Jessica Witter

Jessica Witter-Aladesanmi

Vice President
jessica.witter@compass.com
M: 508-776-6636

Social Media

Instagram LogoInstagram     
Facebook LogoFacebook     

A blurry photo of a street scene with a light.

Awards

RealTrends Verified, 2025

Education



Client Testimonials

Scroll down more

★★★★★
" Jessica, Krystyna, and the whole team here are truly top-notch. Over the years we have worked with them to sell two homes and to buy three homes. Would not work with anyone else. They are extremely responsive and fast-moving with a high sense of urgency, professional, trustworthy, respectful, give great advice on staging, they are honest and have high integrity. They also surround themselves with an amazing network, so always have great connections to stagers, lenders, photographers, insurance reps, etc. who have made deals very smooth every time we have worked with them. Overall great experience and highly recommend. " - subscriptions998

About Jessica
Jessica Witter-Aladesanmi is a Vice President at Compass and co-founder of Witter & Witter, a family-led real estate team serving Boston, Greater Boston, and Cape Cod. With more than $100 million in annual team sales, Jessica has built her business by combining sophisticated market knowledge, thoughtful strategy, and a deeply personal approach to client service.

Jessica represents buyers and sellers across every stage of life—from first-time homebuyers and growing families to seasoned investors, empty nesters, and luxury clients. Whether preparing a property for market, developing a comprehensive launch strategy, or negotiating a complex transaction, she brings clarity, creativity, and calm leadership to every decision. Her approach extends far beyond the transaction itself; she understands that real estate is ultimately about people, families, and the lives they are building.

Known for elevated marketing and an honest, hands-on style, Jessica believes every home deserves a strategy tailored to its story. She pairs Compass’s industry-leading technology and reach with local expertise, strong relationships, and the highly personalized service of a boutique team.

Jessica and the Witter & Witter team have been recognized year after year by RealTrends, while Jessica has also been honored among Boston Common Magazine’s Dynamic Women. A respected voice within the real estate industry, she has taught fellow professionals about online lead conversion and the importance of building meaningful, lasting client relationships.

Her commitment to people extends well beyond real estate. As Vice President of the South Boston Moms Club, Jessica has helped support local families, strengthen neighborhood connections, and contribute to events and initiatives that bring the community together.

Jessica lives in South Boston with her husband, Dare—who is also a valued member of the Witter & Witter team—and their two children, Lorenzo and Gianna. For Jessica, the work is personal: helping people move forward, create opportunity, and find a place where their next chapter can begin.

Jessica Witter-Aladesanmi’s Listings

$3,500,000 | 135 Seaport Boulevard, Unit 2007, Boston, MA 02210
1/40
Listed By CompassUnder Agreement

$3,500,000

2
Bedrooms
1,608
Square Feet

135 Seaport Boulevard, Unit 2007, Boston, MA 02210

$1,575,000 | 12 Salem Street, Cambridge, MA 02139
1/27
Listed By CompassUnder Agreement

$1,575,000

3
Bedrooms
1,519
Square Feet
0.05
Acres

12 Salem Street, Cambridge, MA 02139

$879,000 | 48 Sawyer Avenue, Unit 1, Boston, MA 02125
1/31
Listed By CompassOpen: 10/24 11:30AM - 01:00PM

$879,000

3
Bedrooms
1,553
Square Feet

48 Sawyer Avenue, Unit 1, Boston, MA 02125

$599,000 | 29 Church Street, Braintree, MA 02184
1/25
Listed By Compass

$599,000

2
Bedrooms
1,869
Square Feet
0.17
Acres

29 Church Street, Braintree, MA 02184

a kitchen with a table and chairs
1/15
Listed By Compass

$574,900

2
Bedrooms
1,102
Square Feet

808 Morton Street, Unit 1, Boston, MA 02124

a brick building with a small yard
Listed By Compass

$135,000

Unavailable
Bedrooms
Unavailable
Bathrooms
Unavailable
Square Feet

531 Newbury Street, Boston, MA 02215

Jessica Witter-Aladesanmi’s Transactions

Past Sales
Photo of home

$9,000,000

50 Liberty Dr, Unit 3B & 3C

Boston

an aerial view of houses with yard

$8,000,000

5
Bedrooms
9
Bathrooms
9,780
Square Feet
1.32
Acres

461 Main Street, Osterville, MA 02655

a dining room with furniture a chandelier and wooden floor

$6,775,000

5
Bedrooms
4,861
Square Feet
1.66
Acres

103 Penzance Road, Woods Hole, MA 02543

$5,600,000 | 50 Liberty, Unit 3B, Boston, MA 02210

$5,600,000

2
Bedrooms
2,081
Square Feet

50 Liberty, Unit 3B, Boston, MA 02210

$4,795,000 | 28 Oyster Pond Lane, Chatham, MA 02633

$4,795,000

5
Bedrooms
8
Bathrooms
6,098
Square Feet
1.45
Acres

28 Oyster Pond Lane, Chatham, MA 02633

$4,400,000 | 67 Uncle Alberts Drive, Chatham, MA 02633

$4,400,000

4
Bedrooms
7
Bathrooms
5,578
Square Feet
2.07
Acres

67 Uncle Alberts Drive, Chatham, MA 02633

a living room with furniture and a large window

$3,400,000

2
Bedrooms
1,615
Square Feet

50 Liberty, Unit 3C, Boston, MA 02210

$3,041,135 | 135 Seaport Blvd, Unit 2007 | Boston

$3,041,135

2
Bedrooms
2.5
Bathrooms

135 Seaport Blvd, Unit 2007

Boston

$2,900,000 | 19 Fieldmont Road, Belmont, MA 02478

$2,900,000

5
Bedrooms
6,203
Square Feet
0.61
Acres

19 Fieldmont Road, Belmont, MA 02478

a living room with furniture and a large window

$2,660,000

4
Bedrooms
2,245
Square Feet

60 Chandler Street, Unit 2, Boston, MA 02116

$2,550,000 | 357-359 Beacon Street, Unit 7, Boston, MA 02116

$2,550,000

3
Bedrooms
1,645
Square Feet

357-359 Beacon Street, Unit 7, Boston, MA 02116

an aerial view of house with yard swimming pool and outdoor seating

$2,550,000

5
Bedrooms
4,196
Square Feet
1
Acres

405 Baxter Neck Road, Marstons Mills, MA 02648

$2,280,500 | 135 Seaport Boulevard, Unit 1809, Boston, MA 02210

$2,280,500

2
Bedrooms
1,106
Square Feet

135 Seaport Boulevard, Unit 1809, Boston, MA 02210

a front view of a house with a yard and garage

$2,050,000

4
Bedrooms
4
Bathrooms
3,100
Square Feet
0.96
Acres

149 East Bay Road, Osterville, MA 02655

a living room with furniture potted plant floor to ceiling windows and a flat screen tv

$1,799,000

2
Bedrooms
1,275
Square Feet

100 Lovejoy Wharf, Unit PH3B, Boston, MA 02114

$1,770,000 | 56 Lakeview Drive, Centerville, MA 02632

$1,770,000

5
Bedrooms
5
Bathrooms
4,254
Square Feet
1.69
Acres

56 Lakeview Drive, Centerville, MA 02632

an aerial view of a house with a yard

$1,746,588

4
Bedrooms
4
Bathrooms
3,935
Square Feet
1.54
Acres

89 Old North Road, Pocasset, MA 02559

a view of a big house with a big yard and large trees

$1,725,000

5
Bedrooms
5,797
Square Feet
1.89
Acres

6 Peter Hobart Drive, Hingham, MA 02043

Past Rentals
a room with a couch chairs and chandelier

$9,000

2
Bedrooms

135 Seaport Boulevard, Unit 1907, Boston, MA 02210

a living room with furniture and a potted plant

$6,400

3
Bedrooms

2 A Wellington Street, Unit 2, Boston, MA 02118

$6,250 | 78 Davis Avenue, Unit 1, Brookline, MA 02445

$6,250

3
Bedrooms
3,000
Square Feet
2.30
Acres

78 Davis Avenue, Unit 1, Brookline, MA 02445

a living room with furniture and a flat screen tv

$6,000

3
Bedrooms

171 Phipps Street, Quincy, MA 02169

$5,200 | 773 East 4th Street, Unit 1, South Boston, MA 02127

$5,200

3
Bedrooms
2,000
Square Feet

773 East 4th Street, Unit 1, South Boston, MA 02127

a front view of a residential apartment building with a yard

$5,150

3
Bedrooms

45 L Street, Unit 28, Boston, MA 02127

a living room with furniture and a flat screen tv

$5,000

4
Bedrooms

777 East 4th Street, Unit 3, Boston, MA 02127

$5,000 | 773 East 4th Street, Unit 3, South Boston, MA 02127

$5,000

3
Bedrooms
1,600
Square Feet

773 East 4th Street, Unit 3, South Boston, MA 02127

$5,000 | 773 East 4th Street, Unit 2, South Boston, MA 02127

$5,000

3
Bedrooms

773 East 4th Street, Unit 2, South Boston, MA 02127

$5,000 | 773 East 4th Street, Unit 3, South Boston, MA 02127

$5,000

3
Bedrooms

773 East 4th Street, Unit 3, South Boston, MA 02127

$5,000 | 5 Loring Street, Unit SF HOUSE, Boston, MA 02127

$5,000

4
Bedrooms

5 Loring Street, Unit SF HOUSE, Boston, MA 02127

$4,800 | 40 Traveler Street, Unit 201, Boston, MA 02118

$4,800

2
Bedrooms

40 Traveler Street, Unit 201, Boston, MA 02118

$4,700 | 777 East 4th Street, Unit 2, South Boston, MA 02127

$4,700

4
Bedrooms

777 East 4th Street, Unit 2, South Boston, MA 02127

$4,500 | 773 East 4th Street, Unit 2, South Boston, MA 02127

$4,500

3
Bedrooms

773 East 4th Street, Unit 2, South Boston, MA 02127

a living room with furniture and a flat screen tv

$4,200

3
Bedrooms

157 N Street, Unit 1, Boston, MA 02127

a front view of a residential apartment building with a yard

$3,250

2
Bedrooms

148 West 3rd Street, Unit 3, Boston, MA 02127

$3,200 | 50 Middle Street, Unit 3, Boston, MA 02127

$3,200

2
Bedrooms

50 Middle Street, Unit 3, Boston, MA 02127

$3,000 | 291 West 2nd Street, Unit 2, Boston, MA 02127

$3,000

2
Bedrooms

291 West 2nd Street, Unit 2, Boston, MA 02127