Jessica Witter

Jessica Witter-Aladesanmi

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

Social Media

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A blurry photo of a street scene with a light.

Awards

RealTrends Verified, 2025

Education



Client Testimonials

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" 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
NAR Speaker 2019

Realtor Magazine 30 under 30 Finalist 2015.

With wit, creativity and determination, Jessica Witter has earned her rightful place among the country's leading real estate authorities. She's an exceptional negotiator and marketer, and her elite customer service puts every client at ease.

As the co-founders of the Witter & Witter team, Jessica and her mother Joan, Sotheby's 2013 Massachusetts Realtor of the Year, excel at serving buyers and sellers from Boston to the Cape and everywhere in between. They offer an unrivaled understanding of the marketplace, and they're supported by a full-service team of professionals.

Jessica's path to real estate success was forged by her constant desire to challenge herself, and she first honed her sales skills at a car dealership. Never one to back down from a challenge, she entered real estate in 2009 on the heels of the global financial crisis. With her signature hard work and tenacity, Jessica quickly earned a loyal clientele and developed a talent for training and motivating others.

Jessica was born and raised in West Hyannisport and graduated from Bryant University with a bachelor's in communications and marketing. She is a 2015 Realtor Magazine 30 under 30 finalist and a frequent industry speaker, sales trainer and conference panelist.

Home Style Video at 221 Victory:

Jessica Witter-Aladesanmiā€™s Listings

a living room with furniture and a large window
a living room with furniture fireplace and flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a window
a dining room with wooden floor a chandelier a glass table and chairs
a view of a dining room with furniture window and wooden floor
a kitchen with stainless steel appliances granite countertop a refrigerator a stove a sink and a microwave
a table and chair in a room
a bathroom with a sink and a window
a view of entryway
a bedroom with a bed and wooden floor
a bedroom with furniture and a window
a bedroom with a bed and wooden floor
a bathroom with a sink toilet and shower
a living room with furniture a rug and a window
a view of a workspace with a window and workspace
a front view of a house with a yard
a front view of a house with a yard
a backyard of a house with barbeque oven table and chairs
an aerial view of a house with a yard
a front view of a house with a yard
a picture of a room
a picture of a book and a bed
unknown
$875,000 | 371 Mt Vernon Street, Dedham, MA 02026
1/25
Listed By CompassUnder Agreement

$875,000

4
Bedrooms
1,668
Square Feet
0.14
Acres

371 Mt Vernon Street, Dedham, MA 02026

Jessica Witter-Aladesanmiā€™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
9,780
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
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
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

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
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

an aerial view of a house with a lake view

$1,770,000

5
Bedrooms
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
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

$3,250 | 148 West 3rd Street, Unit 3, Boston, MA 02127

$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