Winchester MA FSBO Homes (25)

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We have 25 homes for sale by owner in Winchester, MA. The median list price in Winchester, MA is $532,251.

Homes For Sale

$1,295,000

4 Bed
2 Bath
2,202 Sqft
0.16 Acre(Lot)

71 Woodside Rd, Winchester, MA

Nestled in the heart of winchester, this charming 4-bedroom, 1.5-bathroom single-family home offers 2,202 square... Read More

Homes For Sale

$925,000

4 Bed
2 Bath
2,172 Sqft
0.3 Acre(Lot)

322 Cambridge St, Winchester, MA

Not your average garrison colonial! you might not expect the bright, open charm waiting within this inviting... Read More

Homes For Sale

$2,499,000

6 Bed
4 Bath
4,667 Sqft
0.26 Acre(Lot)

9 Prospect St, Winchester, MA

Step into a piece of history with this incredibly charming 1895 colonial revival, a home that exudes elegance,... Read More

Homes For Sale

$1,250,000

4 Bed
2 Bath
2,621 Sqft
0.25 Acre(Lot)

61 Westland Avenue, Winchester, MA

Welcome to this oversized cape in a lovely west side neighborhood of winchester. opportunity for a little tlc... Read More

Homes For Sale

$2,850,000

5 Bed
5 Bath
5,044 Sqft
0.23 Acre(Lot)

22 Standish Lane, Winchester, MA

This distinguished residence, built by premier local developer, represents the pinnacle of elegant living!... Read More

Homes For Sale

$1,324,000

3 Bed
4 Bath
2,792 Sqft
0.27 Acre(Lot)

24 Eugene Drive, Winchester, MA

Welcome home to this architect designed 3 plus bedroom, four bath custom cape! spacious rooms within a... Read More

Homes For Sale

$1,599,000

3 Bed
4 Bath
3,351 Sqft
0.34 Acre(Lot)

34 Fells Road, Winchester, MA

Nestled on a peaceful street surrounded by trees, this beautifully updated cape home offers a perfect blend of... Read More

Homes For Sale

$2,900,000

4 Bed
4 Bath
4,325 Sqft
0.45 Acre(Lot)

45 Brooks Street, Winchester, MA

Sprawling expanded cape set on stunning private 1/2 acre lot in coveted brooks neighborhood! the curb appeal... Read More

Homes For Sale

$2,499,000

4 Bed
4 Bath
5,218 Sqft
0.24 Acre(Lot)

31 Lawson Rd, Winchester, MA

Welcome to this gracious colonial, seamlessly blending traditional charm with modern amenities, perfect for... Read More

Homes For Sale

$2,599,000

7 Bed
6 Bath
4,829 Sqft
0.23 Acre(Lot)

89 Wildwood St, Winchester, MA

New construction! this stunning 7-bed, 5.5-bath luxury home boasts high-end finishes and a thoughtfully designed... Read More

Homes For Sale

$3,350,000

6 Bed
5 Bath
5,198 Sqft
0.39 Acre(Lot)

21 Sheffield West, Winchester, MA

Experience the perfect blend of timeless elegance & modern luxury in this stunning 5-6-bedroom home, set on one... Read More

Homes For Sale

$2,850,000

4 Bed
3 Bath
4,276 Sqft
0.47 Acre(Lot)

8 Tanglewood Lane, Winchester, MA

This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for... Read More

Homes For Sale

$3,249,000

7 Bed
6 Bath
6,200 Sqft
0.28 Acre(Lot)

10 Sheffield Road, Winchester, MA

This stunning colonial revival home, situated on one of winchester’s most desirable streets, is just moments... Read More

Homes For Sale

$2,599,000

5 Bed
4 Bath
5,077 Sqft
0.46 Acre(Lot)

276 High Street, Winchester, MA

This stunning, freshly painted, home is located in a picturesque and unique setting, elevated on a small hill... Read More

Active Under Contract

Homes For Sale

$1,745,000

5 Bed
4 Bath
2,848 Sqft
0.46 Acre(Lot)

85 Thornberry Rd, Winchester, MA

Welcome to the highly-coveted westside of winchester, ma. this meticulously maintained colonial-style home is... Read More

Pending

Homes For Sale

$1,199,900

3 Bed
2 Bath
2,060 Sqft
0.11 Acre(Lot)

36 Lebanon Street, Winchester, MA

Nicely updated home in desirable muraco district! this home has been meticulously maintained & features many... Read More

Pending

Homes For Sale

$2,399,000

5 Bed
5 Bath
3,851 Sqft
0.27 Acre(Lot)

7 Rangeley Road, Winchester, MA

**offer accepted/ oh canceled* delightful home in rangeley estates, just outside winchester center! featuring 5... Read More

Homes For Sale

$3,199,000

5 Bed
5 Bath
4,279 Sqft
0.29 Acre(Lot)

51 Wedgemere Avenue, Winchester, MA

Discover the perfect blend of charm & modern elegance in this beautiful home, nestled on one of the most highly... Read More

Homes For Sale

$3,989,000

6 Bed
7 Bath
8,463 Sqft
0.52 Acre(Lot)

26 Swan Road, Winchester, MA

Nestled in the heart of myopia hill, this custom-built home is sure to impress! live your best life at 26 swan... Read More

Homes For Sale

$2,498,000

5 Bed
4 Bath
4,468 Sqft
0.39 Acre(Lot)

74 Hillcrest Parkway, Winchester, MA

Introducing 74 hillcrest parkway! this spacious, modern 5-bedroom home is nestled across the breathtaking... Read More

Winchester - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in Winchester 83

	Average Price
2 Bed Homes For Sale in Winchester (1)	$ 999,999
3 Bed Homes For Sale in Winchester (15)	$ 1,352,253
4 Bed Homes For Sale in Winchester (19)	$ 2,001,158
5+ Bed Homes For Sale in Winchester (48)	$ 3,249,265

AVERAGE PRICE

$ 1,900,669

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 562

Condos For Sale By Owner in Winchester 23

	Average Price
1 Bed Condos For Sale in Winchester (1)	$ 279,000
2 Bed Condos For Sale in Winchester (13)	$ 762,277
3 Bed Condos For Sale in Winchester (7)	$ 1,077,843
4 Bed Condos For Sale in Winchester (2)	$ 1,450,000

AVERAGE PRICE

$ 1,396,474

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 484

Land For Sale By Owner in Winchester 1

	Average Price
Land For Sale in Winchester (1)	$ 1,496,755

AVERAGE PRICE

$ 1,496,755

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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Learn More About Winchester, Massachusetts

Currently there are 83 homes for sale, 23 condos and apartments for sale and 1 vacant land for sale in Winchester

Currently Winchester has 107 properties on the market for sale. The inventory was last updated 04/05/2025. Of these properties, 83 single family homes are for sale by their owners in Winchester, and 23 condos are for sale by their owners in Winchester. The average price of the single family homes for sale in Winchester, is $1,900,669, the average condo price in Winchester, is $1,396,474. The average price per square foot of the active inventory is $349. This is based the living area square footage.

Over the last year, there have been 109 of properties sold in Winchester. Of these properties, 75 single family homes have sold by their owners in Winchester, and 31 condos have sold by their owners in Winchester. The average sales price of the single family homes sold in Winchester, is $1,641,510. Single family homes have been selling for 503 per square foot of living area. The average sales price of the condos for sale in Winchester, is $1,283,309. Condos have been selling for 487 per square foot of living area.

The most active subdivisions with listings for sale in Winchester, are:

If you are thinking of selling your Winchester home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 04/05/2025

Winchester MA FSBO Homes (25)

71 Woodside Rd, Winchester, MA

322 Cambridge St, Winchester, MA

9 Prospect St, Winchester, MA

61 Westland Avenue, Winchester, MA

22 Standish Lane, Winchester, MA

24 Eugene Drive, Winchester, MA

34 Fells Road, Winchester, MA

45 Brooks Street, Winchester, MA

31 Lawson Rd, Winchester, MA

89 Wildwood St, Winchester, MA

21 Sheffield West, Winchester, MA

8 Tanglewood Lane, Winchester, MA

10 Sheffield Road, Winchester, MA

276 High Street, Winchester, MA

85 Thornberry Rd, Winchester, MA

36 Lebanon Street, Winchester, MA

7 Rangeley Road, Winchester, MA

51 Wedgemere Avenue, Winchester, MA

26 Swan Road, Winchester, MA

74 Hillcrest Parkway, Winchester, MA

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Winchester - Statistics and Home Trends

Actives Activity Chart

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

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Learn More About Winchester, Massachusetts

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