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24 Hinds Road, Winchester
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 73529658 MLS
Welcome to the home that has it all! Where thoughtful upgrades meet effortless living. This tastefully updated open-concept home is designed for both quiet nights and grand entertaining. Enjoy one-level living with a stunning sun drenched family room, adjacent dining & renovated kitchen with direct outdoor access, ideal for hosting!The home features 4 generously sized bedrooms, and 3 full baths including the primary suite which is a true private retreat w/lavish oversized bath & private home office. The walk-out lower level features additional living space featuring a family/ game/media space w/ a full bathroom. Outside, you have your own backyard oasis! - enjoy the gazebo overlooking the in-ground pool which was fully transformed w/ a new saltwater system, heater, resurfacing & coping or gather around the fire pit patio for fun summer nights. Oversized garage & plenty of parking. Updated systems, renovated kitchen, and updated baths. Move right into your forever home in Winchester!

24 Hinds Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
18 Grayson Rd, Winchester
$1,738,000
3 Beds ⋅ 3 Baths ⋅ 73526595 MLS
OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with clawfoot tub. From the driveway, enter a newly renovated basement space including mudroom and ample flex space for exercise room or media/play space. Recent updates include a new furnace, water heater and expanded driveway to accommodate additional parking spaces. 1 car garage. Central air, insulated windows and doors, and a programmable thermostat to reduce annual energy costs. Fabulous location, steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds and tennis courts

18 Grayson Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
307 Cross Street, Winchester
$1,730,000
5 Beds ⋅ 5 Baths ⋅ 73508927 MLS
Thoughtfully reimagined & expanded in 2019, this sophisticated colonial offers 5-6 bedrooms & 5 baths with a beautiful open floor plan - perfect for a growing family or multi-generational living. A striking granite kitchen with crisp white cabinetry, premium stainless appliances & oversized island flows seamlessly into the dining area - ideal for everyday living & refined entertaining. A fireplaced living room, office, bedroom & full bath complete this main level. Upstairs, two spacious bedrooms & a family bath complement a serene primary suite with spa-like bath amenities. The 3rd level offers an additional primary suite with luxurious soaking tub & flexible bonus space to use how you choose. A finished walk-out lower level with wet bar, bath, family room, exercise & play space adds further appeal. Acoustic windows enhance comfort throughout. Enjoy the one car garage, fully fenced yard, patio & deck - just moments to parks, town center, major routes, & Winchester's top-rated schools.

307 Cross Street, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
94 Johnson Road, Winchester
$1,715,000
4 Beds ⋅ 3 Baths ⋅ 73525571 MLS
Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated lighting, SS appliances, & new hardwood flooring. A gorgeous primary suite, inviting screened porch, cozy gas fireplace, & functional mudroom add warmth & everyday convenience. All 3 bathrooms were tastefully refreshed in 2024 w/ new showers, vanities, fixtures, & tile. Additional improvements include a new roof, updated exterior siding, finished basement, refinished hardwood floors, freshly painted interior, custom closet systems, new washer/dryer, updated front entry tile, & extensive landscaping w/a new front walkway. Just steps from award winning VO elementary school and Wright Locke Farm.

94 Johnson Road, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
41 Sunset Road, Winchester
$1,700,000
3 Beds ⋅ 2 Baths ⋅ 73520906 MLS
Completely gut renovated in 2023, this stunning home overlooks conservation & offers serene views, privacy & lives like-new construction. The home was thoughtfully redesigned & opened up to feature dramatic soaring vaulted ceilings & an open floor plan, flooded with natural light. The designer kitchen is the centerpiece of the home, showcasing custom cabinetry, paneled appliances, oversized island w/gorgeous natural quartzite countertops, a farmers sink & beautiful details. The wood burning fireplace & wide-plank white oak flooring add warmth. Every space was carefully curated & hand picked, with no detail overlooked. The sunny lower level features a large family room w/ fireplace, full bath, custom laundry room & mudroom. Enjoy a spacious yard & patio perfect for outdoor entertaining & summer dinner parties. Located in a friendly, vibrant neighborhood w/ easy access to town & Boston, this turnkey home offers peaceful surroundings with unmatched convenience. Direct entry 2 car garage.

41 Sunset Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
29 Pilgrim Dr, Winchester
$1,700,000
5 Beds ⋅ 3 Baths ⋅ 73491480 MLS
Beautifully updated home offers generous living spaces & a seamless, open flow. Sun-filled living &dining areas feature hardwood floors, elegant detailing, & a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, & large island that opens to the dining area, which flows into the family room with direct access outdoors - ideal for yard access & entertaining. French doors between the kitchen, dining, & family room help to create a quieter, more private setting for the bedroom & formal living areas. The primary suite provides a private retreat with a full bath, while three additional bedrooms & full bath complete this level. A finished walk-out lower level adds versatility with a fireplace playroom, 5th bedroom, full bath, & laundry - great for guests or multi-generational living. Landscaped grounds & inviting outdoor areas, complemented by an attached garage & ample parking

29 Pilgrim Dr, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
114 Johnson Rd, Winchester
$1,700,000
3 Beds ⋅ 3 Baths ⋅ 73478721 MLS
Welcome Home to this gracious Colonial set on beautifully manicured grounds in one of Winchester’s most sought-after neighborhoods, known for its vibrant community & top-rated schools. An oversized updated kitchen w/ Corian countertops, double ovens & abundant cabinetry anchors the home, opening to an elegant dining room & inviting formal living room. Lovely hardwood floors thruout add warmth & timeless charm. A spectacular four-season sunroom w/ sliders leads to an expansive deck spanning the rear of the home—perfect for gatherings or peaceful mornings. The impressive great room features a dramatic stone fireplace. First floor includes full bath & laundry. Upstairs offers a spacious primary suite w/double closets & spa-like bath w/soaking tub & separate shower, plus 2 bedrooms, full bath & enormous family room w/spiral staircase. Lower level includes playroom, workshop & private office w/ exterior entry. Tandem 2-car garage & 2 driveways -2nd driveway in back. OH Sun 2-4PM SOLD “as-is

114 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Rosemary Kelleher from Listing Office: LAER Realty Partners.
12 Cox Rd, Winchester
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 73511596 MLS
Join me Saturday May 23rd 12-2pm for the 1st Open House at this amazing new price! Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining and leads to a mud room, laundry, and home office . Completing the first floor is half bath off kitchen, a dining room and a front to back, fireplaced, living room with a peaceful screened in porch that creates a serene escape. An expansive deck that overlooks this magnificent property. Upstairs features a beautiful, new, primary en suite with custom walk- in closet. An additional 3 spacious bedrooms and a new full bath complete the second floor. Lower level includes a playroom, a fireplaced den and extensive storage. Close proximity to Vinson-Owen School, Winchester Swin and Tennis Club and Wright Locke Farm, as well as conservation and many walking trails.

12 Cox Rd, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.
10 Farrow Street, Winchester
$1,660,000
4 Beds ⋅ 4 Baths ⋅ 73538441 MLS
Winchester Single Family Home with Attached Garage. Completely rebuilt in 2019, 4 Bedrooms + 2 Home Offices & 3.5 Bathrooms across 2,750+ SF! Two "WFH Offices" with Door & Window for privacy. Open-Concept Kitchen: Quartz Island/Countertops & Stainless Steel Appliances. Induction cooking & Hood Venting. Open-Concept Flows into the Connected Dining Room & Sundrenched Living Room with Wood Burning Pellet Stove! Charming New England feature provides efficient winter heating bills! Glass Sliding Doors bring you Outside to a Large Deck with custom Motorized Awning. Multiple Zones: Forced Central Air + Heating. Mudroom & Storage! Thoughtful design: First Floor Bedroom Suite, 1BR/1BA. Upstairs 3 Large Bedrooms & Laundry Room. Finished Top Level Offers "Future" Expansion? The Unfinished Attic offers Epic Storage! The BACKYARD: Wowie a Tree House! Swing, Slide, Climbing Wall & 2 Sheds. Prime Location: Quiet street, walking distance to the new Lynch Elementary + Middle school + High school.

10 Farrow Street, Winchester

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.
11 Carriage Lane, Winchester
$1,655,000
4 Beds ⋅ 3 Baths ⋅ 73537920 MLS
15K LOT!! Move right into this beautifully updated 4 BR 3 BA open concept home w/stunning rear addition/primary bedroom suite! This impeccably maintained, nicely updated home has a bright & airy open layout w/ abundant natural light streaming through oversized windows. The main living area flows seamlessly from the spacious living room w/beautiful fireplace into the dining room & kitchen. The recently renovated kitchen includes high end appliances, a center island w/ seating & offers clear views of the back yard. Direct access through slider to oversized deck, patio & huge fenced yard with gorgeous perennials. The main floor bedroom wing offers 3 spacious BR's & 2 baths incl the 2 room primary w/office, spa like bath & walk in closet. LL offers add'l BR suite w/ full BA or family room, laundry & storage. Enjoy hardwood floors, central A/C & spacious 2-car garage. This home is perfect for family enjoyment or hosting large gatherings. Located in a vibrant neighborhood near the swim club

11 Carriage Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
5 Willowdale Rd, Winchester
$1,649,900
3 Beds ⋅ 2 Baths ⋅ 73572791 MLS
Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

5 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.
10 Bonad Road, Winchester
$1,620,000
4 Beds ⋅ 3 Baths ⋅ 73530345 MLS
Welcome home to this sun-filled, south-facing 4-bed Colonial in a beloved Winchester neighborhood. Hardwood floors guide you from the gracious foyer into a spacious, fireplaced living room ideal for gatherings. The airy formal dining room flows seamlessly onto a private back deck overlooking a professionally landscaped, fully fenced yard—perfect for al fresco dining & entertaining. The updated chef's kitchen features stainless appliances & a generous island for everyday living. Upstairs, find 4 spacious bedrooms & a redone full bath boasting marble counters & custom tiled shower. The finished lower level provides exceptional flexibility w/ mudroom, full bath & ample flex space for a family room, gym & play area. Outside features a detached 1-car garage & 4-car driveway. Freshly painted inside & out. Fabulous location, blocks from Muraco Elementary, parks, playgrounds, the Fells & commuter routes. Move right in!

10 Bonad Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
38 Salem Street Unit 38, Winchester
$1,610,000
5 Beds ⋅ 4 Baths ⋅ 73513154 MLS
A rare opportunity to enjoy easy, yet refined living in Winchester, this well-maintained newer construction home offers 4-5 bedrooms and 3 ½ baths with a thoughtfully designed open floor plan. The main level features a spacious living area, eat-in kitchen with granite countertops, stainless steel appliances and pantry, along with a ½ bath and practical mudroom for everyday ease. Upstairs, generously proportioned bedrooms provide comfort and flexibility across two levels. The finished lower level with laundry adds valuable living space. Outside, an oversized paver driveway, two-car attached garage and inviting patio overlook a pleasant and private backyard setting. Ideally located just moments to the town center commuter rail, local shops and dining, and nearby schools, including brand new Lynch Elementary School. Move-in ready and offering exceptional value in a sought-after location.

38 Salem Street Unit 38, Winchester

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

6 Oakland Circle, Winchester

Listing courtesy of Listing Agent: Seeme Moreira from Listing Office: Coldwell Banker Realty - Lexington.
17 Cranston Rd, Winchester
$1,560,000
4 Beds ⋅ 3 Baths ⋅ 73480220 MLS
Expanded Cape blends timeless charm with thoughtful updates, offering inviting living spaces designed for comfort and connection. A fireplaced living room with hardwood floors and French doors sets a warm tone, flowing into an elegant dining area accented by custom built-ins and refined detailing. The kitchen serves as the heart of the home, featuring stone countertops, stainless appliances, and a generous island that opens to a sunny dining area with direct access to outdoor living—ideal for everyday enjoyment and entertaining. The main-level primary suite, along with a versatile family room or optional 5th bedroom, provides flexibility for a variety of living needs. Upstairs, 3 additional bedrooms offer comfortable retreats with excellent closet space and natural light. A finished lower level extends the living area with adaptable space and walk-out access to the garage. Outdoor spaces include a welcoming porch, deck, & patio, creating a peaceful setting for gatherings & relaxation.

17 Cranston Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
7 Wainwright Road Unit 107, Winchester
$1,515,000
3 Beds ⋅ 3 Baths ⋅ 73500873 MLS ⋅ ['The Ledges'] BLDG.
Move right into this spacious, light-filled townhouse at The Ledges! This upscale condominium community right outside Winchester center offers the ease of low maintenance living with the feel of a single family home & with the added bonus of a private club w/swimming pool and tennis court! This sought after layout offers a grand FIRST FLOOR PRIMARY bedroom & bath suite. Easy access main floor w/ direct entry from garage features a flowing, casual layout w/ beautiful family room w/ fireplace & vaulted ceilings leading to deck, a spacious dining area, great kitchen with sunny breakfast area, laundry & half bath. Second floor offers a spacious bedroom, loft/office, sitting/ tv room/ or guest room & full bath. The finished walk out lower level includes a generously sized family/ game room, space for additional bedroom, bath & storage! Conveniently located w/ easy access to Winchester center, Whole foods market, major highways & many great restaurants and shops. Only 7 miles from Boston!

7 Wainwright Road Unit 107, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
14 Rangeley Rdg, Winchester
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 73538612 MLS
Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless steel appliances, bedroom/office, bathroom with shower, & mudroom with storage. Hardwood floors extend throughout most of the first floor. Upstairs offers two bedrooms & full bath, including primary bedroom with skylight, large walk-in closet. Lower level provides valuable bonus space ideal for home office, gym, or playroom, plus laundry area & storage. Conveniently located near schools, shopping, restaurants, local amenities, train, parks, trails & outdoor recreation - this home offers a neighborhood setting with easy access to everything the area has to offer. A must see!

14 Rangeley Rdg, Winchester

Listing courtesy of Listing Agent: Peter Rooney from Listing Office: Compass.
28 Emerson Road, Winchester
$1,475,000
3 Beds ⋅ 2 Baths ⋅ 73485803 MLS
Set on a picturesque corner lot in Winchester’s coveted West Side near the Ambrose School, this beautifully preserved mid-century modern home is defined by clean lines, a thoughtful layout, and so many meaningful updates throughout. The main level features a sun-filled, fireplaced living room and a formal dining room with built-ins that flow to an inviting kitchen with stainless-steel appliances. The family room serves as the home’s architectural focal point, distinguished by a cathedral ceiling, expansive picture windows, and a sliding glass door. Two bedrooms and a full bath round out this floor. The lower level adds versatility with a bedroom currently styled as a den, highlighted by a bay window, fireplace, and closet. A spacious exercise room with laundry and storage is complemented by a tastefully renovated porcelain bathroom and direct garage access. Outdoors, landscaped grounds frame a wraparound patio, creating a private setting for enjoyment throughout the seasons.

28 Emerson Road, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
7-9 Ridge St, Winchester
$1,460,000
5 Beds ⋅ 5 Baths ⋅ 73527738 MLS
Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds w/primary suite, office, 2.5 baths, living room, dining room, family room with built-in shelving, eat-in kitchen. Unit 2 2 beds, 1.5 baths, living room, dining room, kitchen, lower level family room. Each unit bodes hardwood floors, in-unit laundry, dedicated basements with high ceilings, driveways, yards with patios. This special home offers flexibility, strong roots & the opportunity to become part of a beloved community. Located in sought after Vinson Owen School within Winchester's top rated school system. Minutes to Winchester Center, 2 MBTA stations direct to Boston & dining!

7-9 Ridge St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
34 Robinhood Road, Winchester
$1,450,000
4 Beds ⋅ 3 Baths ⋅ 73486878 MLS
This spacious four bedroom Colonial is located in the desirable westside neighborhood and Ambrose school. The first level has a fully applianced kitchen followed by a oversized dining room. There is a wood burning fireplace in the spacious living room. A family room is off the kitchen and also an office and half-bath completes this level. The second level has four very large bedrooms. The main bedroom has a walk-in closet and bath. A second bathroom on this level.. Pull down stairs to the attic in the hallway. the lower level has a finished room currently used as a bedroom but has multi uses. Direct access to the 2-car garage. The heated Gunite pool was installed by the current owners along with the enclosed fencing. Home sited on a large level lot. Great location near Whole Foods and Mahoney's. Short ride to the center of town. Desirable Vinson Owen School

34 Robinhood Road, Winchester

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

65 High Street, Winchester

Listing courtesy of Listing Agent: Anna Jung from Listing Office: K Stadium Realty INC.
15 Englewood Road, Winchester
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 73480343 MLS
Cleverly reimagined for modern living, this energy-efficient Craftsman bungalow is ideally located in Winchester with close proximity to the natural beauty of the Middlesex Fells and the shops, dining and commuter rail of the town center. Thoughtfully expanded and renovated, the home features newer systems, windows and roof, among too many other updates to list. A functional mudroom with custom storage welcomes you inside, where the living room flows seamlessly into an exquisite chef’s kitchen with premium appliances, dual sinks and a dining room overlooking the landscaped, fully fenced yard. A spacious bedroom and full bath complete this level. Upstairs offers three additional bedrooms, two full baths and laundry, highlighted by a generous primary suite with walk-in closet and spa-like bath, complete with soaking tub and extra large shower. Owned solar panels, EV charging, a one-car garage, and a versatile lower level with bonus room complete this exceptional offering.

15 Englewood Road, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
205 Washington St., Winchester
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 73503540 MLS
This charming home abounds in style and character. It is Steps to downtown Winchester, where you can enjoy a variety of fine restaurants, easy commute to Boston & be able to walk to all the public schools & St. Mary's .Beautiful natural wood trim & hdwd floors throughout, grace this home. A spacious & sunny kitchen w/ center island, great for entertaining w/ a built-in desk. Large pantry for storage. Lots of cabinets, and stainless steel appliances. The dining room showcases a built-in display china cabinet. Formal living room with a gas f.p. and french doors leading to an informal family room. A wrap around screened- in porch which will expand your lifestyle in the summer, overlooking a front yard with beautiful perennials. Upstairs: 3 bedrooms plus a small office space w/built-ins. Spacious tile bathroom with soaking tub, shower and double sinks. Parking for 3-4 cars. 4th B/R on 3rd floor. EV charger, .Full basement w/sink.

205 Washington St., Winchester

Listing courtesy of Listing Agent: Jayne Zeamer from Listing Office: Coldwell Banker Realty - Boston.
71 Sargent Road, Winchester
$1,399,000
3 Beds ⋅ 4 Baths ⋅ 73501230 MLS
This bright and airy home unfolds into nearly 3,000 sq ft of beautifully designed living space, ideally set in a quiet, established Winchester neighborhood. Cherry cabinet kitchen with stainless steel appliances and skylight and a spacious family room with wet bar, The lowest level great room features a stunning floor-to-ceiling stone-faced gas fireplace with expansive western views. Two home offices and an exercise area offer flexibility for today’s lifestyle. Multiple rooms lead to a fabulous 1133 sq ft decking system. Additional highlights include a 4-zone irrigation system, solar panels, newer heat pumps, and mini splits for heat and central air. Convenient to the Middlesex Fells Reservation with miles of trails for hiking, biking, and outdoor recreation. Enjoy easy access to the Wedgemere Station commuter train. A perfect blend of suburban tranquility, natural surroundings, and commuter convenience, a short distance to Winchester Center shops, dining, and community amenities.

71 Sargent Road, Winchester

Listing courtesy of Listing Agent: Bob Bittelari from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
303 Washington Street, Winchester
$1,367,500
6 Beds ⋅ 2 Baths ⋅ 73526417 MLS
Pleased to present this meticulously maintained and nicely updated two family home in the heart of Winchester! Each spacious unit is one level & features seven rooms including 3 large bedrooms, living room w fplc, dining room w/wainscoting, sunroom, kitchen & updated baths. The generously sized flowing rooms are highlighted by high ceilings, oversized windows, beautiful original woodwork and timeless architectural details; seamlessly blended with thoughtful updates throughout. This home presents an exceptional opportunity for investors, owner occupants w/ an income unit or for multi generational living. Enjoy the private landscaped back yard shaded by mature trees, perfect for relaxing or outdoor gatherings. Ideally located close to town, schools, shops, restaurants, commuter rail, and all Winchester has to offer. The special property combines character space and convenience all in one of the areas most desirable locations, a rare opportunity not to be missed!

303 Washington Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
15 Thornberry Rd, Winchester
$1,360,000
4 Beds ⋅ 3 Baths ⋅ 73529811 MLS
Located on a level corner lot in the desirable Vinson Owen School district and nearby Winchester Swim & Tennis Club, this ranch-style home offers abundant space and a flexible floor plan. The main level features three bedrooms, a full bath, hardwood floors, and a fireplace living room that flows into the dining area and kitchen. A heated sunroom/mudroom with skylights and exposed beams connects to the kitchen, garage, driveway, and backyard deck. A standout feature is the impressive two-story addition with a private entrance, first-floor sitting area, and second-floor bedroom suite with cathedral ceilings, abundant natural light, small kitchenette, and a full bath. The finished lower level has a full bath and two flexible rooms ideal for a family room, office, or gym. Complete with an attached garage, central AC, large deck, and professional landscaping with irrigation, this home offers exceptional space and flexibility in one of Winchester's most sought-after neighborhoods.

15 Thornberry Rd, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
11 Williams Cir, Winchester
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 73554139 MLS
Classic center-entrance Colonial set on a cul-de-sac with a wonderful sense of flow and everyday function. The main level offers formal living and dining rooms, a spacious front-to-back fireplaced family room with first-floor laundry and half bath, plus a bright kitchen with island, dining area, and direct access to the deck. Upstairs, the primary suite includes a walk-in closet and private bath, complemented by three additional bedrooms and a full bath. A two-car under garage connects to the unfinished basement, offering excellent storage and future possibilities. Central air, gas heat, hardwood floors, and a level lot complete this inviting home.

11 Williams Cir, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
7 Wainwright Road Unit 30, Winchester
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 73513982 MLS ⋅ ['The Ledges'] BLDG.
This three bedroom condo in Winchester offers 2025 kitchen and bath updates with a thoughtfully designed, expansive layout across multiple levels. Hardwood floors span the first level with a den and open living and dining area ideal for everyday living and entertaining. The second floor features a generous primary suite with walk-in glass shower and stackable laundry, plus an additional bedroom and full bath. The lower level adds a bedroom, full bath, and office, providing flexible space for guests or work from home. New front windows in 2025 enhance natural light. Enjoy treetop views from the private deck, perfect for watching the sunset. Set within a beautifully landscaped community surrounded by lush greenery, this home blends space, comfort, and modern updates in Winchester.

7 Wainwright Road Unit 30, Winchester

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

1 Orient Street, Winchester

Listing courtesy of Listing Agent: Julie Gibson from Listing Office: Gibson Sotheby's International Realty.
40 Pickering St, Winchester
$1,330,000
4 Beds ⋅ 3 Baths ⋅ 73484617 MLS
This charming home retains period details while delivering flexible modern living. Through the glass-enclosed front porch, the first floor offers an entry stair hall, formal living room, a bedroom or home office with full bath and separate entrance, kid's homework room/drop zone, and - the star of the show - a sun-drenched open plan kitchen/family room with fireplace, massive island, and plenty of space for entertaining. Upstairs, there are three more bedrooms, a full bath and a half-bath, plus laundry and a sitting/play room. However you decide to use the 2400+sf, there's plenty of it. The roof, siding, water line and many windows were new when the sellers bought in 2017. Since then, they have installed new wiring, plumbing, heating and air conditioning. They re-did the kitchen and bathrooms. The floors are refinished, paint refreshed, and insulation upgraded. Outside, the sunny corner lot is partially fenced. Come take a look!

40 Pickering St, Winchester

Listing courtesy of Listing Agent: Timothy Haynes from Listing Office: Keller Williams Realty Signature Properties.

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