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83 Properties

83 Properties Available In Winchester

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MA >Winchester >
Market Insights
14 Grant Rd, Winchester, MA 01890
3D

$2,499,000

Open Sat 10:30AM-12PM

Single Family Home

6 Beds 4.5 Baths 4,200 SqFt

14 Grant Rd, Winchester, MA 01890

Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester'...

Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

4 Aricia Ln, Winchester, MA 01890
1/39 39

$1,900,000

Open Sat 12:30PM-2PM

Single Family Home

4 Beds 4 Baths 5,361 SqFt

4 Aricia Ln, Winchester, MA 01890

Tucked into the tree-lined enclave of Aricia Lane, this striking contemporary residence delivers bold architectural desi...

Listed by The McLaren Team of Compass

26 Olive St, Winchester, MA 01890
3D

$929,000

Open Sat 11:30AM-12:30PM

Single Family Home

3 Beds 2 Baths 1,977 SqFt

26 Olive St, Winchester, MA 01890

Don't miss this rare opportunity to own a charming home with an expansive yard on a quiet cul-de-sac street! This lovely...

Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

4 Chestnut St, Winchester, MA 01890
1/41 41

$1,990,000

Open Sat 12PM-1:30PM

Single Family Home

4 Beds 4.5 Baths 4,474 SqFt

4 Chestnut St, Winchester, MA 01890

Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester's town center, commuter ...

Listed by Tyson Lynch of The Proper Nest Real Estate

85 Loring Ave., Winchester, MA 01890
1/40 40

$1,379,000

Open Sat 12PM-2PM

Single Family Home

3 Beds 2.5 Baths 2,340 SqFt

85 Loring Ave., Winchester, MA 01890

Beautifully updated Colonial in a prime Winchester location. This sun-filled 3-bed, 2.5-bath home features an open-conce...

Listed by Akiko Ghosh of Oyama Investments, Ltd.

3 Socrates Way, Winchester, MA 01890
1/33 33

$1,299,000

Open Sat 12PM-1:30PM

Single Family Home

4 Beds 2.5 Baths 2,570 SqFt

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...

Listed by Pirani & Wile Group of Advisors Living - Winchester

9 Emerson Ct, Winchester, MA 01890
1/41 41

$799,900

Open Sat 11AM-12:30PM

Single Family Home

3 Beds 2 Baths 1,441 SqFt

9 Emerson Ct, Winchester, MA 01890

Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath h...

Listed by The Serrano Team of Leading Edge Real Estate

58 Bacon Street, Winchester, MA 01890
1/40 40

$2,295,000

Open Sat 1PM-2:30PM

Single Family Home

6 Beds 5.5 Baths 5,791 SqFt

58 Bacon Street, Winchester, MA 01890

Timeless elegance & contemporary comfort span four meticulously finished levels.This stately residence boasts 15 rooms, ...

Listed by Real Estate Advisors Group of Coldwell Banker Realty - Belmont

6 Ivy Cir, Winchester, MA 01890
3D

$2,399,000

Open Sat 1:30PM-3PM

Single Family Home

6 Beds 4 Baths 3,728 SqFt

6 Ivy Cir, Winchester, MA 01890

Stunning new construction Colonial tucked away at the end of a quiet cul-de-sac in "The Flats", offering the ideal combi...

Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

1 Fox Hunt Ln, Winchester, MA 01890
1/41 41

$2,250,000

Open Sun 2PM-3:30PM

Single Family Home

5 Beds 5 Baths 5,000 SqFt

1 Fox Hunt Ln, Winchester, MA 01890

Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lo...

Listed by Leigh Ventura of Compass

107 Cambridge Street, Winchester, MA 01890
1/42 42

$2,599,000

Open Sun 1PM-2PM

Single Family Home

6 Beds 4.5 Baths 5,824 SqFt

107 Cambridge Street, Winchester, MA 01890

Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern ...

Listed by Maija Sawyer of William Raveis R.E. & Home Services

35 Harvard Street, Winchester, MA 01890
3D

$1,349,900

Open Sat 11:30AM-1PM

Single Family Home

5 Beds 2 Baths 1,706 SqFt

35 Harvard Street, Winchester, MA 01890

Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted M...

Listed by Joanne Mulkerin of J. Mulkerin Realty

5 Stratford Road, Winchester, MA 01890
1/39 39

$3,599,000

Open Sat 11:30AM-1PM

Single Family Home

6 Beds 4.5 Baths 5,876 SqFt

5 Stratford Road, Winchester, MA 01890

This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester's most s...

Listed by Kim Covino & Co. Team of Compass

162 Swanton Street #162, Winchester, MA 01890
3D

$1,299,000

Open Sat 11AM-12PM

Condo

3 Beds 3.5 Baths 2,136 SqFt

162 Swanton Street #162, Winchester, MA 01890

Opportunity to own the last available end unit! Welcome to 162 Swanton Street, the final new construction townhome by Ro...

Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

10 Girard Rd, Winchester, MA 01890
1/41 41

$1,349,000

Open Sat 1:30PM-2:30PM

Single Family Home

3 Beds 1.5 Baths 3,335 SqFt

10 Girard Rd, Winchester, MA 01890

Unleash Your Vision in Winchester's Coveted West Side! Don't miss this rare chance to transform this Mid-Century Modern ...

Listed by Joanne Hofmann of Coldwell Banker Realty - Lexington

10 Sheffield Road, Winchester, MA 01890
3D

$2,899,000

Open Sat 1PM-2PM

Single Family Home

7 Beds 5.5 Baths 5,864 SqFt

10 Sheffield Road, Winchester, MA 01890

This stunning Colonial Revival home, situated on one of Winchester's most desirable streets, is just moments from the tr...

Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

666 Main St #206, Winchester, MA 01890
1/28 28

$724,999

Open Sat 12PM-1PM

Condo

2 Beds 2 Baths 1,170 SqFt

666 Main St #206, Winchester, MA 01890

Back on Market - buyer got cold feet. Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect ble...

Listed by Sveta Vakhitova of Berkshire Hathaway HomeServices Warren Residential

22 Grove Place #4, Winchester, MA 01890
1/37 37

$859,000

Open Sat 1:30PM-2:30PM

Condo

2 Beds 1 Bath 1,123 SqFt

22 Grove Place #4, Winchester, MA 01890

Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect...

Listed by Kim Covino & Co. Team of Compass

44 Cabot Street, Winchester, MA 01890
3D

$3,249,000

Open Sat 11:30AM-12:30PM

Single Family Home

6 Beds 6.5 Baths 6,028 SqFt

44 Cabot Street, Winchester, MA 01890

Welcome to 44 Cabot Street, a newly built home in one of Winchester's most desirable neighborhoods. Offering over 6,000 ...

Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

80 Arlington Street, Winchester, MA 01890
1/37 37

$3,475,000

Open Sun 12PM-1:30PM

Single Family Home

5 Beds 3.5 Baths 5,632 SqFt

80 Arlington Street, Winchester, MA 01890

This stunning Royal Barry Wills colonial estate, with 11 rooms, 5 bedrooms and 3.5 baths, is nestled alongside the 4th g...

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

54 Wedgemere Avenue, Winchester, MA 01890
1/42 42

$3,099,000

Open Sat 11:30AM-1PM

Single Family Home

6 Beds 3.5 Baths 5,238 SqFt

54 Wedgemere Avenue, Winchester, MA 01890

Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard surrounded by mature plants...

Listed by Kim Covino & Co. Team of Compass

11 Fieldstone Drive, Winchester, MA 01890
3D

$2,899,000

Open Sun 2PM-3PM

Single Family Home

5 Beds 4.5 Baths 6,904 SqFt

11 Fieldstone Drive, Winchester, MA 01890

Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester's most coveted neighborhood. Modern design ...

Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest

147 Highland Ave, Winchester, MA 01890
1/37 37

$1,329,000

Open Sun 1:30PM-2:30PM

Single Family Home

3 Beds 2 Baths 1,884 SqFt

147 Highland Ave, Winchester, MA 01890

Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center inc...

Listed by Kim Covino & Co. Team of Compass

5 Squire Rd, Winchester, MA 01890
1/40 40

$2,000,000

Open Sat 12PM-1:30PM

Single Family Home

6 Beds 3.5 Baths 4,696 SqFt

5 Squire Rd, Winchester, MA 01890

Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours in...

Listed by Alina Wang Team of Coldwell Banker Realty - Lexington

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IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

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Michael Sheehy

Michael Sheehy

+1(978) 580-0224 mike@sheehygroup.com

12 Shirley Road, Andover, Massachusetts, 01810, USA

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IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

SITE MAP

      Home
      Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Sell
      1. Sell My Home
      2. Home Valuation
      About
      1. Team
      2. About Us
      3. Contact Us
      4. Reviews
      Market Snapshot
      Home
default

Michael Sheehy

Michael Sheehy

+1(978) 580-0224 mike@sheehygroup.com

12 Shirley Road, Andover, Massachusetts, 01810, USA

Get My App

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility