Middlesex, MA Homes

/42
$2,299,900 Open Sat 12:30PM - 2PM
- 6 Beds
- 4 Baths
- 4,385 Sq Ft
5 Bacon St, Winchester, MA 01890

This meticulously updated home blends timeless character with modern comfort, offering flexibility as a two-family or multi-generational single-family residence. Prior owners embraced multi-generational living, appreciating the spacious layout and exquisite built-ins that grace both living and dining rooms with elegance and timeless appeal. A grand central staircase links all 3 levels, while

Anne Spry Barrett Sotheby's International Realty

5 Bacon 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
/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

/36
Est $1,359,630 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,823 Sq Ft
7 Wainwright Rd Unit 88, Winchester, MA 01890

7 Wainwright Rd Unit 88, Winchester, MA 01890

/41
$1,599,000
- 3 Beds
- 2.5 Baths
- 2,283 Sq Ft
17 Dennett Rd, Winchester, MA 01890

Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized

Kim Covino Compass

17 Dennett 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
/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

/33
Est $1,669,199 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,327 Sq Ft
7 Wainwright Rd Unit 72, Winchester, MA 01890

7 Wainwright Rd Unit 72, Winchester, MA 01890

/21
$419,900
- 1 Bed
- 1 Bath
- 606 Sq Ft
200 Swanton St Unit 432, Winchester, MA 01890

This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The

Mark Gilson Keller Williams Realty

200 Swanton St Unit 432, Winchester, MA 01890
/11
$2,200 per month
- 1 Bed
- 1 Bath
- 606 Sq Ft
- Condo for Rent
253 Swanton St Unit 428, Winchester, MA 01890

1 bed and 1 bath located in Winchester Highlands. Easy access to downtown and public transportation!

253 Swanton St Unit 428, Winchester, MA 01890
/38
$1,924,000 Sold Jul 10, 2025
- 4,195 Sq Ft
- $459/SF
- 4 Days On Market
- 4 Beds
- 4 Baths
- Built 1995
5 Hastings Rd, Winchester, MA 01890

Rare opportunity on a peaceful cul-de-sac. This extraordinary 4-bedroom, 4-bathroom home is nestled in one of Winchester's most sought-after neighborhoods. For the first time ever, this meticulously maintained residence is available on a street where properties rarely change hands. Bathed in abundant natural light, the thoughtfully designed floor plan showcases generously sized living spaces that

Nancy Pallotta Advisors Living - Winchester

5 Hastings Rd, Winchester, MA 01890

/38
Est $1,600,514 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,368 Sq Ft
7 Wainwright Rd Unit 39, Winchester, MA 01890

7 Wainwright Rd Unit 39, Winchester, MA 01890

/38
$1,650,000 Open Fri 12PM - 1PM
- 4 Beds
- 3.5 Baths
- 2,755 Sq Ft
5 Thornton Rd, Winchester, MA 01890

This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen.

Lynne Russo Better Homes and Gardens Real Estate - The Shanahan Group

5 Thornton 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
/37
$2,200,000 Sold Jul 09, 2025
- 3,901 Sq Ft
- $564/SF
- 4 Days On Market
- 6 Beds
- 3.5 Baths
- Built 2011
20 Elm St, Winchester, MA 01890

Nestled in the highly sought-after "heart" of Winchester Center, this Newer Construction single-family (slightly attached) home offers space & finishes you typically find in 2.5M+ homes! With 10' ceilings and high end finishes throughout, this stunning 5-6 bedroom, 3.5 bath home is just two blocks from the vibrant town center, train station, schools, restaurants & shops! 5190 total sf w/ 3900sf

Kim Covino Compass

20 Elm St, Winchester, MA 01890

/39
Est $1,691,902 Not Listed For Sale
- 2 Beds
- 4 Baths
- 3,655 Sq Ft
7 Wainwright Rd Unit 37, Winchester, MA 01890

7 Wainwright Rd Unit 37, Winchester, MA 01890

/16
$1,150,000 Open Sat 11AM - 12:30PM
- 4 Beds
- 3 Baths
- 1,860 Sq Ft
60 Harvard St, Winchester, MA 01890

Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

Mark Krasnyansky eXp Realty

60 Harvard St, Winchester, MA 01890
/23
$4,000 per month
- 2 Beds
- 2.5 Baths
- 1,700 Sq Ft
- Condo for Rent
41 Church St Unit 1, Winchester, MA 01890

2 bed and 2.5 bath located in Winchester. Easy access to downtown and public transportation!

41 Church St Unit 1, 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

/42
Est $1,814,355 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,901 Sq Ft
7 Wainwright Rd Unit 5, Winchester, MA 01890

7 Wainwright Rd Unit 5, Winchester, MA 01890

/42
$3,750,000
- 6 Beds
- 3.5 Baths
- 4,484 Sq Ft
9 Lakeview Terrace, Winchester, MA 01890

LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room!

Kim Covino Compass

9 Lakeview Terrace, Winchester, MA 01890
/41
$9,400 per month
- 5 Beds
- 4.5 Baths
- 5,016 Sq Ft
- House for Rent
22 Amberwood Dr, Winchester, MA 01890

Fabulous rental opportunity with full wing of an additional in-law suite for multi-generational living at its best. Beautiful designers’ grade high-end finishes throughout! Features separate side entry with inviting south-facing covered porch, a dramatic two-story foyer/ceiling, and the main kitchen that flows into an additional meal prep kitchen area with integrated appliances – Thermador

Anita Lin Coldwell Banker Realty - Lexington

22 Amberwood 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

/41
Est $1,642,024 Not Listed For Sale
- 2 Beds
- 4 Baths
- 5,564 Sq Ft
7 Wainwright Rd Unit 41, Winchester, MA 01890

7 Wainwright Rd Unit 41, Winchester, MA 01890

/42
$2,499,000 Open Sun 12:30PM - 1PM
- 6 Beds
- 4.5 Baths
- 5,824 Sq Ft
107 Cambridge St, Winchester, MA 01890

Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

Maija Sawyer Puleo William Raveis R.E. & Home Services

107 Cambridge St, Winchester, MA 01890
/11
$3,500 per month
- 3 Beds
- 1 Bath
- 1,400 Sq Ft
- Condo for Rent
534 Washington St Unit 2, Winchester, MA 01890

Welcome to this 3-bedroom spacious and bright apartment near the North Reservoir and Middlesex Fells Reservation!!! With many windows, the unit is flooded with natural light. The open-concept living space features a hardwood floor and recessed lighting. Cook with joy in a kitchen that includes granite countertops, a 5-burner stainless steel gas cooktop, and abundant cabinetry. All 3 bedrooms

534 Washington St Unit 2, Winchester, MA 01890
/41
$1,500,000 Sold Jun 30, 2025
- 4,214 Sq Ft
- $356/SF
- 4 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1995
7 Wainwright Rd Unit 117, Winchester, MA 01890

Welcome to the largest unit at The Ledges! This stunning F unit boasts soaring ceilings and an expansive open floor plan, perfect for entertaining or relaxing in style. Custom decorated in a perfect, custom Palm Beach vibe, but easy to change if you don't love it. Sunlight floods the large formal living room, with an attached deck, bifurcated by a gas fireplace that leads to the dining room. A

Nancy Pallotta Advisors Living - Winchester

7 Wainwright Rd Unit 117, Winchester, MA 01890

/42
Est $1,955,208 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,853 Sq Ft
40 Wainwright Rd, Winchester, MA 01890

40 Wainwright Rd, Winchester, MA 01890

/36
$1,349,900 Open Sun 1:30PM - 3PM
- 5 Beds
- 2 Baths
- 1,706 Sq Ft
35 Harvard St, Winchester, MA 01890

Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

Joanne Mulkerin J. Mulkerin Realty

35 Harvard St, Winchester, MA 01890
/14
$2,800 per month
- 2 Beds
- 2 Baths
- 1,452 Sq Ft
- Apartment for Rent
273 Cross St Unit 273, Winchester, MA 01890

Available September 1, 2025! Don’t miss this charming and spacious 6-room duplex townhouse—ready for you to move right in! This well-maintained home features a bright and airy living room and formal dining area, perfect for relaxing or entertaining. The renovated kitchen boasts granite countertops, modern finishes, and a walk-out to your private fenced yard—ideal for seamless indoor-outdoor

coldown jx Phoenix Real Estate Partners, LLC

273 Cross St Unit 273, Winchester, MA 01890
/32
$1,250,000 Sold Jun 30, 2025
- 2,759 Sq Ft
- $453/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 1973
80 Harvard St, Winchester, MA 01890

Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom.

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

80 Harvard St, Winchester, MA 01890

/42
Est $2,887,955 Not Listed For Sale
- 5 Beds
- 6 Baths
- 5,678 Sq Ft
19 Socrates Way, Winchester, MA 01890

19 Socrates Way, Winchester, MA 01890

/39
$3,599,000
- 6 Beds
- 4.5 Baths
- 5,876 Sq Ft
5 Stratford Rd, Winchester, MA 01890

This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

Kim Covino Compass

5 Stratford Rd, Winchester, MA 01890
/38
$7,450 per month
- 4 Beds
- 4 Baths
- 4,650 Sq Ft
- House for Rent
31 Coolidge Rd, Winchester, MA 01890

Available now! 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

Carlos Xu Lexwin Realty

31 Coolidge Rd, Winchester, MA 01890
/42
$2,359,000 Sold Jun 30, 2025
- 3,274 Sq Ft
- $721/SF
- 8 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1985
57 Jefferson Rd, Winchester, MA 01890

Situated on a picturesque corner lot, this exceptional home is nestled in a very desirable neighborhood! Step into a light-filled, open-concept 1st floor, where a soaring beamed ceiling enhances the inviting ambiance. The living room boasts built-in shelves, while the kitchen impresses w/timeless white cabinetry, soapstone counters, SS appliances, large island, & pantry. The dining area, warmed

McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

57 Jefferson Rd, Winchester, MA 01890

/42
Est $2,662,831 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 5,713 Sq Ft
40 Amberwood Dr, Winchester, MA 01890

40 Amberwood Dr, Winchester, MA 01890

/41
$2,899,000 Open Sat 12PM - 1PM
- 7 Beds
- 5.5 Baths
- 5,864 Sq Ft
10 Sheffield Rd, Winchester, MA 01890

This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

Andersen Group Realty Keller Williams Realty Boston Northwest

10 Sheffield Rd, Winchester, MA 01890
/26
$3,995 per month
- 3 Beds
- 2.5 Baths
- 1,823 Sq Ft
- Condo for Rent
171 Swanton St Unit 63, Winchester, MA 01890

Welcome to the Village at Winchester!Experience comfortable living in this spacious 1,823 sq ft townhome nestled in a professionally managed 80-unit complex. This beautiful 3-bedroom, 2.5-bath home features hardwood floors, a cozy fireplace in the living room, and a bright dining area with a skylight that opens to a private patio—perfect for relaxing and entertaining.Additional highlights include

Gary Vrotsos Coldwell Banker Realty - Cambridge

171 Swanton St Unit 63, Winchester, MA 01890
/28
$1,260,000 Sold Jun 30, 2025
- 2,705 Sq Ft
- $466/SF
- 41 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1885
261 Cambridge St Unit 261 G, Winchester, MA 01890

Step into this beautifully renovated historic townhouse that seamlessly blends classic charm with modern updates. This welcoming 3-bedroom, 2.5-bathroom home features elegant finishes, high ceilings and thoughtful details throughout. The main level boasts an open kitchen/family room plan, plus a large dining room and living room, great for entertaining. Upstairs, you'll find generous bedrooms,

Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

261 Cambridge St Unit 261 G, Winchester, MA 01890

/38
Est $1,838,037 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 4,008 Sq Ft
45 Amberwood Dr, Winchester, MA 01890

45 Amberwood Dr, Winchester, MA 01890

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Massachusetts Middlesex County Winchester

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