Refine Search
Map
Sort by
29 Ginn Rd, Winchester
$3,799,000
6 Beds ⋅ 8 Baths ⋅ 73534577 MLS
Exceptional new construction offering approximately 6,000 sq ft of thoughtfully designed living space with 6 bedrooms, 7.5 baths, and a 3-car garage. A striking exterior showcases natural stonework, copper roof accents, copper gutters, and a welcoming covered porch. Inside, custom millwork, wide-plank hardwood floors, soaring ceilings, a floating staircase, and designer finishes create a timeless yet modern aesthetic. The chef's kitchen features Wolf & Sub-Zero appliances, custom cabinetry, and an oversized island, flowing seamlessly into the main living spaces. Expansive glass doors open to a covered outdoor patio area with a stunning stone fireplace. The luxurious primary suite offers a spa-inspired marble bath and oversized custom walk-in closet. The finished lower level includes a recreation room, wet bar, media space, home gym, and additional entertaining areas. Just moments away from Winchester's vibrant downtown center and the commuter rail, this home is a must see!

29 Ginn Rd, Winchester

Listing courtesy of Listing Agent: Peter Kasseris from Listing Office: Serhant.
50 Oxford Street, Winchester
$3,500,000
5 Beds ⋅ 4 Baths ⋅ 73515077 MLS
**OFFER ACCEPTED OPEN HOUSE CANCELED** Set on an oversized lot w/ a stunning in-ground pool, jacuzzi, pool house & expansive level lawn, this exceptional home blends luxury, privacy, & modern living. Expanded & extensively renovated top-to-bottom, the home features an open layout w/ designer kitchen, spacious family room & oversized attached 2-car garage. Walls of windows & French doors overlook the spectacular private yard, creating seamless indoor-outdoor living. The chef’s kitchen offers double islands, custom cabinetry, & high-end Wolfe & Sub-Zero appliances. Flexible 1st flr w/ potential bedrm & adjacent full bath, oversized dining rm, & high ceilings throughout. The beautiful primary suite features vaulted ceilings & full bath. Generously sized secondary bedrooms & large hall bath w/ soaking tub & separate shower complete the second floor. Finished LL w/ gym/media rm, abundant storage & new systems including electrical, plumbing & windows complete this rare Flats offering!

50 Oxford Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
40 Foxcroft Rd, Winchester
$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73485774 MLS
40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows. The chef’s kitchen is appointed with a premium Thermador appliance package and an elegant dry bar with integrated lighting. Custom millwork throughout adds warmth and architectural detail. A home office is located on the main level. The luxurious primary suite offers a custom walk-in closet with built-in lighting and a spa-inspired bath with steam shower. The top level offers two additional bedrooms ideal for guests or play space. The finished lower level includes a media room and home gym. A spacious deck overlooks the backyard, creating the perfect setting for outdoor entertaining.

40 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: The Boston ONE Team from Listing Office: Serhant.
2 Everett Ave, Winchester
$3,230,000
7 Beds ⋅ 6 Baths ⋅ 73488991 MLS
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms, blending timeless architectural details with luxurious modern amenities. Additional highlights include a primary suite with walk-in closet and sitting room, large entertainment room, 3 car garage, and close proximity to downtown and commuter rail. Don’t miss this rare opportunity to own a truly remarkable estate.

2 Everett Ave, Winchester

Listing courtesy of Listing Agent: Joan Francis Sullivan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
39 Town Way, Winchester
$3,200,000
6 Beds ⋅ 7 Baths ⋅ 73442521 MLS
Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to life! First floor offers a mudroom, half bath, office/living room, bedroom w/ full bath & a stunning high-end kitchen open to the dining room & spacious family room w/ fireplace, leading to a deck & large yard! The second floor features four generous bedrooms & three full baths, including a luxurious primary suite w/ a spa-like bath & walk-in closet, plus a convenient laundry room. The third floor includes an additional bedroom w/ rec/lounge area & oversized full bath! The walk out finished lower level provides a large recreation room, gym & full bath..perfect for family fun or entertaining. Reach out today for a site visit and a tour of this fabulous home to be completed by early spring 2026!

39 Town Way, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
257 High Street, Winchester
$3,150,000
5 Beds ⋅ 7 Baths ⋅ 73499287 MLS
OPEN HOUSE CANCELLED 4/12 **OFFER ACCEPTED** Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or everyday living & entertaining. Must see this fabulous home~

257 High Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
12 Salisbury Street, Winchester
$3,100,000
6 Beds ⋅ 5 Baths ⋅ 73496654 MLS
Welcome home to this stunning colonial on one of Winchester's most beloved streets. Featuring 6 bedrooms and 4.5 baths, this has been extensively renovated, creating space to spread out and truly live. Rich hardwood floors, 3 fireplaces, and a gracious flow make every room feel warm and inviting. The gourmet kitchen- complete with granite countertops, a large island, butlers pantry, wine chiller, double dishwashers and stainless appliances- is the heart of the home. The primary suite is a true retreat with a fireplace, walk-in closets, and spa bath with soaking tub. A sun room, custom mud room, finished basement, and 3rd-floor bedrooms offer room for everyone and everything. Outside, a bluestone patio, wood burning fireplace, covered deck, enclosed porch, professional landscaping and irrigation system create a beautiful and private setting, while a 2-car detached garage and 6-car paved driveway provide exceptional storage and parking. Surely a highlight of Winchester's spring market!

12 Salisbury Street, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
54 Johnson Rd, Winchester
$3,100,000
5 Beds ⋅ 8 Baths ⋅ 73474290 MLS
This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builders commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, wine fridge, coffee bar, charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite & full third floor w/ hardwood floors & bath. The expansive lower level offers a family room, movie theatre, game room, gym plus private entry separate living quarters w/full in-law/au-pair suite w/ kitchen, 2nd laundry,BR & bath

54 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
25 Myopia Road, Winchester
$3,100,000
4 Beds ⋅ 4 Baths ⋅ 73471735 MLS
A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining room, chef’s kitchen adorned by enchanting breakfast area and an inviting living &family room anchored by a stone fireplace. The upstairs primary suite is a private retreat w/ its own balcony, dressing rooms, cedar closet & a spa-inspired bath. The private backyard—with its historic stone hunter gazebo, fire pit, mature trees and layered plantings—offers both openness and seclusion. Within close proximity to Winchester Country Club and offering a swift commute to Boston & major highways, this exceptional property delivers privacy and prestige in one of Winchester’s most desirable enclave.

25 Myopia Road, Winchester

Listing courtesy of Listing Agent: Wenjun Cao from Listing Office: Engel & Volkers Boston.
27 Everett Ave, Winchester
$3,100,000
6 Beds ⋅ 6 Baths ⋅ 73468691 MLS
This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are beautifully preserved, elevated by the warm glow of restored hardwood floors. Generous, light-filled rooms unfold with grace and scale throughout. A newly designed chef's kitchen, new baths, walk-in pantry w/laundry and a classic butler’s pantry with wine refrigerator are some of the highlights. Anchoring the home is an expansive family room, framed by floor-to-ceiling windows overlooking a park-like lawn. A rare offering where architectural pedigree, thoughtful architecture and renovation, and exceptional land converge.

27 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
4 Lawrence St, Winchester
$3,070,000
6 Beds ⋅ 8 Baths ⋅ 73524328 MLS
A beautifully renovated and expanded Colonial in the Flats, blending old-world charm with modern living that suits a myriad of needs. The main home features high ceilings, restored original woodwork, and updated systems throughout. The kitchen invites the outdoors in with views of the private, tree-lined backyard with mature plantings, an expansive covered patio, and firepit for cozy evenings. The 2nd floor offers 4 beds and 3 baths, including a stunning primary suite with cathedral ceilings, marble bath, and sun deck access. A third-floor flex space adds a bar and bath. The bi-level in-law/au-pair suite is complete with full bath and kitchenette. Add a detached two-car garage with 2nd-story finished living area, bar, and full bath, and there are multiple offerings for autonomy, extended-stay guests, an au-pair, or teens seeking their own space. A rare opportunity to call this exceptional oasis home in the heart of the Flats, with Winchester Center and the commuter rail close by.

4 Lawrence St, Winchester

Listing courtesy of Listing Agent: Burbs to Boston from Listing Office: Compass.
115 Church St, Winchester
$2,975,000
7 Beds ⋅ 6 Baths ⋅ 73512327 MLS
Distinguished Colonial Revival located in the desirable “Flats" neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace and built-ins. Formal living and dining rooms offer generous proportions and period character. Second floor hosts a primary with en suite bath, a second en suite bedroom, and two additional bedrooms served by a hall bath. Renovated third floor features wide pine floors, a full bath, and flexible space for offices or bedrooms. Recreation room has a wet bar, half bath, and a balcony. Situated on a .41-acre corner lot that boasts a large flagstone patio, a basketball court and driveway access from Wedgemere Avenue. Minutes to Winchester Center, commuter rail, schools, and conservation trails.

115 Church St, Winchester

Listing courtesy of Listing Agent: Jennifer Ryer from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
56 Yale Street, Winchester
$2,830,000
5 Beds ⋅ 4 Baths ⋅ 73491616 MLS
Gracefully appointed in the sought after "Flats" this stunning Colonial has been superbly expanded & transformed into 4 levels of living space, offering a perfect blend of timeless details with well thought-out quality renovations. The front entry makes a striking first impression! Inside every turn is rich w/ detail- fireplace LR, elegant dining rm, crown molding, wainscoting, HW flrs & an exquisite built-in cabinet. The award-winning kitchen is nothing short of spectacular, with 2 walk-in pantries, wet bar & many outstanding features. You'll love the sunken family rm, adjoining mud rm, & bath. French doors extend the living space to a serene outer setting featuring mahogany deck & an alfresco kitchen. The luxurious primary suite is a stunner w/ spa-like marble bath, steam shower, walk-in closet & unique nursery/office. The finished lower level,2c gar, EZ access to the commuter rail & center of town complete this distinctive home. A rare offering & wonderful opportunity!

56 Yale Street, Winchester

Listing courtesy of Listing Agent: Patricia Fitzgerald from Listing Office: Brad Hutchinson Real Estate.
7 Cliff Street, Winchester
$2,800,000
6 Beds ⋅ 4 Baths ⋅ 73509698 MLS
Gracious 1890 colonial on .3 acre lot on dead end overlooking Middlesex Fells. Close to I-93, town center, train, and top Winchester schools (Lincoln Elementary). Welcoming front porch leads to a beautiful foyer. First floor features a living room with wood FP and bookshelves, and a large family room with gas FP accessing a side porch, a back deck and the kitchen. Renovated kitchen has large island, built-in desk and casual eating area. Formal dining room, half bath, mudroom, and pantry at the back staircase complete the 1st floor. Upstairs, the primary suite showcases a tub, shower, double sinks, plus walk-in closet. 3 additional bedrooms share a tiled bath. 3rd floor has another full bath, 2 more bedrooms and an office for a variety of uses. Finished basement houses a large rec room, laundry and mechanical rooms, plus generous storage. Highlights include central air, 2 car garage plus 4 driveway spaces, rear deck, side porch, beautiful landscaping and sprinkler system. Offers 5/5 4p.

7 Cliff Street, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
74 Wedgemere Avenue, Winchester
$2,793,000
5 Beds ⋅ 5 Baths ⋅ 73499151 MLS
The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and beautifully appointed baths throughout. The elegant kitchen overlooks a large, level backyard with direct access to a bluestone patio—ideal for entertaining—set against acres of serene conservation. The second floor offers a gracious primary suite with bath, plus four additional bedrooms and two full baths. The finished lower level features high ceilings, a fireplace, full bath, sauna, and direct yard access.

74 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
15 Yale St, Winchester
$2,700,000
7 Beds ⋅ 4 Baths ⋅ 73510619 MLS
Beautifully renovated 5 bedroom, 11 room home w 2 home offices located in the desirable FLATS area of town. An inviting front porch welcomes you into this special home showcasing the charm & character of historic Winchester, with amenities and layout desired today. Magazine worthy kitchen/dining/ family room! Open concept first floor with 3 rooms directly overlooking gorgeous and private rear yard w/ deck, patio, mature landscape and an abundance of privacy. Oversized 2 car garage is a huge bonus and rarely found in this part of town! Second floor includes 3 beds, 2 full baths & laundry room. 3rd level offers 3 sun drenched oversized Bedrooms w/ full ceiling height & full bath. Primary bedroom suite w/ spa like bath; oversized steam shower w/body sprays/bench/surround sound, radiant flooring & towel warmer plus a large newly constructed walk in coset! Close to the center & train to Boston. Ambrose School*

15 Yale St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
21 Bellevue Avenue, Winchester
$2,650,000
5 Beds ⋅ 4 Baths ⋅ 73506730 MLS
Exquisite home nestled in sought after Winchester neighborhood! This breathtaking home checks all the boxes on the wish list! Welcoming sun-filled entry foyer, soaring ceilings, gleaming hardwood floors & open concept flow. Inviting living room w/gas fireplace. Fabulous gourmet kitchen complete w/ Viking appliances, walk-in-pantry, dining area, coffee/wet bar & wine chiller. Sliding doors open to deck w/ serene wooded views overlooking level fenced in backyard. Elegant dining room, Family room w/stone fireplace adjacent to in-law or home office suite w/lush bath & separate entrance. Second floor offers luxurious master suite featuring spa-like marble bath w/oversized shower & soaking tub, dressing room, office nook & private deck retreat. 3 additional generous sized bedrooms w/ensuite baths & laundry room. Lower level features a spacious media/game room that opens to backyard & mudroom w/ direct access to oversized 2 car garage/work space. Highest quality systems & finishes throughout!

21 Bellevue Avenue, Winchester

Listing courtesy of Listing Agent: Giordana Fioravanti Smith from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
45 Bacon Street, Winchester
$2,650,000
7 Beds ⋅ 8 Baths ⋅ 73479961 MLS
Situated at the corner of Ginn Road neighborhood, this home was custom built by a premier local builder- with its dramatic design, it is a must see! Ideally located near town center w/ easy access to the commuter rail, Mystic lakes trails & beach, Ginn playground & the vibrant town center. This 7000sf, 7 BR home is perfectly designed for todays living w/ au-pair & multi generational options. A dramatic two-story foyer with stunning lit cove ceiling welcomes you into the home & flows into the formal living and dining spaces. The oversized chef’s kitchen features high end cabinetry, top-tier stainless appliances, large granite island w/dining area & fireplace. The inviting family room is just off the kitchen;The primary suite offers a lavish walk-in closet, large bath w/radiant heat & steam shower. Four additional bedrooms include en-suite baths, plus a separate-entry au pair suite. The finished lower level includes a bar, flexible family room/bonus space, gym & storage. Floor plan att'd

45 Bacon Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
2 Priscilla Lane, Winchester
$2,649,000
4 Beds ⋅ 4 Baths ⋅ 73485423 MLS
Under construction / Beautifully crafted 4 bedroom home offering thoughtful design, quality finishes & an ideal layout. The open-concept 1st floor is both spacious & welcoming, perfect for entertaining & everyday living. The chef’s kitchen features quartz countertops, stainless appliances, large center island w/seating & pantry. The kitchen flows seamlessly into the generous family room w/ gas fireplace & sliders leading to a large deck w/ private yard. The main level also includes a formal dining room w/ wainscoting, & a tray ceiling, a functional mudroom w/ bench seating, & a stylish half bath. Upstairs, the expansive primary suite offers 2 walk-in closets a luxurious bath with double vanities, soaking tub, & oversized shower. 3 additional bedrooms, a full hall bath, & convenient laundry room complete the 2nd floor. The finished LL provides a versatile media room,a full bath, & abundant storage. Two-car garage w/ direct entry. Convenient location close to town, train & Boston!

2 Priscilla Lane, Winchester

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.