Gayle Winters & Co. Real Estate -Compass

Gayle Winters & Co. Real Estate -Compass Gayle Winters & Co. Real Estate
Real Estate Advisor-CRS
New Construction-Investor Premier Realtor and team servicing the Boston and Northshore area.
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08/19/2026

Discover the timeless appeal of 53 Sheridan Circle, an exceptional 3-4 bedroom, 3-bath residence offering sophisticated modern living, generous proportions, and an enviable Wellesley location. Built in 2008 and thoughtfully designed with high ceilings throughout, the home welcomes you with an elegant sense of scale and beautiful maple and bamboo hardwood floors that flow seamlessly from room to room. The custom kitchen makes a statement with rich red cabinetry, creating a warm and distinctive gathering space for everyday living and entertaining. The spacious primary suite offers a private retreat, complete with a luxurious en-suite bath, oversized walk-in closet, and private balcony overlooking the grounds. A finished attic provides additional versatile living space, ideal for a home office, guest retreat, studio, or playroom. The walkout lower level offers exceptional potential for future finished living space, with high ceilings and a steel support beam already in place, while abundant basement storage keeps everyday life effortlessly organized. Outdoors, beautifully maintained grounds create a private setting with a garden area, patio, and deck, providing multiple spaces for outdoor dining, entertaining, or simply enjoying the seasons. A two-car garage adds convenience and ample storage, while thoughtful infrastructure includes 200-amp electrical service, a French drain system surrounding the home's perimeter, and an 80-gallon lifetime storage water tank. Ideally situated near Fiske Elementary School and offering easy access to Route 95 and the Massachusetts Turnpike, 53 Sheridan Circle combines refined comfort, exceptional flexibility, and the enduring appeal of one of Wellesley's most sought-after communities.

08/04/2026

Thinking about selling this fall? Buyers out looking in September and October tend to be serious — they want to close before the holidays, inventory is lighter than the spring rush, and well-prepared homes stand out instead of competing with a flood of new listings. If a sale is on your radar — this fall, next spring, or you're just curious what your home could bring right now — I'd love to chat. No pressure, just a straightforward conversation. Reach out anytime. 🏡

Your trusted agent for more than just listings-I help you access both on market and off-market properties to find the ri...
07/28/2026

Your trusted agent for more than just listings-I help you access both on market and off-market properties to find the right fit!

07/10/2026

Opportunity in Melrose – Bring Your Buyers This Weekend

If you have buyers looking to get into Melrose, 265 Main Street is a property you’ll want them to see. This home offers a fantastic opportunity for the next owner to refresh, personalize, and build equity in a highly desirable location.

With solid bones and great potential, it’s an ideal option for buyers who are ready to make a home their own while getting into a competitive market at an attractive value point.

We’ll be hosting open houses this weekend:
Saturday & Sunday, 11:00 AM – 12:30 PM

Feel free to stop by—we’d love to see you there.

Please reach out if you’d like additional details or a private showing.

617-699-0310/781-520-1361

The market evolves. Technology evolves. The best agents do too. This summer, I'm investing six weeks into coaching, stra...
07/06/2026

The market evolves. Technology evolves. The best agents do too. This summer, I'm investing six weeks into coaching, strategy and skill-building so I can continue showing up as the best possible advisor for my clients. Whether it's negotiating a stronger offer, navigating a changing market, or finding new ways to create opportunities, my goal is always the same: helping you achieve the best possible outcome. Growth never stops and neither do I. ☀️📈 ******erma %inUS

Welcome to 57 Glendale Avenue, a gorgeous 3 bed 2.5 bath home in Melrose! Fully renovated throughout, this property offe...
06/26/2026

Welcome to 57 Glendale Avenue, a gorgeous 3 bed 2.5 bath home in Melrose! Fully renovated throughout, this property offers a blend of character, functionality & modern finishes. The kitchen features custom cabinetry, quartz countertops, an oversized island, farmhouse sink, beverage fridge, built-in microwave & stainless steel appliances. White oak flooring throughout, modern lighting & abundant natural light enhance the living spaces. The bathrooms are beautiful with marble finishes & distinctive design details. Significant improvements include updated plumbing, electrical, HVAC, insulation, roofing, siding, windows, doors, drainage & waterproofing. Additional energy-efficiency enhancements have also been completed. Outside, enjoy a farmer’s porch with composite decking, stonework, landscaped grounds, microclover lawn & updated exterior lighting. Conveniently located near downtown Melrose, this move-in-ready home offers quality updates, thoughtful design & comfortable living spaces.

I am incredibly honored and grateful to share that I have been recognized in the top 1.5% of real estate agents in the U...
06/08/2026

I am incredibly honored and grateful to share that I have been recognized in the top 1.5% of real estate agents in the United States by RealTrends. This milestone is not something I reached alone—it is a direct reflection of the trust my clients place in me every single day.

To my clients, thank you for allowing me to be part of such important moments in your lives. Whether buying, selling, or investing, your confidence in me means everything, and I never take it for granted. To my team, thank you for your dedication, hard work, and commitment to excellence. Your support behind the scenes is what makes everything possible, and I am so proud of what we continue to build together.

I am deeply appreciative and truly grateful for every referral, every conversation, and every opportunity to serve. This recognition motivates me even more to continue delivering the highest level of service and care to each and every one of you.

Thank you for being part of this journey with me.
.5%realtors

06/04/2026

Executive Assistant — Join a Top 1% Real Estate Team
This is not your average assistant role.
If you thrive in fast-paced environments, love being the person who makes everything run seamlessly, and want to work side-by-side with a top-producing agent—keep reading.
I’m looking for a high-level Executive Assistant to become my right hand in a growing, high-performance real estate business serving Greater Boston.
This role is for someone who is sharp, proactive, and thrives under pressure. You don’t wait for instructions—you anticipate, execute, and elevate everything around you.
What You’ll Be Doing
Running point on listings from contract to market: coordinating photography, building MLS listings, and managing launches
Being boots-on-the-ground at properties: walk-throughs, inspections, staging, and vendor coordination
Executing standout events: broker opens, open houses, and high-end listing launches
Managing a fast-moving calendar and inbox with precision
Acting as a key liaison between clients, vendors, and our team to deliver a seamless experience
Handling day-to-day operational and personal support to keep the business running at a high level
Who You Are
You think ahead and solve problems before they happen
You stay calm, focused, and effective in high-pressure situations
You’re highly organized, detail-obsessed, and take pride in ex*****on
You’re tech-savvy (MLS, DocuSign/Dotloop, CRM systems like Follow Up Boss)
You have reliable transportation and are ready to be in the field across Greater Boston
Real estate or executive assistant experience is a strong plus
The Opportunity
Full-time, local role with significant in-person involvement
Competitive compensation with strong upside for the right person
Direct access to top-level real estate operations and mentorship
If this sounds like you—and you’re ready to step into a role where you can truly grow and make an impact—I want to hear from you.
Send me a private message and tell me why you’re the right fit.

06/02/2026

Welcome to 57 Glendale Avenue, a beautifully renovated 3-bedroom, 2 full and 1 half bathroom home where timeless charm meets exceptional modern craftsmanship in the heart of a premium location in Melrose. Extensively renovated from top to bottom, this stunning property has been thoughtfully reimagined with high-end finishes, quality construction, and meticulous attention to detail throughout. Every space feels warm, inviting, and effortlessly functional, creating a home that is as beautiful as it is comfortable.

The heart of the home is the spectacular designer kitchen, featuring all new Bosch appliances including an industrial-style 800 Series gas/electric combo range, custom Schrock cabinetry, quartz countertops with dramatic full slab backsplash, oversized island, Kohler farmhouse sink, matte black pot filler, built-in KitchenAid microwave, beverage refrigerator, and elegant under-cabinet and toe-kick lighting. Custom details like Legrand screwless wall plates and sleek Fittes HVAC vents elevate the space even further.

Throughout the home, you’ll find beautiful new white oak flooring, custom millwork, designer lighting, all new windows and doors, and thoughtfully designed living spaces filled with natural light. The bathrooms blend luxury and character with artisan finishes including Turkish marble sink, handmade Moroccan fixtures, marble tile, and a custom circular window handmade in Portugal.

Beyond the cosmetic updates, the home has undergone an extensive systems renovation with all new plumbing, electrical, HVAC, insulation, roofing, siding, drainage, and waterproofing improvements. Energy-efficient upgrades including HERS certification, Rockwool insulation, foamboard exterior wrapping, and modern mechanical systems provide comfort, efficiency, and peace of mind for years to come.

Outside, the property continues to impress with a welcoming farmer’s porch with Azek decking, new stone walls and stairs, lush microclover sod, updated exterior lighting, and professionally improved landscaping. This is a rare opportunity to own a truly turnkey home where classic New England character and modern luxury come together seamlessly. Call for private showing 617-699-0310

Address

Winchester, MA
01890

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