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$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.
$2,000,000
3 Beds ⋅ 3 Baths ⋅ 73449729 MLS
Royal Barry Wills former home! – An architectural treasure nestled on over 1 acre of land in one of Winchester’s most serene and private settings. Designed by the renowned architect Royal Barry Wills, this iconic Cape Cod residence showcases timeless elegance with its signature gambrel roof, cypress shingle exterior, and classic New England design. Inside, three magnificent fireplaces, exquisite millwork, and a beautiful stained-glass door create a sense of warmth and refinement. The inviting eat-in kitchen opens to a charming screened porch, perfect for quiet mornings or evening gatherings overlooking the lush rose gardens. Three spacious bedrooms w/ a large primary suite on the first floor with 2.5 baths. Completing this exceptional property is a distinctive garden gazebo, an architectural complement to the main home. The possibilities are endless...a rare opportunity to own a piece of the towns heritage, blending historic craftsmanship in a top country club location!

5 Wood Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,250
3 Beds ⋅ 1 Baths ⋅ 73453034 MLS
Townhouse available 12/1! This Townhouse offers spacious 3 bedrooms, living room, kitchen and 1 full bath. There have been many updates with hardwood flooring through out, new kitchen floor, and painting in all rooms. Basement has Washer and Dryer Hook ups and 2 parking spots. There is a backyard and deck coming off kitchen. Tenant is to shovel driveway and walkway in winter months. There is a charge for Trash it is 330 for the year. Trash needs to be brought to Transfer Station.Note: I will post new pictures of kitchen once floor is complete.

317 Cross Street Unit 317, Winchester

Listing courtesy of Listing Agent: Robin Griffiths from Listing Office: J. Mulkerin Realty.
$2,175,000
3 Beds ⋅ 3 Baths ⋅ 73452553 MLS ⋅ ['Winning Farm'] BLDG.
Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in sunroom and enjoy the peaceful wooded backdrop—your own private oasis. The luxurious first-floor primary retreat offers an oversized spa-like bathroom, a large walk-in closet, and direct access to the convenient first-floor laundry. Upstairs, you’ll find two generous bedrooms, a full bath, and a cozy loft ready to be tailored to your needs. The finished lower level provides a spacious family room and ample storage. With a two-car garage and maintenance-free living, this exceptional home offers comfort, elegance, and ease in one perfect package.

19 Gershon Way Unit 1, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$1,850,000
6 Beds ⋅ 4 Baths ⋅ 73457013 MLS
This stately Victorian offers an exceptional blend of preserved character and modern functionality across its generous, well-appointed layout. Sunlit rooms highlight hardwood floors, detailed millwork, bay windows, and a graceful fireplace, creating a warm and elegant flow throughout the main level. The expansive kitchen features stone counters, a central island, French doors, and direct access to the porch and patio for effortless indoor-outdoor living. Upper levels provide inviting bedrooms, including a spacious primary suite with its own bath, walk-in closet and balcony. A versatile third-floor retreat/ legal apartment with treetop views—complete with additional kitchen, living area, full bath, and its own exterior deck—enhances the home’s flexibility. Set on a beautifully landscaped lot with mature trees, stone accents, and abundant outdoor space, this remarkable property offers a standout combination of scale, charm, and convenience near local amenities.

7-7A Brooks St, Winchester

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

189 High Street, Winchester

Listing courtesy of Listing Agent: from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,502,500
3 Beds ⋅ 4 Baths ⋅ 73447418 MLS ⋅ ['The Ledges'] BLDG.
Exceptional 3 Bedroom 3 1/2 Bath Highly Desired End Unit Townhome at The Ledges! Main Level Features include: Inviting Sun-Filled Entry Foyer, Gleaming Hardwood Floors, Cathedral Ceilings, Granite/Stainless Chef's Kitchen w/Breakfast Room, Formal Dining Room, Living Room w/Gas Fireplace and Private Deck overlooking Tranquil Wooded Setting. Family Study w/ Custom Built-ins, Luxurious Primary Bedroom Suite w/Dual Walk in Closets and Spa-Like Bath. The Second Level offers a Spacious Bedroom, W-I-C, Full Bath and Office. Finished Lower Level Oversized 3rd Bedroom Retreat w/Relaxing Sitting Area and Full Bath. Professionally Landscaped Courtyard Patio with Mature Plantings. Amenities include Pool, Pickle Ball/Tennis Courts and Clubhouse to Enjoy! Convenient to Winchester Center and Major Routes!

7 Wainwright Rd Unit 118, Winchester

Listing courtesy of Listing Agent: Giordana Fioravanti Smith from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,950
1 Baths ⋅ 73464830 MLS
Sparkling, recently renovated studio with amazing views of a beautifully landscaped garden and pond. This rental is SHORT TERM and comes fully furnished. White cabinet kitchen features stainless steel appliances, tiled backsplash and a marble top peninsula with seating.The main area has hardwood floors and glass sliders out to a good sized balcony, letting in plenty of natural light. In the hall leading to the bath is a double closet. The bathroom was recently refreshed with a new vanity, mirror, shower, tiled floor and lighting. The rent covers heat, hot water, internet, and electricity. Professionally management on-site. Convenient to town shops, restaurants and commuter rail. Explore the nearby Tri-Community Greenway with 10.6 miles for biking and walking. A "just right" place to land for a sabbatical or transition to a new home.

200 Swanton St Unit 502, Winchester

Listing courtesy of Listing Agent: Susan Murie from Listing Office: Aikenhead Real Estate, Inc..
$2,450,000
6 Beds ⋅ 5 Baths ⋅ 73456410 MLS
Offers due Tuesday, 11/25 @ 10am. With 6 bedrooms & 5 full baths, this beautifully crafted new construction located at the end of a cul-de-sac delivers refined style, a modern layout & effortless living. The open layout showcases a chef’s kitchen with an oversized island, quartz counters & Thermador appliances, seamlessly connecting to the dining & living rooms, both with their own gas fireplace. Detailed millwork, coffered ceilings & built-ins elevate every space. A 1st floor bedroom provides flexibility for guests or a home office. The 2nd floor features 5 bright, airy bedrooms including a serene primary suite with tray ceiling, spa-like bath, soaking tub, walk-in shower & custom closet, plus separate laundry. The 3rd floor & finished lower level offer ideal space for a gym, playroom, media or bonus rooms. Enjoy a lrg, fenced yard & 2-car garage with direct mudroom entry. Prime location near McDonald Field, downtown, schools & commuter rail, with easy access to 93/95.

29 Shepard Ct, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$1,930,000
4 Beds ⋅ 3 Baths ⋅ 73452706 MLS
Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M. Ramsay, this home blends timeless Tudor charm with modern updates. Features include 4 bedrooms, 2.5 baths, renovated kitchen, cozy family area, & a spacious living room with a striking fireplace. The finished third floor adds extra living space, along with the finished lower level, currently set up as a home gym. Built in 1929, the home boasts exceptional craftsmanship, with steel I-beams & wire lath plaster walls. A detached two-car garage & peaceful yard complete the property, making this a once-in-a-lifetime chance to own a historic home in one of Winchester's most sought-after neighborhoods.

8 Felsdale Close, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$1,392,500
3 Beds ⋅ 3 Baths ⋅ 73444073 MLS
Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering seamless access to a large deck and level, fenced backyard--ideal for relaxing or entertaining. Upstairs you'll find 3 generous bedrooms with ample closets, including a main suite with bath and a second, full bath. Just below the main level is a versatile office or fitness room, laundry area with extra freezer and storage, and garage entry. The inviting lower-level family room boasts great natural light, a wood stove/fireplace, half bath, and a walk-in cedar closet. This warm, welcoming home offers exceptional light, layout, and location! Property is leased until 7/31/2026-well worth the wait!

53 Bacon Street, Winchester

Listing courtesy of Listing Agent: Taleen Chiofaro from Listing Office: Leading Edge Real Estate.
$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.
$2,090,000
6 Beds ⋅ 4 Baths ⋅ 73411839 MLS
This stunning Victorian home, in the style of Painted Ladies w/ soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & Boston. The house lives as a harmonious single family with a second kitchen on the 1st floor (multigenerational living potential). It has 6 beds & 4 baths, over 4,385 SF of living area on 3 flrs. Features include 2 covered porches, renovated garage, butler’s pantries, built-in cabinetry, new interior & exterior paint, & ample outdoor space. Upgrades include high-velocity A/C throughout, 2 new gas water heaters, restored chimney, a gas F/P, oversized custom walk-in closet, & fenced-in side yard. Professionally landscaped, mature fruit trees, flower & vegetable gardens & 2 extra cobblestone parking spots complete the outdoor space. Full, unfinished walkout basement with a high ceiling has endless possibilities. Don't miss this rare opportunity in Winchester!

5 Bacon St, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$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.
$1,399,000
4 Beds ⋅ 5 Baths ⋅ 73454901 MLS ⋅ ['4-6 Wyman Court'] BLDG.
Another Tree Top Group masterpiece –Welcome to 4 Wyman Court! New full gut renovation townhome with 2,500 sq. ft., 4 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 4th bedroom, 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!

4 Wyman Court Unit 4, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$1,558,200
3 Beds ⋅ 3 Baths ⋅ 73448388 MLS
Nestled directly across from the breathtaking Middlesex Fells Reservation, this home offers the perfect blend of charm, space, and potential. This classic 3-bedroom, 2.5 bath Cape is beautifully situated on over half an acre in one of Winchester’s most desirable locations. The home features mostly hardwood floors throughout, a brand-new roof, and a newer heating and AC system. The second floor includes three bedrooms, including a primary suite with a walk-in closet. The first floor offers a spacious eat-in kitchen, a formal dining room, an office, and a front-to-back living room with fireplace with access to a sun porch. The lower level is ideal for a family room, complete with a fireplace. The generous lot provides exciting expansion potential without sacrificing yard space. Surrounded by nature and endless recreation opportunities just steps from your front door, this home is being sold as is and presents an incredible opportunity to make it your own.

82 Hillcrest Parkway, Winchester

Listing courtesy of Listing Agent: from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$900,000
3 Beds ⋅ 1 Baths ⋅ 73428179 MLS
Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for today’s lifestyle just moments from Winchester Center, award-winning schools, and the commuter rail. NEW roof, NEW walkway & patio, NEW hot water heater, NEW fence, NEW garage doors, NEW insulation, Updated kitchen, refinished hardwood floors, gas cooking, and immaculate throughout...This home isn’t just move-in ready—it’s brimming with potential to make it uniquely yours!

571 Washington St, Winchester

Listing courtesy of Listing Agent: Wilson Group from Listing Office: Keller Williams Realty.
$6,500
4 Beds ⋅ 4 Baths ⋅ 73441172 MLS
A grand home with a perfect mix of serenity and entertaining spaces. The main level has endless possibilities with its ability to provide cozy living areas and also an open concept with great flow. Fully equipped modern kitchen with tons of storage and island, Formal dining room with custom built ins, french doors to separate or open up spaces, front to back fireplace between the massive family room and home office/reading room with floor to ceiling windows and skylights - perfect place to enjoy the ever changing seasons while cuddled up to the fireplace. The multiple french doors open to the secluded patio space surrounded by a beautiful wooded tree line conjoining the 2 spaces into a perfect summer oasis. Upstairs has 4 large bedrooms, a main bath and an en suite. The main bedroom has custom built ins, hardwood floors thru out, expansive lower level that seems to never end, wet bar, pool table, 3/4 bath storage closets and small bonus room, This is a must see home!

31 Coolidge Street Unit 31, Winchester

Listing courtesy of Listing Agent: Sheri O'Connor from Listing Office: Plunkett Properties.
$2,000
1 Beds ⋅ 1 Baths ⋅ 73421998 MLS
Spacious top floor 1 bedroom with private deck with stunning pond views. Convenient location to public transportation, shopping and restaurants. Heat, hot water and electricity included. Laundry and extra storage in the building. 1 parking spot. No smoking and no pets.

200 Swanton St Unit 713, Winchester

Listing courtesy of Listing Agent: Brunna Henrique from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.
$1,865,000
7 Beds ⋅ 3 Baths ⋅ 73457068 MLS
Gracious Center Entrance colonial situated in top Flats location on a desirable corner lot. This home has all the charm of yesteryear and has many custom features including a beautiful front staircase with window seats, hardwood floors and sunny rooms. Attractive cherry cabinet kitchen with granite island. Large front to back living room has fireplace and is situated next to enclosed porch. Elegant dining room has attractive gumwood paneling..Second floor has four bedrooms including primary suite with full bath. Third floor has three additional bedrooms or use space as artist loft.or office space.Desirable location close to town and trains.While this house requires some updating and is being sold as is, it is well worth the investment for size ,location and potential.

1 Copley Street, Winchester

Listing courtesy of Listing Agent: Nannette Shanahan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,499,000
5 Beds ⋅ 4 Baths ⋅ 73449686 MLS
Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flower beds—in the exclusive yard. This home offers four levels of sun-filled space. The main level features 9’ ceilings, an open floor plan, and a chef’s kitchen with Viking appliances, large center island, with direct slider access to the fabulous private yard & patio. Upstairs includes a serene primary suite with walk-in closet and spa-like bath, plus two add’l bedrooms, full bath, & laundry. The third floor provides two more bedrooms and a full bath, ideal for guests, au- pair/ nannies or offices. A spacious lower-level family room, garage access, and storage complete this exceptional home with easy access to the center, schools, and train making it easy to enjoy all Winchester has to offer!

209 Washington St Unit 209, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$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.
$2,400,000
6 Beds ⋅ 4 Baths ⋅ 73454149 MLS
This beautifully updated Winchester residence combines timeless Garrison-style architecture with elegant modern finishes, creating a seamless space for everyday living. The inviting foyer leads to a sunlit living room, where wide-plank oak flooring flows into a stunning chef’s kitchen equipped with a spacious pantry, double ovens, and an oversized island—perfect for both cooking and gathering. Just off the kitchen, the formal dining room shares a double-sided fireplace with a library or study, offering flexible space for work or relaxation. With six bedrooms and three and a half baths, the home is thoughtfully laid out. The serene primary suite features a spa-inspired bath, while a full-size laundry room is conveniently located just down the hall. The finished garden level adds even more versatility with two bedrooms, a full bath, a living area, and a wet bar—ideal for guests, a home gym, office, or extended family stays. This home blends historic character w/today’s modern comfort

9 Norfolk Rd, Winchester

Listing courtesy of Listing Agent: Jody Fricia Geany from Listing Office: Citylight Homes LLC.
$940,000
2 Beds ⋅ 2 Baths ⋅ 73449918 MLS
Charming Spanish-style home in desirable Winchester! This unique property features a beautiful terracotta roof and timeless architectural details. The first floor welcomes you with a foyer which leads to an astounding great room, perfect for entertaining or hosting family gatherings. The kitchen opens seamlessly to the dining area. Additionally an inviting enclosed patio provides space to relax or enjoy morning coffee. A cozy sitting area and convenient half bath complete the main level. Upstairs, you’ll find two comfortable bedrooms and a renovated full bathroom with modern finishes. The lower level offers an unfinished basement ideal for storage or future expansion, plus an attached garage for added convenience. Whether you’re an investor seeking potential or an end user looking for a fixer-upper, this home presents an incredible opportunity in one of Winchester’s most sought-after neighborhoods.

446 Highland Ave, Winchester

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

26 N Gateway, Winchester

Listing courtesy of Listing Agent: Robert Dell from Listing Office: Homes Unlimited.
$2,400,000
5 Beds ⋅ 5 Baths ⋅ 73460779 MLS
Meticulous full-home reconstruction on peaceful Laurel Hill Lane by Mark Stephen Development. Completely reimagined and expanded, this 5-bed, 4 full/2 half bath residence blends modern function with sophisticated design. Custom cabinetry and beautifully curated finishes define every room. A first-floor en-suite enhances flexibility, while the living room’s striking custom marble surround creates an elegant focal point. The open-plan layout connects a chef’s kitchen, dining area, and a sun-filled bonus room ideal for play, work, or relaxation. A fully finished basement provides additional space for recreation, fitness, or media. The attached garage and generous wrap-around driveway offer convenience, and the elevated backyard delivers privacy and an impressive sense of space. An exceptional opportunity in one of Winchester’s most sought-after neighborhoods.

19 Laurel Hill Ln, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Gibson Sotheby's International Realty.
$2,450,000
4 Beds ⋅ 3 Baths ⋅ 73455307 MLS
One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef's kitchen anchors the main level with high-end finishes and a seamless flow for living and entertaining. The living room is sunny and inviting, featuring an impressive fireplace, timeless details, and a beautiful view of the gorgeous backyard. The adjoining dining room offers a refined space for gatherings with its classic architectural charm. The new primary suite includes a spa-inspired bath and custom walk-in closet, while additional bathrooms have been fully renewed with elegant finishes. Architectural extensions enhance natural light and expand the home’s functionality. Outside, the refreshed exterior and professionally designed landscaping deliver exceptional curb appeal and serene outdoor living. A rare opportunity for turnkey sophistication in Winchester.

30 Prospect St, Winchester

Listing courtesy of Listing Agent: Karima Alami from Listing Office: Compass.
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73449320 MLS
Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living space that flows nicely between the formal living room, dining room, kitchen, office and family room, all of which have picturesque views. Many recent updates including kitchen, baths, roof, heating & de-leading; making this lovely home move in ready! 3 to 4 bedrooms, 2 1/2 baths w/ a finished walk out basement w/ mud room, laundry, rec. room, storage and gym area. The setting is simply gorgeous with expansive rolling green lawn offering plenty of room for future expansion.Enjoy your morning coffee from deck appreciating all that nature offers, plus spectacular sunsets in the western skies!

32 Woodside Road, Winchester

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

50 Lincoln Street, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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