4388 Sailmaker Circle, Chattanooga, TN 37416

$1,750,000

Step into a lifestyle defined by ease and unforgettable vistas. Perched above the big deep water of Chickamauga Lake, this masterfully designed five-bedroom, five-and-a-half-bath residence captures the essence of sophisticated living in one of Chattanooga's most coveted gated waterfront communities, Windward Pointe. Just twenty minutes from Scenic City downtown… Read More Chattanooga yet a world away tucked into this private and established Tennessee River enclave. With almost 5000 square feet of meticulously crafted interior space, 3400 of it on the main level! -and an additional 1,000+ square feet of covered outdoor living — every corner of this home is an invitation to relax, entertain or simply savor the good life. Expansive walls of glass pull in panoramic water views from nearly every angle. Step inside, where chiseled travertine tile and soaring 18 foot ceilings set the tone for a home steeped in refined detail, meaningful upgrades and well executed updates. The heart of the home is the great room -a spectacular gathering space open to the kitchen and wet bar with fireplace and large-scale windows leading out to the first of three covered patios all looking out to those stunning waterfront views. Imagine morning coffee on the terrace, the breeze off the river gently drifting in, or evenings spent unwinding in front of the fire as the sunset reflects off the water below. A spectacular outdoor space takes advantage of the view as well, with an outdoor kitchen, sparkling crystal clear pool, hot tub and extensive flagstone decking. The kitchen is a dream for the culinary enthusiast: furniture quality cabinetry, high-end appliances including a 48 inch Dacor gas range with double ovens and second prep space with wet bar. A casual dining space off the kitchen, bathed in natural light and framed by 180-degree views of the lake, makes every meal feel special. At the front of the home, a substantial formal dining room - filled with natural light. The main-level primary suite is a private retreat, designed to restore and inspire. Wake each morning to the quiet dance of herons over the river or soft sound of the waterfall from your private pool, through a full wall of windows. The spa-inspired en suite bath features dual vanities, a jetted soaking tub, and a generous walk-in shower, every element selected to elevate the everyday. A second bedroom reimagined just off the primary suite offers endless opportunity for use. Upstairs, two additional bedrooms with two full baths offer privacy and comfort, including a secluded sitting area or office and kitchenette-complete with stainless steel sink, microwave, compact refrigerator, and cabinetrymaking overnight stays both comfortable and convenient.. A broad driveway leads to a spacious three-car garage, offering seamless access for residents and guests. Impeccably maintained and move-in ready, this is a home that lives grandly yet intimately, balancing luxurious appointments with a deep sense of warmth and welcome. This is a place to build memories, to soak in the views that change with every season. Come stand on the terrace, breathe in the river air, and see for yourself. You just may never want to leave. Windward Pointe Showplace Home. No Place Like It! Read Less

Courtesy of Linda Brock, Real Estate Partners Chattanooga LLC.

Listing Snapshot

Days Online

105

Last Updated

Nov 20, 2025

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

4,558

Lot Size

0.31 Acres

Year Built

2008

MLS Number

1514700

30 Days Snapshot Of 37416

$342k

+24%

(avg) sold price

-8%

homes sold

-30%

(avg) days on market

Snapshot

Area Map

Additional Details

Building

Building area total: 4,558, Living area: 4,558, 2 stories, Built in 2008

Cooling

"Central Air", "Electric", "Multi Units"

Exterior Features

"Gas Grill", "Lighting", "Outdoor Grill", "Rain Gutters"

Fireplaces

"Family Room", "Gas Log", "Gas Starter", "Outside"

Floors

"Hardwood", "Tile"

Garage

3 spaces

Heating

"Central", "Natural Gas"

Home Owner's Association

Association amenities: "Boating", "Gated", "Park", "Picnic Area", "Powered Boats Allowed", Association fee: $1,600

Interior Features

"Breakfast Room", "Built-in Features", "Ceiling Fan(s)", "Chandelier", "Coffered Ceiling(s)", "Crown Molding", "Double Shower", "Double Vanity", "Dumbwaiter", "En Suite", "Entrance Foyer", "Granite Counters", "High Ceilings", "Open Floorplan", "Primary Downstairs", "Recessed Lighting", "Separate Dining Room", "Separate Shower", "Sitting Area", "Tub/shower Combo", "Walk-In Closet(s)", "Wet Bar"

Lot

"Landscaped", "Level", "Sloped", "Views", 0.31 acres, Lot size area: 0, 13,433 square feet

Parking

"Garage", "Garage Door Opener", "Kitchen Level", "Off Street"

Pool

"Heated", "Outdoor Pool", "Private", "Salt Water", "Waterfall"

Sewer

"Public Sewer"

Taxes

Tax annual amount: $12,126

Utilities

"Cable Connected", "Electricity Connected", "Natural Gas Connected", "Phone Connected", "Sewer Connected", "Water Connected", "Underground Utilities"

Windows

"Insulated Windows"

Find The Perfect Home

'VIP' Listing Search

Whenever a listing hits the market that matches your criteria you will be immediately notified.

Join The List

Mortgage Calculator

Selling price

Down payment

Term (years)

Interest rate (%)

Monthly Payment

4388 Sailmaker Circle

'VIP' Listing Search

Schools In The Area

Similar Listings

Find My Dream Home

1. Neighborhoods

2. Home Type

3. Send