Homes for Sale in 01890

/42
$1,350,000

Open Sat 1PM - 3PM
- 4 Beds
- 3 Baths
- 2,690 Sq Ft
423 Washington St, Winchester, MA 01890

Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The inviting living room is enhanced by a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast

Danielle Fleming MA Properties

423 Washington St, Winchester, MA 01890
/36
$999,900

Open Thu 4:30PM - 5:30PM
- 4 Beds
- 2 Baths
- 1,719 Sq Ft
258 Cross St, Winchester, MA 01890

Welcome to 258 Cross Street, a masterfully updated Winchester Colonial blending timeless character, modern comfort, and everyday function. Set on a level, fenced corner lot, this 4 bed, 2 bath home offers endless outdoor opportunity to relax, entertain, play, or dine al fresco. Inside, hardwood floors, crown molding, arched openings, bay windows, and ornate detail bring warmth and personality.

Justin Blankenship

Fiv Realty Co

258 Cross St, Winchester, MA 01890
/40
$2,380,000

Open Sat 2:30PM - 4PM
- 4 Beds
- 4.5 Baths
- 3,881 Sq Ft
14 Hillside Ave, Winchester, MA 01890

Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom

Rebecca Huang William Raveis R.E. & Home Services

14 Hillside Ave, Winchester, MA 01890
/42
$1,100,000

Open Sat 12:30PM - 1:30PM
- 4 Beds
- 2 Baths
- 2,085 Sq Ft
41 Cross St, Winchester, MA 01890

Freshly painted side-entrance Colonial offering space, flexibility, and a prime Winchester location. The expansive eat-in kitchen flows seamlessly into the dining area and family room, creating an ideal layout for everyday living and entertaining. The main level includes a bedroom or office, full bath, mudroom with laundry, and is well-suited for one-level living. Upstairs features three

Andersen Group Realty Keller Williams Realty Boston Northwest

41 Cross St, Winchester, MA 01890
/2
$1,099,000
- 3 Beds
- 1.5 Baths
- 1,711 Sq Ft
150 Cambridge St, Winchester, MA 01890

Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for

Diane Plunkett Plunkett Properties

150 Cambridge St, Winchester, MA 01890
/7
$374,900
- 1 Bed
- 1 Bath
- 606 Sq Ft
200 Swanton St Unit 412, Winchester, MA 01890

Welcome to this well-maintained 1-bedroom, 1-bathroom condo in the highly desirable Winchester Parkview community. Offering comfortable living at an affordable price, this inviting home is located in a professionally managed building with excellent amenities, including elevator service, on-site management, and an in-ground swimming pool. The HOA fee covers heat, AC, hot water, and electricity,

Wei Wang

WW Real Estate LLC

200 Swanton St Unit 412, Winchester, MA 01890
/41
$1,725,000

Open Thu 5:30PM - 6:30PM
- 5 Beds
- 3.5 Baths
- 3,722 Sq Ft
117 Highland Ave, Winchester, MA 01890

Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and

Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

117 Highland Ave, Winchester, MA 01890
/36
$2,199,000

Open Sat 12:30PM - 1:30PM
- 4 Beds
- 3.5 Baths
- 3,210 Sq Ft
26 N Gateway, Winchester, MA 01890

Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the

Pirani & Wile Group Gibson Sotheby's International Realty

26 N Gateway, Winchester, MA 01890
/35
$1,649,000
- 4 Beds
- 3.5 Baths
- 2,768 Sq Ft
10 Farrow St, Winchester, MA 01890

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

Collin Bray Century 21 Cityside

10 Farrow St, Winchester, MA 01890
/38
$1,699,000
- 4 Beds
- 3 Baths
- 2,707 Sq Ft
11 Carriage Ln, Winchester, MA 01890

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

Kim Covino Compass

11 Carriage Ln, Winchester, MA 01890
/32
$1,225,000

Open Sat 12:30PM - 1:30PM
- 3 Beds
- 3 Baths
- 1,736 Sq Ft
38 Robinhood Rd, Winchester, MA 01890

Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open

Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

38 Robinhood Rd, Winchester, MA 01890
/42
$1,999,900

Open Thu 4:30PM - 6PM
- 4 Beds
- 3.5 Baths
- 3,286 Sq Ft
15 Fieldstone Dr, Winchester, MA 01890

Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless

Anne Spry Barrett Sotheby's International Realty

15 Fieldstone Dr, Winchester, MA 01890
/42
$3,199,000
- 5 Beds
- 4.5 Baths
- 5,406 Sq Ft
10 Rangeley Rd, Winchester, MA 01890

Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a

Karima Alami Compass

10 Rangeley Rd, Winchester, MA 01890
/42
$2,400,000
- 5 Beds
- 3.5 Baths
- 4,591 Sq Ft
21 Willowdale Rd, Winchester, MA 01890

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

Kim Covino Compass

21 Willowdale Rd, Winchester, MA 01890
/32
$1,330,000
- 3 Beds
- 3 Baths
- 2,145 Sq Ft
7 Wainwright Rd Unit 47, Winchester, MA 01890

Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub.

Felicity Tuttle Better Homes and Gardens Real Estate - The Shanahan Group

7 Wainwright Rd Unit 47, Winchester, MA 01890
/39
$3,799,000
- 6 Beds
- 7.5 Baths
- 6,000 Sq Ft
29 Ginn Rd, Winchester, MA 01890

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

The Boston ONE Team Serhant

29 Ginn Rd, Winchester, MA 01890
/41
$1,899,000
- 4 Beds
- 2.5 Baths
- 3,091 Sq Ft
9 Brookside Place, Winchester, MA 01890

This completely remodeled home is nestled on a dead end street off Brookside Road, offering a serene/ natural setting with unmatched privacy. This home offers 4 bedrooms, and 2.5 baths with three spacious finished levels. The completely reimagined open concept main floor features a stunning kitchen open to dining area and large family room, plus a separate living room, mudroom, half bath and

Kim Covino Compass

9 Brookside Place, Winchester, MA 01890
/12
$829,000
- Land
- 19,166 Sq Ft
- $1,884,091 per Acre
14 Cross St, Woburn, MA 01801

Improved Land Opportunity - Developers, Contractors, Investors and Future single-family homeowners – recently reconfigured 14 Cross Street located immediately over the WINCHESTER line is an attractive sized residential lot consisting of 19,277 square feet of land (see attached recorded plan, Lot 1) Lot is zoned R-2 (Per Building Department - single or 2 family residential structure permitted.)

Donna Bozza Barrett Sotheby's International Realty

14 Cross St, Woburn, MA 01801
/30
$729,000

Open Sat 11AM - 12PM
- 2 Beds
- 2.5 Baths
- 1,431 Sq Ft
171 Swanton St Unit 7, Winchester, MA 01890

Easy living awaits at The Village, where this well-maintained, freshly painted, townhouse offers a functional layout, desirable amenities, and a convenient Winchester location. The main level features hardwood floors, an oversized living room with gas fireplace, an open dining area, and kitchen with direct access to a private patio overlooking the beautifully landscaped grounds. A half bath and

Pirani & Wile Group Gibson Sotheby's International Realty

171 Swanton St Unit 7, Winchester, MA 01890
/41
$699,900

$49K PRICE DROP
- 3 Beds
- 4 Baths
- 1,380 Sq Ft
23 Shepard Ct Unit U23, Winchester, MA 01890

Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, 2 half baths, and a flexible third-floor suite perfect as a primary bedroom, guest space, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019

Nancy Zhang Zhenning Fairview Partners International LLC

23 Shepard Ct Unit U23, Winchester, MA 01890
/39
$1,499,000

$51K PRICE DROP
- 5 Beds
- 5 Baths
- 3,360 Sq Ft
7 Ridge St, Winchester, MA 01890

Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds

Paul Cirignano The Synergy Group

7 Ridge St, Winchester, MA 01890
/42
$2,529,000

$70K PRICE DROP Pre-Foreclosure
- 5 Beds
- 3.5 Baths
- 5,230 Sq Ft
78 Bacon St, Winchester, MA 01890

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,

Kim Covino Compass

78 Bacon St, Winchester, MA 01890
/40
$1,799,000
- 4 Beds
- 3 Baths
- 3,366 Sq Ft
94 Johnson Rd, Winchester, MA 01890

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

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

94 Johnson Rd, Winchester, MA 01890
/12
$2,399,000

Open Sat 11AM - 12PM $400K PRICE DROP
- 5 Beds
- 4 Baths
- 5,083 Sq Ft
53 Winford Way, Winchester, MA 01890

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

Andersen Group Realty Keller Williams Realty Boston Northwest

53 Winford Way, Winchester, MA 01890
/19
$505,000

Open Sat 12PM - 1PM
- 2 Beds
- 1 Bath
- 822 Sq Ft
200 Swanton St Unit 303, Winchester, MA 01890

Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and

Joan Powell

REMAX Andrew Realty Services

200 Swanton St Unit 303, Winchester, MA 01890
/27
$1,850,000

Open Sat 11AM - 12:30PM $75K PRICE DROP
- 5 Beds
- 4 Baths
- 3,315 Sq Ft
8 Hawthorne Rd, Winchester, MA 01890

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.

Elaine Song Coldwell Banker Realty - Lexington

8 Hawthorne Rd, Winchester, MA 01890
/13
$414,500
- 2 Beds
- 1 Bath
- 1,121 Sq Ft
22 Arthur St, Winchester, MA 01890

This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped

Karen Morand MCO Realty Service, LLC

22 Arthur St, Winchester, MA 01890
/38
$3,600,000

Open Sat 12:30PM - 1:45PM
- 6 Beds
- 6.5 Baths
- 7,400 Sq Ft
2 Atherton Rd, Winchester, MA 01890

This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is

Brooke Zarbano Regatta Realty

2 Atherton Rd, Winchester, MA 01890
/36
$1,199,000

$26K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,235 Sq Ft
53 Lake St, Winchester, MA 01890

Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

Kim Covino Compass

53 Lake St, Winchester, MA 01890
/32
$2,795,000

Open Sun 1PM - 2:30PM
- 4 Beds
- 4.5 Baths
- 5,233 Sq Ft
18 Middlesex St, Winchester, MA 01890

This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the

Tina Natale Luxury Living Real Estate

18 Middlesex St, Winchester, MA 01890
/33
$1,150,000
- 5 Beds
- 3 Baths
- 2,186 Sq Ft
63-65 Harvard St, Winchester, MA 01890

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

Beth Sager Group Keller Williams Realty Boston Northwest

63-65 Harvard St, Winchester, MA 01890
/35
$3,149,000

Open Sun 12PM - 2PM $101K PRICE DROP
- 5 Beds
- 5.5 Baths
- 6,500 Sq Ft
8 Priscilla Ln, Winchester, MA 01890

Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef’s kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and

The Pezzano Group Rise Signature Homes

8 Priscilla Ln, Winchester, MA 01890
/31
$1,199,000

Open Sat 10AM - 12PM $100K PRICE DROP
- 3 Beds
- 3.5 Baths
- 2,420 Sq Ft
129 Washington St Unit 131, Winchester, MA 01890

Prime Winchester location just moments from Winchester Center, within walking distance to elementary, middle, high school, downtown and commuter rail. Ideal for commuters and locals alike. This townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that

The Mary Scimemi Team Leading Edge Real Estate

129 Washington St Unit 131, Winchester, MA 01890
/42
$2,450,000

$145K PRICE DROP
- 4 Beds
- 3.5 Baths
- 4,403 Sq Ft
50 Brooks St, Winchester, MA 01890

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 &

Kim Covino Compass

50 Brooks St, Winchester, MA 01890
/36
$2,000,000
- 6 Beds
- 5 Baths
- 3,403 Sq Ft
6 Ivy Cir, Winchester, MA 01890

Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

Valerie Post Engel & Volkers Boston

6 Ivy Cir, Winchester, MA 01890
/41
$2,099,000

$101K PRICE DROP
- 6 Beds
- 4.5 Baths
- 6,900 Sq Ft
16 Glenwood Ave, Winchester, MA 01890

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

Kim Covino Compass

16 Glenwood Ave, Winchester, MA 01890
/41
$2,099,000

$101K PRICE DROP
- 6 Beds
- 4.5 Baths
- 6,900 Sq Ft
16 & 16A Glenwood Ave, Winchester, MA 01890

Must see! sprawling 2-3 family beautifully renovated & expanded home 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,

Kim Covino Compass

16 & 16A Glenwood Ave, Winchester, MA 01890
/40
$3,379,000
- 7 Beds
- 7.5 Baths
- 8,540 Sq Ft
37 Mayflower Rd, Winchester, MA 01890

Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

Kim Covino Compass

37 Mayflower Rd, Winchester, MA 01890
/36
$2,799,000

$51K PRICE DROP
- 6 Beds
- 7 Baths
- 6,968 Sq Ft
14 Nassau Dr, Winchester, MA 01890

Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

Weidong Li WINN Real Estate & Consulting

14 Nassau Dr, Winchester, MA 01890
/30
$364,900
- 1 Bed
- 1 Bath
- 613 Sq Ft
200 Swanton St Unit 717, Winchester, MA 01890

Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

Cameron Moniz Coldwell Banker Realty - Lexington

200 Swanton St Unit 717, Winchester, MA 01890

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Massachusetts Middlesex County Winchester 01890

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