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$270,000
1 Beds ⋅ 1 Baths ⋅ 73439236 MLS
Immaculate, studio condominium within the desirable Parkview Condominiums in Winchester. The large private balcony overlooks a beautiful wildlife pond, and the grounds are meticulously landscaped. The kitchen features tile flooring, updated granite countertops, and a breakfast bar. The Condominium amenities include: in-ground swimming pool, barbecue area, large parking area with plenty of overnight guest parking, on-site laundry rooms, on-site management, and private storage units. The low condo fee includes: heat, hot water, trash services, electricity, and air conditioning. Winchester is a quaint and charming New England town, only 8 miles north of Boston. This amazing location is only two blocks from Winchester center, shops, restaurants, parks, and the commuter rail. Don’t miss this exceptional opportunity!

200 Swanton St Unit 636, Winchester

Listing courtesy of Listing Agent: Michael Masci from Listing Office: North Atlantic Realty Group.
$2,400
1 Beds ⋅ 1 Baths ⋅ 73472950 MLS
Completly remodeled 5years ago (only one tenant since). This generously sized first floor unit within a two-family home is located a convenient side street. Take advantage of the beautiful bright turn-key space. Off-street parking for 1 car, hardwood floors throughout, stained glass window in the living room highlights the homes original detail and close proximiity to Winchester center, major routes and all Winchester has to offer.

43 Harvard St Unit 1, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$4,200
3 Beds ⋅ 2 Baths ⋅ 73467846 MLS
Move into a well-maintained 3-bedroom, 1.5-bathroom single-family home in quiet Winchester neighborhood. The house featuring central AC, in-home laundry, and garage parking. The finished lower level provides extra living space. Enjoy your own lovely, private backyard. You're within walking distance to McClennen Park, Wright-Locke Farm, and the scenic Whipple Hill conservation area—boasting 120 acres of protected land and miles of walking trails.* Pictures was taken before current family move in

12 James St, Winchester

Listing courtesy of Listing Agent: Giang Nguyen from Listing Office: Harmony Hill Realty LLC.
$1,500
1 Baths ⋅ 73476975 MLS
ALL utilities included! Enjoy serene pond views from this sun-filled 4th-floor studio at Parkview Condominiums in Winchester. Step onto your private balcony and take in the peaceful scenery of swans, ducks, and koi fish gliding across the water — a tranquil setting that feels like your own private retreat. Inside, the thoughtfully designed layout offers a bright and spacious living area, a separate kitchen space, and a full bath, along with additional storage in the building. This professionally managed community features elevator access, on-site maintenance, laundry with newer machines, an outdoor pool, BBQ area, ample resident parking, and convenient guest parking. With heat, hot water, electricity, and central air all included in the rent, this is an exceptional value. No pets and no smoking. Schedule your showing today — this one won’t last.

200 Swanton Unit 408, Winchester

Listing courtesy of Listing Agent: Stefanos Galouzis from Listing Office: Coldwell Banker Realty - Waltham.
$1,427,000
3 Beds ⋅ 4 Baths ⋅ 73473597 MLS ⋅ ['The Ledges'] BLDG.
CANCELED OPEN HOUSE - offer accepted. Ready to not worry about shoveling or taking care of a yard?  Come have carefree living at the Ledges in Winchester.  Delight in a small, manageable courtyard that you can view from your eat-in kitchen table.  Enjoy a 2-car garage, laundry and a gorgeous primary suite on the main living level. Living room has gas fireplace, built-ins, access to nice deck and is open to the dining area. PLUS 2 bedrooms, 2 more full baths, office, loft and family room on other levels. Plenty of options for family and guests.  Current owner replaced LR/DR/Primary carpet with lovely hardwood floors!! This unit is in the section of the Ledges that looks out over Sucker Brook Conservation Area where the seasonal beauty and birds never end!  Think you'll feel cramped if you downsize?  Not here!  The soaring ceiling in the living room (with skylight) and primary bedroom bring grandeur and plenty of natural light. Fantastic community w/ pool, clubhouse and tennis court.

7 Wainwright Road Unit 15, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,580,000
3 Beds ⋅ 3 Baths ⋅ 73471034 MLS
Welcome to 10 Trinity Road, an inviting split-level home located on a low-traffic cul-de-sac in a desirable Winchester neighborhood. The main level features an open-concept kitchen that flows into the family and dining areas, ideal for everyday living and entertaining. Three bedrooms and two full baths complete this level, including a primary bedroom with an ensuite bath. The lower level provides flexible space with walk-out access to the backyard, perfect for a playroom, office, or guest area, plus a half bath and laundry. A heated attached two-car garage adds year-round convenience. With natural light throughout and a functional layout close to schools, town amenities, and commuter routes, this home offers a fantastic opportunity to enjoy Winchester living.

10 Trinity Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$1,380,000
4 Beds ⋅ 4 Baths ⋅ 73470827 MLS
Thoughtfully designed newer construction townhome offering the feel and privacy of a single family home. This 4 bed, 3.5 bath home features a sought-after 1st floor primary suite, sun-filled interiors, and dramatic ceiling height that enhances the home’s bright, airy feel. Hardwood floors and a gas fireplaced family room flow to sliders leading to a private deck, patio, and fenced yard. The kitchen is well-appointed with quartz countertops and high-end appliances, ideal for everyday living and entertaining. The second floor offers two spacious bedrooms, a full bath, laundry, & a versatile loft, perfect for a home office, lounge, or play space, creating an open yet highly functional layout. The finished lower level includes a private suite with full bath & walk-in closet, plus additional storage to keep everyday living organized. Ideally located close to downtown shops, Packer Tennis Courts, Lynch, McCall & WHS, commuter rail, Tri-Community Bike Path, and easy access to Routes 93 & 95.

36 Middlesex St Unit 36, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$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.
$1,830,000
4 Beds ⋅ 2 Baths ⋅ 73461235 MLS
Welcome to this beautifully maintained Colonial in a highly desirable family neighborhood directly across from a scenic conservation area. The main level offers a bright, seamless flow with a living room, dining room, updated kitchen, full bath, family room, and a sunroom opening to the backyard. Upstairs features three comfortable bedrooms and a full bath, while the third-floor bonus room offers excellent flexibility for a fourth bedroom, office, or studio. The finished lower level adds even more living space with a laundry room, storage room, and a versatile area ideal for a playroom, media room, or home gym. Outside, enjoy a private, fully fenced yard with an inground pool, perfect for entertaining. A rare combination of space, comfort, and lifestyle.

35 Glen Grn, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$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.
$2,380,000
5 Beds ⋅ 6 Baths ⋅ 73466648 MLS
Move-in ready home on Winchester’s highly desirable West Side, set on a quiet street with a bright, inviting layout. The first floor offers a sun-filled primary suite, a kitchen with granite countertops and adjacent flexible space ideal for casual dining or family room use, plus a formal dining room, living room, and half bath. Upstairs features a second primary suite, a guest en-suite, two additional bedrooms, a full bath, and laundry. The fully finished basement provides versatile space perfect for a home gym, media room, playroom, or other lifestyle needs. Outside, enjoy a spacious stone patio surrounded by mature trees for exceptional privacy. Ideally located within walking distance to the newer Vinson-Owen Elementary School and just minutes to downtown Winchester’s restaurants, shops, coffee spots, and the commuter rail to North Station, with easy highway access and only 7 miles to Boston.

8 Buckman Dr, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$1,800,000
3 Beds ⋅ 4 Baths ⋅ 73466421 MLS
This beautiful, move-in-ready Cape has been thoughtfully renovated from top to bottom. Oversized front walks lead to a charming front porch and into a welcoming foyer that opens to a sun-filled open-concept layout with fire-placed family room, dining area, and kitchen—ideal for everyday living and entertaining. A bright bonus room off the kitchen with wall-to-wall windows and heat/AC offers year-round enjoyment. The first-floor primary suite features hardwood floors, double closets, and a spa-like bath with double vanity and glass-enclosed tiled shower. The second floor features two front-to-back bedrooms, each with a private tiled bath. The finished lower level provides direct access to the 2-car garage, mudroom and flexible space—perfect for a home gym, office, media room, hang-out area or if wanted, a potential ADU with some vision. A stunning home offering comfort, style, and versatility. Open House Sat & Sun 11:30–1.

61 Westland Ave, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$258,000
1 Baths ⋅ 73455836 MLS ⋅ ['The Parkview'] BLDG.
Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include an in-ground swimming pool, barbecue area, large parking area with additional overnight guest parking, on-site laundry, on-site management, and private storage units. Ideally located near downtown Winchester, the commuter rail, and major highways.

200 Swanton Street Unit 234, Winchester

Listing courtesy of Listing Agent: Devin Caglayan from Listing Office: All County Select Property Management.
$945,000
3 Beds ⋅ 2 Baths ⋅ 73453920 MLS
This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to entertain. Enjoy morning coffee or evening relaxation on the unheated 3-season porch overlooking the yard, with seasonal views of the Boston skyline. The lower level features high ceilings with a heating and cooling unit already installed, offering great potential for 200+ sqft of future finished space. Additional highlights include a one-car garage under and a convenient layout with timeless appeal. Nestled beside conservation land, this home provides a peaceful, natural setting where you can enjoy watching birds and local wildlife right from the yard. Make this one yours for 2026!

139 High Street, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$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.
$750,000
2 Beds ⋅ 2 Baths ⋅ 73466541 MLS ⋅ ['Wedgewood Place'] BLDG.
Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry hook-ups, garage parking, elevator and access to an in-ground pool. Enjoy the landscaped waterfront grounds or take a short walk to Winchester Center, coffee shops, restaurants, and the commuter rail. Move-in ready and perfectly located! Sold in As-Is condition.

666 Main St Unit 312, Winchester

Listing courtesy of Listing Agent: Walace Nogueira from Listing Office: Fellsway Realty, LLC.
$1,335,000
4 Beds ⋅ 3 Baths ⋅ 73466016 MLS
Welcome to 112 Wendell Street, a bright and inviting 4-bed, 3-bath colonial on a desirable corner lot with a flexible floor plan. The sun-filled kitchen features abundant cabinetry, stainless steel appliances, & quartz countertops, opening to a spacious dining area and living room with hardwood floors throughout. The main level includes a large bedroom & full bath, while three additional bedrooms & full bath complete the second floor. An expansive finished lower level with a full bath, laundry room and walk-out access to the yard offers exceptional versatility for recreation, home office space and storage. Outside, enjoy a generous yard and patio ideal for entertaining, featuring an EV charging station & smart irrigation system. Conveniently located near the newly updated McDonald Field with playground and tennis courts, parks, downtown Winchester shops and dining, commuter options, the new Lynch Elementary School, this home offers comfort, space, and flexibility for todays lifestyle

112 Wendell St, Winchester

Listing courtesy of Listing Agent: Steve McKenna & The Home Advantage Team from Listing Office: Gibson Sotheby's International Realty.
$2,150,000
4 Beds ⋅ 5 Baths ⋅ 73463596 MLS
Sophisticated updates and a bright, open layout define this beautifully appointed Winchester Fells home. Generous living spaces and thoughtful design enhance both everyday comfort and entertaining. The gourmet kitchen flows seamlessly into inviting gathering areas, while French doors and multiple outdoor access points create an effortless indoor–outdoor connection. Two dedicated home offices offer outstanding flexibility, and four full baths provide ease and convenience throughout. The front-to-back primary suite serves as a serene retreat with spacious closets and a private ensuite bath. Surrounded by mature landscaping that ensures beauty and privacy, this home combines timeless charm with a versatile floor plan—an exceptional blend of space, style, and location next to the scenic trails and lakes of the Fells.

7 Appalachian Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$340,000
1 Beds ⋅ 1 Baths ⋅ 73463453 MLS ⋅ ['Parkview Condominiums'] BLDG.
Welcome to easy, carefree living in this one-bedroom, one-bathroom condo located in a well-managed Winchester community offering amenities and beautifully maintained grounds. This inviting unit features a private sixth-floor porch with a lovely view of the landscaped grounds, providing a peaceful spot to relax and unwind. The condo fee includes heat, hot water, and electricity, offering value and predictable monthly expenses. The unit also includes one deeded parking space, along with guest parking for visitors. Residents enjoy access to a swimming pool and park-like grounds featuring tranquil ponds, charming bridges, and a pergola, all professionally maintained for year-round enjoyment. Convenient laundry facilities are located within the building, adding to the ease of everyday living. With a functional layout and strong bones, this home offers excellent potential for updates and equity growth, all within a desirable Winchester location!

200 Swanton St Unit 630, Winchester

Listing courtesy of Listing Agent: Angela Hirtle from Listing Office: Lyv Realty.
$3,150
2 Beds ⋅ 3 Baths ⋅ 73470597 MLS
Townhouse - Absolutely Gorgeous @ Winchester Crossing - Enjoy the Charm and Privacy of Your Own Private Entrance - Heated 2-Car Garage - Bright and Spacious - Open Floor Plan - Living Room w/Balcony and Gas Fireplace, 2 BDs, 2.5 BAs, Granite Countertops, Stainless Steel Appliances, Maple Cabinets, Eat-in Kitchen, Gleaming Hardwood Floors, High Ceilings, Lots of Storage and Large Closets. This Townhouse is Private and is set Back from Street - Convenient Location - Minutes to the new Lynch School - Two Commuter Train Stations and Winchester Center - easy access to Routes 93 and 128. Enjoy Winchester and all its Amenities.

400 Cross Unit 403, Winchester

Listing courtesy of Listing Agent: Lucille Murray from Listing Office: Gibson Sotheby's International Realty.
$3,700
3 Beds ⋅ 3 Baths ⋅ 73457614 MLS
Welcome to 11 Elmwood, just steps from Winchester Center. You’ll love being able to stroll to your morning coffee, grab dinner with friends, browse the local shops, or catch the commuter rail without ever needing your car. Inside, this home offers three levels of comfortable living space plus a finished basement that works beautifully as a quiet office, a cozy hangout spot, or simply extra storage. The main floor features beautiful wood floors and an easy, open layout that makes everyday living feel effortless. The kitchen includes double ovens, granite counters, and a wine fridge, and opens directly to a private deck — perfect for warm evenings or enjoying your morning coffee outdoors. Upstairs, the primary bedroom offers a generous walk-in closet and in-unit laundry. The third floor holds two additional bedrooms filled with natural light and flexible enough to adapt to your lifestyle. One off-street parking space is included. Available January 1st.

11 Elmwood Avenue Unit 11, Winchester

Listing courtesy of Listing Agent: from Listing Office: Leading Edge Real Estate.
$3,300
2 Beds ⋅ 2 Baths ⋅ 73448953 MLS
Welcome to 7 Conant Road! This unit offers a spacious open floor plan with 1,338 square feet, featuring two bedrooms and two full bathrooms, including a roomy primary suite. Enjoy open concept living with nice flow from the kitchen to the living room & dining area. Updated & move-in ready, the bedrooms are large, complete with generous closet space. This rental showcases modern charm with an in-unit washer and dryer for your ease. Enjoy the perks of the building, like an inground swimming pool, elevator, and gym. Parking is a breeze with an assigned spot and ample extra guest parking. This updated unit is ready for you to move in and make it your own — come check it out!

7 Conant Road Unit 21, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$5,500
5 Beds ⋅ 5 Baths ⋅ 73436408 MLS
A rare find! Newer construction rental home/ attached single family/ featuring 5 bedrooms & 4 baths over 4 finished levels, close to Winchester center and Muraco Elementary School. This great home features large spacious rooms, a sunny granite kitchen w/ maple cabinets, hardwood floors/ open concept w/ family room & a gas fireplace w/ sliders that lead to a spacious deck overlooking a fenced in yard. High ceilings throughout, formal dining room, primary suite on second floor w/fplc & private bath, plus two additional bedrooms & second floor laundry w/ machines included. The third level features two bedrooms w/ carpet and full bath. Lower level family room/ gym/ rec room/ Central AC, plenty of parking ~call for a private showing!

378 Washington Street Unit 378, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,641,000
5 Beds ⋅ 2 Baths ⋅ 73251461 MLS
Picture perfect cape style home across from the Lynch Elementary School. This beautiful home on a corner lot checks all the boxes with 4/5 bedrooms on 2 floors and 2 full baths. Extra bonus space in lower level for home office or gym. Huge, beautiful yard that is perfect for outdoor recreation. Pretty eat in kitchen has direct entry to deck. This custom built home has been lovingly maintained and updated.

149 Horn Pond Brook Rd, Winchester

Listing courtesy of Listing Agent: Nancy Ciampa McLaughlin from Listing Office: Redfin Corp..
$1,290,000
6 Beds ⋅ 4 Baths ⋅ 73461412 MLS
Rare Duplex style residence just minutes from the train, downtown shops & restaurants, Rt. 93 & 128, school, MacDonald Field and only 7 miles to Boston! Unit 46 features a modern kitchen with granite counter tops, a Wolfe gas stove, ample cabinet space and a three quarter bath and laundry is nearby. The dining room with a built-in china cabinet seamlessly flows into the living room. Upstairs you'll find three bedrooms, an office/den and full bath. There are two spacious, unfinished, unheated rooms on the third level offering potential for additional living space. Recent updates to #46 include a gas fired boiler, hot water heater & electric panel. Unit 48 has the same number of rooms and bedrooms and there is a half bath with laundry off the eat-in kitchen and one unfinished, unheated room on the third level. Both units include front porch's. The rear yard is spacious and fenced in with parking for three cars and room to expand. Make an appointment to see this home soon!

46-48 Swanton Street, Winchester

Listing courtesy of Listing Agent: Leeman & Gately from Listing Office: Compass.
$1,965,000
4 Beds ⋅ 4 Baths ⋅ 73458603 MLS
Welcome to 46 Church Street. This spacious, beautifully maintained, Paul Whitney built home is just outside the heart of Winchester center with easy access to the commuter rail, schools, restaurants, and shopping. Offering flexible living areas and abundant room throughout, the residence features four bedrooms, three and a half bathrooms, two dedicated home offices, and a generously sized bonus room that can be adapted to serve a variety of purposes – including conversion to an additional primary suite. An additional guest suite on the lower level provides even more versatility. This property also includes an attached two-car garage, owned solar panels that can help lower electric costs, and an inviting outdoor space with a private backyard and patio. With its thoughtful layout and extensive living area, this home can accommodate a wide range of lifestyle needs. Don’t miss this opportunity to enjoy downtown living!

46 Church St, Winchester

Listing courtesy of Listing Agent: Joan Francis Sullivan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$6,900
3 Beds ⋅ 3 Baths ⋅ 73457875 MLS
No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim and white culinary grade kitchen equipped with Sub Zero refrigerator and top of the line Blue Star chef's gas range. 23' x 16' Living room overlooks 33' x 13.5 ' Enormous private outdoor veranda with marine grade mahogany flooring, cedar millwork, gas fireplace, ceiling fans, amazing outdoor kitchen with gas commercial grill tied in to domestic gas line. Unlike any executive, luxury rental in town. Short distance to Town Center, shops, village cafes, restaurants, and Commuter line Train stations. First class construction with no expense spared, in a modern & wonderfully finished residence.

846 Main Street Unit 3, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
$955,225
4 Beds ⋅ 2 Baths ⋅ 73454629 MLS
Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest exposure, eat-in kitchen, half bath, and access to the garage. Four bedrooms and full bath upstairs. Above grade finished basement with full windows walks out onto a natural backyard. Desirable west end location on Thornberry Hill. Vinson-Owen Elementary School and Winchester Swim & Tennis Club in the neighborhood. Close proximity to Winchester Center, surrounding towns, shopping, dining, area businesses, events and culture, parks, trails, and conservation lands. Convenient to Downtown Boston.

41 Squire Road, Winchester

Listing courtesy of Listing Agent: from Listing Office: Charlesgate Realty Group, llc.
$7,000
4 Beds ⋅ 4 Baths ⋅ 73425800 MLS
No Broker Fee! Beautifully updated 4-bedroom single-family home in a top Winchester neighborhood. Over 3,200 sq ft of space with multiple living areas, a flexible layout, and a private yard—ideal for families, professionals, or anyone needing room to spread out. The main level offers an open kitchen with stainless appliances and granite counters, dining area, and two bright living spaces with access to a large private deck. Upstairs features a primary suite with spa bath plus two additional bedrooms with a shared Jack-and-Jill bath. A fully finished lower level provides exceptional flexibility for an au pair suite, guest space, home office, or gym, with direct walk-out access to the yard. Convenient to Winchester Center, schools, the Fells, and commuter routes to Boston and Cambridge.Additional features: in-unit laundry, central air, 1-car garage + driveway parking, landscaped yard, landlord covers water/sewer and landscaping.

29 Wainwright Rd, Winchester

Listing courtesy of Listing Agent: Helen Stefan from Listing Office: Gibson Sotheby's International Realty.
$8,500
4 Beds ⋅ 4 Baths ⋅ 73464986 MLS
OH January 10 11-12PM! This exceptional ranch-style home offers the ease of one-floor living with a private, serene feel while remaining close to everyday conveniences. Pets are welcome, making this a rare and flexible rental opportunity. The home features a gracious entry leading into a spacious, light-filled family room with soaring skylights, an open layout ideal for living and entertaining, and elegant crown molding throughout. The updated primary bath offers a modern, spa-like retreat, and the home is further enhanced by updated systems for added comfort and efficiency. Additional lower-level living space provides flexible options for a media room, home office, guest area, or bonus space. A standout feature is the oversized 4-car garage, perfect for vehicle storage, a workshop, home gym, or extra storage. Ideally located highly sought after public schools, restaurants, Whole Foods, and a variety of shopping and lifestyle amenities. Equipped with 2 EV charging ports & new W/D.

23 Olde Village Drive, Winchester

Listing courtesy of Listing Agent: Ngoc Anh Goldstein from Listing Office: Leading Edge Real Estate.

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