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4388 Sailmaker Circle

Chattanooga, TN 37416

5 beds
6 baths
4,558 sqft
13,433 sqft lot
$427 per sqft
2008 build
– on site

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 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!

Listing courtesy of CHTMLS / Real Estate Partners Chattanooga LLC

Last checked: Checking… • Last updated Jun 16, 2025 •

MLS# 1514700 —

The Building

Year Built:

2008
New Construction:

false
Structure Type:

House
Construction Materials:

Brick, Stone, Stucco
Levels:

Two
Stories:

2
Stories Total:

None
Roof:

Asphalt, Shingle
Basement:

false
Foundation Details:

Brick/Mortar, Stone
Exterior Features:

Gas Grill, Lighting, Outdoor Grill, Rain Gutters
Window Features:

Insulated Windows
Patio And Porch Features:

Covered, Front Porch, Patio, Porch - Covered, Terrace
Security Features:

Gated Community, Smoke Detector(s)
Building Area Total:

4558.0
Above Grade Finished Area:

4558.0

Interior

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
Furnished:

None
Flooring:

Hardwood, Tile
Fireplace:

true
Fireplaces Total:

2
Fireplace Features:

Family Room, Gas Log, Gas Starter, Outside
Laundry Features:

Laundry Room, Main Level
Zoning Description:

None

Room Dimensions

Living Area:

4558.0
Living Area Units:

None
Living Area Source:

Appraiser

Location

Directions:

Hwy 58 North, left on Webb Rd, left on Sailmaker into Windward Pointe.
Latitude:

35.101184
Longitude:

-85.186539

The Property

Parcel Number:

120j D 003
Property Type:

Residential
Property Subtype:

Single Family Residence
Property Condition:

Updated/Remodeled
Direction Faces:

None
Possible Use:

None
Other Structures:

None
Lot Features:

Landscaped, Level, Sloped, Views
Lot Size Acres:

0.31
Lot Size Area:

0.31
Lot Size Dimensions:

100.0X133.66
Lot Size SqFt:

13433.0
Lot Size Units:

Acres
Lot Size Source:

None
Additional Parcels:

false
Zoning:

None
Topography:

None
Fencing:

Fenced
View:

Lake, River, Trees/Woods
View:

true
Pool Private:

No
Waterfront:

false
Waterfront Features:

Lake, Lake Privileges, Navigable Water, River Access
Road Frontage Type:

Private Road
Road Surface Type:

Paved
Road Responsibility:

Private Maintained Road

Listing Agent

Contact info:

Taxes

Tax Legal Description:

LT 42 WINDWARD POINTE SUB PB58 PG12 1
Tax Annual Amount:

12125.81

Beds

Bedrooms Total:

5

Baths

Total Baths:

5.5
Total Baths:

6
Full Baths:

5
Half Baths:

1
Three Quarter Baths:

None
Quarter Baths:

None
Partial Baths:

None

The Listing

Home Warranty:

false

Heating & Cooling

Heating:

Central, Natural Gas
Heating:

true
Cooling:

Central Air, Electric, Multi Units
Cooling:

true

Utilities

Utilities:

Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Sewer Connected, Water Connected, Underground Utilities
Water Source:

Public
Sewer:

Public Sewer
Electric:

None

Appliances

Appliances:

Wine Refrigerator, Microwave, Ice Maker, Gas Water Heater, Free-Standing Gas Range, Double Oven, Disposal, Dishwasher, Bar Fridge

Schools

Elementary School:

Harrison Elementary
Elementary School District:

None
Middle Or Junior School:

Brown Middle
Middle Or Junior School District:

None
High School:

Central High School

The Community

Subdivision Name:

Windward Pointe
Senior Community:

false
Community Features:

Curbs, Fishing, Gated, Lake, Park
Association:

true
Association Amenities:

Boating, Gated, Park, Picnic Area, Powered Boats Allowed
Association Fee:

1600.0
Association Fee Frequency:

Annually
Association Fee 2:

None
Association Fee 2 Frequency:

None
Pets Allowed:

None
Spa:

true
Spa Features:

Above Ground, Heated, Private
Pool Features:

Heated, Outdoor Pool, Private, Salt Water, Waterfall

Parking

Garage:

true
Garage Spaces:

3.0
Attached Garage:

true
Carport:

false
Parking Features:

Garage, Garage Door Opener, Kitchen Level, Off Street

Monthly cost estimate

Asking price

$1,950,000

Expense	Monthly cost
Mortgage	$10,441
Taxes	$1,010
Insurance	$536
Utilities	$192 See report
Total	$12,179/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Transit Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
6/13/25 Jun 13, 2025	Listed / Active	CHTMLS	$1,950,000	90.2% (15.9% / YR)
10/4/19 Oct 4, 2019		CHTMLS	$1,025,000

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This house located in Dupont - Murray Hills, Chattanooga, TN 37416 is currently for sale for $1,950,000. 4388 Sailmaker Circle is a 4,558 square foot house with 5 beds and 6 baths that has been on Estately for 5 days. 4388 Sailmaker Circle is in the Dupont - Murray Hills neighborhood of Chattanooga and has a WalkScore® of 2, making it car-dependent. This house is in the attendance area of Central High School, Brown Middle School, and Harrison Elementary School.

Listing Courtesy of: CHTMLS and Real Estate Partners Chattanooga LLC.

Information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed accurate by the MLS. © 2025 Chattanooga Association of REALTORS®