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6 Wyman Court Unit 6, Winchester
$1,379,000
3 Beds ⋅ 5 Baths ⋅ 73458347 MLS ⋅ ['4-6 Wyman Court'] BLDG.
Another Tree Top Group masterpiece –Welcome to 6 Wyman Court! New full gut renovation townhome with 2,722 sq. ft., 3 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center island, opening to bright living & dining areas w/ custom cabinetry & hardwood floors. The 2nd level offers a serene en-suite primary w/ private deck, a spacious 2nd bedroom, full bathroom, 2nd floor laundry, & includes a versatile loft ideal for office or lounge. The 3rd floor hosts a 2nd en-suite primary w/ double closets. Finished lower level boasts a home office/flex space, full bathroom, family room w/ built-ins, & wet bar! Additional highlights include a 1-car garage, an extra off-street parking space, & EV charger readiness. Luxury, location & design—your perfect Winchester townhome awaits!

6 Wyman Court Unit 6, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
32 Oak St., Winchester
$1,375,000
4 Beds ⋅ 3 Baths ⋅ 73459273 MLS
Prime location near town center! This renovated 4-bed, 3-bath home is nestled in a private setting, walking distance to Winchester center and commuter rail to downtown Boston, nearby Middlesex Fells Reservation, High School, shops, and restaurants. Recent upgrades include new basement vinyl flooring (2025), stunning kitchen and second-floor bath renovation (2021), and new Bosch boiler and hot water heater (2018) and more. The sunlit kitchen dazzles with quartz countertops, stainless steel appliances, custom cabinetry, and a generous island. A warm living room with a wood-burning fireplace, elegant dining room with access to sunroom, 1st floor bedroom, and full bath complete the main level. Upstairs offers three inviting bedrooms and a beautifully updated bath with a double-sink vanity. Walk-out lower level provides entertaining family room, a flexible bonus room for office/guest, wet bar, full bath and laundry. Outside enjoy a spacious flat backyard, patio, and electric car charger.

32 Oak St., Winchester

Listing courtesy of Listing Agent: Julia and Joanne (Guozhen) Team from Listing Office: Keller Williams Realty-Merrimack.
19 Cox Road, Winchester
$1,375,000
3 Beds ⋅ 2 Baths ⋅ 73363545 MLS
Charming three-bedroom ranch on spectacular 20,000sf west side lot abutting conservation! The updated granite kitchen with newer appliances leads to the open concept dining room overlooking the beautiful, private yard. The spacious living room features a fplc & bay window; a sunroom, 3 spacious bedrooms, 1 bath & garage complete the main level; the lower level offers a large rec/ family room w fplc, bath and laundry/ storage. This home would be wonderful to enjoy as-is or renovate/ expand/ rebuild & create your dream home! Don't miss this opportunity!

19 Cox Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
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.
4 Sargent Rd, Winchester
$1,355,000
4 Beds ⋅ 3 Baths ⋅ 73441705 MLS
Welcome to the Winchester Highlands! This inviting 4-bedroom, 2.5-bath home blends comfort and character in the desirable Lincoln School District—just a short distance to downtown Winchester, the commuter rail, I-93, and the Middlesex Fells. A sun-filled living room with custom stone fireplace flows seamlessly into the dining area, perfect for gatherings. The kitchen offers a vented gas range, light maple cabinetry, and a peninsula with views of the private backyard oasis featuring a stone patio and tree lined property. Enjoy easy single-level living with four bedrooms and 1.5 baths on the main floor, including a spa-inspired bath with walk-in shower and whirlpool tub not to mention hardwood floors throughout. The finished lower level offers a family room, home gym, full bath, laundry, and direct garage access. Thoughtfully maintained with many homeowner improvements, this home combines warmth, functionality, and timeless appeal in one of Winchester’s most sought-after neighborhoods.

4 Sargent Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
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.
95 Irving Street Unit 95, Winchester
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 73459193 MLS
Beautiful newer-construction home in a wonderful Muraco school location! This meticulous 4-bed, 3.5-bath property offers modern living with an inviting open-concept layout & high ceilings spanning across 4 finished levels with attached garage! The stunning chef’s kitchen features high-end appliances, large island & abundant storage, flowing seamlessly into the dining area & living room with a gas fireplace, perfect for everyday living and entertaining. A slider leads out to the expansive fenced yard w/ patio for outdoor enjoyment. The second level offers 3 spacious BR’s& 2 BA including the primary suite w/ spa-like bath & great closet space. The finished 3rd floor.provides a fantastic bonus/media room, home office, fitness space, or guest suite w/ a full bath!.. the finished LL adds more family space! Central air & thoughtful finishes throughout make this home truly turn-key.Enjoy easy access to schools, town center & commuter rail all nearby!—don’t miss this exceptional opportunity

95 Irving Street Unit 95, Winchester

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

3 Chesterford Terrace, Winchester

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

6 Marchant Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
12 Canterbury Road, Winchester
$1,325,000
3 Beds ⋅ 3 Baths ⋅ 73450862 MLS
Tucked along a quiet side street in the sought-after Ambrose School district, this spacious ranch offers comfort, convenience, and endless possibilities. With nearly 2,000 square feet of living space, the home features seven rooms, including a large living room w/ fireplace that anchors the easy, natural flow. Three spacious bedrooms and two and a half full baths make one-level living effortless, and the property is handicapped accessible for added comfort and flexibility. A full, unfinished basement provides additional potential for expansion or storage. Set on a flat, 10,000-square-foot lot, this property is ideal for those seeking single-floor living, as well as those eager to reimagine, renovate, and expand without losing yard space. Don’t miss this wonderful opportunity to add your own touches to a warm home with close proximity to the commuter rail into Boston, charming town center, shops, parks, restaurants, Mystic Lake, and more.

12 Canterbury Road, Winchester

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

12 Hancock St, Winchester

Listing courtesy of Listing Agent: Elena Langlois from Listing Office: Compass.
7 Thornberry Road, Winchester
$1,310,000
5 Beds ⋅ 2 Baths ⋅ 73417760 MLS
The land alone is worth this price!! 15Ksf lot & a newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept kitchen w/ high end appliances & quartz counters w/ island seating, adjacent dining w/ soaring ceilings, step down the living room w/fplc & walls of glass overlooking large lot w/ patio & fire pit. 4 spacious BR's plus finished LL perfect family/playroom, plus BR #5 or office. Enjoy the convenience of a 2-car garage and additional driveway parking, with ready connections for EV's. Located just minutes from top-rated schools, parks, shopping, & a variety of dining options, this home offers the best of suburban living w/ easy access to Boston~A tremendous value!

7 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
46-48 Swanton Street, Winchester
$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.
40 Sargent Road, Winchester
$1,290,000
3 Beds ⋅ 2 Baths ⋅ 73437800 MLS
Nestled in Winchester’s coveted Lincoln School district, this classic Colonial offers timeless charm, modern comfort, and unbeatable curb appeal! Situated on a beautiful corner lot, the property features a detached 2-car garage and welcoming exterior that sets the tone for what awaits inside. The main level boasts a warm and inviting living room with a wood-burning fireplace, perfect for cozy evenings. A flexible office or playroom offers additional space for today’s lifestyle needs, while the formal dining room provides a wonderful setting for gatherings and special occasions. The kitchen boasts easy access to the patio and yard, ideal for outdoor entertaining and everyday enjoyment. Upstairs, you’ll find 3 bedrooms, including a spacious primary suite with dual closets and a private walk-out area — which could be the perfect retreat for your morning coffee. Available for the first time in over 40 years, this cherished home is ready to be passed down from one loving owner to the next.

40 Sargent Road, Winchester

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

2 Eaton Ct, Winchester

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

6 Alden Lane, Winchester

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

11 Ridge Street, Winchester

Listing courtesy of Listing Agent: Yvonne Logan from Listing Office: Coldwell Banker Realty - Lexington.
104 Church Street, Winchester
$1,255,000
4 Beds ⋅ 2 Baths ⋅ 73435935 MLS
This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded updated kitchen & family area open to gorgeous deck overlooking the beacon hill style yard featuring a quaint patio/ entertaining space. Formal living & dining w three-season porch perfect for relaxing. Upstairs, the primary suite feels like a retreat with skylights, cathedral ceiling, loft, and private balcony. Three bedrooms and a study on 2 share a bath, with flexible space on the third floor featuring a loft and two rooms. Outside, the deck and patio create a private oasis with tranquil views. 2 separate garages. Conveniently located in the Flats location near Wedgemere Station and Winchester’s vibrant downtown, this home delivers space, character & Ambrose elementary just up the hill!

104 Church Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
87 Wendell Street, Winchester
$1,250,000
4 Beds ⋅ 2 Baths ⋅ 73500869 MLS
Beautifully renovated 4BR home situated across from McDonald field & playground offering a desirable floor plan ideal for entertaining & easy living. Enter into a lovely sun porch/ mudroom leading to the main level featuring a bright and airy open floor plan w/gorgeous wide plank hickory flooring, many windows, high ceilings & stunning renovated kitchen showcasing high-end appliances & a spacious center island. The versatile 1st floor also offers a large bedroom suite w/ full bath providing the perfect option for a primary suite, guest suite or family room. Upstairs includes 3 additional bedrooms & full renovated hall bath. Tucked away on the third floor, a peaceful retreat/ ideal home office space. An oversized yard w/ new trex deck is ideal for play, bbq's and offers potential space for an ADU! Enjoy a vibrant cheerful neighborhood & a turnkey property w/ many recent thoughtful updates. Close to town & train to Boston! Don't miss this great home in the NEW Lynch Elementary district!

87 Wendell Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
35 Harvard Street, Winchester
$1,250,000
5 Beds ⋅ 2 Baths ⋅ 73434284 MLS
Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well as 3 sunlit bedrooms which include a primary bedroom with private ensuite bath. The walk up third floor is appointed with 2 additional bedrooms and ample storage space. Additional highlights include central air, storage shed, sprinkler system and fully fenced in yard. The home sits with convenient access to major highways, Winchester center and the commuter rail.

35 Harvard Street, Winchester

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

12 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
10 Winchester Pl Unit 301, Winchester
$1,225,000
2 Beds ⋅ 2 Baths ⋅ 73437251 MLS ⋅ ['Winchester Place'] BLDG.
Elegant and expansive condo with soaring ceilings in the sought-after Winchester Place, just moments from the vibrant town center, boutique shops, idyllic Mill Pond, newly improved commuter rail, and so much more. Offering over 1,500 square feet of refined living, this home showcases gleaming wood floors, sun-filled open living room with a dedicated dining areas for hosting, and a beautifully designed kitchen with built-in cabinets, abundant counter space, and direct access to a private deck. The spacious primary suite features a full bath with a soaking tub, complemented by a second well-appointed bedroom. Enjoy the convenience of in-unit laundry, two deeded garage spaces, your own basement storage room, and modern amenities like central air and a cozy fireplace, adding to the timeless appeal of this exceptional home.

10 Winchester Pl Unit 301, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
40 Englewood Rd, Winchester
$1,218,000
4 Beds ⋅ 2 Baths ⋅ 73497917 MLS
Nestled on a quiet, tree-lined street near the Fells, this charming Cape with classic dormers blends timeless character with thoughtful updates. The sun-filled kitchen features granite countertops and overlooks a peaceful backyard, while the breezeway between the one-car garage and kitchen offers an ideal mudroom or expansion potential. A beautifully updated first-floor bath includes radiant heated floors and a spacious glass-enclosed shower. A flexible first-floor bedroom or office adds versatility, and the fireplaced living and dining rooms provide inviting spaces for everyday living and entertaining. Custom built-ins enhance both charm and function. Upstairs are two generously sized front-to-back bedrooms and a full bath with radiant heat. The lower level offers a finished fourth bedroom with separate entrance, laundry, and a bonus room ideal for a gym, playroom, or office. Convenient to the Fells, the Muraco School, shops, restaurants, and major commuter routes.

40 Englewood Rd, Winchester

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

8-10 Oak St, Winchester

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

52 Middlesex Street Unit 52, Winchester

Listing courtesy of Listing Agent: The North Star Group from Listing Office: Keller Williams Realty Evolution.

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