mud room, 1/2 bath & direct access to heated 2 car garage & laundry. An expansive deck and patio overlook the sunny private yard. Don't miss this great opportunity to customize and create your dream home in Winchester! Enjoy our great community offering top rated schools, 2 train stations, restaurants shops, & more with easy access to Boston, Arlington/ Cambridge!!

16 Ridge 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.
26 N Gateway, Winchester
$1,070,000
2 Beds ⋅ 1 Baths ⋅ 73340651 MLS
LOCATION, LOCATION, LOCATION This has it.....Current building is a 2 bedroom ranch with lr,dr,k.needing TLC..Great potential for a Complete rebuild and/or restoration All offers must be on attached OFFER TO PURCHASE form and prior to entering property the attached " Hold Harmless" agreement must be signed. All offers must include the OTP, Proof of funds and/or preapproval and copy of $1,000.00 deposit check...An additional $50,000.00 will be required with P&S.Property is being sold :".AS IS".Sellers make no warranties or representations of any kind...Buyers to do their own due diligences'

26 N Gateway, Winchester

Listing courtesy of Listing Agent: Robert Dell from Listing Office: Homes Unlimited.
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.
7 Trinity Rd, Winchester
$1,055,000
3 Beds ⋅ 3 Baths ⋅ 73462880 MLS
Welcome to 7 Trinity Road, a warm & inviting split level home tucked away on a quiet side street in sought after Winchester. From the moment you step inside, the home feels welcoming & comfortable, offering 3 bed & 2.5 baths with a layout that easily supports both everyday living & entertaining. Your foyer provides a convenient place to arrive home, with direct access to the attached garage. The main level features a bright living room with a wood burning fireplace, perfect for cozy evenings as the holidays approach, along with a dining area & a kitchen that opens to an enclosed sunroom overlooking the backyard, an ideal space to relax or gather with friends. Fresh paint throughout enhances the light & inviting feel. The lower level offers a comfortable family room with a second wood burning fireplace, a private office, laundry area, & a 3/4 bath. Set on a generous 0.38 acre lot... Steps away from the Winchester Country Club and nearby Ball field, playground & Wright Lock Farm.

7 Trinity Rd, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.
36 Elmwood Ave Unit 4, Winchester
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 73423932 MLS ⋅ ['Allegro'] BLDG.
Welcome to this stunning 2-bedroom, 2-bathroom condo, built in 2021 and being offered by its original owner. Perfectly situated in the center of Winchester, this home is designed for effortless one-level living and offers the best of modern convenience and timeless style with an open and airy floor plan with oversized windows which fill the space with natural light. The gourmet kitchen flows seamlessly into the living and dining areas, which opens directly to a private outdoor balcony. Both bedrooms are generously sized, each with its own full bathroom, including a spacious primary suite for comfort and privacy. For added convenience, the condo includes in-unit laundry, extra storage in the garage area, an underground parking space, and elevator access within the building. Step outside and enjoy being just moments away from Winchester's charming shops, restaurants, and newly renovated commuter rail, making this the perfect blend of convenience and luxury.

36 Elmwood Ave Unit 4, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
41 Englewood Rd, Winchester
$1,038,500
3 Beds ⋅ 2 Baths ⋅ 73438045 MLS
Discover this charming raised ranch set on an oversized lot in one of Winchester’s most desirable neighborhoods. Enjoy the convenience of an attached garage and a wide driveway with ample parking for multiple vehicles. Step outside to a spacious, fenced-in yard and deck—perfect for gatherings, play, or simply relaxing. Inside, the sun-filled living room features gleaming hardwood floors and a cozy fireplace, opening seamlessly to the dining room and kitchen. Three comfortable bedrooms and a full bath complete the main level. The lower level offers a welcoming family room with a second fireplace and a dedicated storage room for added functionality. Ideally located just minutes from downtown Winchester, the brand-new commuter rail station, and with easy access to Boston, this home blends comfort, convenience, and charm. Loved by one family for many years—now it’s ready to become yours!

41 Englewood Rd, Winchester

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.
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.
353-355 Washington Street, Winchester
$1,025,000
6 Beds ⋅ 2 Baths ⋅ 73470713 MLS
Investor alert! About one mile from an array of shops, restaurants, & the commuter rail to Boston, this Winchester multi-family is a rare opportunity waiting to be redesigned! Held by the same family for many years, the property offers substantial square footage & endless potential for those ready to roll up their sleeves. While it requires significant renovation, the reward will be well worth the effort. The classic wood exterior provides timeless character while an addition off the upper level offers valuable extra living space. Each apartment includes fully applianced kitchens & in-unit laundry. Explore the possibilities: convert to a single-family home, pursue a condo conversion, or live in one unit while generating rental income from the other. The main-level unit may be shown at open house only; the upper unit is available for private showings. An exceptional chance to invest in Winchester, known for its top-rated schools, charming neighborhoods, and unbeatable lifestyle!

353-355 Washington Street, Winchester

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

320 Washington St, Winchester

Listing courtesy of Listing Agent: John D. Conroy from Listing Office: East Coast Realty, Inc..
9 Sylvester Court, Winchester
$1,015,000
4 Beds ⋅ 2 Baths ⋅ 73444775 MLS
Tucked away on a private cul-de-sac in one of Winchester’s most desirable neighborhoods, this adorable 4-bedroom, 1.5-bath single-family cape style home with full rear dormer offers a rare opportunity to renovate, expand, and build equity in a prime location. Set in the brand new **Lynch School District**, this property is ideal for homeowners, investors, or builders looking to customize and add value. The home features a traditional floor plan with sun-filled rooms, hardwood floors with great outdoor space on a generously sized lot. It is the perfect canvas to customize and add your personal touch! Large bedrooms, bright sunny rooms, large newer windows, gleaming hardwood floors and so much curb appeal. Located just minutes from Winchester Center, the commuter rail, schools, and major routes. Don’t miss your chance to own in a top-tier neighborhood with strong potential to build equity. Bring your vision and make 9 Sylvester Court your own!

9 Sylvester Court, Winchester

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.