I graduated from Staples High School in 1981, so walking through the school again during our class reunion was already pretty special.
But getting a look backstage at the theater was a real trip down memory lane.
Staples Players has been part of the Westport community since 1959—and today, the program gives students opportunities not only to perform, but also to work behind the scenes as technicians and instrumentalists.
⬅️ Click image for a video clip!
And now, this part of Staples is getting an upgrade.
The auditorium is undergoing improvements to its stage rigging, lighting, sound and other technical systems—helping keep this long-running theater program ready for the next generation.
A personal look inside Staples High School—from a Class of 1981 graduate who recently returned for her reunion
If you’re considering a move to Westport, Connecticut, one of the questions you’re likely to have is: What is Staples High School really like?
The answer is more interesting than a school ranking or a list of statistics.
Staples is a large, comprehensive public high school with a remarkably broad range of academic, athletic, artistic and extracurricular opportunities. It is also a school with a long history in Westport—and one that has changed considerably since I walked its halls as a student.
I was reminded of that recently when I returned to Staples for my Class of 1981 reunion.
Our reunion included a tour of the school, and walking through the building again after 45 years was a wonderful opportunity to see what has changed, what has stayed the same, and what today’s Staples students have available to them.
For families already living in Westport—or considering a move here—I thought I’d share some of what I learned and some of the questions I hear most often.
Where is Staples High School?
Staples High School is located at 70 North Avenue in Westport and serves students in grades 9 through 12.
The school is part of the Westport Public Schools system. Current school materials describe Staples as a comprehensive high school with approximately 1,850 students, offering a broad curriculum as well as extensive opportunities outside the classroom.
For families moving into Westport, permanent residency in the town is the primary requirement for enrollment. Owning property or paying taxes in Westport, by itself, does not establish school residency.
What is Staples High School known for?
Academics are certainly an important part of the Staples experience, but one thing that stood out to me during my recent visit was how much more there is going on beyond the traditional classroom.
Staples currently offers more than 150 extracurricular opportunities, including clubs, athletics, art, music and theater. The school describes these activities as an important part of helping students discover their interests, develop teamwork and creative problem-solving skills, and build relationships within the school community.
That breadth is one of the things I think prospective families should understand about Staples.
There isn’t just one definition of a successful Staples student.
A student may be deeply focused on academics. Another may discover a passion for theater, music, journalism, radio, athletics, technology or community involvement. And many students combine several of those interests.
That variety was very evident during our tour.
Staples Players: A Westport Tradition That Continues
One of the things I was particularly excited to see again was the performing arts program.
Staples Players has a long-standing reputation for excellence, and the current Staples website describes the organization as being famous for producing some of the best student theater in the country. It is a year-round program with opportunities not only for actors, but also for students interested in technical theater and instrumental music.
The theater department offers courses including Theater I: Acting Fundamentals, Theater II: Advanced Acting, Theater III: Acting Technique and Theater III: Directing. Students also have opportunities to participate in major productions, Studio Theater productions and the One Act Play Festival.
During our reunion tour, I was able to see behind the scenes, including areas of the theater that are currently undergoing renovation.
During our reunion tour, I was able to see behind the scenes, including areas of the theater that are currently undergoing renovation.
That was particularly fun for me because I remember Staples from a very different era.
And there’s more than one performance space.
⬅️ Click image for the quick tour!
Staples also has a Black Box Theater, which provides a more intimate setting for student productions and other performances. The school’s theater information describes Studio Theater productions and student-organized performances taking place in the Black Box and other venues.
For a community with such a strong artistic identity, having these kinds of opportunities within a public high school is pretty remarkable.
More Than Theater: Music, Media and Radio
The arts at Staples extend well beyond the stage.
Current Staples materials highlight programs in art, music, theater, media and technology education, among other areas.
And during our tour, I came across something that I don’t remember from my own high-school days: an ON AIR/radio space.
Staples actually has a long history of student broadcasting. The school’s current handbook identifies WWPT-FM 90.3, a student radio station, as one of the school’s facilities.
For students interested in communications, journalism, broadcasting or media production, this is the kind of hands-on experience that can turn an interest into a real skill.
And Staples has other ways for students to tell stories and engage with the community, including Inklings, the school’s student news organization. One of our classmates brought an Inklings issue from 1981, which we were comparing to the May 2026 issue!
Athletics Are a Major Part of the Staples Experience
Staples also has extensive athletic facilities and programs.
During our tour, I photographed the pool, field house, track, and field, which give a good visual sense of the scale of the school’s athletic offerings.
The school maintains a dedicated athletics department, with sports registration, coaching resources, student-athlete information and NCAA guidance for students considering collegiate athletics.
For families with student-athletes, that combination of competitive athletics and college-planning resources can be an important consideration.
What About Academics at Staples?
Staples describes its curriculum as “broad and deep,” with the goal of helping students develop programs of study around their individual strengths, interests, challenges and post-high-school goals.
The school offers Advanced Placement opportunities as well as a wide range of courses across traditional academic departments and more specialized areas.
The current program extends beyond the standard core subjects to include areas such as:
Art
Music
Theater
Media
Technology education
Culinary arts
Career and vocational offerings
Online learning opportunities
The current new-student guide also highlights more than 100 co-curricular clubs, while the newer extracurricular resource lists more than 150 offerings across clubs, athletics, music and theater.
For parents moving to Westport, that distinction matters.
The question isn’t simply, “Is Staples a good school?”
A better question is:
Does Staples offer opportunities that fit my particular child?
With its size and breadth, there is a good chance that students can find an academic, artistic, athletic or extracurricular niche that genuinely interests them.
What Happens After Staples?
For many families, college preparation is naturally an important consideration.
Staples has a dedicated school counseling department and resources addressing college applications, financial aid, scholarships, military pathways and athletics in the college admissions process. The principal told us that the majority of students continue onto college, with approximately 93-96% attending four-year schools.
But one of the things I also appreciated hearing during our reunion was the emphasis on helping students prepare for their own next chapter, rather than assuming there is only one definition of success.
That philosophy is consistent with Staples’ stated mission of helping students pursue individual strengths, interests and post-high-school goals.
A Global Perspective
One of the most interesting parts of our reunion was hearing from the principal about the experiences available to students today—including travel opportunities to destinations around the world.
That was a striking reminder of how much the definition of a high-school education has expanded.
Students can learn about another culture in a classroom.
But actually experiencing that culture, traveling with classmates and teachers, and seeing another part of the world firsthand can create an entirely different kind of learning.
This was one of the details I found particularly meaningful because it reflects something I noticed throughout the tour: Staples seems to be trying to prepare students not just for the next test or the next school, but for a much larger world.
How Did Staples Get Through COVID?
Our principal also talked with us about the school’s experience during COVID.
For those of us who graduated decades ago, it was fascinating to hear what it took to keep a large public high school community functioning through such an extraordinary disruption.
The experience was a reminder that a school isn’t simply a building or a curriculum.
It’s a community of students, teachers, administrators and families—and maintaining that community during a crisis required an enormous amount of adaptation.
“No Hate Here” and Creating a Welcoming School Community
Another thing I noticed as we walked through the building was the messaging throughout the school about belonging and inclusion.
I photographed bulletin boards and signs, including “No Hate Here”, a Pride board and the “Respect for Life” mantra permanently etched into the school’s seal.
These aren’t academic statistics, but they are part of what a school communicates about its culture.
The Westport Public Schools describes the community as valuing a town that is welcoming to people of all kinds and encourages students to engage with the broader community.
As someone returning to Staples after 45 years, I found these visual reminders particularly interesting.
The building may have changed.
The technology has certainly changed.
The opportunities have expanded enormously.
But the idea that a school is also a community remains just as important.
What Surprised Me Most About Returning to Staples?
Probably the sheer breadth of opportunity.
When I attended Staples, I obviously experienced it through the lens of a teenager in the late 1970s and early 1980s.
Returning as an adult—and now as a Realtor who spends so much time talking with families about what it is like to live in Westport—gave me an entirely different perspective.
I wasn’t looking at Staples wondering which class I would take next.
I was looking at it through the eyes of a parent considering a move.
I noticed the athletic facilities.
The performing arts.
The theater spaces.
The radio studio.
The bulletin boards.
The classrooms.
The opportunities for travel.
The range of extracurricular activities.
And perhaps most of all, I noticed how much there is for a student to discover.
That may be one of the best things about a comprehensive high school of this size.
Staples High School: Frequently Asked Questions
Is Staples High School a public school?
Yes. Staples High School is the public high school serving Westport, Connecticut, for grades 9–12.
Where is Staples High School located?
Staples is located at 70 North Avenue, Westport, CT 06880.
How many students attend Staples High School?
Current Staples enrollment information describes approximately 1,850 students in grades 9–12.
Does Staples High School offer AP classes?
Yes. Staples offers Advanced Placement courses, with information maintained through its school counseling department.
What extracurricular activities are available at Staples?
Staples currently lists more than 150 extracurricular offerings, including clubs, athletics, music and theater.
Does Staples have a theater program?
Yes. Staples has a dedicated theater department and the renowned Staples Players, along with Studio Theater and One Act opportunities.
Does Staples have a Black Box Theater?
Yes. The school uses its Black Box Theater for Studio Theater and other student performances.
Does Staples have a radio station?
Yes. Staples’ handbook identifies WWPT-FM 90.3 as the school’s radio station.
Does Staples offer athletics?
Yes. Staples has a dedicated athletics department and a broad interscholastic athletics program, with resources for student-athletes and families.
What middle schools feed into Staples?
Westport’s public-school system includes Bedford Middle School and Coleytown Middle School, which serve Westport students before they move on to Staples.
Do you have to live in Westport to attend Staples?
For ordinary public-school enrollment, yes. Westport residency is the primary requirement for enrollment. Simply owning property or paying taxes in Westport does not establish residency for school purposes.
A Realtor’s Perspective: Why Schools Matter When You’re Moving to Westport
When people move to Westport, they are rarely buying a house in isolation.
They’re choosing a community.
They’re thinking about commute times, beaches, parks, restaurants, cultural opportunities, neighbors, recreation—and, for families with children, schools.
That’s why I think it is important for prospective buyers to look beyond a school ranking.
Visit the town.
Explore the neighborhoods.
Understand the school system.
Ask questions.
And think about whether the community—and the opportunities available within it—fit your family’s particular needs.
For me, returning to Staples after 45 years made that perspective especially personal.
I first knew Staples as a student.
Today, I know it as a Realtor, a Westport-area resident and someone who helps people make decisions about where they want to live.
And now I have had the unusual opportunity to see it from both sides.
A Special Connection to a Neighborhood Home
My recent return to Staples also happened at an interesting time professionally.
I’m preparing to bring a wonderful home to the market—a home located just down the road from Staples.
That gave my reunion visit an additional perspective.
As I walked through Staples again, I found myself thinking about what today’s families are looking for when they choose Westport—not simply in a home, but in the lifestyle and community surrounding it.
That’s ultimately what makes Westport such a special place to call home.
If you’re considering buying or selling in Westport, Fairfield or the surrounding coastal communities, I’m always happy to share what I know about the neighborhoods, schools, lifestyle and real estate market.
— Linda Raymond, Realtor | William Raveis Real Estate | 203-912-4440
Discover the best farmers markets in Fairfield, Westport and Black Rock, CT, including locations, days, hours and what to expect from a local Realtor.
Click image to view video! =>
Looking for farmers markets in Fairfield or Westport, Connecticut? One of the things I love about living in this part of Fairfield County is how easy it is to make shopping local part of everyday life.
On a summer morning, you can walk through a farmers market, pick up fresh Connecticut-grown produce, flowers, bread or something delicious for dinner, and run into friends and neighbors along the way.
For me, that is part of what makes Fairfield and Westport such appealing places to live. The farmers markets aren’t simply places to buy food. They’re places where you experience the community.
Here are a few local farmers markets worth knowing about.
Fairfield Farmers Market: Sunday on Sherman Green
If you’re in Fairfield on a Sunday morning, head downtown to Sherman Green for the Fairfield Farmers Market.
The 2026 market runs Sundays from 10 a.m. to 2 p.m., rain or shine, through October 11. Now in its 11th season, the market features more than 40 farms, food producers and artisan vendors.
You’ll find many of the things you’d hope to see at a traditional farmers market: seasonal fruits and vegetables, flowers, bread and baked goods, honey, eggs, meat, fish, mushrooms, pickles, prepared foods, artisan products and more.
But what I especially enjoy is the atmosphere.
Sherman Green becomes a gathering place on Sunday mornings. There are vendors and shoppers, families and friends, and often music and community activities. It’s a chance to do some shopping while also getting out into the community.
Fairfield Farmers Market 📍 Sherman Green, downtown Fairfield 📅 Sundays ⏰ 10 a.m.–2 p.m. 📆 2026 season through October 11 🌧️ Rain or shine
Shout outs to some of the market contributors! (in order of appearance)
Just west of Fairfield, the Farmers’ Market of Black Rock offers another convenient weekend option.
The 2026 market is held Saturdays from 9 a.m. to 1 p.m. at St. Ann Church, 481 Brewster Street in Bridgeport’s Black Rock neighborhood, running from June 13 through October 31.
Black Rock has its own distinctive neighborhood character, and the farmers market fits naturally into that walkable, community-oriented atmosphere. In fact, our friend, Marion who works at Gabagool in Fairfield, makes her home made crepes on Saturday mornings for the Black Rock Farmer’s Market!
If you’re spending a Saturday morning exploring Black Rock, the market is an easy stop to add to the itinerary.
Farmers’ Market of Black Rock 📍 St. Ann Church, 481 Brewster Street, Bridgeport 📅 Saturdays ⏰ 9 a.m.–1 p.m. 📆 2026 season through October 31
Westport Farmers’ Market: Thursday at Imperial Avenue
Westport’s farmers market has a slightly different rhythm because it takes place on Thursday, making it a great midweek opportunity to shop local.
The Westport Farmers’ Market runs from May 7 through November 5, 2026, Thursdays from 10 a.m. to 2 p.m. at 50 Imperial Avenue.
The market focuses on fresh, local, healthy and seasonal food and describes its mission as supporting local producers and sustainable, healthy growing practices. It is also a non-GMO market.
You’ll find everything from produce and flowers to baked goods, bread, honey, prepared foods, coffee and other locally produced specialties.
There’s also an especially nice community component. Through its Farmers + School + Community program, the market works with Staples High School culinary students to prepare meals using ingredients sourced from the market for people served by Homes with Hope’s community kitchen.
Why Farmers Markets Are Part of the Fairfield County Lifestyle
For someone considering a move to Fairfield, Westport or the surrounding communities, farmers markets might seem like a small detail.
I don’t think they are.
When people ask me what it’s really like to live here, I often find that the answer isn’t just about the house. It’s about the things you can do on an ordinary Tuesday, Thursday or Sunday.
It’s recognizing a neighbor at the farmers market.
It’s having places where you naturally become part of the community.
Those everyday experiences are an important part of the lifestyle appeal of Fairfield and Westport.
And that’s one reason I enjoy creating local guides like this. Real estate isn’t just about houses and property values. It’s also about helping people understand what their life could look like once they move here.
Three Local Markets, Three Different Experiences
One of the nice things about living in this area is that you don’t have to choose just one.
Sunday: Fairfield Farmers Market on Sherman Green Saturday: Farmers’ Market of Black Rock Thursday: Westport Farmers’ Market
Each has its own setting and personality, so if you enjoy shopping local, it’s worth exploring all three.
And if you’re new to Fairfield County, visiting a farmers market can be a surprisingly good way to get a feel for a neighborhood. Look around. Listen to the conversations. Notice who lives there, what people are buying and how people use the surrounding streets and public spaces.
That’s the kind of local detail you won’t necessarily find just looking at houses.
A Local Realtor’s Perspective
As a Realtor specializing in Fairfield and Westport, one of my favorite parts of my job is helping people look beyond the four walls of a house.
A home is important—but so is the community around it.
When buyers are deciding between Fairfield, Westport, Southport, Black Rock or another Fairfield County neighborhood, I encourage them to spend some time here as if they already lived here.
And, if it’s market day, stop by a farmers market.
You may learn more about whether a community feels right for you in an hour of simply being there than you will from looking at dozens of property photos online.
Planning a Visit?
Before heading out, check the individual market’s website or social media for the most current vendor information, special events and any weather-related changes.
And if you visit one of these markets, I’d love to know: Which is your favorite?
More Fairfield & Westport Local Guides
I’m continually adding local information about the communities, neighborhoods, beaches, restaurants, events and lifestyle that make Fairfield County such a special place to call home.
If you’re thinking about buying or selling a home in Fairfield, Westport or the surrounding area, I’m always happy to share what I know about the local market and the communities I know and love.
Linda Raymond William Raveis Real Estate Fairfield & Westport, Connecticut
It’s August! ☀️ The market was hot in July! Here’s a summary of the Fairfield and Westport CT single-family markets compared to a year ago.
July 2026 Takeaways 📝
Housing Supply: Months of housing supply continued to be limited with 2.7 months in Fairfield and 3.6 in Westport at the end of July, showing a continued sellers’ market.
Price Selection: Homes sold across all price points, between $433K to $4.2M in Fairfield and from $1.2M to $8.986M in Westport.
Competition: The median price was still up from a year ago due to continued high demand and low supply. Homes sold an average of 5-6% over the asking price, however this reflected a wide range.
Market Time: The time from list to contract was brisk, averaging less than 30 days in both towns! Almost all listings (over 96%) sold in 90 days or less.
Buyer Takeaway: Buyers can work with their agents to plan the best offer approach based on their needs and the conditions specific to their home of interest, since competition is still case-by-case.
Seller Takeaway: The successful sellers were those who priced competitively to draw buyers in quickly and invested in the steps needed to present their property in it’s best possible light to ensure buyers felt a strong and positive emotional connection when they arrived.
Below are the William Raveis Local Housing Data charts from July.
Every spring and early summer, something remarkable happens along Connecticut’s shoreline. As the tides rise, thousands of horseshoe crabs emerge under the cover of darkness to continue a ritual that has remained largely unchanged for hundreds of millions of years.
The past two summers, I had the opportunity to volunteer with Project Limulus at Southport Beach CT, helping researchers safely tag horseshoe crabs as part of an ongoing conservation effort. Spending a morning alongside scientists, volunteers, and families gave me an even greater appreciation for these extraordinary animals and the role they play in keeping Long Island Sound healthy.
As a coastal Connecticut Realtor specializing in Fairfield, Southport, and Westport, I believe one of the greatest privileges of living here is being surrounded by an incredible coastal ecosystem. Protecting it helps preserve the quality of life that makes our shoreline communities so special.
Here are ten things you may not know about horseshoe crabs.
1. Despite Their Appearance, They Can’t Bite or Pinch You
Horseshoe crabs often surprise people with their armored shells and long pointed tails. Fortunately, they’re completely harmless to humans.
They have no teeth, no stingers, and no claws capable of pinching. Their tail, called a telson, isn’t a weapon—it’s simply a tool they use to flip themselves over if waves leave them upside down.
2. They’ve Been Around Since Before the Dinosaurs
Horseshoe crabs have survived for more than 445 million years, making them one of Earth’s oldest living species.
They’ve lived through multiple mass extinctions, the age of dinosaurs, and even the Ice Age. Few living creatures can claim such an extraordinary history.
3. The Males Really Do Wear “Boxing Gloves”
One of the easiest ways researchers identify males and females is by looking at their front pincers.
Male horseshoe crabs have distinctive hook-shaped claws that resemble tiny boxing gloves. These specialized claws allow the male to hold onto the female during spawning as she lays eggs along the shoreline.
Once you know what to look for, it’s surprisingly easy to tell them apart.
4. They’re Living Ecosystems
A single horseshoe crab supports an entire community of marine life.
Their shells often become home to algae, barnacles, mussels, slipper shells, and other organisms, creating miniature ecosystems wherever they travel.
In many ways, they’re not just part of the ecosystem—they’re ecosystems themselves.
5. Their Eggs Feed Thousands of Migrating Birds
Each female can lay tens of thousands of eggs during spawning season.
Those nutrient-rich eggs become a vital food source for migrating shorebirds traveling thousands of miles along the Atlantic Flyway. Without healthy horseshoe crab populations, many bird species would struggle to complete their migrations successfully.
Healthy beaches support healthy wildlife.
6. Their Blood Has Saved Countless Human Lives
One of the most remarkable facts about horseshoe crabs is that their blue blood has transformed modern medicine.
Their blood contains specialized cells that clot instantly in the presence of harmful bacterial toxins. Scientists developed a test using this natural reaction that helps ensure vaccines, intravenous medications, implantable medical devices, and many injectable pharmaceuticals are free from dangerous bacterial contamination before reaching patients.
Research involving horseshoe crabs has also contributed to advances in vision science and has inspired innovations used in specialized surgical materials and wound care.
7. Their Eyes Are Unlike Almost Any Other Animal
Horseshoe crabs have multiple eyes positioned around their bodies, each serving different purposes.
Their unique visual system has been studied for decades and has expanded scientists’ understanding of how vision and the nervous system process light and movement—research that has influenced both medicine and neuroscience.
8. Their Population Has Been Declining
Although horseshoe crabs have survived for hundreds of millions of years, modern challenges have put increasing pressure on their populations.
Habitat loss, shoreline development, harvesting, and climate-related changes have all contributed to population declines in parts of their range.
That’s why monitoring and conservation efforts are so important.
9. Project Limulus Has Been Protecting Long Island Sound for Decades
Project Limulus began in 1997 to better understand and conserve horseshoe crab populations throughout Long Island Sound.
Since then, volunteers and researchers have tagged approximately 98,000 horseshoe crabs, collecting valuable information about migration patterns, longevity, spawning behavior, and population trends.
One of the project’s greatest strengths is its commitment to public education. Community volunteers—including local residents like me—work alongside scientists to collect meaningful data while learning firsthand why these remarkable animals matter.
Every tagged horseshoe crab contributes another piece to a much larger puzzle.
The information collected through Project Limulus helps scientists make informed conservation decisions that benefit wildlife, coastal habitats, and ultimately everyone who enjoys Long Island Sound.
Living along Connecticut’s shoreline means being stewards of an extraordinary environment. Whether you’re walking Southport Beach, kayaking in the Sound, or simply enjoying the beauty of our coastline, horseshoe crabs are quietly playing an essential role beneath the surface.
Horseshoe crabs are tagged in NY, CT, MA, and RI. They tend to travel long distances!
If you find a horseshoe crab with a white disc please call 1-888-LIMULUS (1-888-546-8587) to report the tag number, location (specific beach), date you found the crab, and if the crab was alive or dead.
If you see a yellow cinch tags call 203-365-7577 to report the tag number, location (which beach), date you found the crab, and if the crab was alive or dead.
Please return live crabs to the water.
I’m grateful to have participated in this year’s Project Limulus event and look forward to volunteering again. Experiences like these remind me why I’m so passionate about our coastal communities—not only for the beautiful homes they offer, but also for the incredible natural resources that make Fairfield, Southport, and Westport such special places to live.
Have you ever spotted horseshoe crabs along Connecticut’s shoreline? I’d love to hear about your experience—or better yet, consider volunteering at a future Project Limulus event. It’s a memorable way to give back to one of our region’s most remarkable natural treasures.
Fairfield and Westport Connecticut have been home to a seller’s market for about six years now. However, this doesn’t mean every homeowner can decide to sell tomorrow and ensure a win. The reality is that most homeowners have their own unique circumstances and priorities, and most homes are not show-ready the day they decide to move. But alignment between the seller and their agent on the desired outcomes and how to get there, will get the successful sale and a fresh start well on the way.
Result – Sold for $151,000 above list in 10 days while meeting the seller’s timing and outcome goals.
Address: 120 Saddle View Road, Fairfield
List Price: $1,199,000
Sale Price: $1,350,000
Amount Above List: $151,000
Percent Above List: 13%
Days on Market: 10
For more than three decades, this Fairfield home was the center of family life.
A family of five—including two adult sons, a close family friend, and the homeowners—filled the house with decades of memories after purchasing it in 2007. Weekends were spent tackling home improvement projects, hosting backyard barbecues, and enjoying life in their close-knit Lake Mohegan neighborhood.
Their home evolved along with their family. Over the years they completed numerous improvements, including adding a second story, opening interior walls, relocating the kitchen, creating beautiful landscaping, and building a new pool deck. Every project reflected the pride they took in their home and their love of living there.
Although they knew they would eventually move to Florida to be closer to family, there never seemed to be a reason to rush.
Then everything changed.
While vacationing in Florida, the husband experienced an unexpected medical emergency. His doctors prohibited him from flying home for at least six months, leaving his wife to balance full-time caregiving with mounting medical bills and the overwhelming task of preparing a home that wasn’t remotely ready to sell.
With several family members still living in the house—and decades’ worth of belongings filling every room—she wasn’t sure where to begin.
That’s when she called me.
Step 1: Establishing the Seller’s Priorities
Before discussing pricing or marketing, we talked about what mattered most.
Her goals were clear:
Sell as quickly as possible.
Achieve the highest possible sale price.
Create a plan that reduced as much stress as possible during an already difficult time.
Those priorities became the foundation for every decision that followed.
Step 2: Developing the Right Strategy
We agreed that success would depend on attracting buyers immediately rather than “testing the market.”
The home had excellent bones and had been lovingly maintained, but it was still functioning as a busy family home. Furniture placement reflected everyday living instead of showcasing the home’s space and flow, and years of accumulated belongings made it impossible for buyers to appreciate its full potential.
Rather than trying to market the house as-is, we created a step-by-step roadmap that would maximize both presentation and value.
Step 3: Strategic Pricing
Once the preparation plan was in place, we selected a pricing strategy designed to generate immediate interest.
Instead of pricing at the upper limit of perceived value, we positioned the home competitively to encourage strong traffic and multiple offers. When paired with excellent presentation, this approach often creates the strongest negotiating position.
Step 4: A Coordinated Plan
Selling the home wasn’t a single event—it was a carefully managed process.
Our roadmap included:
Finding a rental home
Negotiating the lease
Developing the pricing and marketing strategy
Moving the family
Clearing out decades of belongings
Pre-marketing & neighborhood showcasing
Painting the interior from top to bottom
Replacing dated light fixtures and bulbs
Deep cleaning, including windows & carpets
Updating curtains and shower curtains
Professional staging
Professional photography, video, and digital media
Launching the listing
Implementing my custom comprehensive marketing plan
Negotiating offers
Resolving missing permit issues
Successfully closing the sale
Each step built on the previous one, allowing the home to reach the market in its best possible condition.
Step 5: Connecting the Sellers with Trusted Resources
One of the biggest challenges wasn’t the marketing—it was logistics.
Over the course of the project, I coordinated trusted local professionals to facilitate every phase of the move, including home clean-out experts, painters, cleaners, contractors, stagers, an attorney partner, town officials, and other service providers. Having the right team in place and keeping them on track transformed what initially felt overwhelming into a manageable and productive process.
When life changes unexpectedly, having an experienced agent and advocate to facilitate the plan can make all the difference.
The Takeaway
This sale wasn’t successful simply because the home sold.
It was successful because the sellers and their Realtor shared the same vision and collaborated from the very beginning.
When homeowners and their agent have a true meeting of the minds—agreeing on priorities, pricing strategy, preparation, and execution—the selling process becomes far more efficient and far less stressful.
Whether you’re relocating across town, downsizing after decades in one home, or navigating an unexpected life event, having a thoughtful plan and committing to the process before your home hits the market can make a significant difference in both your experience and your final sale price.
They automatically take the ‘marriage vow’. They give unconditional love -in sickness and in health until death due us part- and only want the same in return. They are an ever-present uplifting energy in your life. They are as social as we are, needing attention, interaction, stimulation, encouragement, protection, discipline, education, rewards, love, and togetherness.
Roger (Havanese from a breeder in NY) and Charlie (terrier mix from Pet Finders) were the odd couple! But they were brothers who adored each other, sibling rivalry and all! They also adored us, and we adored them!
We lost Charlie in March of 2026 to heart failure at the age of 16. Roger at 15, was healthy but completely changed. We couldn’t console him. Despite double the walks each day, extra treats, new puzzles, more time at home… it wasn’t enough. We weren’t enough. He couldn’t bounce back. He stopped eating, didn’t move all day… lost all his strength. He died of a broken heart in June.
But we know we gave them both a fun and loving life, and they did the same in return, as long as they could. So I want to share some of the memories below, and let them live here on my blog, where we can come back and visit anytime. ❤️🐾❤️🐾
Feel free to share a comment or story about your loving pet at the bottom of this page.
Featuring first-floor bedrooms, four full baths, an enviable private fenced backyard, and easy access to beaches, commuter rail, and Fairfield’s town centers, this home checks all the boxes. Ideally located steps from the Lake with serene dog-friendly nature trails, fresh-water swimming beach, and sprinkler area, this beautifully updated home with 3,328 square feet on three levels and .68 acres offers the perfect blend of space, convenience, and lifestyle.
Designed for flexible modern living, the home features multiple entrances, open-flow, and a large eat-in kitchen with an oversized island and direct access to the backyard for seamless indoor-outdoor entertaining.
The second floor offers two primary suite options, another guest bedroom and a full hall bath. The main suite is a private retreat with a vaulted ceiling, walk-in closets, a generous proportioned spa-inspired bath, and a balcony overlooking the backyard. An open flex space with a picture window creates an ideal home office, reading nook, or homework area. Convenient upstairs laundry completes the upper floor.
The lower level offers additional flex rooms perfect for a gym, playroom, media room, or workshop, while the attic, basement, garage, and shed provide exceptional storage.
Enjoy comfort , energy-efficiency, and peace of mind year-round with central air, (2 HVAC systems), extra insulation, and programmable thermostats in this generator-ready home.
Enjoy access to award-winning schools, peaceful nature, Long Island Sound beaches, shopping, dining, libraries, performance venues, Sportsplex, and two train stations.
With Fairfield and Westport Connecticut real estate markets favoring sellers since 2020, it’s easy to assume that every home magically flies off the shelf. The reality is that the homeowners who seek a savvy agent, align with the strategy they propose, and take advantage of the resources they provide are the ones who enjoy success!
Buyers in this market are competing aggressively- only for the homes they fall in love with and truly want.
Every successful sale is the result of more than marketing alone. It begins with a shared commitment between homeowner and agent, followed by strategic planning, careful preparation, and ongoing collaboration throughout the process.
Result – Sold for $255,000 above list in 13 days while meeting the seller’s timing goals.
Property: 494 Pequot Court, Southport Village
List Price: $1,495,000
Sale Price: $1,750,000
Percent Above Asking: 17%
Days on Market: 13
Aligned Vision
We met to confirm the end-goal and priorities before a plan was established. The goal was to sell quickly for the highest price, but remain in the property for an extra month or so to finish a work commitment.
ProposedPlan
In my role of sharing information to help my client make informed decisions, I told her that optimal presentation and attractive pricing were both key success factors before creative and comprehensive marketing could begin. We toured the property together, and I compiled a list of key selling points, potential objections, and recommendations for how to get top dollar. We drafted a schedule together and got to work.
I connected my seller with an excellent local attorney upfront, because the antique home had numerous property easement changes on the deed over the years, so we could be proactive in sorting that out.
Conservative pricing
We reviewed the market data on both town-wide and neighborhood levels, and then looked at the closest comparable sales and potential competition for her property. We agreed to price conservatively to attract buyers and elicit enthusiasm versus critique when they came through. This also created competition for the home.
I invited a handful of agents from my office for a preview and endorsement of our price since there was very little immediate market data available to pinpoint a number.
Intentional home prep
Since curb appeal makes the first impression, we began there. A tree in front of the house was cute when she bought it three years earlier, but it since grew to hide the charming front porch and adorable covered terrace beneath, two key assets of the home. So it was important to the mission to remove it. The brick terrace had also been covered by a layer of green growth since it was last purchased.
So I connected her with my best landscaper to complete a full landscape refresh including tree removal, weeding, trimming, power-washing, and mulching.
The interior was well-maintained and had been updated by the prior owner, but it was packed full of large-scale furnishings from a prior residence that was more than three times the size. Most of the furnishings were cherished finds from chic furniture stores or specialty antique shops. So we focused on what had the biggest impact. We relocated some chairs to open the space and showcase the fireplace. We moved smaller pieces from window sills into storage to capitalize on the beautiful views of the gardens. And we identified other pieces that could be stored in the garage or sold.
That’s when I shared my estate sale contacts who helped to sell several armoires and an extra bed.
We used staging as a key marketing strategy to showcase the home’s assets and best use of space, streamline the focal points, and make a powerful emotional impression for buyers starting with the first glance at the curb.
Strategic timing& comprehensive marketing
It was going to take a few weeks to get the home ready amidst my client’s work and family obligations, but once the paperwork was complete, I began a marketing campaign to promote the Southport Village neighborhood where the house was located. This included a series of blog posts about the history and amenities of Southport Village that were shared across multiple social media channels.
Southport Village Video Shoot
Because the location was as much of an asset as the house itself, we filmed clips all over town, which also drew attention and conversation about the upcoming sale among passers by.
Once the house preparation was complete, I brought in my professional photography, video, drone, and floor plan crew.
The rollout capitalized on an in-office announcement just before the listing approached the market, use of the Coming Soon status in the Multiple Listing Service, and a yard sign with my agent rider to build momentum and pre-fill the upcoming showing schedule. This was followed by activating the listing for showings along with a full promotion on all websites and social channels to announce the new listing, broker tour, and the weekend of open houses.
I shared the new listing launch with my vast network via text thread, networking groups, social media groups, and email contacts.
The beautiful professional images and video were shared across dozens of websites and social media channels, email, and printed brochures, so that news could reach everyone wherever they were and whenever they were looking, 24/7.
Potential roadblock
My client had replaced the cedar roof on the detached garage with a licensed contractor but without obtaining a permit. Our buyer insisted that the seller obtain the permit before closing. The added layer was that the house was in the Southport Historic District and a flood zone, so those two departments needed to sign off in addition to the building and zoning departments in order to close the permit.
I connected my client with the Fairfield zoning department and historic commission to begin the permitting process. Ultimately, I also had to press them to come out for the final inspection in time for the closing!
Resources provided
Landscapers, staging insights, estate planners, photographers, videographers, drone specialists, the right attorney, town officials, office colleagues, and my vast network were key resources I provided to my client as we worked together to implement the plan.
This network, along with the countless technology platforms, digital subscriptions, and APPs I employ, helped to pull it all together.
The result
Several showings were pre-scheduled for the first few days of the active listing. The broker tour and two open houses had a non-stop flow of interested agents and potential buyers. We received an offer well-above the list price right away. We knew we could not keep that buyer waiting but wanted to honor the previously scheduled showings and open houses. So we made an offer deadline of noon on Monday, and by then, we had three offers to review. We reviewed the benefits and risks of each offer, accepted one, and sold the house for $255,000 (17%) above the asking price with a rent-back to my client at an agreed-upon rate, for a month and a half.
Fairfield and Westport CT Real Estate Guide 