Middlesex, MA Homes

/32
$1,475,000 Open Sat 11AM - 1PM
- 4 Beds
- 2.5 Baths
- 2,590 Sq Ft
7 Sherman Place, Winchester, MA 01890

Welcome to this exceptional 4-bedroom, 2.5 bath townhome on a cul-de-sac with idyllic private garden, feels like a single-family. This 2,500+ SF, sun-filled, open concept design provides ample space for family living & entertaining. Features include 9ft high ceilings, gas fireplace & oversized windows throughout. Chef’s kitchen w/ expansive granite countertops & upgraded appliances. Dining room

Ides Figueiredo Coldwell Banker Realty - Brookline

7 Sherman Place, Winchester, MA 01890
Explore North Main
/33
$6,900 per month
- 4 Beds
- 3.5 Baths
- 2,800 Sq Ft
- House for Rent
37 Rumford St, Winchester, MA 01890

This 4-bed,3.5-bath custom-designed and built in 2012 townhouse feels like a single family. Step onto the welcoming farmer’s porch into an open, airy layout with natural light streaming through large windows. It features gleaming wood floors and a chef’s kitchen with stainless steel appliances, granite countertops, custom cabinets, and a beautifully designed kitchen island. Living room has a

37 Rumford St, Winchester, MA 01890
/32
$1,280,000 Sold Jul 16, 2025
- 2,137 Sq Ft
- $599/SF
- 21 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2015
18 Hemingway St, Winchester, MA 01890

This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st

Julia Xie Keller Williams Realty-Merrimack

18 Hemingway St, Winchester, MA 01890

/39
Est $1,231,071 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,664 Sq Ft
10 Chesterford Rd E, Winchester, MA 01890

10 Chesterford Rd E, Winchester, MA 01890

/40
$1,199,000 Pending
- 4 Beds
- 2.5 Baths
- 2,566 Sq Ft
70 Woodside Rd, Winchester, MA 01890

Have you ever dreamed of owning a house with a white picket fence? Here it is! Eight rooms, four bedrooms, 2.5 baths. Corner lot with backyard patio, shed and one car garage. The large living room with many windows and a fireplace opens to the dining room. French doors from the dining room lead to a room that can be used as a family room, play room for the kids, or another bedroom. The

Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

70 Woodside Rd, Winchester, MA 01890
/33
$8,450 per month
- 4 Beds
- 3.5 Baths
- 3,500 Sq Ft
- House for Rent
10 Farrow St, Winchester, MA 01890

Single Family Home rental in Winchester. NO BROKERS FEE. Available 8/5, 8/15, 9/1. Completely rebuilt from ground up in 2019 w/Attached 1 Car Garage. 4 Beds, 3.5 baths & 3500SF w/ 2 dedicated home offices. Modern kitchen w/Quartz Countertops, Stainless Steel Appliances & Venting for cooking. Open concept has an Island connecting dining & living spaces. Sundrenched Living Room offers a wood

Collin Bray Century 21 Cityside

10 Farrow St, Winchester, MA 01890
/39
$2,200,000 Sold Jul 14, 2025
- 3,896 Sq Ft
- $565/SF
- 11 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2016
4 Fairfield Place, Winchester, MA 01890

NEWER CONSTRUCTION 4 bed 3.5 bath colonial located in a great neighborhood right outside Winchester center! Enjoy all the area has to offer just outside your door including restaurants, shops, schools, train to Boston, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! This warm and welcoming, gently lived in home showcases 3900sf of space on 3 levels with 4 large

Kim Covino Compass

4 Fairfield Place, Winchester, MA 01890

/42
Est $1,168,931 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,657 Sq Ft
8 Chesterford Rd E, Winchester, MA 01890

8 Chesterford Rd E, Winchester, MA 01890

/39
$1,149,000 Pending
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
83 Canal St Unit 85, Winchester, MA 01890

This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary

Mary O'Hagan Barrett Sotheby's International Realty

83 Canal St Unit 85, Winchester, MA 01890
/4
$2,650 per month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- House for Rent
7 Salem St, Winchester, MA 01890

Charming "doll house" cottage. Lovely, historic one-bedroom home situated on conveniently located lot in beautiful Winchester. Walk to restaurants, MBTA buses & trains. 2 Off street Parking spaces.

7 Salem St, Winchester, MA 01890
/40
$1,635,000 Sold Jul 11, 2025
- 2,470 Sq Ft
- $662/SF
- 6 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2012
35 Rumford St Unit 35, Winchester, MA 01890

This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering—whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High

Elena Langlois Compass

35 Rumford St Unit 35, Winchester, MA 01890

/35
Est $1,944,959 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,846 Sq Ft
12 Ardley Place, Winchester, MA 01890

12 Ardley Place, Winchester, MA 01890

/40
$1,600,000 Pending
- 5 Beds
- 2 Baths
- 2,331 Sq Ft
149 Horn Pond Brook Rd, Winchester, MA 01890

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

Nancy McLaughlin Redfin Corp.

149 Horn Pond Brook Rd, Winchester, MA 01890
/35
$7,500 per month
- 3 Beds
- 2.5 Baths
- 2,900 Sq Ft
- Apartment for Rent
846 Main St Unit III, Winchester, MA 01890

No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

Anthony Marino The Marino Group Collection

846 Main St Unit III, Winchester, MA 01890
/34
$2,000,000 Sold Jun 02, 2025
- 3,039 Sq Ft
- $658/SF
- 7 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1927
11 Chesterford Rd E, Winchester, MA 01890

Stunning waterfront home on Little Winter Pond offers the perfect blend of modern design and serene natural beauty! Thoughtfully updated, the home welcomes you with a striking entry, soaring vaulted ceilings, and walls of windows that flood the space with natural light and frame breathtaking pond views. The stylish kitchen with adjacent dining area featuring custom bench seating flows seamlessly

Joseph Pollack Redfin Corp.

11 Chesterford Rd E, Winchester, MA 01890

/37
Est $1,412,415 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,350 Sq Ft
8 Parker Rd, Winchester, MA 01890

8 Parker Rd, Winchester, MA 01890

/35
$1,060,000 Pending
- 5 Beds
- 2.5 Baths
- 2,849 Sq Ft
62 Richardson St, Winchester, MA 01890

Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/

Frank Ventresca Strategy Street

62 Richardson St, Winchester, MA 01890
/33
$4,000 per month
- 4 Beds
- 1.5 Baths
- 1,300 Sq Ft
- Townhouse for Rent
848 Main St, Winchester, MA 01890

**Elegant Winchester Home Near Wright Pond and Downtown Amenities**Spacious 4-bedroom, 1.5-bathroom townhouse style unit - located close to Winchester Center, with a park across the street and Wright Pond and Park nearby.Enjoy top rated Winchester schools nearby.Open-concept kitchen with granite countertops, island, pantry, and space for your table, plus hardwood floors, central

848 Main St, Winchester, MA 01890
/33
$699,900 Sold May 30, 2025
- 1,326 Sq Ft
- $528/SF
- 4 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1890
32 Clark St, Winchester, MA 01890

A true diamond in the rough, Whether you're a first-time homebuyer, a savvy investor, or someone looking to customize a home to their liking, this residence presents the perfect blend of potential and location. This 2 bedroom single family home makes for a great condo alternative. Don't miss this rare chance to break into the Winchester market and enjoy all this town has to offer from it's great

Rodrigo Serrano Leading Edge Real Estate

32 Clark St, Winchester, MA 01890

/39
Est $1,679,968 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,592 Sq Ft
59 Woodside Rd, Winchester, MA 01890

59 Woodside Rd, Winchester, MA 01890

/36
$7,500 per month
- 3 Beds
- 2.5 Baths
- 2,900 Sq Ft
- Apartment for Rent
846 Main St Unit IV, Winchester, MA 01890

No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

Anthony Marino The Marino Group Collection

846 Main St Unit IV, Winchester, MA 01890
/31
$948,000 Sold May 29, 2025
- 1,469 Sq Ft
- $645/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1928
79 Sylvester Ave, Winchester, MA 01890

Discover where form meets function in this beautifully maintained home, ideally located near Winchester Center. Nestled on a neighborhood street, with Horn Pond, bike paths, local schools, commuter rail, & downtown shops just moments away, this home offers a quintessential location. Thoughtfully updated, the kitchen, exterior, and bedrooms reflect pride of ownership, showcasing care and attention

Anne Spry Barrett Sotheby's International Realty

79 Sylvester Ave, Winchester, MA 01890

/29
Est $1,089,778 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,630 Sq Ft
7 Brantwood Rd, Winchester, MA 01890

7 Brantwood Rd, Winchester, MA 01890

/36
$1,600,000 Sold Apr 30, 2025
- 2,809 Sq Ft
- $570/SF
- 7 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2004
24 Water St, Winchester, MA 01890

Discover the warmth and charm of this inviting New England Colonial, newly built in 2004. This sun-filled home features three bedrooms, 3.5 bathrooms, and a flexible floor plan. First floor features a large family room, dining room, updated kitchen with SS appliances, abundant custom cabinetry, a half bath, mudroom, and a separate living room. Second floor offers a sizable primary suite with a

Domingo Medina Coldwell Banker Realty - Lexington

24 Water St, Winchester, MA 01890

/40
Est $1,764,175 Not Listed For Sale
- 4 Beds
- 2 Baths
- 3,395 Sq Ft
4 Ardley Rd, Winchester, MA 01890

4 Ardley Rd, Winchester, MA 01890

/42
$2,200,000 Sold Mar 07, 2025
- 3,676 Sq Ft
- $598/SF
- 12 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1940
6 Ardley Place, Winchester, MA 01890

Tucked away on a dead-end street, 6 Ardley Place blends classic character with modern comforts. Beautifully expanded with a complete renovation & redesign in 2013, this home offers a warm & inviting atmosphere w/elegant finishes throughout. The heart of the home is a stunning chef’s kitchen, featuring a 10 foot walnut island, Viking gas stove, beautiful cabinetry, & flows into the family room

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

6 Ardley Place, Winchester, MA 01890

/40
Est $1,266,828 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,202 Sq Ft
71 Woodside Rd, Winchester, MA 01890

71 Woodside Rd, Winchester, MA 01890

/25
$1,450,000 Sold Feb 10, 2025
- 2,632 Sq Ft
- $551/SF
- 3 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1911
48 Water St Unit 50, Winchester, MA 01890

Embrace elegance and convenience with this exquisite townhouse that's been meticulously designed. This residence presents a generous 4-bedroom, 3.5-bathroom, ample space for relaxation and entertainment across its three expansive levels. The heart of this home is the open floor plan, where natural light cascades over fine finishes that align with the rhythm of your daily life. Culinary

Chris Kostopoulos Keller Williams Realty

48 Water St Unit 50, Winchester, MA 01890

/22
Est $1,429,194 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,495 Sq Ft
166 Pond St, Winchester, MA 01890

166 Pond St, Winchester, MA 01890

/42
$2,799,000 Sold Jan 30, 2025
- 4,324 Sq Ft
- $647/SF
- 68 Days On Market
- 5 Beds
- 6 Baths
- Built 1938
16 Ardley Place, Winchester, MA 01890

Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene cul-de-sac & private hilltop oasis just minutes from the new Lynch Elementary School opening in 2025. Enjoy proximity to Horn Pond recreation areas & seasonal views of Winter Pond. Featuring 5 Bed,4 Full baths, 2-half with 2 ensuites plus a

Ann Norberg Coldwell Banker Realty - Lexington

16 Ardley Place, Winchester, MA 01890

/42
Est $2,538,223 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 4,659 Sq Ft
10 Norfolk Rd, Winchester, MA 01890

10 Norfolk Rd, Winchester, MA 01890

/25
$1,000,000 Sold Dec 23, 2024
- 2,355 Sq Ft
- $425/SF
- 11 Days On Market
- 6 Beds
- 4 Baths
- Built 1900
37-39 Middlesex St, Winchester, MA 01890

Motivated Sellers! Wonderful 2 Family on a quiet side street area just off Wedge Pond. Welcome to 37 - 39 Middlesex Street, Winchester. Lack of inside pictures is to protect privacy of the tenants and NOT an indication of poor condition. This is a very solid Two-Family Large Backyard with tremendous privacy behind property abutting Town owned land. Reciprocal side by side duplex with separate

Craig Celli Century 21 North East

37-39 Middlesex St, Winchester, MA 01890

/42
Est $1,747,167 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 3,180 Sq Ft
85 Pond St, Winchester, MA 01890

85 Pond St, Winchester, MA 01890

/24
$962,000 Sold Dec 18, 2024
- 1,890 Sq Ft
- $509/SF
- 21 Days On Market
- 3 Beds
- 2 Baths
- Built 1969
25 Hemingway St, Winchester, MA 01890

Discover the potential of this charming and well-maintained 2-story Cape-style home, offering both comfort and privacy in a highly desirable Winchester location. Conveniently situated near a public elementary school, public transportation, healthcare services, and a variety of dining options, this home ensures easy access to everything you need. Featuring 3 spacious bedrooms and 2 full baths, the

Andersen Group Realty Keller Williams Realty Boston Northwest

25 Hemingway St, Winchester, MA 01890

/42
Est $1,519,227 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,562 Sq Ft
32 Woodside Rd, Winchester, MA 01890

32 Woodside Rd, Winchester, MA 01890

/26
$1,725,000 Sold Dec 18, 2024
- 3,143 Sq Ft
- $549/SF
- 75 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1939
7 Ardley Rd, Winchester, MA 01890

Spacious 4-bedroom colonial home w/a Nantucket vibe, sited on manicured lawns in a cul-de-sac neighborhood! Just a block from the newly being built elementary school, close to the bike path, Horn Pond & hiking trails, this property is sure to please! 7 Ardley Road features a flowing & welcoming floor plan w/lots of natural light. Beautiful gleaming hardwood flooring is found in the living room

Vantage Point Team William Raveis R.E. & Home Services

7 Ardley Rd, Winchester, MA 01890

/32
Est $1,344,507 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,894 Sq Ft
114 Pond St, Winchester, MA 01890

114 Pond St, Winchester, MA 01890

/34
$1,580,000 Sold Nov 29, 2024
- 2,650 Sq Ft
- $596/SF
- 26 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1900
78 Middlesex St, Winchester, MA 01890

Amazing transformation of a Classic Colonial carefully reimagined for today's busy lifestyle. Living room with gas fireplace opens to the family room, oversized hi-end kitchen with island, stainless & granite, dining room with sliders to the yard with a stone patio for outside entertaining, a mud room & 1/2 bath. Upstairs has a primary bedroom suite, bath with 2 separate vanities, walk-in custom

Marjie and Phil Advisors Living - Arlington

78 Middlesex St, Winchester, MA 01890

/40
Est $1,264,902 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,919 Sq Ft
94 Pond St, Winchester, MA 01890

94 Pond St, Winchester, MA 01890

/42
$1,650,000 Sold Nov 15, 2024
- 2,887 Sq Ft
- $572/SF
- 4 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1931
64 Woodside Rd, Winchester, MA 01890

Discover classic charm & modern luxury in this beautifully renovated colonial. Nestled in desirable neighborhood close to town, soon-to-be new Lynch Elementary, Winter & Horn Pond! Abundant natural light & hardwood floors throughout. Enjoy the spacious LR w/cozy gas fireplace, stunning home office w/custom built-ins & playroom for family time. Inviting formal dining room & eat-in kitchen perfect

Kim Covino Compass

64 Woodside Rd, Winchester, MA 01890

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County Winchester North Main

Learn more about living in North Main

Home Trends in North Main, MA

On average, homes in North Main, Winchester sell after 114 days on the market compared to the national average of 70 days. The median sale price for homes in North Main, Winchester over the last 12 months is $575,000, down 16% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$575,000

Median Single Family Sale Price

$575,000

Median 2 Bedroom Sale Price

$390,000

Average Price Per Sq Ft

$298

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.00

Median List Price

$575,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-16%

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