Judy Michaelis

Judy Michaelis Judy Michaelis has been a highly sought-after Westport, CT real estate agent over the last three decades. Personal attention.

Judy has earned a reputation as a hardworking broker, dedicated to maximizing the value of your home’s sale. Judy Michaelis has been bringing financial expertise and acumen to her Fairfield County real estate practice since 1993. Having raised a family in Westport, CT, she has a reputation as a hard-working broker, on both sides of the transaction, dedicated to getting the job done. With over $340

M in closed sales to date, Judy is a member of the Coldwell Banker® brand’s Presidential Premier group, which represents the top 1% of sales associates internationally. Having begun her real estate career as a Certified Public Accountant specializing in real estate partnerships and taxation at a Big-Four accounting firm in New York City, Judy's credentials include a B.B.A. in Accounting/Marketing and a Master's degree in Taxation. With a real understanding of the local marketplace, whether representing buyers or sellers, all clients are guided through the process with attention to detail and a very high level of expertise and professionalism. Believing that buying and selling real estate is one of the most unique transactions many will undertake, one that is both financial and emotional, Judy meets each client where they are—first time buyer, down-sizer, up-sizer, investor or builder—while solid relationships with resourceful and acclaimed stagers help your property show its best side.

92% of all home buyers use the internet to research the marketplace. Known for her innovative marketing skills, as a listing broker, Judy puts the power of the internet, including social media, to work on every listing. Her objective is to sell your house, netting you the highest proceeds in the shortest amount of time. Buyers benefit from her deep understanding of the market place and its historical underpinnings—key to finding the right house at an accurate price. At work, guiding buyers + sellers through the process, happily and successfully—for over 23 years. Proven results, with Judy Michaelis.

🏡 Under Contract | 6 Twin Circle Drive, Westport, CT 🎉Exciting news — this extraordinary Colonial in Westport, CT is off...
06/16/2026

🏡 Under Contract | 6 Twin Circle Drive, Westport, CT 🎉

Exciting news — this extraordinary Colonial in Westport, CT is officially under contract!

Beautifully set on a quiet cul-de-sac, this Westport luxury home features a resort-style backyard with pool and spa, a rare post-tension concrete tennis court, and a gourmet chef's kitchen with high-end appliances — just moments from Longshore, Compo Beach, and downtown Westport.

We're thrilled to have matched this special property with a buyer who's one step closer to calling it home.

Thank you to everyone who toured, attended the open house, or shared their support. Stay tuned for updates as we move through the next steps. ✨

📲 Thinking about buying or selling in Westport, CT? Call, text, or email me — I'd love to help.

Judy Michaelis | 📞 203-247-5000
✉️ [email protected]

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉🏠 22 Sturges Commons, Westport, CT💲 Listed Price: $3,500,000📍 Near the Hunt Club — a distinguished Colonia...
06/11/2026

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉

🏠 22 Sturges Commons, Westport, CT
💲 Listed Price: $3,500,000

📍 Near the Hunt Club — a distinguished Colonial on a beautifully landscaped acre in one of Westport's most coveted walking neighborhoods, just one traffic light from Greens Farms Station.

📆 Thursday, June 11
🕐 11:00 AM – 1:00 PM

📆 Sunday, June 14
🕐 2:00 PM – 4:00 PM

▪️ 5 beds 🛌 | 6 full + 2 half baths 🛁
▪️ 1 acre 🌳 | 4,911 Sq. Ft. 🏡
▪️ 3-car attached garage 🚘🚘🚘

✨ The gourmet chef's kitchen opens to a step-down family room with soaring ceilings and abundant natural light — the true heart of the home. Formal living and dining rooms offer elegant entertaining spaces, while 5 ensuite bedrooms, a third-floor office or yoga retreat, and a finished lower level with gym, media room, and playroom deliver exceptional flexibility.

🌳 Fully fenced backyard with a sparkling pool and spa, expansive dining and gathering areas, and plenty of room for sports and play.

📲 Can't make it? Call, text, email, or DM for a private showing.

Judy Michaelis | 📞 203-247-5000
📧 [email protected]

🏡 Under Contract | 32 Webb Road, Westport, CT 🎉Exciting news — this stunning newly built 2026 Colonial in Westport, CT i...
06/04/2026

🏡 Under Contract | 32 Webb Road, Westport, CT 🎉

Exciting news — this stunning newly built 2026 Colonial in Westport, CT is officially under contract!
Thoughtfully designed from the ground up, this Westport luxury home features a chef's kitchen, a primary suite with a private balcony, a cul-de-sac setting, and a fully approved pool permit — just half a mile from Compo Beach.

We're thrilled to have matched this special property with a buyer who's one step closer to calling it home.

Thank you to everyone who toured, attended the open house, or shared their support. Stay tuned for updates as we move through the next steps. ✨

📲 Thinking about buying or selling in Westport, CT? Call, text, or email me — I'd love to help.

Judy Michaelis | 📞 203-247-5000
✉️ [email protected]

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉🏠 28 Bulkley Avenue N., Westport, CT💲 Listed Price: $2,500,000📍 Greens Farms — a beautifully renovated 179...
05/28/2026

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉

🏠 28 Bulkley Avenue N., Westport, CT
💲 Listed Price: $2,500,000

📍 Greens Farms — a beautifully renovated 1799 antique Colonial blending original architectural detail and six fireplaces with modern luxury, on a flat half-acre one light to the Greens Farms train.

📆 Saturday, May 30
🕐 2:00 PM – 4:00 PM

▪️ 5 beds 🛌 | 3 full + 2 half baths 🛁
▪️ 0.50 acres 🌳 | 5,793 Sq. Ft. 🏡
▪️ 2-car attached garage 🚘🚘

✨ At the center is a chef's kitchen with Sub-Zero refrigerator, Wolf range, and custom cabinetry, opening to a sun-filled family room. The primary suite features an oversized dressing room and a spa-like bath with soaking tub and steam shower. Six fireplaces and antique details carry through formal rooms that feel both elegant and welcoming. The finished lower level adds a game room, wine cellar, and flexible recreation space.

🌳 Flat half-acre lawn with room for a future pool — ideal for sports, gatherings, and gardens.

📲 Can't make it? Call, text, email, or DM for a private showing.

Judy Michaelis | 📞 203-247-5000
📧 [email protected]

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉🏠 28 Bulkley Avenue N., Westport, CT💲 Listed Price: $2,700,000📍 Greens Farms — a beautifully renovated 179...
05/07/2026

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉

🏠 28 Bulkley Avenue N., Westport, CT
💲 Listed Price: $2,700,000

📍 Greens Farms — a beautifully renovated 1799 antique Colonial blending historic charm with modern luxury, on a flat pool-worthy lot just one light to the Greens Farms train.

📆 Thursday, May 7
🕐 11:00 AM – 1:00 PM

📆 Saturday, May 9
🕐 2:00 PM – 4:00 PM

▪️ 5 beds 🛌 | 3 full + 2 half baths 🛁
▪️ 0.50 acres 🌳 | 5,793 Sq. Ft. 🏡
▪️ 2-car attached garage 🚘🚘

✨ Chef's kitchen with Sub-Zero refrigerator, Wolf range, and custom cabinetry opens to a sun-filled family room. Six fireplaces, antique architectural details, and formal rooms create elegant, welcoming spaces.

Primary suite features an oversized dressing room and spa-like bath with soaking tub and steam shower. Finished lower level includes a game room, wine cellar, and flexible recreation space.

🌳 Expansive flat lawn with room for sports, gatherings, gardens, or a future pool.

📲 Can't make it? Call, text, email, or DM for a private showing.

Judy Michaelis | 📞 203-247-5000
📧 [email protected]

05/04/2026

🎉 𝑪𝑶𝑴𝑰𝑵𝑮 𝑺𝑶𝑶𝑵 🎉

🏠 28 Bulkley Avenue N., Westport, CT 06880
💲Offered at $2,700,000

📍 One of Westport's original homes—built in 1799 and beautifully renovated to blend historic character with modern luxury, offering timeless charm, rich warmth, architectural detail, and exceptional convenience just one light to Greens Farms train. Set on a flat, half-acre property with room for a potential pool in the sought-after Long Lots neighborhood.

📆 Thursday, May 7
🕛 11:00 PM – 1:00 PM

📆 Saturday, May 9
🕛 2:00 PM – 4:00 PM

▪️ 5 beds 🛌 | 3 full & 2 half baths 🛁
▪️ 0.50 acres 🌳 | 5,793 Sq. Ft. 🏡
▪️ 2-car attached garage with mudroom access 🚘
▪️ 6 fireplaces 🔥

Inside:
— Stunning chef’s kitchen with Sub-Zero refrigerator, Wolf range, custom cabinetry, and generous prep space opening to a sun-filled family room
— 9-foot-plus ceilings and hardwood floors throughout the main level with wide-plank character
— Formal dining room, den, and dedicated home office—each with a fireplace and French doors
—Generous family room and living room designed for relaxed gathering and entertaining
— Luxurious primary suite with oversized dressing room, abundant closets, gas log fireplace, and spa-inspired bath with soaking tub
— Three remodeled bedrooms upstairs with exposed beams and hardwood floors
— Beautifully finished lower level with game room, wine cellar, and flexible recreation space

Outside:
— Flat, cleared half-acre lot with endless potential for sports, gardens, entertaining, or future pool
— Front porch, patio, and mudroom complete the package
— Minutes to downtown Westport, Compo Beach, Long Lots Elementary, and the Westport Metro-North station

Comment "LINK" and I'll send you the full listing details. 🏡

📲 Call, text, email, or DM for more information or to be the first to schedule a private showing.

Judy Michaelis | 📞 203-247-5000
📧 [email protected]

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉🏠17 Loren Lane, Westport, CT 06880💲Offered at $1,375,000📍 Beautifully updated and ideally set on a fabulou...
05/01/2026

🎉 𝑶𝑷𝑬𝑵 𝑯𝑶𝑼𝑺𝑬 🎉

🏠17 Loren Lane, Westport, CT 06880
💲Offered at $1,375,000

📍 Beautifully updated and ideally set on a fabulous flat property in one of Westport's most desirable walk-to-town neighborhoods—where comfort, function, and everyday lifestyle meet just minutes from Main Street.

📆 Saturday, May 2
🕛 2:00 PM – 4:00 PM

▪️ 4 beds 🛌 | 2 full & 1 half baths🛁
▪️ 0.34 acres🌳 | 2,000 Sq. Ft. 🏡
▪️ Attached garage with direct mudroom access 🚘

Inside:
— Sun-filled living spaces anchored by a wood-burning fireplace
— Updated kitchen built for daily living and entertaining
— Oversized den for relaxing, gathering, or play
— Mudroom with direct garage access
— Finished lower level with dedicated gym, home office, and rec space
— Four spacious bedrooms upstairs

Outside:
— Flat 0.34-acre level yard, ideal for entertaining and play
— Minutes to Main Street shopping and dining, the Westport Library, Compo Beach, and Longshore Club Park

Comment "LINK" and I'll send you the full listing details. 🏡

📲 Call, text, email, or DM for more information or to be the first to schedule a private showing.

Judy Michaelis | 📞 203-247-5000
📧 [email protected]

04/30/2026

📣🏡Westport Homeowners🏡📣

Equity is earned. Many homeowners discuss their equity, but unfortunately, a significant number of them leave it on the table. When everything was at stake, they sold their home for less than the market value or agreed to less-than-ideal terms. The good news is that such costly mistakes can be avoided. I’ve learned a lot over my lengthy real estate career, selling homes right here in Westport.

Today’s video wraps up my list of the 15 most important lessons:

11. Go easy on the fads!🚫
- Avoid overdosing on trends you’ll regret. The Barbie Pink kitchen maybe?

12. Waterproof the basement!💧
- Your future self will thank you.

13. Get that home inspection🛠️
- Get a professional home inspection every five years and stay ahead of potential
issues. If it is broken, fix it as soon as possible.

14. Landscaping is noticed first!🌳
- Buyers notice, and it takes a while to mature, so it's never too early to start
planting.

15. Tidy homes sell for more!🧹
- Organized clutter-free homes always sell for more.

As they say, experience is the best teacher. It’s certainly been mine, and I hope you’ve picked up some useful insights from these past few videos. If you or someone you know is considering selling, it would be my pleasure to meet and discuss how best to proceed.

📲If you’re looking to sell your home in Westport, call, text, email, or direct message me today - I’d love to chat with you and help you on your home journey!🏡

Judy Michaelis | 203-247-5000 | [email protected]

04/28/2026

🎉 𝑪𝑶𝑴𝑰𝑵𝑮 𝑺𝑶𝑶𝑵 🎉

🏠17 Loren Lane, Westport, CT 06880
💲Offered at $1,375,000

📍 Beautifully updated and ideally set on a fabulous flat property in one of Westport's most desirable walk-to-town neighborhoods—where comfort, function, and everyday lifestyle meet just minutes from Main Street.

📆 Thursday, April 30 🕚 11:00 AM – 1:00 PM

📆 Saturday, May 2 🕛 2:00 PM – 4:00 PM

▪️ 4 beds 🛌 | 2 full & 1 half baths🛁
▪️ 0.34 acres🌳 | 2,000 Sq. Ft. 🏡
▪️ Attached garage with direct mudroom access 🚘

✨ Updated kitchen opens seamlessly to sun-filled living spaces anchored by a charming wood-burning fireplace—designed for daily living and easy entertaining.

✨ Oversized den offers exceptional space for relaxing, gathering, or play, while the mudroom with direct garage access adds the practical convenience today's buyers love.

✨ Finished lower level delivers outstanding flexibility with dedicated gym space, private home office, and additional room for recreation, media, or storage.

✨ Level, flat backyard is ideal for entertaining, play, and outdoor enjoyment year-round.

📍 Conveniently located near downtown Westport, Main Street shopping and dining, Metro North train, Compo Beach, Longshore Club Park, and the Westport Library.

📲 Call, text, email, or DM for more information or to be the first to schedule a private showing.

Judy Michaelis | 📞 203-247-5000
📧 [email protected]

04/28/2026

📣🏡Westport Homeowners🏡📣

Choosing to list your Westport home for sale is, in a way, stepping out into the unknown.

Results vary, and what I know for certain is that strategy matters. Timing matters.
Experience matters. So today’s video resumes my list of the 15 most important lessons
I’ve learned in selling Westport Real Estate. Focusing on lessons six through ten.

In today’s video, I’ll cover five of the 15 most important lessons I’ve learned:

6. Your home needs to be staged! Everyone does.🏡

7. Bring in the realtor, 6 to 12 months before you’re ready to sell.📅

8. Private sales never get you top dollar!💰

9. Real Estate is a long-term investment! Don’t buy unless you have a 5 to 7-year
timeline.⏳

10. 80% or more of what you’re looking for in a home, that’s your home.🏠

Wisdom comes through experience, reflection, and learning from both success and
failure. So if you know someone who is looking to make a move, this video might be
exactly what they need to do wisely.

📲If you’re looking to sell your home in Westport, call, text, email, or direct message me
today - I’d love to chat with you and help you on your home journey!🏡

Judy Michaelis | 203-247-5000 [email protected]

Address

355 Riverside Avenue
Westport, CT
06880

Opening Hours

Monday 9am - 8pm
Tuesday 9am - 8pm
Wednesday 9am - 8pm
Thursday 9am - 8pm
Friday 9am - 8pm

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