$1,299,000 Custom-built in 2019 by respected local builder John Gildernew Construction, this exceptional 6-bedroom, 4-bath home is located in the desirable Maggie Bluff community, just past Covenant College on Lookout Mountain. Offering a flexible, accessibility-minded floor plan, the home is well suited for main-level living, multigenerational households, working from home, and entertaining. Inside, the open-concept main level features beautiful hardwood floors and wide, easy-flow living spaces. A dedicated office with custom built-ins is conveniently located just off the entry. The main-level primary suite provides the ease of one-level living, while an additional bedroom suite with a Murphy bed creates a welcoming space for guests, extended family, or a second office. The two-car garage also offers space for a future accessibility ramp if desired. The kitchen opens seamlessly to the living area and is complemented by an impressive butler's pantry with generous storage and prep space. A separate galley provides the perfect setting for a coffee bar, beverage center, or additional serving area. The screened porch extends the living space outdoors and offers a peaceful place to enjoy morning coffee, quiet afternoons, and cool fall evenings. Upstairs, a second primary suite provides added privacy and flexibility. Three additional bedrooms, a full hall bath, another dedicated office, a spacious bonus room ideal for a media room, playroom, or home gym, and an upstairs laundry room complete the second level. Connections are also available for a future main-level laundry area. The wooded property is filled with mature trees and beautiful natural rock formations, creating privacy and plenty of room to explore. The generous area to the left of the home offers possibilities for thoughtfully expanding the usable outdoor space while preserving the property's natural setting. Additional quality features include an encapsulated crawl space, an extensive French drain and downspout drainage system designed to direct water away from the foundation, and energy-efficient LP TechShield radiant-barrier roof decking that helps reduce attic heat. With dual primary suites, two home offices, multiple living and recreation spaces, peaceful wooded surroundings, and a thoughtfully designed floor plan, this custom Lookout Mountain home offers exceptional space and versatility for every season of life. 6 Beds ⋅ 4 Baths ⋅ 1542510 MLS Custom-built in 2019 by respected local builder John Gildernew Construction, this exceptional 6-bedroom, 4-bath home is located in the desirable Maggie Bluff community, just past Covenant College on Lookout Mountain. Offering a flexible, accessibility-minded floor plan, the home is well suited for main-level living, multigenerational households, working from home, and entertaining. Inside, the open-concept main level features beautiful hardwood floors and wide, easy-flow living spaces. A dedicated office with custom built-ins is conveniently located just off the entry. The main-level primary suite provides the ease of one-level living, while an additional bedroom suite with a Murphy bed creates a welcoming space for guests, extended family, or a second office. The two-car garage also offers space for a future accessibility ramp if desired. The kitchen opens seamlessly to the living area and is complemented by an impressive butler's pantry with generous storage and prep space. A separate galley provides the perfect setting for a coffee bar, beverage center, or additional serving area. The screened porch extends the living space outdoors and offers a peaceful place to enjoy morning coffee, quiet afternoons, and cool fall evenings. Upstairs, a second primary suite provides added privacy and flexibility. Three additional bedrooms, a full hall bath, another dedicated office, a spacious bonus room ideal for a media room, playroom, or home gym, and an upstairs laundry room complete the second level. Connections are also available for a future main-level laundry area. The wooded property is filled with mature trees and beautiful natural rock formations, creating privacy and plenty of room to explore. The generous area to the left of the home offers possibilities for thoughtfully expanding the usable outdoor space while preserving the property's natural setting. Additional quality features include an encapsulated crawl space, an extensive French drain and downspout drainage system designed to direct water away from the foundation, and energy-efficient LP TechShield radiant-barrier roof decking that helps reduce attic heat. With dual primary suites, two home offices, multiple living and recreation spaces, peaceful wooded surroundings, and a thoughtfully designed floor plan, this custom Lookout Mountain home offers exceptional space and versatility for every season of life. 60 Maggie Bluff, Lookout Mountain
$500,000 Panoramic views, privacy, acreage, and exceptional versatility come together at 365 Meadowbrook Lane in Middleton Estates. Set on 2.45 acres, this beautifully maintained 4 bedroom, 4 full bath home offers a rare combination of peaceful surroundings and convenient access to Chattanooga, approximately 25 to 30 minutes away. Designed to showcase its stunning setting, the main level features soaring cathedral style windows that fill the home with natural light. The open living and dining areas create an inviting space for everyday living and entertaining, while the well appointed kitchen offers a center island with bar seating and direct access to the glass enclosed sun porch. Open the screens and enjoy the perfect indoor outdoor setting for morning coffee, entertaining, or taking in the scenery. The primary suite provides a private retreat with direct access to the expansive back deck, where a newly installed hot tub awaits. Two additional bedrooms, two full bathrooms, and a generously sized laundry room complete the main level. The fully finished basement adds incredible flexibility with a private entrance and interior access. This separate living area includes a full kitchen, living room, large bedroom, full bathroom, laundry area, and bonus room. Perfect for guests, multigenerational living, an in law suite, home office, or potential rental opportunity. Outside, the large upper deck takes full advantage of the breathtaking valley views. A two car garage and spacious workshop with exterior access provide plenty of room for storage, hobbies, or projects. A Generac whole home generator adds valuable peace of mind. Residents of Middleton Estates enjoy a tranquil community setting with access to a beautiful 5 acre pond and open green space. With its incredible views, flexible living spaces, generous acreage, and prime location, this is a property that offers both the serenity of the mountains and the convenience of being close to the city! 4 Beds ⋅ 4 Baths ⋅ 1542007 MLS Panoramic views, privacy, acreage, and exceptional versatility come together at 365 Meadowbrook Lane in Middleton Estates. Set on 2.45 acres, this beautifully maintained 4 bedroom, 4 full bath home offers a rare combination of peaceful surroundings and convenient access to Chattanooga, approximately 25 to 30 minutes away. Designed to showcase its stunning setting, the main level features soaring cathedral style windows that fill the home with natural light. The open living and dining areas create an inviting space for everyday living and entertaining, while the well appointed kitchen offers a center island with bar seating and direct access to the glass enclosed sun porch. Open the screens and enjoy the perfect indoor outdoor setting for morning coffee, entertaining, or taking in the scenery. The primary suite provides a private retreat with direct access to the expansive back deck, where a newly installed hot tub awaits. Two additional bedrooms, two full bathrooms, and a generously sized laundry room complete the main level. The fully finished basement adds incredible flexibility with a private entrance and interior access. This separate living area includes a full kitchen, living room, large bedroom, full bathroom, laundry area, and bonus room. Perfect for guests, multigenerational living, an in law suite, home office, or potential rental opportunity. Outside, the large upper deck takes full advantage of the breathtaking valley views. A two car garage and spacious workshop with exterior access provide plenty of room for storage, hobbies, or projects. A Generac whole home generator adds valuable peace of mind. Residents of Middleton Estates enjoy a tranquil community setting with access to a beautiful 5 acre pond and open green space. With its incredible views, flexible living spaces, generous acreage, and prime location, this is a property that offers both the serenity of the mountains and the convenience of being close to the city! 365 Meadowbrook Lane, Trenton
$310,000 Welcome home to this beautifully crafted new construction home, thoughtfully situated on a spacious ±0.55 acre lot with a large level backyard perfect for entertaining, play, or future additions. Priced at $310,000 this home offers upscale finishes and effortless functionality that includes an attached 2-car garage, concrete driveway, and covered front porch that welcomes you in. Step inside to an open-concept layout designed for modern living, complete with luxury vinyl plank flooring and a vaulted ceiling in the master suite. The kitchen showcases sleek granite countertops, large island offering workspace and eating space, stainless steel appliances, and abundant cabinet space, all flowing seamlessly into the living and dining areas. Retreat to the spacious owner's suite featuring a custom tiled walk-in shower with glass doors for a spa-like experience. Additional highlights include a laundry closet for convenience, back deck for grilling or relaxing, and stylish curb appeal from every angle. This is a new construction without compromise, perfectly blending quality, style, and value. Eligible for 100% USDA financing! 3 Beds ⋅ 2 Baths ⋅ 1540864 MLS Welcome home to this beautifully crafted new construction home, thoughtfully situated on a spacious ±0.55 acre lot with a large level backyard perfect for entertaining, play, or future additions. Priced at $310,000 this home offers upscale finishes and effortless functionality that includes an attached 2-car garage, concrete driveway, and covered front porch that welcomes you in. Step inside to an open-concept layout designed for modern living, complete with luxury vinyl plank flooring and a vaulted ceiling in the master suite. The kitchen showcases sleek granite countertops, large island offering workspace and eating space, stainless steel appliances, and abundant cabinet space, all flowing seamlessly into the living and dining areas. Retreat to the spacious owner's suite featuring a custom tiled walk-in shower with glass doors for a spa-like experience. Additional highlights include a laundry closet for convenience, back deck for grilling or relaxing, and stylish curb appeal from every angle. This is a new construction without compromise, perfectly blending quality, style, and value. Eligible for 100% USDA financing! 870 Michaels Road, Trenton
$543,000 ***Sellers offering $25,000 concession for buyers.*** Tucked away in a setting of true seclusion and privacy, this charming log cabin offers a rare blend of natural beauty and refined comfort. Located within the gated community of Cloudland at Lookout, the home is stunning both inside and out. Set on 3.36 mostly level acres, the property features established walking trails that extend into more than 10 acres of untouched surrounding land, creating a peaceful retreat immersed in nature. Inside, soaring 25-foot vaulted ceilings highlight the main living area and continue into the bedrooms, filling the home with light and a sense of grandeur. A handcrafted spiral wood staircase leads to a spacious loft of over 750 square feet, overlooking the living and dining areas--perfect for additional living space, a studio, or a private escape. Whether you visit by day or by night, the atmosphere is consistently serene, offering a timeless sense of calm and charm in an exceptional mountain setting. 3 Beds ⋅ 4 Baths ⋅ 1540323 MLS ***Sellers offering $25,000 concession for buyers.*** Tucked away in a setting of true seclusion and privacy, this charming log cabin offers a rare blend of natural beauty and refined comfort. Located within the gated community of Cloudland at Lookout, the home is stunning both inside and out. Set on 3.36 mostly level acres, the property features established walking trails that extend into more than 10 acres of untouched surrounding land, creating a peaceful retreat immersed in nature. Inside, soaring 25-foot vaulted ceilings highlight the main living area and continue into the bedrooms, filling the home with light and a sense of grandeur. A handcrafted spiral wood staircase leads to a spacious loft of over 750 square feet, overlooking the living and dining areas--perfect for additional living space, a studio, or a private escape. Whether you visit by day or by night, the atmosphere is consistently serene, offering a timeless sense of calm and charm in an exceptional mountain setting. 181 Hampton Way, Rising Fawn
$498,500 ESCAPE to your own private mountain retreat! Nestled on a peaceful cul-de-sac atop Lookout Mountain, this custom-built home offers unmatched privacy while being just minutes from McLemore Golf Resort, only 20 minutes to Cloudland Canyon State Park, and surrounded by endless outdoor recreation. THIS incredible property is ready for your mini farm or hobby farm, featuring a goat house and pasture, chicken coop, three-sided barn with attached workshop, a large pasture perfect for horses or donkeys, and an additional large barn with concrete floors, four storage rooms, and abundant space for equipment and supplies. There's also a small dog pen, a large fenced dog run, mature apple trees, blueberry bushes, and wild blackberry bushes. You will love relaxing on the screen porch off the kitchen - great for entertaining or enjoy your morning coffee. There is also a deck off porch with a ramp if needed! IMSIDE, you'll love the spacious open floor plan with beautiful hardwood floors! The oversized great room features a cozy fireplace; vaulted ceiling and custom cabinets and shelves on each side of the fireplace and flows seamlessly into the kitchen, complete with granite countertops, ample cabinetry, stainless steel appliance and a dining area highlighted by a large bay window. THE spacious primary suite is a true retreat with a bay window sitting area, tray ceiling, luxurious bath featuring a travertine walk-in tiled shower, double vanities, and plenty of space to unwind. Two additional bedrooms and a full bath are privately located on the opposite side of the home in a desirable split-bedroom layout. UPSTAIRS, you'll find a large bonus room with its own heat & air system, full bath and walk-out attic storage--perfect as a guest suite, home office, or recreation room. Plus large attic off bonus room for storage. ADDITIONAL features include a 20K whole-house generator, well, if needed and city water, a sealed and professionally cleaned crawlspace, a two-year-old HVAC system IF YOU/VE HAVE BEEN DREAMING OF PEACEFUL, COUNTRY LIVING WITHOUT SACRIFICING CONVENIENCE, THIS ONE-OF-A-KIND LOOKOUT MOUNTAIN PROPERTY - READY TO WELCOME YOU HOME! 3 Beds ⋅ 3 Baths ⋅ 1538539 MLS ESCAPE to your own private mountain retreat! Nestled on a peaceful cul-de-sac atop Lookout Mountain, this custom-built home offers unmatched privacy while being just minutes from McLemore Golf Resort, only 20 minutes to Cloudland Canyon State Park, and surrounded by endless outdoor recreation. THIS incredible property is ready for your mini farm or hobby farm, featuring a goat house and pasture, chicken coop, three-sided barn with attached workshop, a large pasture perfect for horses or donkeys, and an additional large barn with concrete floors, four storage rooms, and abundant space for equipment and supplies. There's also a small dog pen, a large fenced dog run, mature apple trees, blueberry bushes, and wild blackberry bushes. You will love relaxing on the screen porch off the kitchen - great for entertaining or enjoy your morning coffee. There is also a deck off porch with a ramp if needed! IMSIDE, you'll love the spacious open floor plan with beautiful hardwood floors! The oversized great room features a cozy fireplace; vaulted ceiling and custom cabinets and shelves on each side of the fireplace and flows seamlessly into the kitchen, complete with granite countertops, ample cabinetry, stainless steel appliance and a dining area highlighted by a large bay window. THE spacious primary suite is a true retreat with a bay window sitting area, tray ceiling, luxurious bath featuring a travertine walk-in tiled shower, double vanities, and plenty of space to unwind. Two additional bedrooms and a full bath are privately located on the opposite side of the home in a desirable split-bedroom layout. UPSTAIRS, you'll find a large bonus room with its own heat & air system, full bath and walk-out attic storage--perfect as a guest suite, home office, or recreation room. Plus large attic off bonus room for storage. ADDITIONAL features include a 20K whole-house generator, well, if needed and city water, a sealed and professionally cleaned crawlspace, a two-year-old HVAC system IF YOU/VE HAVE BEEN DREAMING OF PEACEFUL, COUNTRY LIVING WITHOUT SACRIFICING CONVENIENCE, THIS ONE-OF-A-KIND LOOKOUT MOUNTAIN PROPERTY - READY TO WELCOME YOU HOME! 1390 Tatum Gulf Road, Cloudland
$1,298,900 Unparalleled mountain retreat in the gated community of Lookout Highlands. (4 bds/4bths) All finishes completed in 2026, this architectural masterpiece effortlessly blends modern sophistication with warm cabin elements. Sitting on 6.62 private, wooded acres, this estate offers a secluded ''forest island'' feel while boasting rare dual-street access with two private driveways for ultimate convenience. Every inch of this 3,438 square foot home showcases exceptional craftsmanship, modern day comforts, and high-end finishes designed for lavish entertaining and serene daily living. The Great Room: Anchored by a striking stone, pass-through fireplace and designer lighting, the main living area frames stunning lines of sight straight through to the mature, beautifully preserved forest backdrop. Chef's Kitchen & Butler's Pantry: A true gathering hub featuring custom cabinetry, a massive island with seating, wolf gas/electric range with a custom hood, and an in-counter microwave. The adjacent butler's pantry features charming half-glass doors, extensive storage, and a full fridge size freezer. The kitchen refrigerator is 100% refrigeration space. Primary Suite: A secluded wing offering a true resort-style retreat, complete with a massive luxury walk-in closet system and a spa-like en-suite bath. Flexible Accommodations: On the main wing, a second bedroom with an adjacent full bath currently serves as a grand executive office. On the opposite wing, two additional upstairs bedrooms flank a private balcony living room, offering the perfect balance of privacy and connectivity. Elite Bathrooms: All 4 full bathrooms have been meticulously designed, featuring floor-to- ceiling custom tile and premium cabinetry. Three baths feature dual shower heads, and the front-of-house bathroom includes a custom setup perfect for a luxury dog-washing station. The owners transformed the oversized, fully climate-controlled garage into an extension of the luxury home itself. 4 Beds ⋅ 4 Baths ⋅ 1537841 MLS Unparalleled mountain retreat in the gated community of Lookout Highlands. (4 bds/4bths) All finishes completed in 2026, this architectural masterpiece effortlessly blends modern sophistication with warm cabin elements. Sitting on 6.62 private, wooded acres, this estate offers a secluded ''forest island'' feel while boasting rare dual-street access with two private driveways for ultimate convenience. Every inch of this 3,438 square foot home showcases exceptional craftsmanship, modern day comforts, and high-end finishes designed for lavish entertaining and serene daily living. The Great Room: Anchored by a striking stone, pass-through fireplace and designer lighting, the main living area frames stunning lines of sight straight through to the mature, beautifully preserved forest backdrop. Chef's Kitchen & Butler's Pantry: A true gathering hub featuring custom cabinetry, a massive island with seating, wolf gas/electric range with a custom hood, and an in-counter microwave. The adjacent butler's pantry features charming half-glass doors, extensive storage, and a full fridge size freezer. The kitchen refrigerator is 100% refrigeration space. Primary Suite: A secluded wing offering a true resort-style retreat, complete with a massive luxury walk-in closet system and a spa-like en-suite bath. Flexible Accommodations: On the main wing, a second bedroom with an adjacent full bath currently serves as a grand executive office. On the opposite wing, two additional upstairs bedrooms flank a private balcony living room, offering the perfect balance of privacy and connectivity. Elite Bathrooms: All 4 full bathrooms have been meticulously designed, featuring floor-to- ceiling custom tile and premium cabinetry. Three baths feature dual shower heads, and the front-of-house bathroom includes a custom setup perfect for a luxury dog-washing station. The owners transformed the oversized, fully climate-controlled garage into an extension of the luxury home itself. 454 Highland Forest Circle, Menlo
$275,000 INVESTMENT OPPORTUNITY ALERT! This fully furnished and functional money maker is waiting on its next buyer. In only 11 months as a short term rental, this cabin has grossed over $36,000! The potential for the future is growing through word of mouth and a great star rating with AIRBNB. Seller just installed several new mini split unit systems for heating and air. Added additional furniture so the home sleeps more people, a custom dining table to share meals together and a lot of extra decor to match the setting. Wether you are looking for your next investment or just looking for a place to enjoy the outdoors, this is a great opportunity. Call the listing agent with any questions. 2 Beds ⋅ 3 Baths ⋅ 1534272 MLS INVESTMENT OPPORTUNITY ALERT! This fully furnished and functional money maker is waiting on its next buyer. In only 11 months as a short term rental, this cabin has grossed over $36,000! The potential for the future is growing through word of mouth and a great star rating with AIRBNB. Seller just installed several new mini split unit systems for heating and air. Added additional furniture so the home sleeps more people, a custom dining table to share meals together and a lot of extra decor to match the setting. Wether you are looking for your next investment or just looking for a place to enjoy the outdoors, this is a great opportunity. Call the listing agent with any questions. 65 Rocky Top Trail, Trenton
$339,000 Tucked away on Lookout Mountain, this beautifully handcrafted cabin offers the kind of peace and charm most people only find on vacation. Just minutes from Cloudland Canyon and McLemore Golf Resort, the setting alone is enough to make you slow down, and once you step inside, it only gets better. Vaulted ceilings and thoughtful design create an open, airy feel, while custom cabinetry and granite countertops add a refined touch to the rustic character. The layout features two bedrooms plus a loft, giving you flexibility for guests, a home office, or additional sleeping space. A stackable washer and dryer are neatly tucked into a laundry closet for convenience without sacrificing space. Outside is where this property truly shines. A screened back porch invites you to unwind without the bugs, while the wraparound porch gives you front row views of the surrounding woods. There is even an outdoor shower, along with a hot tub that is perfect for relaxing under the stars. A storage shed and custom handcrafted carport add both function and charm. Designed with energy efficiency and low maintenance in mind, this home allows you to spend more time enjoying your surroundings and less time worrying about upkeep. Whether you are looking for a full time escape, a second home, or a short term rental opportunity, this property checks all the boxes. If living like you are on vacation is the goal, this one delivers. 2 Beds ⋅ 2 Baths ⋅ 1534072 MLS Tucked away on Lookout Mountain, this beautifully handcrafted cabin offers the kind of peace and charm most people only find on vacation. Just minutes from Cloudland Canyon and McLemore Golf Resort, the setting alone is enough to make you slow down, and once you step inside, it only gets better. Vaulted ceilings and thoughtful design create an open, airy feel, while custom cabinetry and granite countertops add a refined touch to the rustic character. The layout features two bedrooms plus a loft, giving you flexibility for guests, a home office, or additional sleeping space. A stackable washer and dryer are neatly tucked into a laundry closet for convenience without sacrificing space. Outside is where this property truly shines. A screened back porch invites you to unwind without the bugs, while the wraparound porch gives you front row views of the surrounding woods. There is even an outdoor shower, along with a hot tub that is perfect for relaxing under the stars. A storage shed and custom handcrafted carport add both function and charm. Designed with energy efficiency and low maintenance in mind, this home allows you to spend more time enjoying your surroundings and less time worrying about upkeep. Whether you are looking for a full time escape, a second home, or a short term rental opportunity, this property checks all the boxes. If living like you are on vacation is the goal, this one delivers. 15 Sassafras Trail, Rising Fawn
$1,295,000 A once in a lifetime opportunity to own this fabulous picture-perfect farm/residence on 6.7 acres in Wildwood, Georgia. This charmer has a stocked pond, a 6-stall barn with a concrete floor, party pavilion, practice tee box and green, and privacy. The home was built in 1970 but has undergone several renovations. The most recent update is a family room with a vaulted ceiling, stone woodburning fireplace, built in bookcases and a wet bar. Other improvements include all new windows and gutters, 9 raised flower beds and a recently sealed driveway. There is a smoke house, tractor barn, and a corn crib that has been turned into an adorable one bedroom/bath guest cottage. The property is fenced all around. The primary bedroom is downstairs with an adjacent sitting room/den. A new bathroom and walk-in closet were added to enhance the liveabilty of this WONDERFUL HOME. Please note there is a guest house in the back of the property and some of the furniture will remain. Recently a 6 POUND BASS was caught in the pond. August 15 Open house 12-2 A light lunch provided. Come on over! 4 Beds ⋅ 4 Baths ⋅ 1521525 MLS A once in a lifetime opportunity to own this fabulous picture-perfect farm/residence on 6.7 acres in Wildwood, Georgia. This charmer has a stocked pond, a 6-stall barn with a concrete floor, party pavilion, practice tee box and green, and privacy. The home was built in 1970 but has undergone several renovations. The most recent update is a family room with a vaulted ceiling, stone woodburning fireplace, built in bookcases and a wet bar. Other improvements include all new windows and gutters, 9 raised flower beds and a recently sealed driveway. There is a smoke house, tractor barn, and a corn crib that has been turned into an adorable one bedroom/bath guest cottage. The property is fenced all around. The primary bedroom is downstairs with an adjacent sitting room/den. A new bathroom and walk-in closet were added to enhance the liveabilty of this WONDERFUL HOME. Please note there is a guest house in the back of the property and some of the furniture will remain. Recently a 6 POUND BASS was caught in the pond. August 15 Open house 12-2 A light lunch provided. Come on over! 148 Carroll Road, Wildwood