Refine Search
Map
Sort by
7-7A Brooks St, Winchester
$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.
20 Grove Pl, Winchester
$1,850,000
5 Beds ⋅ 4 Baths ⋅ 73455673 MLS
From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a sitting area complete this level. The third floor provides space for additional bedrooms or an office. The finished lower level includes a family room, wine cellar, sauna, gym, and full bath. Enjoy a tree-lined backyard with deck and hot tub, perfect for entertaining. The home office opens to the yard and attached two-car garage with Level 2 EV charger. Central A/C and a Tesla solar roof with 27 KW battery storage complete this stunning home.

20 Grove Pl, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
35 Glen Grn, Winchester
$1,830,000
4 Beds ⋅ 2 Baths ⋅ 73461235 MLS
Welcome to this beautifully maintained Colonial in a highly desirable family neighborhood directly across from a scenic conservation area. The main level offers a bright, seamless flow with a living room, dining room, updated kitchen, full bath, family room, and a sunroom opening to the backyard. Upstairs features three comfortable bedrooms and a full bath, while the third-floor bonus room offers excellent flexibility for a fourth bedroom, office, or studio. The finished lower level adds even more living space with a laundry room, storage room, and a versatile area ideal for a playroom, media room, or home gym. Outside, enjoy a private, fully fenced yard with an inground pool, perfect for entertaining. A rare combination of space, comfort, and lifestyle.

35 Glen Grn, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
10 Graystone Cir Unit 10, Winchester
$1,825,000
2 Beds ⋅ 4 Baths ⋅ 73508182 MLS ⋅ ['Graystone At Winchester'] BLDG.
Tucked within the coveted enclave of Graystone, this exceptional townhouse offers a rare blend of scale, privacy, and refined living. Among the largest residences in the community, this impeccably maintained 2-bedroom, 3.5-bath home unfolds across more than 3,800 square feet of thoughtfully designed space. Sunlight pours through expansive windows, illuminating gracious living and entertaining areas that flow seamlessly from room to room. The interiors are polished yet inviting, with generous proportions that allow for both elegant gatherings and comfortable everyday living. The first floor primary suite is large and inviting; another full bedroom suite is on the second floor, along with an expansive office and a cozy den. A rare walk-out patio on the lower level opens directly to a serene, forested backdrop—an uncommon offering that creates a private retreat, perfect for morning coffee or evening relaxation surrounded by nature.

10 Graystone Cir Unit 10, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
19 Glengarry Road, Winchester
$1,825,000
6 Beds ⋅ 4 Baths ⋅ 73418086 MLS
A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic details throughout, from original woodwork, beautiful fireplaces & hardwood floors to cozy, sun filled living spaces incl. a dreamy sun porch overlooking gorgeous back yard. 4 bedrooms & 2 baths on the 2nd floor, while the 3rd floor offers 2 additional beds. Full basement with flex living spaces including an additional bed or office & full bath. A large yard awaits with access/ frontage all the way to Grassmere Ave. With easy access to schools, shops, restaurants & the commuter rail, you’ll enjoy the best of Winchester living with unmatched convenience & one of the best neighborhoods around!

19 Glengarry Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
16 Glenwood Ave, Winchester
$1,820,000
6 Beds ⋅ 5 Baths ⋅ 73507145 MLS
Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac in the Lynch School district

16 Glenwood Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
12 Wincrest Drive, Winchester
$1,810,000
6 Beds ⋅ 5 Baths ⋅ 73492714 MLS
West Side! Set on a beautiful, serene oversized 1/2 acre lot, this turn key 2006* 5–6 bedroom, 4.5 BA home offers the perfect blend of space, comfort, & style. This home was completely renovated & expanded in 2004 offering an open floor plan w/ kitchen & dining area that flow seamlessly into an oversized family room w/ walls of windows showcasing the gorgeous yard. The main floor also offers living/ dining plus 2 bedrooms & a full bath. The luxurious primary suite w/vaulted ceilings is a true retreat, boasting a spacious walk-in closet & spa-like bath with double vanity, soaking tub & shower. 2 additional 2nd fl bedrooms offer large rooms w/ fun loft spaces. Enjoy the sun filled lower level w/ a sunny family room w/ fireplace, office or BR & bath. 2 car attached garage, & central AC complete this home. Enjoy panoramic views of the tranquil yard from nearly every room. Ideally located near Whipple Hill Conservation trails, VO Elementary w easy access to major routes/ Boston & Cambridge

12 Wincrest Drive, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
18 Graystone Circle Unit 18, Winchester
$1,800,000
3 Beds ⋅ 3 Baths ⋅ 73551306 MLS ⋅ ['Graystone At Winchester'] BLDG.
OFFER ACCEPTED-OH CANCELLED!Discover luxury & convenience in this impeccably maintained 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a 1st floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas fireplace, gleaming hardwood floors & soaring cathedral ceilings w/ skylights, leading to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, the spacious second bedroom, full bath plus an oversized loft family room area w/ potential to wall off a portion for 3rd bedroom, & a cozy a den/ office The walkout LL has high ceilings & offers opportunity to finish 1440SF for gym/rec room, media room, storage or anything you desire!

18 Graystone Circle Unit 18, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
61 Westland Ave, Winchester
$1,800,000
3 Beds ⋅ 4 Baths ⋅ 73466421 MLS
This beautiful, move-in-ready Cape has been thoughtfully renovated from top to bottom. Oversized front walks lead to a charming front porch and into a welcoming foyer that opens to a sun-filled open-concept layout with fire-placed family room, dining area, and kitchen—ideal for everyday living and entertaining. A bright bonus room off the kitchen with wall-to-wall windows and heat/AC offers year-round enjoyment. The first-floor primary suite features hardwood floors, double closets, and a spa-like bath with double vanity and glass-enclosed tiled shower. The second floor features two front-to-back bedrooms, each with a private tiled bath. The finished lower level provides direct access to the 2-car garage, mudroom and flexible space—perfect for a home gym, office, media room, hang-out area or if wanted, a potential ADU with some vision. A stunning home offering comfort, style, and versatility. Open House Sat & Sun 11:30–1.

61 Westland Ave, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
8 Hawthorne Road, Winchester
$1,775,000
5 Beds ⋅ 4 Baths ⋅ 73522773 MLS
Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees. The open-concept living and dining area provides a seamless flow, ideal for hosting gatherings or simply relaxing with guests. Family room w/window seat and built-ins, leads to a sunny deck. Next level, you enter an en-suite bedroom and two large additional Bdrms with an updated bath. Two more Bdrms on the upper level can be utilized for a guest or family member w/ultimate flexibility. Lower level, there are Power Rm, Laundry Rm, Dog Spa & Study. This residence provides the ideal blend of functionality and style. Close to Vinson Owen School. This dream home provides easy access to everything!

8 Hawthorne Road, Winchester

Listing courtesy of Listing Agent: H. Elaine Song from Listing Office: Coldwell Banker Realty - Lexington.
35 Hollywood Rd, Winchester
$1,755,000
4 Beds ⋅ 5 Baths ⋅ 73485418 MLS
Tucked at the end of a cul-de-sac and bordering the Fells, this classic brick-and-wood Colonial blends generous living spaces with comfortable, easy flow. The fireplaced living room and spacious dining room are filled with natural light and framed by peaceful woodland views. The kitchen features stone counters, stainless appliances, and a peninsula that connects to the dining area and opens to a vaulted, beamed family room with fireplace and French doors to the outdoors. A home office offers added flexibility. Upstairs, four inviting bedrooms include a tranquil primary suite with walk-in, cedar closet and private bath, and a second bedroom with its own ensuite bath. The walk-out lower level offers additional living space with a playroom, wet bar, and full bath. Porch, patio, and fenced yard create welcoming outdoor areas, complemented by central air and an attached 2 car garage. With its thoughtful layout and cul-de-sac setting near the Fells, this home offers enduring appeal.

35 Hollywood Rd, Winchester

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

24 Hinds Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
15 Westland Ave, Winchester
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 73438722 MLS
OFFER ACCEPTED OH SUNDAY CANCELLED Taken down to the studs, this renovated and reimagined center entrance Colonial offers timeless elegance and modern comfort in one of Winchester’s most desirable neighborhoods. The gracious foyer gives way to a front-to-back living room anchored by a wood-burning fireplace with custom mantle. An adjacent sun-filled, south-facing room provides the perfect space for an office, den, or playroom. Nestled between the dining room and charming covered back porch, the expanded kitchen features a large island, white cabinetry, under-cabinet lighting, quartz countertops and SS appliances. A stylish powder room with beadboard and designer wallpaper completes the first floor. Upstairs the bright and spacious primary suite features a full bath and walk-in closet. Three additional bedrooms, a second full bath, and walk-up attic access complete this level. The lower level offers versatile living space, dedicated laundry room, and mudroom with direct exterior access

15 Westland Ave, Winchester

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

18 Grayson Rd, Winchester

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

307 Cross Street, Winchester

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

94 Johnson Road, Winchester

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

41 Sunset Road, Winchester

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

29 Pilgrim Dr, Winchester

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

114 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Rosemary Kelleher from Listing Office: LAER Realty Partners.
77 Washington St, Winchester
$1,700,000
5 Beds ⋅ 4 Baths ⋅ 73428068 MLS
This isn’t just a house — it’s a front-row seat to the good life, where you can walk to shops, schools, cafés, restaurants, and everything the town has to offer! This 5-bedroom, 3.5-bath Victorian sits proudly in the heart of Winchester Center, in the highly coveted Lincoln School district. Original hardwood floors, soaring ceilings, and stunning architectural details give this home its timeless character, while the updated kitchen and spacious rooms bring modern comfort to everyday living. With its gorgeous design and generous layout, it’s perfect for hosting friends or enjoying quiet evenings at home. And the best part? The backyard offers a quiet space with a dining patio, garden and pergola....it's like a secret garden in the heart of the action. A full basement with good ceiling height offers plenty of expansion possibilities. An ample primary suite, excellent closets and big bedrooms combine with young systems/roof and ample parking!

77 Washington St, Winchester

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

12 Cox Rd, Winchester

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

10 Farrow Street, Winchester

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.
4 Aricia Ln, Winchester
$1,656,000
4 Beds ⋅ 5 Baths ⋅ 73397190 MLS
Rare 5-car garage on a quiet, tree-lined cul-de-sac in one of Winchester’s most exclusive enclaves! Offering both serene privacy and seamless connectivity, 4 Aricia is perfectly positioned within walking distance to a coveted elementary school and Wright-Locke Farm, and minutes from the commuter rail and Routes 128 & 93. Set on nearly .5 acres of manicured grounds, the home’s exterior is framed by mature plantings, sculpted gardens, and a sweeping lawn that creates a resort-like sense of arrival. Inside, contemporary touches meet everyday comfort with soaring vaulted ceilings, skylights, and floor-to-ceiling windows that fill the home with natural light, while hardwood floors and a central fireplace anchor the open-concept living and dining spaces. A built-in wet bar makes entertaining effortless, and the spacious kitchen with breakfast nook, pantry, laundry room, and direct access to a sprawling deck and stone patio connect indoor comfort with outdoor beauty.

4 Aricia Ln, Winchester

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

11 Carriage Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
4 Oakland Cir, Winchester
$1,651,000
3 Beds ⋅ 2 Baths ⋅ 73426639 MLS
Welcome to 4 Oakland Circle, a spacious home tucked away on a desirable cul-de-sac in Winchester. Thoughtfully designed with oversized rooms and a versatile layout, this residence provides comfort and flexibility for a variety of lifestyles. The main level features expansive living and dining areas along with a 1st floor primary bedroom option that opens onto a private deck, plus a dedicated home office perfectly suited for remote work. Upstairs, the private primary bedroom offers a generous retreat, accompanied by a well-sized third bedroom. Large windows bring in abundant natural light, creating a warm and inviting atmosphere throughout. Step outside to enjoy the beautiful backyard, an ideal space for entertaining, gardening, or simply relaxing in a peaceful setting. With its generous floor plan, tranquil location, and close proximity to Winchester’s vibrant center, schools, this home presents an exceptional opportunity to enjoy both space and convenience.

4 Oakland Cir, Winchester

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

5 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.
149 Horn Pond Brook Rd, Winchester
$1,641,000
5 Beds ⋅ 2 Baths ⋅ 73251461 MLS
Picture perfect cape style home across from the Lynch Elementary School. This beautiful home on a corner lot checks all the boxes with 4/5 bedrooms on 2 floors and 2 full baths. Extra bonus space in lower level for home office or gym. Huge, beautiful yard that is perfect for outdoor recreation. Pretty eat in kitchen has direct entry to deck. This custom built home has been lovingly maintained and updated.

149 Horn Pond Brook Rd, Winchester

Listing courtesy of Listing Agent: Nancy Ciampa McLaughlin from Listing Office: Redfin Corp..
73 Grove St, Winchester
$1,627,000
4 Beds ⋅ 3 Baths ⋅ 73435608 MLS
This stunning 4-bedroom Center Entrance Colonial in the desirable Ambrose School District has been beautifully updated for modern living. A complete first-floor renovation features a reimagined layout with a custom-designed kitchen boasting Thermador and Bosch appliances, marble and quartzite counters, walk-in pantry, and a bar w/ beverage fridge. Spacious, light-filled rooms showcase gleaming hardwood floors, three fireplaces, and two staircases, blending timeless character with today’s style. The inviting living room w/ stone fireplace opens through French doors to a Trex deck & expansive backyard, perfect for entertaining. The primary suite offers vaulted ceilings, walk-in closet, & spa-like bath w/ soaking tub & walk-in shower. Additional highlights include central air, mudroom off 2-car garage, updated baths, & enhanced insulation throughout. Conveniently located near Winchester Center & the train station, this move-in ready home offers comfort, elegance, and everyday convenience!

73 Grove St, Winchester

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

10 Bonad Road, Winchester

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

38 Salem Street Unit 38, Winchester

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

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.