Cindy Raney & Team

Cindy Raney & Team Fairfield County luxury real estate advice & local lifestyle for those living in/moving to CT.

Featured in USA Today, CBS News, Better Homes & Gardens.
$700MM+ sold.

02/28/2026

LIFE ON OLD ACADEMY ROAD // It is not simply a street within Greenfield Hill. It is one of the addresses that helps define it.

The homes are set on mature, beautifully maintained properties. Stone walls, established landscaping, and a quiet pride of ownership reflect long-term care and investment.

There’s a reason buyers wait for opportunities here. And when they’re fortunate enough to find one, they tend to hold onto it.

Turnover is rare. That alone says it all.

📍1380 Old Academy Road
Fairfield, CT
$2,595,000

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Luxury Real Estate • Real Estate • Luxury Living • Luxury Homes • Fairfield County • CT Living • Connecticut Lifestyle • Living in Fairfield County • Real Estate Teams in Fairfield, CT • Luxury Real Estate Agents • Fairfield Realtors • Homes for Sale Under $3M in Fairfield, CT

YOU’RE INVITED // On Old Academy, neighbors arrive and remain. If they move, they move within. Homes aren’t stepping sto...
02/27/2026

YOU’RE INVITED // On Old Academy, neighbors arrive and remain. If they move, they move within. Homes aren’t stepping stones. They’re chosen carefully and kept.

1380 Old Academy was built with that same intention. A gravel courtyard arrival behind a stone wall. Estate-scale grounds with a putting green, pool, and stone terraces. Interiors that expand when the house is full and settle with ease when it’s quiet. A home that evolves alongside the life lived inside it.

Join us tomorrow, February 28th from 12-2pm to tour this beautiful home and enter to win custom spring planters from !

JUST LISTED // Set behind a stone wall in Greenfield Hill, 1830 Old Academy Road is designed to live beautifully across ...
02/26/2026

JUST LISTED // Set behind a stone wall in Greenfield Hill, 1830 Old Academy Road is designed to live beautifully across seasons. Multiple fireplaces ground the main living areas, while a considered layout allows the home to adapt easily from quiet mornings to full gatherings.

Outdoors, the courtyard arrival, pool, porch, and open lawn create spaces meant to be enjoyed rather than simply admired.

Stop by one of our upcoming open houses to experience it for yourself:
• Thursday, February 26 | 11am–2pm
• Saturday, February 28 | 12pm–2pm

📍1380 Old Academy Road
Fairfield, CT
$2,595,000

MISSING THE MARKET // Every seller worries about timing. Not because they don’t understand the market, but because they ...
02/25/2026

MISSING THE MARKET // Every seller worries about timing. Not because they don’t understand the market, but because they don’t want to get it wrong.

The truth is, there is rarely a single “perfect” moment to sell. Markets move gradually, shaped by buyer behavior, supply levels, pricing signals, and sentiment that rarely makes headlines.

What worked even a few weeks ago may not apply today. And what applies to one home may not apply to yours.

So instead of focusing only on timing, the real conversation should be about strategy.

With pricing, presentation, and positioning aligned to current conditions, sellers are able to move forward confidently and decisively, instead of reacting to the market.

If you’re thinking about selling this year, we’re happy to help you understand what the market is actually doing right now, and what that means for your home.

INTERNATIONAL SOCIETY OF EXCELLENCE // We are honored to share that our team has been recognized with Coldwell Banker Re...
02/22/2026

INTERNATIONAL SOCIETY OF EXCELLENCE // We are honored to share that our team has been recognized with Coldwell Banker Real Estate LLC’s highest distinction, the International Society of Excellence.

While awards are meaningful, what matters most to us is what this represents for our clients.

It reflects the trust our sellers place in us when positioning their homes with care and strategy. It reflects the guidance our buyers rely on when navigating important decisions with confidence. It reflects the preparation, market insight, and attention to detail that go into every transaction.

Real estate is never just about numbers. It is about people, timing, and thoughtful ex*****on.

We are grateful to the buyers and sellers who allow us to do this work, and we remain focused on serving you with clarity, discretion, and results.

02/21/2026

ARCHITECTURE AS LIGHT // Light isn’t a feature here. It’s part of the structure.

At 1380 Old Academy Road, light is drawn in from every angle. Bay windows carry it deep into the living spaces. Dormers and skylights introduce it from above. Tall ceilings allow it to move freely rather than pause at the perimeter.

The result is depth and a softness that shifts beautifully from morning through evening.

📍1380 Old Academy Road
Fairfield, CT
$2,595,000
For more information, visit https://cindyraney.com/properties/1380-old-academy-road-fairfield-ct-us-06824-24153510

02/20/2026

COLLECTIVE SALON // Last week, Cindy and Jason were invited to Palm Beach for an intimate gathering of top agents and industry leaders shaping the future of luxury real estate.

These aren’t just dinners. They’re working rooms. Conversations around shifting buyer behavior, global demand, emerging marketing strategies, and how high-end properties are being positioned and sold right now.

We invest time in rooms like this for one reason: to bring that insight back to our clients.

Because in a market where outcomes depend on precision, exposure, and strategy, staying connected at this level isn’t extra. It’s part of how we advise, price, and position your home more effectively.

OUTDOOR LIVING // Grounds that live as fully as the house itself.At 1380 Old Academy Road, the setting unfolds with inte...
02/19/2026

OUTDOOR LIVING // Grounds that live as fully as the house itself.

At 1380 Old Academy Road, the setting unfolds with intention. Beyond the stone wall entrance and paved drive, a gravel courtyard arrival gives way to curated, private grounds designed for both gathering and retreat.

A Gunite pool edged in stone terraces anchors summer afternoons. An outdoor fireplace draws everyone back together as the light fades. The putting green adds a playful layer that feels integrated into the landscape.

Tucked to the side, a porch lined with rocking chairs invites slower moments, morning coffee, late conversations, and everything in between. Manicured lawns, mature trees, and full irrigation ensure the property feels composed in every season.

Outdoor living here isn’t an afterthought. It’s part of the rhythm of the home.

📍1380 Old Academy Road
Fairfield, CT
$2,595,000
For more information, visit https://cindyraney.com/properties/1380-old-academy-road-fairfield-ct-us-06824-24153510

02/18/2026

NEW TO FAIRFIELD // We’re excited to welcome Flour Water Salt Bread to Fairfield. Known for their incredible pastries and beautifully crafted bread, they’ve long been a favorite in Darien, New Canaan, and Greenwich, and now firmly part of the Fairfield food scene.

The kind of place that turns a simple morning into something to look forward to.

JUST SOLD // With its meadow, orchard, barn, and multiple outbuildings, this was one of the most special and unique prop...
02/17/2026

JUST SOLD // With its meadow, orchard, barn, and multiple outbuildings, this was one of the most special and unique properties we’ve ever brought to market.

Our sellers had poured a tremendous amount of heart and investment into making it what it is: a lifestyle of luxury, retreat, and play.

They came to us with an aspirational number in mind. One that reflected both their financial commitment and emotional connection. While we recommended a more conservative price, we understood what it meant to them to aim high.

So we built the strategy accordingly.

We put our full marketing muscle behind the sale, crafting a narrative that brought the property to life and leaning into what made it irreplaceable. We priced strategically, anticipating negotiation with the goal of landing close to their range.

The result? A sale remarkably close to their target, and a strategy executed with precision.

Address

355 Riverside Avenue
Westport, CT
06880

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