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Welcome to 307 Massey Lane, an exquisite Williamsburg-style residence where timeless architectural beauty, refined craftsmanship, and understated luxury come together in the heart of Lookout Mountain's prestigious Fairyland community. Walk Your Child to School! Located steps away, 307 Massey Lane offers the wonderful opportunity to walk to Fairyland Elementary School, recognized in Georgia's 2025 statewide awards with Platinum Honors for Highest Performing and Silver Honors for Greatest Gains. Embrace the charm of mountain living with the Lookout Mountain Golf Club, the charming Town Hall, Starbucks, and the iconic Rock City Gardens all within walking distance. Gracefully situated on just under half an acre of beautifully level grounds, along a quiet dead-end street--both rare finds on Lookout Mountain! Offering three bedrooms, two and a half baths, and a spacious backyard with ample room for a future addition, this home presents exceptional possibilities. The versatile den could also serve as a fourth bedroom, home office, or additional living space. Authentic details, including charming skeleton key locks, and crown moulding, reflect the home's classic appeal and distinctive craftsmanship. Nine-foot ceilings, rich heart of pine hardwood floors, and custom interior wood shutters create an atmosphere of understated sophistication. The beautiful, sun-filled kitchen is the heart of the home, thoughtfully appointed with a new French-door refrigerator, KitchenAid stainless steel dishwasher, and KitchenAid gas cooktop with electric oven. Perfect for entertaining, gathering with loved ones, and creating lasting memories, this cheerful space effortlessly combines everyday functionality with timeless appeal. The primary suite is a retreat of exceptional scale, mirroring the grandeur of the downstairs great room, complete with its own stunning fireplace. This remarkable retreat offers luxury and comfort, creating a private sanctuary within the home. Two original wood- burning fireplaces, converted to gas, add warmth and ambiance to the inside living spaces, while a third charming stone fireplace on the outdoor stone patio provides an enchanting setting for intimate gatherings, relaxed evenings, and year-round outdoor enjoyment. The level backyard, complete with an invisible dog fence, offers exceptional space for outdoor activities, pets, gardening, or simply enjoying the beauty and tranquility of this coveted mountain setting. An extraordinary location in the heart of Fairyland, offering the timeless charm of Lookout Mountain living, with beloved local landmarks just a stroll away...this is a rare opportunity to enjoy one of the mountain's most treasured settings. Call me today for your private showing. Owner/Agent. Buyer to verify any and all information deemed important, including square footage, acreage, HOA information, and school zoning. Information is deemed reliable but not guaranteed.

3 Beds ⋅ 3 Baths ⋅ 1546271 MLS

Welcome to 307 Massey Lane, an exquisite Williamsburg-style residence where timeless architectural beauty, refined craftsmanship, and understated luxury come together in the heart of Lookout Mountain's prestigious Fairyland community. Walk Your Child to School! Located steps away, 307 Massey Lane offers the wonderful opportunity to walk to Fairyland Elementary School, recognized in Georgia's 2025 statewide awards with Platinum Honors for Highest Performing and Silver Honors for Greatest Gains. Embrace the charm of mountain living with the Lookout Mountain Golf Club, the charming Town Hall, Starbucks, and the iconic Rock City Gardens all within walking distance. Gracefully situated on just under half an acre of beautifully level grounds, along a quiet dead-end street--both rare finds on Lookout Mountain! Offering three bedrooms, two and a half baths, and a spacious backyard with ample room for a future addition, this home presents exceptional possibilities. The versatile den could also serve as a fourth bedroom, home office, or additional living space. Authentic details, including charming skeleton key locks, and crown moulding, reflect the home's classic appeal and distinctive craftsmanship. Nine-foot ceilings, rich heart of pine hardwood floors, and custom interior wood shutters create an atmosphere of understated sophistication. The beautiful, sun-filled kitchen is the heart of the home, thoughtfully appointed with a new French-door refrigerator, KitchenAid stainless steel dishwasher, and KitchenAid gas cooktop with electric oven. Perfect for entertaining, gathering with loved ones, and creating lasting memories, this cheerful space effortlessly combines everyday functionality with timeless appeal. The primary suite is a retreat of exceptional scale, mirroring the grandeur of the downstairs great room, complete with its own stunning fireplace. This remarkable retreat offers luxury and comfort, creating a private sanctuary within the home. Two original wood- burning fireplaces, converted to gas, add warmth and ambiance to the inside living spaces, while a third charming stone fireplace on the outdoor stone patio provides an enchanting setting for intimate gatherings, relaxed evenings, and year-round outdoor enjoyment. The level backyard, complete with an invisible dog fence, offers exceptional space for outdoor activities, pets, gardening, or simply enjoying the beauty and tranquility of this coveted mountain setting. An extraordinary location in the heart of Fairyland, offering the timeless charm of Lookout Mountain living, with beloved local landmarks just a stroll away...this is a rare opportunity to enjoy one of the mountain's most treasured settings. Call me today for your private showing. Owner/Agent. Buyer to verify any and all information deemed important, including square footage, acreage, HOA information, and school zoning. Information is deemed reliable but not guaranteed.

307 Massey Lane, Lookout Mountain

$595,000

Enjoy the beauty and charm of Lookout Mountain from this inviting 3-bedroom, 2-bath home, ideally situated on a lovely 0.62-acre setting with a beautiful year round view. Offering 2,212 square feet of comfortable, one-level living, this property presents a wonderful opportunity to enjoy an exceptional location while creating a home that reflects your own personal style. The ease of a single-level floor plan, combined with the home's generous living space and peaceful surroundings, makes this an appealing opportunity for a variety of buyers. A NEW roof (October 2026) and HVAC system just 5 years old provide valuable peace of mind, allowing you to focus on making the home your own. Walking distance from the Lookout Mountain Golf Course and situated on a private brow road, this property offers an inviting canvas and endless potential. 1606 Fairy Dell Trail is a wonderful place to begin your next chapter.

3 Beds ⋅ 2 Baths ⋅ 1546092 MLS

Enjoy the beauty and charm of Lookout Mountain from this inviting 3-bedroom, 2-bath home, ideally situated on a lovely 0.62-acre setting with a beautiful year round view. Offering 2,212 square feet of comfortable, one-level living, this property presents a wonderful opportunity to enjoy an exceptional location while creating a home that reflects your own personal style. The ease of a single-level floor plan, combined with the home's generous living space and peaceful surroundings, makes this an appealing opportunity for a variety of buyers. A NEW roof (October 2026) and HVAC system just 5 years old provide valuable peace of mind, allowing you to focus on making the home your own. Walking distance from the Lookout Mountain Golf Course and situated on a private brow road, this property offers an inviting canvas and endless potential. 1606 Fairy Dell Trail is a wonderful place to begin your next chapter.

1606 Fairy Dell Trail, Lookout Mountain

1300 Cinderella Road Road, Lookout Mountain

$639,900

Welcome to 1300 Cinderella Road, a beautifully updated 4-bedroom, 3-bath home in one of Lookout Mountain's most sought-after neighborhoods. Just steps from Fairyland Elementary, Starbucks, and Rock City, this property offers the perfect blend of convenience and community. The thoughtful floor plan highlights a split-bedroom layout with three spacious bedrooms and two full baths on one side, while the brand-new private primary suite occupies the opposite wing, complete with dual walk-in closets and a beautiful bath. Large windows fill the home with natural light, creating a warm and inviting atmosphere throughout the living spaces. The updated kitchen flows seamlessly to the screened porch and spacious fenced yard, making this home perfect for both everyday living and entertaining. A large attic provides excellent storage space. Even more recent upgrades include a new roof, a newly paved driveway, and an encapsulated crawl space--offering both comfort and long-term durability. With its modern updates, functional design, and walkable location, this move-in ready home is a rare find in Fairyland.

4 Beds ⋅ 3 Baths ⋅ 1545840 MLS

Welcome to 1300 Cinderella Road, a beautifully updated 4-bedroom, 3-bath home in one of Lookout Mountain's most sought-after neighborhoods. Just steps from Fairyland Elementary, Starbucks, and Rock City, this property offers the perfect blend of convenience and community. The thoughtful floor plan highlights a split-bedroom layout with three spacious bedrooms and two full baths on one side, while the brand-new private primary suite occupies the opposite wing, complete with dual walk-in closets and a beautiful bath. Large windows fill the home with natural light, creating a warm and inviting atmosphere throughout the living spaces. The updated kitchen flows seamlessly to the screened porch and spacious fenced yard, making this home perfect for both everyday living and entertaining. A large attic provides excellent storage space. Even more recent upgrades include a new roof, a newly paved driveway, and an encapsulated crawl space--offering both comfort and long-term durability. With its modern updates, functional design, and walkable location, this move-in ready home is a rare find in Fairyland.

1300 Cinderella Road Road, Lookout Mountain

$649,000

Located at the top of Lookout Mountain in the heart of desirable Fairyland, this move-in-ready, one-level home offers approximately 2,845 sq ft with a flowing floor plan ideal for everyday living and entertaining. Features include a formal living room with fireplace, separate dining room, updated kitchen with custom cabinetry and granite countertops, breakfast area, and spacious family room with stamped concrete flooring, and an Isokern stacked-stone fireplace. The main-level primary suite adds convenience. Enjoy the level, fenced backyard from the covered deck or screened porch. Updates include a remodeled kitchen, bathroom updates, new roof and gutters, privacy fence, tankless water heater, natural gas service, and sealed crawlspace and attic. With generous living spaces, thoughtful updates, and a sought-after Fairyland location, this home is a must-see! .

4 Beds ⋅ 2 Baths ⋅ 1545093 MLS

Located at the top of Lookout Mountain in the heart of desirable Fairyland, this move-in-ready, one-level home offers approximately 2,845 sq ft with a flowing floor plan ideal for everyday living and entertaining. Features include a formal living room with fireplace, separate dining room, updated kitchen with custom cabinetry and granite countertops, breakfast area, and spacious family room with stamped concrete flooring, and an Isokern stacked-stone fireplace. The main-level primary suite adds convenience. Enjoy the level, fenced backyard from the covered deck or screened porch. Updates include a remodeled kitchen, bathroom updates, new roof and gutters, privacy fence, tankless water heater, natural gas service, and sealed crawlspace and attic. With generous living spaces, thoughtful updates, and a sought-after Fairyland location, this home is a must-see! .

214 Hardy Road, Lookout Mountain

$1,425,000

Experience the allure of Lookout Mountain living, where an enchanting setting, enhanced seasonal views, and thoughtful updates create a home that feels both refined and inviting. Built by renowned George Getter, this brick residence sits on a private 1.4-acre lot offering winter views and lush wooded privacy in the summer. Inside, the home features four bedrooms and three full baths. The recently renovated primary ensuite includes a double vanity, heated marble floors, a standing shower, and a large marble soaking tub. The primary closet offers custom shelving along with three additional storage closets--plus two dedicated silver closets elsewhere in the home--ensuring exceptional storage throughout. The updated kitchen includes a keeping room with a cozy fireplace, perfect for relaxed evenings at home. A sunroom at the back of the house provides a peaceful spot to enjoy the views, while the formal living and dining rooms open directly onto the back deck, creating an effortless flow for everyday living and entertaining. The lower level offers an additional living room with fireplace, two more bedrooms, and a full bath--ideal for guests, teens, or multi-generational living. The garage features epoxy floors and a dedicated work area. Come see why 100 Fairy Trail might just be your next fairytale!

4 Beds ⋅ 3 Baths ⋅ 1544817 MLS

Experience the allure of Lookout Mountain living, where an enchanting setting, enhanced seasonal views, and thoughtful updates create a home that feels both refined and inviting. Built by renowned George Getter, this brick residence sits on a private 1.4-acre lot offering winter views and lush wooded privacy in the summer. Inside, the home features four bedrooms and three full baths. The recently renovated primary ensuite includes a double vanity, heated marble floors, a standing shower, and a large marble soaking tub. The primary closet offers custom shelving along with three additional storage closets--plus two dedicated silver closets elsewhere in the home--ensuring exceptional storage throughout. The updated kitchen includes a keeping room with a cozy fireplace, perfect for relaxed evenings at home. A sunroom at the back of the house provides a peaceful spot to enjoy the views, while the formal living and dining rooms open directly onto the back deck, creating an effortless flow for everyday living and entertaining. The lower level offers an additional living room with fireplace, two more bedrooms, and a full bath--ideal for guests, teens, or multi-generational living. The garage features epoxy floors and a dedicated work area. Come see why 100 Fairy Trail might just be your next fairytale!

100 Fairy Trail, Lookout Mountain

$1,235,000

Two primary suites, a screened porch tucked into the trees, and room to spread out on Lookout Mountain. Built in 2019 by John Gildernew Construction, this custom six-bedroom, four-bath home offers approximately 4,011 square feet in the Maggie Bluff community, just past Covenant College. The main living area brings together hardwood floors, ceiling beams, a fireplace, and an open connection to the kitchen and dining space. A generous island, gas cooking, and an impressive butler's pantry provide room for everyday meals and larger gatherings, while a separate galley offers additional space for coffee, beverages, or serving. Step onto the screened porch to enjoy morning coffee or a quiet evening overlooking the wooded surroundings. The main-level primary suite offers a comfortable retreat, while an additional main-level bedroom with a Murphy bed provides flexibility for guests or another workspace, with a full bath also on this level. A dedicated office with custom built-ins sits just off the entry. Upstairs, a second primary suite provides a separate retreat, complemented by three additional bedrooms, a full hall bath, another office, and a spacious bonus room for movies, hobbies, or a home gym. The laundry room is upstairs, with connections available for a future main-level laundry area. Set on approximately 0.9 acre, the property features mature trees, natural rock formations, and a peaceful setting. A two-car garage adds everyday convenience. With distinct spaces to gather, work, and unwind, 60 Maggie Bluff offers the flexibility to make the home your own.

6 Beds ⋅ 4 Baths ⋅ 1542510 MLS

Two primary suites, a screened porch tucked into the trees, and room to spread out on Lookout Mountain. Built in 2019 by John Gildernew Construction, this custom six-bedroom, four-bath home offers approximately 4,011 square feet in the Maggie Bluff community, just past Covenant College. The main living area brings together hardwood floors, ceiling beams, a fireplace, and an open connection to the kitchen and dining space. A generous island, gas cooking, and an impressive butler's pantry provide room for everyday meals and larger gatherings, while a separate galley offers additional space for coffee, beverages, or serving. Step onto the screened porch to enjoy morning coffee or a quiet evening overlooking the wooded surroundings. The main-level primary suite offers a comfortable retreat, while an additional main-level bedroom with a Murphy bed provides flexibility for guests or another workspace, with a full bath also on this level. A dedicated office with custom built-ins sits just off the entry. Upstairs, a second primary suite provides a separate retreat, complemented by three additional bedrooms, a full hall bath, another office, and a spacious bonus room for movies, hobbies, or a home gym. The laundry room is upstairs, with connections available for a future main-level laundry area. Set on approximately 0.9 acre, the property features mature trees, natural rock formations, and a peaceful setting. A two-car garage adds everyday convenience. With distinct spaces to gather, work, and unwind, 60 Maggie Bluff offers the flexibility to make the home your own.

60 Maggie Bluff, Lookout Mountain

$335,000

Welcome to 184 Middle Road, a beautifully designed modern craftsman cottage offering the ultimate one-level mountain lifestyle on coveted Lookout Mountain, Georgia. This 3 bedroom, 2 bath home is tucked away on a scenic, serene lot surrounded by towering mature trees, perfectly balancing peaceful privacy with everyday convenience. Your tour begins with entry to an airy, open-concept floor plan designed for effortless living and entertaining, anchored by a functional kitchen with rich granite countertops, a large center island, an abundance of cabinet space, and stainless steel appliances. The split-bedroom layout ensures maximum privacy, highlighted by a spacious primary suite with its own private elevated deck, the perfect spot for morning coffee or evening stargazing, and a convenient staircase leading directly down to the sprawling, fully fenced backyard. The large, shade-filled backyard offers a safe haven for pets, play, or gardening under a canopy of mature trees. While you will feel worlds away in your private mountain oasis, you are only minutes from Lookout Mountain's premier amenities, including nearby hiking trails and scenic Lula Lake Land Trust for outdoor adventure, mountain favorites like Mountain Market, Massey's Kitchen, and Canopy Coffee and Wine Bar for local dining and coffee, and less than a 25-minute drive to the bustling heart of downtown Chattanooga. Whether you are seeking a full-time mountain residence, a low-maintenance retreat, or a lucrative rental asset, this Lookout Mountain gem is a rare opportunity for the buyer ready to enjoy mountain living without sacrificing convenience, so call today to schedule your private tour. Information is deemed reliable but not guaranteed. Buyer to verify any and all information they deem important.

3 Beds ⋅ 2 Baths ⋅ 1541621 MLS

Welcome to 184 Middle Road, a beautifully designed modern craftsman cottage offering the ultimate one-level mountain lifestyle on coveted Lookout Mountain, Georgia. This 3 bedroom, 2 bath home is tucked away on a scenic, serene lot surrounded by towering mature trees, perfectly balancing peaceful privacy with everyday convenience. Your tour begins with entry to an airy, open-concept floor plan designed for effortless living and entertaining, anchored by a functional kitchen with rich granite countertops, a large center island, an abundance of cabinet space, and stainless steel appliances. The split-bedroom layout ensures maximum privacy, highlighted by a spacious primary suite with its own private elevated deck, the perfect spot for morning coffee or evening stargazing, and a convenient staircase leading directly down to the sprawling, fully fenced backyard. The large, shade-filled backyard offers a safe haven for pets, play, or gardening under a canopy of mature trees. While you will feel worlds away in your private mountain oasis, you are only minutes from Lookout Mountain's premier amenities, including nearby hiking trails and scenic Lula Lake Land Trust for outdoor adventure, mountain favorites like Mountain Market, Massey's Kitchen, and Canopy Coffee and Wine Bar for local dining and coffee, and less than a 25-minute drive to the bustling heart of downtown Chattanooga. Whether you are seeking a full-time mountain residence, a low-maintenance retreat, or a lucrative rental asset, this Lookout Mountain gem is a rare opportunity for the buyer ready to enjoy mountain living without sacrificing convenience, so call today to schedule your private tour. Information is deemed reliable but not guaranteed. Buyer to verify any and all information they deem important.

184 Middle Road, Lookout Mountain

$230,000

This amazing updated home on a Private lot on top of Lookout Mountain, features 4 bedrooms and 3 full bathrooms. Sitting on Flat level .63 acre lot. Kitchen and Living are are open concept. Stainless steel appliances. Butcher block countertops. LVP throught the home. Metal roof with new gutters. All 4 bedrooms are large in size. The Master is on front left side with nice size on suite full bathroom. 2 bedrooms to the right that share a full bath and an additonal bedroom in the back of the home with a full on suite bath as well. Laundry room off the kitchen. French doors leading out to the back deck to enjoy the summer and fall weather! This home is ideal for the Lineman in Training in Trenton Ga. It is also minutes from Covenant College! Motivated Seller!! Seller will give up to $10,000 in buyer concessions at closing.

4 Beds ⋅ 3 Baths ⋅ 1539971 MLS

This amazing updated home on a Private lot on top of Lookout Mountain, features 4 bedrooms and 3 full bathrooms. Sitting on Flat level .63 acre lot. Kitchen and Living are are open concept. Stainless steel appliances. Butcher block countertops. LVP throught the home. Metal roof with new gutters. All 4 bedrooms are large in size. The Master is on front left side with nice size on suite full bathroom. 2 bedrooms to the right that share a full bath and an additonal bedroom in the back of the home with a full on suite bath as well. Laundry room off the kitchen. French doors leading out to the back deck to enjoy the summer and fall weather! This home is ideal for the Lineman in Training in Trenton Ga. It is also minutes from Covenant College! Motivated Seller!! Seller will give up to $10,000 in buyer concessions at closing.

89 Alexander Way, Lookout Mountain

$360,000

This property offers several excellent possibilities for your family. Whether you need an in-law apartment, a multi-generational space, a separate area for a college student, or the option to generate long-term or short-term rental income, this home can accommodate your needs. The main house features 3 bedrooms, 1.5 baths, hardwood floors, and a kitchen equipped with a gas stove and dishwasher, totaling approximately 1,524 square feet. It also includes a deck perfect for enjoying morning coffee or grilling, alongside a yard for outdoor space. Additionally, there is a separate studio apartment offering approximately 440 square feet with an open floor plan includes kitchen with stove and refrigerator, and full bath. The property is conveniently located near the town of Lookout Mountain and close to Covenant College and Cloudland Canyon State Park.

3 Beds ⋅ 3 Baths ⋅ 1539825 MLS

This property offers several excellent possibilities for your family. Whether you need an in-law apartment, a multi-generational space, a separate area for a college student, or the option to generate long-term or short-term rental income, this home can accommodate your needs. The main house features 3 bedrooms, 1.5 baths, hardwood floors, and a kitchen equipped with a gas stove and dishwasher, totaling approximately 1,524 square feet. It also includes a deck perfect for enjoying morning coffee or grilling, alongside a yard for outdoor space. Additionally, there is a separate studio apartment offering approximately 440 square feet with an open floor plan includes kitchen with stove and refrigerator, and full bath. The property is conveniently located near the town of Lookout Mountain and close to Covenant College and Cloudland Canyon State Park.

1294 Highway 157, Lookout Mountain

$1,365,000

Perched atop Lookout Mountain on a beautifully wooded, oversized lot, 1117 Mountain Terrace Rd offers the perfect blend of privacy, charm, and everyday convenience just minutes from downtown Chattanooga. This thoughtfully renovated Tudor style ranch is a true retreat, where timeless character meets modern comfort. Step inside to a welcoming foyer with hardwood floors throughout, flanked by a formal dining room and a classic living room, perfect for entertaining or relaxing at home. The heart of the home is the chef's kitchen featuring granite countertops, top of the line stainless appliances, an island, and breakfast bar, all opening to the inviting family room with custom built ins and a cozy fireplace. The main level also includes a guest bedroom with a full bath, plus a half bath and laundry. Upstairs, the primary suite is a private escape with a second fireplace, spacious bath, and dressing room. Two additional bedrooms each offer private en suite baths, along with a second laundry room and office space. Outside, enjoy a peaceful patio overlooking the private backyard, ideal for grilling and unwinding in the quiet mountain setting. Recent updates include fresh paint, new light fixtures, an expanded driveway, and a new retaining wall. Meticulously maintained and move in ready, this Lookout Mountain home is ready to welcome its next owners. Schedule your private showing today.

4 Beds ⋅ 5 Baths ⋅ 1533767 MLS

Perched atop Lookout Mountain on a beautifully wooded, oversized lot, 1117 Mountain Terrace Rd offers the perfect blend of privacy, charm, and everyday convenience just minutes from downtown Chattanooga. This thoughtfully renovated Tudor style ranch is a true retreat, where timeless character meets modern comfort. Step inside to a welcoming foyer with hardwood floors throughout, flanked by a formal dining room and a classic living room, perfect for entertaining or relaxing at home. The heart of the home is the chef's kitchen featuring granite countertops, top of the line stainless appliances, an island, and breakfast bar, all opening to the inviting family room with custom built ins and a cozy fireplace. The main level also includes a guest bedroom with a full bath, plus a half bath and laundry. Upstairs, the primary suite is a private escape with a second fireplace, spacious bath, and dressing room. Two additional bedrooms each offer private en suite baths, along with a second laundry room and office space. Outside, enjoy a peaceful patio overlooking the private backyard, ideal for grilling and unwinding in the quiet mountain setting. Recent updates include fresh paint, new light fixtures, an expanded driveway, and a new retaining wall. Meticulously maintained and move in ready, this Lookout Mountain home is ready to welcome its next owners. Schedule your private showing today.

1117 Mountain Terrace, Lookout Mountain

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