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4388 Sailmaker Cir, Chattanooga

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.

5 Beds ⋅ 6 Baths ⋅ 3059916 MLS ⋅ CLOSED Status ⋅ 0.31 Acres ⋅ 37416 Zip Code

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.

4388 Sailmaker Cir, Chattanooga

4490 Sailmaker Cir, Chattanooga

Unparalleled Luxury with Iconic Lake and River Views. Welcome to a masterfully designed and meticulously crafted home, offering breathtaking vistas of Chickamauga Lake and the Tennessee River. Nestled in an exclusive, gated community, this 5-bedroom, 4.5-bath residence, with over 5,000 square feet of living space, perfectly blends timeless design with enduring quality, creating one of Chattanooga's premier luxury living experiences. Every corner of this home radiates sophistication. The impeccable curb appeal is evident from both the main drive, leading to a two-car garage, and the lower-level access to a rare third garage—an exceptional convenience for guests or multigenerational living. Inside, elegant black-and-white tile greets you at the entry, setting the tone for a home rich with hardwood floors, soaring ceilings, designer lighting, and expansive windows framing jaw-dropping river views at every turn. The gorgeous great room, anchored by a stunning fireplace, seamlessly brings the outdoors in, offering an inviting space to relax or entertain. The open-concept kitchen is adorned with sleek custom cabinetry, top-tier stainless steel appliances, Wolf gas range and an expansive walk-in pantry. An inviting casual dining area, framed by panoramic water views, promises an uplifting daily dining experience. The formal dining room, thoughtfully positioned beside a private office, offers a versatile layout—perfect for elegant dinners or a secluded sitting area. The main-level primary suite is a sanctuary unto itself, where an entire wall of windows showcases mesmerizing river vistas. Awaken each day to the graceful dance of birds over the water. The spa- inspired en-suite bath features dual vanities, a jetted soaking tub, and an indulgent walk-in shower, that might tempt you to linger a little longer. Upstairs, a private bedroom with en-suite bath sits on one side of the home, while two additional bedrooms share a stylish Jack-and-Jill bath on the other conne

5 Beds ⋅ 5 Baths ⋅ 2820874 MLS ⋅ CLOSED Status ⋅ 0.33 Acres ⋅ 37416 Zip Code

Unparalleled Luxury with Iconic Lake and River Views. Welcome to a masterfully designed and meticulously crafted home, offering breathtaking vistas of Chickamauga Lake and the Tennessee River. Nestled in an exclusive, gated community, this 5-bedroom, 4.5-bath residence, with over 5,000 square feet of living space, perfectly blends timeless design with enduring quality, creating one of Chattanooga's premier luxury living experiences. Every corner of this home radiates sophistication. The impeccable curb appeal is evident from both the main drive, leading to a two-car garage, and the lower-level access to a rare third garage—an exceptional convenience for guests or multigenerational living. Inside, elegant black-and-white tile greets you at the entry, setting the tone for a home rich with hardwood floors, soaring ceilings, designer lighting, and expansive windows framing jaw-dropping river views at every turn. The gorgeous great room, anchored by a stunning fireplace, seamlessly brings the outdoors in, offering an inviting space to relax or entertain. The open-concept kitchen is adorned with sleek custom cabinetry, top-tier stainless steel appliances, Wolf gas range and an expansive walk-in pantry. An inviting casual dining area, framed by panoramic water views, promises an uplifting daily dining experience. The formal dining room, thoughtfully positioned beside a private office, offers a versatile layout—perfect for elegant dinners or a secluded sitting area. The main-level primary suite is a sanctuary unto itself, where an entire wall of windows showcases mesmerizing river vistas. Awaken each day to the graceful dance of birds over the water. The spa- inspired en-suite bath features dual vanities, a jetted soaking tub, and an indulgent walk-in shower, that might tempt you to linger a little longer. Upstairs, a private bedroom with en-suite bath sits on one side of the home, while two additional bedrooms share a stylish Jack-and-Jill bath on the other conne

4490 Sailmaker Cir, Chattanooga

4581 Sailmaker Cir, Chattanooga

Set above the deep, glistening waters of Chickamauga Lake within the long-established, gated enclave of Windward Pointe, this exceptional home embodies modern transitional design, everyday comfort, and a lifestyle of relaxation and effortless access to the water. Just 15 minutes from both downtown Chattanooga and the Chattanooga Airport, immersed in the tranquility of living alongside the Tennessee River, you remain remarkably close to the energy and conveniences of the Scenic City. Just five years young, the home immediately impresses with its street presence, framed by mature landscaping and backed by dense hardwoods. The wide covered front porch comfortably welcomes guests into a light and open floor plan that unfolds in an easy seamless flow.Whether gathering friends for an evening of conversation or savoring a quiet morning on your screened in porch overlooking the tree-framed community greenspace, the design allows every moment to feel both connected and restorative, inviting quiet moments for peace and relaxation at every turn. Warm toned engineered hardwoods run throughout the primary living spaces, combining refined style with lasting durability and virtually no upkeep. The main-level primary suite offers a private retreat designed for restoration, complete with a spa-like bath where a soaking tub invites you to unwind and an en suite laundry makes for minimal effort with the tasks of the day to day rush. Second, full laundry room is located on upper level. Upstairs,thoughtful design, and a second well-appointed laundry room, confirm that livability was never sacrificed for style. Three additional bedrooms and two full baths are complemented by a generous bonus or media room. The upper level easily provides space to allow for a home office, fitness space, craft room or reading haven. The polished floor plan accommodates large families and grand hosting while keeping the footprint ideal for one level living.

4 Beds ⋅ 4 Baths ⋅ 3061514 MLS ⋅ CLOSED Status ⋅ 0.19 Acres ⋅ 37416 Zip Code

Set above the deep, glistening waters of Chickamauga Lake within the long-established, gated enclave of Windward Pointe, this exceptional home embodies modern transitional design, everyday comfort, and a lifestyle of relaxation and effortless access to the water. Just 15 minutes from both downtown Chattanooga and the Chattanooga Airport, immersed in the tranquility of living alongside the Tennessee River, you remain remarkably close to the energy and conveniences of the Scenic City. Just five years young, the home immediately impresses with its street presence, framed by mature landscaping and backed by dense hardwoods. The wide covered front porch comfortably welcomes guests into a light and open floor plan that unfolds in an easy seamless flow.Whether gathering friends for an evening of conversation or savoring a quiet morning on your screened in porch overlooking the tree-framed community greenspace, the design allows every moment to feel both connected and restorative, inviting quiet moments for peace and relaxation at every turn. Warm toned engineered hardwoods run throughout the primary living spaces, combining refined style with lasting durability and virtually no upkeep. The main-level primary suite offers a private retreat designed for restoration, complete with a spa-like bath where a soaking tub invites you to unwind and an en suite laundry makes for minimal effort with the tasks of the day to day rush. Second, full laundry room is located on upper level. Upstairs,thoughtful design, and a second well-appointed laundry room, confirm that livability was never sacrificed for style. Three additional bedrooms and two full baths are complemented by a generous bonus or media room. The upper level easily provides space to allow for a home office, fitness space, craft room or reading haven. The polished floor plan accommodates large families and grand hosting while keeping the footprint ideal for one level living.

4581 Sailmaker Cir, Chattanooga

4531 Sailmaker Cir, Chattanooga

BUILDING LOTS - BREATHTAKING VIEWS OF LAKE, GATED COMMUNITY, CONVENIENT, SURROUNDING HOMES MAKE FOR EXCELLENT INVESTMENT. LOTS RANGE FROM $125,000-$150,000.

3540669 MLS ⋅ CLOSED Status ⋅ 0.2 Acres ⋅ 37416 Zip Code

BUILDING LOTS - BREATHTAKING VIEWS OF LAKE, GATED COMMUNITY, CONVENIENT, SURROUNDING HOMES MAKE FOR EXCELLENT INVESTMENT. LOTS RANGE FROM $125,000-$150,000.

4531 Sailmaker Cir, Chattanooga

Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.

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