Hero Real Estate

Winthrop, MA Real Estate

Your Trusted Greater Boston Realtor

I represent buyers and sellers in Winthrop and across Greater Boston — from Marblehead and Swampscott to Newton, Wellesley, Belmont, Hingham and Weymouth. With Bowdoin Real Estate Partners, I pair real market knowledge with a patient, honest process my clients consistently rate 5 stars.

Why Work With Me

Why Work With Me

My clients keep writing the same thing: I never pressured them. One buyer told Zillow I "never pressured us into making an offer on a home we didn't love or waive contingencies," and another spent more than a year searching with me before we found the right house. That's the standard I hold myself to. As a REALTOR® with Bowdoin Real Estate Partners — a team with 119+ closed sales and a $295K–$2M price range across Greater Boston — I have the data and the deal experience to price sharply, negotiate hard, and tell you the truth about a property. But I also bring a financial professional's background to the table, which means we talk plainly about numbers: carrying costs, resale, renovation math, what a bidding war actually costs you. Whether you're buying your first condo in Winthrop, trading up to a forever home, or selling and buying at the same time (I've done both in one transaction for clients), you'll get a straight answer, a fast reply, and a guide who is genuinely enjoyable to spend a Saturday with. Professional, caring, and fun — that's how my clients describe working with me, and I'd rather earn that than rush you into a closing.

Greater Boston Market Expertise

I work an unusually wide map, on purpose. Winthrop is my hub — a peninsula community where knowing the difference between Winthrop Highlands, Point Shirley and Cottage Hill changes what you should pay. From there I serve the North Shore in Marblehead and Swampscott, the South Shore in Hingham and Weymouth, the suburbs in Wellesley, Newton and Belmont, and neighborhoods throughout Boston and East Boston. That range matters when you're deciding where to live, not just which house to buy: I can compare commutes, school considerations, condo-fee structures, flood and coastal factors, and price-per-square-foot across all of them in one conversation. Backed by my team's active pipeline of sales, listings and rentals, I'm looking at real closed numbers every week — not last quarter's headlines.

Buyers & Sellers

Full representation on both sides, including simultaneous sale-and-purchase transactions.

No-Pressure Guidance

Clients say I never pushed them to offer on a home they didn't love.

Greater Boston Reach

Winthrop, Boston, Marblehead, Swampscott, Hingham, Weymouth, Wellesley, Newton, Belmont.

Prompt Communication

Reviewers consistently note fast, reliable responses at every stage of the deal.

Your Journey Home

Your Journey Home

We start with a conversation about the outcome you want and the numbers behind it — budget, timeline, financing, and what you're willing to trade. For buyers, I set up a focused search, tour properties with an honest running commentary on condition and value, and write offers strategically so you're competitive without waiving the protections that matter. For sellers, I walk your home room by room, recommend only the prep that returns real money, price it against live comparables, and market it to the Greater Boston buyer pool through my team's network. From there I manage inspections, appraisals, lender deadlines and the closing table, keeping you updated before you have to ask. And if you're selling and buying at once, I sequence both so you're never homeless and never carrying two payments longer than necessary.

Homes for sale in Winthrop

Featured listings currently on the market

Property at 32 Irwin St, Winthrop, MA 02152
1 / 37
Active

$1,049,900

32 Irwin St, Winthrop, MA 02152

6 bds
|
4 ba
|
2949 sqft
MLS® 735343853 Family
The Aland Realty Group LLC - Michael Giannone
Property at 23-25 Fremont St, Winthrop, MA 02152
1 / 23
Active

$1,250,000

23-25 Fremont St, Winthrop, MA 02152

6 bds
|
3 ba
|
3420 sqft
MLS® 735888913 Family
Coldwell Banker Realty - Boston - Alla Rossi
Property at 129 Strandway, Winthrop, MA 02152
1 / 34
Active

$1,275,000

129 Strandway, Winthrop, MA 02152

4 bds
|
3 ba
|
2599 sqft
MLS® 73585487Single Family Residence
Redfin Corp. - Kyle Macnichol
Property at 63 Harbor View Ave, Winthrop, MA 02152
1 / 41
Active
Open

$1,500,000

63 Harbor View Ave, Winthrop, MA 02152

4 bds
|
2 ba
|
2852 sqft
MLS® 73582288Multi Family
Brian J. Perrin Real Estate - Brian Perrin
Property at 94 Winthrop Shore Dr, Winthrop, MA 02152
1 / 42
Active

$1,095,000

94 Winthrop Shore Dr, Winthrop, MA 02152

2 bds
|
3 ba
|
2649 sqft
MLS® 73577096Single Family Residence
Compass - The Movement Group
Property at 174 Bartlett Road, Winthrop, MA 02152
1 / 42
Active

$2,100,000

174 Bartlett Road, Winthrop, MA 02152

5 bds
|
5.5 ba
|
6224 sqft
MLS® 73550891Single Family Residence
Blue Sky Realty - Atiyeh Cassidy
Property at 3 Seal Harbor Rd #PH33, Winthrop, MA 02152
1 / 41
Active

$1,230,000

3 Seal Harbor Rd #PH33, Winthrop, MA 02152

3 bds
|
3 ba
|
1913 sqft
MLS® 73560746Condominium
Charlesgate Realty Group, llc - Cathie Curran
Property at 63-69 Putnam St, Winthrop, MA 02152
1 / 5
Active

$2,250,000

63-69 Putnam St, Winthrop, MA 02152

16 bds
|
14 ba
|
10000 sqft
MLS® 735318295+ Family - 5+ Units Up/Down
Leading Edge Real Estate - The Bill Butler Group

Client Testimonials

What My Clients Say

Every review below came from a real closing — first-time buyers, move-up buyers, and sellers across Winthrop, Boston and the North Shore. The words that repeat are the ones I'm proudest of: stress-free, no pressure, prompt, and "got us into our forever home."

“Jenny was our best decision of 2025! Without her knowledge, unwavering energy, HONESTY, and amazing sense of humor, we would not have landed in our dream house. We started working with Jenny as first-time homebuyers in March 2025, and she guided us through countless home visits during our search (wh...”

Terra B.

Verified Direct Review•Mar 2025

“Jenny did an incredible job with helping my partner and I find the perfect home for us. She never pressured us into making an offer on a home we didn't love or waive contingencies. Bought a single family home in 2023 in Beverly, MA.”

Jess Andrews

Verified Zillow Review•Jun 2023

“Jenny did an amazing job getting us in our forever home and selling our condo. She had great knowledge of the market and the area. She's very professional, highly recommend. Bought and sold a single family home in 2023 in Winthrop, MA.”

Anthony Fucillo

Verified Zillow Review•Mar 2023

Frequently Asked Questions