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47 Yale Street, Winchester
$2,600,000
6 Beds ⋅ 5 Baths ⋅ 73516849 MLS
Timeless 1920 brick Tudor in the heart of the Flats neighborhood combines all of today’s modern amenities with classic architectural charm to create an exceptional home for modern living offering 6 bedrooms, 3 full and 2 half baths. A welcoming entry opens to a sun-filled living room with custom built-ins, fireplace, and French doors to a private office. The open dining room flows into a chef’s kitchen with oversized island, abundant storage, and adjoining family room ideal for everyday living and entertaining. A custom mudroom, walk-in pantry, and half bath complete the first floor. The primary suite offers ensuite bath and walk in closet. 3 additional bedrooms, a full bath and convenient laundry room complete the second floor. The third floor offers two additional bedrooms, a full bath and ample storage. The finished lower level includes recreation, gym, playroom space, half bath, second laundry room and unfinished storage. Manicured grounds, two-car garage, C/A and irrigation.

47 Yale Street, Winchester

Listing courtesy of Listing Agent: Molly Nolan Byrne from Listing Office: Coldwell Banker Realty - Belmont.
15 York Road, Winchester
$2,600,000
5 Beds ⋅ 4 Baths ⋅ 73510389 MLS
This 5-bed colonial was built in 2017 and offers a bright open floor plan ideal for today’s lifestyle. The kitchen features a large quartz island, breakfast nook, and flows into dining and living areas with gas fireplace. Sliders open to a private lot with stone patio and fire pit. First floor includes half bath, pantry, and an enormous mudroom with cubbies for everyone. The oversized primary suite offers a marble bath and bonus space for a gym or office. Two large bedrooms and full bath on second floor. Third floor adds two bedrooms, a full bathroom, and laundry room. Finished basement provides additional living space perfect for play room or game room, with ample storage. Two-car detached garage with overhead flex space. Modern construction, updated finishes, and a true neighborhood setting makes this home a perfect fit!

15 York Road, Winchester

Listing courtesy of Listing Agent: Nannette Shanahan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
48 Salisbury Street, Winchester
$2,600,000
5 Beds ⋅ 4 Baths ⋅ 73419963 MLS
Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink, granite counters, and second dishwasher make this a wonderful home for entertaining. The second floor features a primary suite with walk-in closet & marble bath w/ soaking tub, 3 generous bedrooms with a full hall bath, and a laundry-ready closet. The lower level offers an excellent option for guests with a bedroom & ¾ bath, plus an office, laundry room & playroom. Plentiful closets & functional storage space abound throughout this home. The professionally landscaped yard is a welcoming spot to entertain on the deck & bluestone patio, or relax & play in the flat back yard.

48 Salisbury Street, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
2 Edgewater Place, Winchester
$2,575,000
4 Beds ⋅ 5 Baths ⋅ 73498843 MLS
A quiet cul-de-sac near the Mystic Lakes sets the stage for this exceptional Royal Barry Wills residence, masterfully reimagined. Every inch reflects elevated craftsmanship and a refined sense of luxury, with bespoke finishes and thoughtfully curated amenities throughout. The main level unfolds with effortless elegance, anchored by a state-of-the-art chef’s kitchen featuring custom cabinetry, Thermador appliances, dual ovens and wet bar. An inviting family room with soaring cathedral ceilings and sliders to the deck creates a seamless indoor-outdoor flow. Multiple dining areas offer versatility for both intimate gatherings and grand entertaining, complemented by a stunning gas fireplaced living room with a sunlit bay window. A private office, study, sunroom and 4 beautifully appointed bedroom suites complete the interior. Outside, a newly renovated yard w/ an outdoor living room, play space, rock walls and secondary patio offer natural sanctuary. Top location, close to town & Ambrose.

2 Edgewater Place, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
2 Abby Rd, Winchester
$2,575,000
4 Beds ⋅ 5 Baths ⋅ 73492061 MLS
Tucked on a quiet cul-de-sac within an exclusive enclave of homes, this newer residence offers a harmony of refined living and natural beauty. Just moments from the trails and vistas of the Middlesex Fells Reservation, this home is ideally positioned for those who value serenity and effortless access to the outdoors. Thoughtfully designed, it unfolds with an airy, open-concept where a sunlit kitchen, dining area, and family room create an inviting backdrop for everyday living and elegant entertaining. The family room exudes warmth and sophistication, while the chef’s kitchen impresses with an expansive center island and a suite of premium Thermador appliances. A first-floor office or den, paired with a full bath, offers versatility. Upstairs, the primary suite is a true retreat, with soaring ceilings, a spa-inspired bath, and a generous walk-in closet. 3 other roomy bedrooms complete this floor. A full finished basement is a true bonus, with direct walk-out access to the back.

2 Abby Rd, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
10 Viking Road, Winchester
$2,549,000
4 Beds ⋅ 4 Baths ⋅ 73518600 MLS
Discover this stunning, freshly updated 4 bedroom, 4 BA oversized brick ranch with open layout & soaring cathedral beamed ceilings on a gorgeous lot with new in-ground pool! The first floor boasts a spectacular custom kitchen with stainless steel appliances, high-end Monogram appliances, two dishwashers & oversized island with seating & rare granite countertops. Relax in the family room with walls of windows overlooking the resort style heated in-ground gunite pool & plenty of yard space. The thoughtfully designed bedroom wing features a sun-filled primary with en-suite marble bath, plus 3 add'l spacious bedrooms and full guest bath. An expansive mudroom provides seamless access to 2 car garage and add'l full bath. Fully finished lower level with exterior access is perfect for entertaining with game/media room, gym, full bath, generously sized laundry room & a custom-designed dog wash room! Outside, you will love the heated pool surrounded by lush landscape. Move right in & enjoy!

10 Viking Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
29 Shepard Ct, Winchester
$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.
30 Prospect St, Winchester
$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.
382 S. Border Road, Winchester
$2,450,000
6 Beds ⋅ 6 Baths ⋅ 73442428 MLS
NEW HIGH-END CONSTRUCTION - 13 Rms - 6 BD's - 5.5 BA's You will be captivated by the grand entrance - attention to detail - high coffered 10' ceilings and excellent flow that leads you to the magnificent Open Floor Plan - custom-designed Kitchen which is the heart of this home. no expense was spared; custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm w/FP, Dining Rm, Butler Pantry, Mud Rm, Laundry, Powder Rm and Guest BD w/BA. The 2nd flr offers 4 BD's w/BA's, gorgeous Master Suite w/BA and Laundry, FP and custom-designed oversized Walk-in Closet. Finished Lower Level has spacious Family/Game Rm w/custom cabinets and Bar, Office/Exercise Rm and full BA - perfect space for a NANNY/IN-LAW SUITE. Professionally landscaped Yard, Patio - Deck - oversized 2-Car Garage - plenty of land for a pool; Enjoy Winchester amenities, minutes to Center, top-rated Schools, Fells Reservation, Parks, Restaurants, Shopping, Commuter Train, major routes - 8 miles to Boston.

382 S. Border Road, Winchester

Listing courtesy of Listing Agent: Lucille Murray from Listing Office: Gibson Sotheby's International Realty.
49 Sheridan Circle, Winchester
$2,409,000
5 Beds ⋅ 5 Baths ⋅ 73534811 MLS
Like new, built in 2014, this exceptional home offers generous living space, a flexible floor plan, & quality finishes throughout. Situated on a large corner lot in a desirable Winchester neighborhood, the home features a spacious kitchen that opens to the family room w/ fireplace, creating the perfect gathering space. A sun-filled living room & formal dining room provide additional areas for entertaining & everyday living. The oversized primary suite includes a beautiful bath & 2 walk-in closets. Three additional large bedrooms, a full bath, & convenient second-floor laundry complete the 2nd level. The newly finished 3rd floor offers media/ bedroom w/full bath, providing excellent flexibility for guests, a home office, au pair suite, or potential in-law space. The finished lower level includes a rec room, full bath & abundant storage. Outside, enjoy the expansive yard w/ patio, fruit trees & plenty of space for recreation, gardening & more! Don't miss this one!

49 Sheridan Circle, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
112 Highland Avenue, Winchester
$2,400,000
6 Beds ⋅ 4 Baths ⋅ 73515135 MLS
Timeless Victorian grandeur meets modern living in this iconic Winchester home situated on the corner of Wilson Street w/ easy access to Fells trails! This recently renovated sun-filled 6 BR 4 BA home offers nearly 5000 ft.² of beautifully scaled living spaces filled w/ extraordinary architectural charm & elegant details featuring a brand new state of the art gorgeous kitchen w/ Wolf & Sub Zero appliances. A stunning staircase showcases a wall of colorful leaded glass complimented by high ceilings, intricate millwork & dramatic details throughout. The expansive rebuilt wrap-around porch offers wonderful space to enjoy summer evenings & host gatherings. The great layout provides flexibility for entertaining, working from home or extended living needs. The striking façade & stately presence creates an unforgettable first impression ideally located near Winchester Center, commuter rail, shops, restaurants & top rated schools. located in one of Winchester's most sought after neighborhoods

112 Highland Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
216 Highland Avenue, Winchester
$2,400,000
5 Beds ⋅ 4 Baths ⋅ 73511014 MLS
Welcome to this fully updated 5 BR, 3.5 BA Victorian showcasing elegant period detail throughout, including intricate woodwork, moldings, high ceilings & hardwood floors. The main level features a gourmet eat-in kitchen w/ quartz island & high-end stainless appliances, opening to a custom butler’s pantry w/ additional oven, sink & wine chiller. A sun-filled family room w/French doors leads to the patio, along w/ a fireplaced living room w/ built-ins, & formal dining room. Home includes 2 primary bedroom options, one on the 2nd floor & a private 3rd-floor primary suite w/ fireplace & full bath. The 2nd level also has 3 additional spacious bedrooms & two full baths, while the 3rd floor features a dramatic great room w/ beamed ceiling.Additional highlights include partially finished basement & newer heat & AC. Enjoy a wrap-around porch, patio & large fenced yard. Ideally located near town center, Middlesex Fells Reservation, Commuter Rail, Lincoln Elementary, Middle School, & Highschool.

216 Highland Avenue, Winchester

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

8 Buckman Dr, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
50 Brooks Street, Winchester
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 73510897 MLS
Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home & continues into the formal dining room, breakfast nook, formal living room & home office. The primary suite offers a ensuite bath & large walk in closet. 3 additional bedrooms & a full bath complete the 2nd floor. The finished lower level w/ full bath offers great space for movie nights, kids play space or guest area & gym. This property is complete w/ a 2 car garage & gorgeous level lot. The back yard features an expansive deck, patio & fenced in yard. This home truly has it all! Sought after Brooks neighborhood is close to town, Wedgemere train station & Brooks town forest. Don't miss this one!!

50 Brooks Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
15 Gershon Way Unit 15, Winchester
$2,325,000
3 Beds ⋅ 4 Baths ⋅ 73495350 MLS
Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual dining and entertaining. Dining area with coffered ceilings, fireplaced living room, and bonus screened porch to enjoy the view of the lush conservation land and walking trails. The luxurious primary retreat offering a spa-like bath with double vanities .Laundry room and 1/2 bath round out the main level. Upper level boasts 2 additional bedrooms, a full bath and flexible, cozy loft space. Amazing, walk out lower level includes a full gym, patio for grilling, built in cabinets, full bath and spectacular, custom built wine cellar Two car garage. This opportunity is not to be missed!

15 Gershon Way Unit 15, Winchester

Listing courtesy of Listing Agent: Moira Lown from Listing Office: Coldwell Banker Realty - Wellesley.
15 Gershon Way Unit 15, Winchester
$2,325,000
3 Beds ⋅ 4 Baths ⋅ 73495315 MLS ⋅ ['Winning Farm'] BLDG.
Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual dining and entertaining. Dining area with coffered ceilings, fireplaced living room, and bonus screened porch to enjoy the view of the lush conservation land and walking trails. The luxurious primary retreat offering a spa-like bath with double vanities .Laundry room and 1/2 bath round out the main level. Upper level boasts 2 additional bedrooms, a full bath and flexible, cozy loft space. Amazing, walk out lower level includes a full gym, patio for grilling, built in cabinets, full bath and spectacular, custom built wine cellar Two car garage. This opportunity is not to be missed!

15 Gershon Way Unit 15, Winchester

Listing courtesy of Listing Agent: Moira Lown from Listing Office: Coldwell Banker Realty - Wellesley.
78 Bacon Street, Winchester
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73526460 MLS
Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR, mudroom, stylish 1/2 bath & home office/sunroom complete this floor. Upstairs you'll find five spacious bedrooms and two full baths including the most perfect primary suite w/gorgeous bath plus a sitting room. Many updates include new hardwood floors, new high end Pella windows, updated electrical, heating and cooling systems finished lower level offers excellent recreation Enjoy the great landscaped yard with patio, lawn and sports court! For sure a favorite gathering spot for family and friends.

78 Bacon Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
30 Rangeley Road, Winchester
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73526416 MLS
Welcome to this distinctive home set on a lush landscaped lot in Winchesters historic and highly sought after Rangeley Estates neighborhood. Just moments from the town Center, this hidden gem offers a rare opportunity to renovate, expand & create your dream home in one of the towns premier locations. Rich in character and timeless appeal the sun-filled home features, five bedrooms, 3.5 baths, gleaming hardwood floors, updated electrical, updated heating and a newer roof; beautiful perennial gardens and mature landscape surround the property~ the level backyard is stunning with flowering perennial gardens & specimen trees showcasing the ideal setting. The first floor offers high ceilings, spacious rooms & an oversized screen porch plus sunroom with walls of windows & 2 fireplaces. The second level offers 3 large bedrooms & 2 baths including the primary suite w/ full bath. The third floor offers 2 additional bedrooms & another full bath. Detached 2 car garage and oversized driveway.

30 Rangeley Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
53 Winford Way, Winchester
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73525195 MLS
OPEN HOUSE CANCELLED. Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home! Located within the Winchester School District

53 Winford Way, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
12 Yale St, Winchester
$2,300,000
4 Beds ⋅ 3 Baths ⋅ 73480345 MLS
Timeless architecture blends beautifully with curated updates designed for modern living in this classic Colonial. Sunlight pours into the newly renovated gourmet kitchen, where beautiful cabinetry, premium appliances, and thoughtful design create an inviting heart of the home for both everyday living and elegant entertaining. A gracious front-to-back living room offers exceptional scale and flow, anchored by a fireplace and an abundance of natural light. Attached, a charming three-season sunroom provides a tranquil retreat, seamlessly connecting indoor comfort with the beauty of the outdoors. 4 bedrooms and 2 baths complete the second floor. Bonus: extra 900 unfinished square feet in the attic just waiting for your ideas! The basement offers one of the best finished areas we've seen, with vintage hardwood floors and a fireplace. A thoughtfully landscaped yard feels like a private oasis, with room for play or private mornings. Impeccably maintained, in a prime Flats location.

12 Yale St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
2 York Road, Winchester
$2,255,000
4 Beds ⋅ 4 Baths ⋅ 73537657 MLS
Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized shower, soaking tub & double vanity. A second en-suite bedroom, two additional bedrooms & full bath complete the second floor. The partially finished lower level provides flexible bonus space. Outdoors, enjoy a private sports court & expansive fenced yard, ideal for recreation & entertaining. An attached 2-car garage, including one heated bay, adds convenience. Ideally located adjacent to Town Forest walking trails and just minutes from Wedgemere Station, downtown Winchester, schools, parks, and commuter routes. A rare opportunity to enjoy comfort, recreation & convenience in a sought-after location.

2 York Road, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
6 Davey Ln, Winchester
$2,250,000
4 Beds ⋅ 4 Baths ⋅ 73554545 MLS
Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.
14 Grant Rd, Winchester
$2,250,000
6 Beds ⋅ 5 Baths ⋅ 73438521 MLS
Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space and offers a peaceful retreat. Enjoy the flexibility of dual primary suites on both the first & second floors, providing exceptional layout options for multi-generational living or guest accommodations. The mudroom w/ dual closets adds everyday functionality and style, while the finished lower level includes a full bathroom and versatile flex space—ideal for a home office, gym, or playroom. Located in the sought-after Muraco School District w/ easy access to I-93, this home combines luxury, convenience, and thoughtful design. Don’t miss your chance to own this exceptional new build in Winchester!

14 Grant Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
15 Cabot St, Winchester
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 73502658 MLS
Set in one of Winchester’s most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece—generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools.

15 Cabot St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
10 Edgehill Road, Winchester
$2,200,000
7 Beds ⋅ 4 Baths ⋅ 73490604 MLS
Offer Accepted. Open houses cancelled. This exceptional Colonial Revival home in a sought-after Winchester neighborhood blends craftsmanship, thoughtful updates and a design layout perfect for entertaining and modern day living. A welcoming front porch introduces a double entry foyer, high ceilings with crown molding and period detail that flow through the formal dining and living room with fireplace to the family room, kitchen and butler’s pantry. Oversized windows drench hardwood floors with sunshine. Keep the French doors open to access the patio and fenced-in back yard, perfect for play. This well-proportioned home includes 2 primary suites, 5 additional bedrooms plus a 2nd floor office with bead board. Enjoy the private, renovated 3rd floor as an owner sanctuary, work space, or kid zone! With abundant storage, partially finished lower level rec room and 2-car garage this home has it all; including, a location close to the town center, schools, and train, close to Boston/Cambridge.

10 Edgehill Road, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
89 Wildwood St, Winchester
$2,200,000
7 Beds ⋅ 6 Baths ⋅ 73455053 MLS
Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half bath complete the first level. Upstairs, find five bedrooms, three full bathrooms & a laundry room outfitted with custom cabinetry & sink. The front to back primary suite has double walk in closets & an ensuite with dual vanities. Finished lower level features an additional guest suite & playroom, hangout space or gym. Conveniently located close to town, 89 Wildwood offers the best of Winchester living. Showings begin at first Open House Saturday 11/15 12:30-2!

89 Wildwood St, Winchester

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
19 Gershon Way Unit 1, Winchester
$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.
21 Willowdale Road, Winchester
$2,170,000
5 Beds ⋅ 4 Baths ⋅ 73534988 MLS
New construction 2019, this impressive 4-5-bedroom, 4.5-bath custom built East side colonial offers exceptional space and a highly sought-after floor plan. The chef's eat-in kitchen features a large center island, abundant cabinetry & sunny dining area that seamlessly blends w/ the spacious family room w built ins & fireplace. Sun-filled living and dining rooms are connected by a double-sided fireplace, creating ideal gathering spaces. The stunning oversized primary includes a beautiful bath w/ shower & soaking tub & large walk-in closet. 3 additional generously sized bedrooms and full bath complete the upper level. The finished lower level offers a media room with a 4th fireplace, a BR/Office, full bath & mudroom area. w/direct access to the garage.Enjoy the large yard and patio, perfect for outdoor entertaining. Conveniently located near Winchester center, parks, & commuter routes, this turn-key home combines modern construction, generous living space, and quality finishes throughout

21 Willowdale Road, Winchester

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

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