Jessica Silipo

Jessica Silipo

Real Estate Agent

Specialties

Buyer's Agent, Listing Agent, Appraisal, Staging, Property Management, Landlord

Education

Seton Hall University - Bachelor's Degree, Journalism, and Public Relations

Client Testimonials

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​ ★★★★★
"Jess was very helpful in getting us a wonderful apartment. I highly recommend her to anyone who is looking for a place to rent in the city. She went out of her way to leave a positive recommendation for us in our application. Thank you for all the help Jess!"

★★★★★
"I couldn't have been happier with the way Jessica Anderson handled my wife and I through the entire real estate process. We had no idea what we were doing and Jessica was with us every step of the way. She explained everything that we didn't understand about the process clearly and respectfully. She communicated and met with us when it was convenient for our schedules. She helped us find our dream apartment in a easy stress free and timely manner that was completely catered to OUR experience,wants, and needs."

★★★★★
"Jessica is a professional and a great negotiator for all of her customers on both sides of the lease or sale. She follows through on all deals never leaving her customers hanging and goes above and beyond to make a deal workout."


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About Jessica
Jessica Silipo is a Winchester, Massachusetts real estate agent with Kim Covino & Co. at Compass, the #1 real estate team in Massachusetts by sales volume according to RealTrends Verified rankings based on 2025 sales data.Born and raised in Winchester, Jessica continues to call the town home and brings firsthand knowledge of Winchester, Greater Boston and the North Shore to every client she works with. Known for her strong work ethic, attention to detail and thorough understanding of the local real estate market, Jessica is a trusted resource for both buyers and sellers. Her deep roots in the community, combined with her knowledge of surrounding towns and neighborhoods, allow her to provide valuable insight throughout every step of the buying or selling process. Jessica’s passion for architecture, decorating and remodeling brings another level of expertise to her work. Buyers often rely on her eye for design to identify homes with potential and envision what a property could become, while sellers benefit from her ability to recognize improvements that can enhance a home’s presentation and appeal. Whether buying or selling in Winchester, the Greater Boston area or the North Shore, Jessica combines local expertise, market knowledge and a great eye for design to help her clients make confident real estate decisions.

Jessica Silipo’s Transactions

Past Sales
$3,825,000 | 5 Cambridge St | Wedgemere

$3,825,000

5
Bedrooms
5
Bathrooms

5 Cambridge St

Wedgemere

a view of a swimming pool and outdoor space

$3,675,000

3
Bedrooms
2,641
Square Feet
1.86
Acres
$3,520,000 | 20 Lorena Road, Winchester, MA 01890

$3,520,000

6
Bedrooms
6,085
Square Feet
0.27
Acres
a front view of a house with a garden

$3,440,000

7
Bedrooms
6,388
Square Feet
0.34
Acres
$3,200,000 | 74 Salisbury St

$3,200,000

3
Bedrooms
1.5
Bathrooms

74 Salisbury St

$3,125,000 | 8 Kay Tiffany Way | Lexington

$3,125,000

8 Kay Tiffany Way

Lexington

$2,950,000 | 7 Ledgewood Road, Winchester, MA 01890

$2,950,000

5
Bedrooms
4,648
Square Feet
0.94
Acres
$2,900,000 | 34 Ledgewood Road, Winchester, MA 01890

$2,900,000

5
Bedrooms
4,700
Square Feet
0.46
Acres
$2,900,000 | 11 Niles Lane, Winchester, MA 01890

$2,900,000

5
Bedrooms
7,103
Square Feet
0.38
Acres
an aerial view of a house

$2,850,000

4
Bedrooms
4,325
Square Feet
0.45
Acres
$2,799,000 | 32 Ledgewood Road, Winchester, MA 01890

$2,799,000

5
Bedrooms
4,900
Square Feet
0.30
Acres
$2,775,000 | 18 Wedgemere Avenue, Winchester, MA 01890

$2,775,000

5
Bedrooms
5,116
Square Feet
0.34
Acres
$2,625,000 | 16 Chestnut Street, Winchester, MA 01890

$2,625,000

6
Bedrooms
6,100
Square Feet
0.39
Acres
$2,625,000 | 3 Alice Lane, Winchester, MA 01890

$2,625,000

5
Bedrooms
6,000
Square Feet
0.23
Acres
$2,599,000 | 8 Glengarry Road, Winchester, MA 01890

$2,599,000

5
Bedrooms
4,525
Square Feet
0.19
Acres
$2,599,000 | 22 McCall Rd

$2,599,000

5
Bedrooms
5
Bathrooms

22 McCall Rd

$2,500,000 | 6 Sheffield Road | Wedgemere

$2,500,000

5
Bedrooms
4.5
Bathrooms

6 Sheffield Road

Wedgemere

a front view of a house with garage

$2,499,000

5
Bedrooms
5,600
Square Feet
0.30
Acres
Past Rentals
a balcony with furniture and wooden floor

$11,500

5
Bedrooms
a front view of a house with a yard

$7,500

5
Bedrooms
a front view of a house with a yard

$7,200

5
Bedrooms
$7,200 | 65 Church Street, Winchester, MA 01890

$7,200

5
Bedrooms
a view of a city

$6,500

2
Bedrooms
a front view of a house with garden

$5,800

5
Bedrooms
a front view of a house with garden

$5,750

5
Bedrooms
a front view of a house with garden

$5,700

5
Bedrooms
$5,200 | 1 Irving Street, Unit 1, Winchester, MA 01890

$5,200

5
Bedrooms
a living room with furniture and a flat screen tv

$4,900

4
Bedrooms
a view of a house with a yard

$4,900

3
Bedrooms
$4,500 | 49 Edward Dr, Unit 18B | Boston

$4,500

49 Edward Dr, Unit 18B

Boston

a front view of a house with a porch

$4,500

4
Bedrooms
a living room with furniture and a couch

$4,500

4
Bedrooms
1,720
Square Feet
22.96
Acres
a kitchen with a sink appliances and a counter space

$4,400

2
Bedrooms
$4,400 | 67 Church Street, Unit 67, Winchester, MA 01890

$4,400

2
Bedrooms
a pathway of a house with a yard

$4,300

3
Bedrooms
a living room with furniture a flat screen tv and a fireplace

$4,200

2
Bedrooms