Middlesex, MA Homes

/40
$2,199,000
- 5 Beds
- 3.5 Baths
- 6,232 Sq Ft
5 Azalea Rd, Winchester, MA 01890

NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials

Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

5 Azalea Rd, Winchester, MA 01890
Explore West Side
/20

$2,585 - $7,000 per month

Sanctuary Winchester West

Studio - 3 Beds

416 Cambridge St, Winchester, MA 01890

The Sanctuary at Winchester West makes living your best life as easy as walking through your front door. Contemporary design and state-of-the-art amenities offer modern luxury at your fingertips. With shopping and a Whole Foods right next door, this community provides convenience at every turn.

416 Cambridge St, Winchester, MA 01890
/42
$2,500,000 Sold Aug 27, 2025
- 4,215 Sq Ft
- $593/SF
- 4 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1955
12 Olde Lyme Rd, Winchester, MA 01890

*** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates

Mary Beth McGillicuddy Engel & Völkers , South Shore

12 Olde Lyme Rd, Winchester, MA 01890

/42
Est $2,853,598 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 6,265 Sq Ft
228 Ridge St, Winchester, MA 01890

228 Ridge St, Winchester, MA 01890

/38
$2,350,000
- 5 Beds
- 3.5 Baths
- 5,006 Sq Ft
276 High St, Winchester, MA 01890

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

Kim Covino Compass

276 High St, Winchester, MA 01890
/3
$4,800 per month
- 3 Beds
- 2.5 Baths
- 2,339 Sq Ft
- House for Rent
12 Trinity Rd, Winchester, MA 01890

Don’t miss the opportunity to lease this beautifully maintained multi-level single-family home, nestled on a quiet and private dead-end street. Recently updated with fresh interior paint and refinished hardwood floors, this spacious residence offers over 2,300 square feet of comfortable living space. Enjoy central A/C, a generous kitchen with an open-concept dining area—perfect for both everyday

Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

12 Trinity Rd, Winchester, MA 01890
/33
$1,240,000 Sold Aug 20, 2025
- 2,570 Sq Ft
- $482/SF
- 9 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1966
3 Socrates Way, Winchester, MA 01890

Unlock the potential of this tri-level home in one of Winchester’s sought-after neighborhoods! Set on a 20,000 sq ft lot, this 4 bed, 2.5 bath, 1966-built home offers 2,116 sf of living space, a 2 car garage, & endless possibilities for renovation or redevelopment. The main level features a formal living room, dining room, & kitchen leading to a deck overlooking the backyard. A cozy family room

Pirani & Wile Group Advisors Living - Winchester

3 Socrates Way, Winchester, MA 01890

/30
Est $1,977,719 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,696 Sq Ft
5 Squire Rd, Winchester, MA 01890

5 Squire Rd, Winchester, MA 01890

/41
$1,900,000
- 4 Beds
- 5 Baths
- 5,361 Sq Ft
4 Aricia Ln, Winchester, MA 01890

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

The McLaren D'Agostino Team Compass

4 Aricia Ln, Winchester, MA 01890
/24
$6,900 per month
- 4 Beds
- 4 Baths
- 3,639 Sq Ft
- House for Rent
31 Coolidge Rd, Winchester, MA 01890

Welcome to this beautifully renovated and maintained colonial at a very quiet street in a desirable neighborhood with easy commute to schools, Boston, highways and MBTA train stations. The 1st floor offers a foyer with formal dining room and living room in either sides. The kitchen, with island and full breakfast/dining area, flows into a family room that transitions to a private office with

Carlos Xu Lexwin Realty

31 Coolidge Rd, Winchester, MA 01890
/19
$1,820,000 Sold Aug 19, 2025
- 3,784 Sq Ft
- $481/SF
- 5 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1974
109 Thornberry Rd, Winchester, MA 01890

Ideally located in one of Winchester’s most desirable neighborhoods, this classic Colonial blends timeless design with thoughtful updates. At the heart of the home, the beautifully updated kitchen features a generous center island, opening to a spacious family room with a slider leading to a large deck overlooking the expansive, level backyard - perfect for summer entertaining. Just off the

Andrew Martini Compass

109 Thornberry Rd, Winchester, MA 01890

/40
Est $1,371,759 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,529 Sq Ft
15 Wincrest Dr, Winchester, MA 01890

15 Wincrest Dr, Winchester, MA 01890

/42
$1,999,000 Pending
- 4 Beds
- 3.5 Baths
- 4,731 Sq Ft
6 Samoset Rd, Winchester, MA 01890

Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up

Anne Spry Barrett Sotheby's International Realty

6 Samoset Rd, Winchester, MA 01890
/26
$8,800 per month
- 4 Beds
- 3.5 Baths
- 3,500 Sq Ft
- House for Rent
35 Thornberry Rd, Winchester, MA 01890

One Month Free and No Broker Fee! Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms,

Frank Celeste Gibson Sotheby's International Realty

35 Thornberry Rd, Winchester, MA 01890
/42
$1,775,000 Sold Aug 15, 2025
- 3,150 Sq Ft
- $563/SF
- 6 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1961
19 Pilgrim Dr, Winchester, MA 01890

Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

Gorfinkle Group eXp Realty

19 Pilgrim Dr, Winchester, MA 01890

/33
Est $1,549,030 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,034 Sq Ft
10 Carriage Ln, Winchester, MA 01890

10 Carriage Ln, Winchester, MA 01890

/42
$2,349,900 Pending
- 5 Beds
- 5 Baths
- 3,940 Sq Ft
17 Wagon Wheel Rd, Winchester, MA 01890

Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends

Yifei Wang Dreamega International Realty LLC

17 Wagon Wheel Rd, Winchester, MA 01890
/38
$1,627,000 Sold Jul 31, 2025
- 2,853 Sq Ft
- $570/SF
- 7 Days On Market
- 5 Beds
- 4 Baths
- Built 1930
32 Oneida Rd, Winchester, MA 01890

Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

32 Oneida Rd, Winchester, MA 01890

/42
Est $1,469,914 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,125 Sq Ft
47 Thornberry Rd, Winchester, MA 01890

47 Thornberry Rd, Winchester, MA 01890

/36
$1,980,000 Pending
- 5 Beds
- 3.5 Baths
- 4,378 Sq Ft
4 Fieldstone Dr, Winchester, MA 01890

Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, and over 20,000 sq ft of beautifully landscaped grounds. The sun-drenched interior features an open-concept kitchen and dining room with five fully opening doors leading to a bright four-seasons sunroom—perfect for gatherings year-round.

Wenli Zheng Fairview Partners International LLC

4 Fieldstone Dr, Winchester, MA 01890
/42
$1,650,000 Sold Jul 30, 2025
- 2,646 Sq Ft
- $624/SF
- 18 Days On Market
- 3 Beds
- 4 Baths
- Built 1957
50 Johnson Rd, Winchester, MA 01890

One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins.

Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

50 Johnson Rd, Winchester, MA 01890

/35
Est $1,664,154 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,926 Sq Ft
16 Nassau Dr, Winchester, MA 01890

16 Nassau Dr, Winchester, MA 01890

/33
$3,600,000
- 6 Beds
- 7.5 Baths
- 8,866 Sq Ft
20 Amberwood Dr, Winchester, MA 01890

Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

Wei Wang WW Real Estate LLC

20 Amberwood Dr, Winchester, MA 01890
/40
$1,551,000 Sold Jul 15, 2025
- 3,186 Sq Ft
- $487/SF
- 5 Days On Market
- 3 Beds
- 4.5 Baths
- Built 1988
7 Wainwright Rd Unit 13, Winchester, MA 01890

Welcome to The Ledges, Winchester’s premier townhouse community! This extraordinary F Style corner unit is truly one of a kind with soaring ceilings, sun-filled spaces, and rare flat backyard space with two decks. A landscaped courtyard leads to a gracious foyer and transitions into an expansive open layout. The chef’s kitchen opens to the dining rm and features ss appliances, granite countertops

Nancy Pallotta Advisors Living - Winchester

7 Wainwright Rd Unit 13, Winchester, MA 01890

/36
Est $1,594,158 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,171 Sq Ft
94 Johnson Rd, Winchester, MA 01890

94 Johnson Rd, Winchester, MA 01890

/35
$1,379,000
- 5 Beds
- 2 Baths
- 3,033 Sq Ft
7 Thornberry Rd, Winchester, MA 01890

Priced to SELL this newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept

Kim Covino Compass

7 Thornberry Rd, Winchester, MA 01890
/37
$1,390,000 Sold Jul 15, 2025
- 2,388 Sq Ft
- $582/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1963
26 Ridge St, Winchester, MA 01890

Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and offers both comfort and style. The newly renovated kitchen features upscale appliances and custom quartz countertops, perfect for everyday living and entertaining alike.Hardwood floors, two fireplaces, a sunlit living room, and a separate family room create inviting spaces

Dream Team Dreamega International Realty LLC

26 Ridge St, Winchester, MA 01890

/32
Est $1,618,198 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,622 Sq Ft
104 Thornberry Rd, Winchester, MA 01890

104 Thornberry Rd, Winchester, MA 01890

/24
$1,249,900
- 3 Beds
- 2.5 Baths
- 2,458 Sq Ft
59 Johnson Rd, Winchester, MA 01890

Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and

Angela Zhang Greatland Real Estate LLC

59 Johnson Rd, Winchester, MA 01890
/42
$1,540,000 Sold Jul 11, 2025
- 2,814 Sq Ft
- $547/SF
- 5 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1970
21 Johnson Rd, Winchester, MA 01890

This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring all 4 bedrooms on the second floor, the layout includes a spacious primary w/ an en-suite bath as well as a fully updated hall bath. The main level offers an elegant family room w/ soaring ceilings, a cozy fireplace, recessed lighting & a slider leading to the deck. The

Stefanie Clifford Keller Williams Realty Boston Northwest

21 Johnson Rd, Winchester, MA 01890

/34
Est $2,046,384 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,000 Sq Ft
133 Johnson Rd, Winchester, MA 01890

133 Johnson Rd, Winchester, MA 01890

/42
$3,799,900
- 7 Beds
- 7.5 Baths
- 7,429 Sq Ft
11 Viking Rd, Winchester, MA 01890

Prepare to be captivated by the elegance of 11 Viking Rd. This magnificent home, boasting over 7,000 square feet of luxurious living space, offers an unparalleled opportunity for discerning buyers seeking the ultimate in comfort, style, and sophistication.Step inside and discover a world of meticulous details and thoughtful design. With 7 generously sized bedrooms and 7.5 exquisitely appointed

The McLaren D'Agostino Team Compass

11 Viking Rd, Winchester, MA 01890
/16
$1,050,000 Sold Jul 11, 2025
- 2,621 Sq Ft
- $401/SF
- 48 Days On Market
- 4 Beds
- 2 Baths
- Built 1952
61 Westland Ave, Winchester, MA 01890

Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

61 Westland Ave, Winchester, MA 01890

/39
Est $1,911,815 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,046 Sq Ft
73 Thornberry Rd, Winchester, MA 01890

73 Thornberry Rd, Winchester, MA 01890

/42
$3,699,000
- 7 Beds
- 7.5 Baths
- 7,982 Sq Ft
54 Johnson Rd, Winchester, MA 01890

This newly constructed home faces Old Village Dr. & 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

Kim Covino Compass

54 Johnson Rd, Winchester, MA 01890
/39
$2,200,000 Sold Jun 30, 2025
- 3,818 Sq Ft
- $576/SF
- 0 Days On Market
- 4 Beds
- 4 Baths
- Built 1967
1 Saint Augustine Ct, Winchester, MA 01890

Tucked away on a private cul-de-sac shared with just two lucky neighbors, this classic New England Colonial is the total package. With 4 bedrooms, 3 baths, and gleaming hardwood floors throughout, it strikes the perfect balance between timeless charm and fresh, move-in-ready style. The front-to-back living room is flooded with natural light—ideal for everything from morning coffee to impromptu

Nancy Pallotta Advisors Living - Winchester

1 Saint Augustine Ct, Winchester, MA 01890

/35
Est $1,809,180 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,224 Sq Ft
22 Berkshire Dr, Winchester, MA 01890

22 Berkshire Dr, Winchester, MA 01890

/42
$1,599,000 Pending
- 3 Beds
- 2.5 Baths
- 2,541 Sq Ft
9 Pilgrim Dr, Winchester, MA 01890

Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

9 Pilgrim Dr, Winchester, MA 01890
/40
$1,877,000 Sold Jun 30, 2025
- 2,813 Sq Ft
- $667/SF
- 26 Days On Market
- 3 Beds
- 2 Baths
- Built 1930
20 Seneca Rd, Winchester, MA 01890

Welcome home to this picture-perfect Colonial, tucked away in a quiet, sought-after neighborhood just steps from Ambrose! Boasting gorgeous curb appeal & a warm, welcoming feel, this home offers the best of comfort & convenience.Step inside to a bright & open first floor designed for effortless entertaining, featuring oversized windows that flood the space with amazing natural light.The spacious

Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

20 Seneca Rd, Winchester, MA 01890

/42
Est $2,246,527 Not Listed For Sale
- 5 Beds
- 4 Baths
- 4,620 Sq Ft
5 Partridge Ln, Winchester, MA 01890

5 Partridge Ln, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County Winchester West Side

Learn more about living in West Side

Home Trends in West Side, MA

On average, homes in West Side, Winchester sell after 22 days on the market compared to the national average of 52 days. The median sale price for homes in West Side, Winchester over the last 12 months is $1,589,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,589,000

Median Single Family Sale Price

$1,773,024

Median 2 Bedroom Sale Price

$1,070,000

Average Price Per Sq Ft

$497

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.80

Median List Price

$1,637,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

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