37356 Homes under $500,000

Welcome to Monteagle, TN, a hidden gem nestled in the heart of the scenic Cumberland Plateau, where the captivating beauty of nature meets the charm of small-town living. Zip code 37356 encompasses this picturesque community, renowned for its stunning landscapes, vibrant local culture, and friendly atmosphere.

Monteagle is an ideal destination for those seeking a tranquil lifestyle without sacrificing modern conveniences. With a range of homes available under $500,000, this area offers excellent opportunities for first-time buyers, families, and retirees alike. Whether you’re drawn to cozy cottages, spacious family homes, or charming bungalows, Monteagle has something to suit every taste and budget.

One of the most appealing aspects of living in Monteagle is the abundance of outdoor activities. Surrounded by lush forests and breathtaking views, residents can enjoy hiking, biking, and exploring the nearby South Cumberland State Park, which boasts stunning waterfalls and scenic trails. Additionally, the community is known for its rich history and vibrant arts scene, with local festivals, farmer's markets, and charming shops adding to its allure.

Living in Monteagle means embracing a lifestyle that values community, nature, and affordability. With homes under $500,000, you can experience the best of what this charming town has to offer without breaking the bank. Discover your perfect home in Monteagle, where every day feels like a retreat in this beautiful corner of Tennessee!

Newest 37356 Homes under $500,000

$239,000

4 Beds ⋅ 1 Baths ⋅ 3602146 MLS ⋅ ACTIVE Status ⋅ 0.46 Acres ⋅ 37356 Zip Code

Property being sold AS IS. Estate sale. This is a lovely older home. Roof, CHA and water heater newer.This home has 4 bedrooms and 1 full bath.Buyer or Buyers Agent to verify all information.

36 Dove St, Monteagle

$450,000

6 Beds ⋅ 4 Baths ⋅ 3541023 MLS ⋅ ACTIVE Status ⋅ 0.3 Acres ⋅ 37356 Zip Code

Welcome to 162 1st Street in Monteagle, Tennessee, a beautifully updated home situated on the iconic Cumberland Plateau just minutes from local schools, scenic parks, world-class hiking trails, major interstates, and local favorites like the Mountain Goat Market and High Point restaurants. Step through the front door into an inviting living room flooded with natural light. Adjacent to the main living space is a sleek, modern kitchen that serves as an inviting culinary experience. This well thought out floor plan offers optimal privacy, featuring two bedrooms and a full bathroom on one side, perfect for hosting guests or creating a quiet retreat away from the main living quarters. The back wing houses the primary suite alongside additional supporting bedrooms and another full bathroom. In this wing, heated floors ensure luxurious comfort on chilly winter mornings. The primary bedroom welcomes you with vaulted ceilings, a generous walk-in closet with built-in organizers, and an ensuite bathroom designed as a spa-like oasis. Step through the sliding glass doors directly onto the upstairs covered deck overlooking the extraordinary backyard. This top deck wraps around to the front of the home, offering effortless indoor-outdoor living. Downstairs, the finished basement boasts a massive living space flexible enough for a home gym, hobby area, or game room, alongside a cozy den centered around a wood-burning fireplace. You will also find abundant extra storage and a convenient half bath for pool guests. Skip the overpriced movie theaters and host unforgettable movie nights in your private home cinema, complete with custom floor lighting. Slide open the basement doors to access a lower deck tailored for sunbathing beside the private pool and hot tub. With endless room to spread out, expansive outdoor entertainment areas, and premium amenities throughout, this charming property is truly a one of a kind. Call today for your private tour

162 1st Street, Monteagle

$249,900

1 Beds ⋅ 1 Baths ⋅ 3530227 MLS ⋅ ACTIVE Status ⋅ 0.89 Acres ⋅ 37356 Zip Code

Proven vacation rental property history. The fabulous Serenity by the Falls tiny home. Being sold with all contents. Cozy home near trail head for the falls. This property is ready for new owners. The Retreat at Deer Lick Falls is close to hiking trails, Monteagle proper, High Point Restaurant, Zip-lining, The Caverns, Sewanee and much much more! Seller offering 1% buyer incentive to buy down rate, closing costs, etc. Lender credit of $2300 being offer with preferred lender.

484 Deer Lick Trail, Monteagle

$229,900

1 Beds ⋅ 1 Baths ⋅ 3527468 MLS ⋅ ACTIVE Status ⋅ 1 Acres ⋅ 37356 Zip Code

Owner financing options available! Welcome to The Retreat At Deer Lake! You don't want to miss this amazing opportunity to own your own vacation get away. ~ Two homes available that are nestled beautifully in the woods with a short walk to the waterfall or hiking trails ~ Currently being rented through the Deer Lick rental site ~ Firepit ~ Playground ~ Private primary bedroom ~ The Monteagle area has so much to offer, tucked in the lush forests on the mountains between Nashville and Chattanooga ~ The Retreat at Deer Lick Falls was the first premier tiny home community ~ The area features abundance of hiking trails leading to the roaring falls ~ Guests can enjoy a concert at the Caverns for a truly unique experience.

75B Deer Lick Trail, Monteagle

$199,900

2 Beds ⋅ 1 Baths ⋅ 3527344 MLS ⋅ ACTIVE Status ⋅ 0.286 Acres ⋅ 37356 Zip Code

STR-approved investor opportunity at The Cozy Cottage, The Retreat at Deer Lick Falls. Tucked into a private, wooded lot (Lot #30) with the deck opening steps away from a trail leading to a private waterfall, a rare find even for Monteagle. Already operating as a turnkey vacation rental with built-in demand from the tiny home travel market. Retreat ownership extends beyond this lot: owners get full access to sister communities Sunset Bluff and Water's Edge, including additional trails, fire pits, gazebos, a lake, and playgrounds. Centrally positioned for weekend tourism: 45 min to Chattanooga, 90 to Nashville, 150 to Atlanta. Flexible use as a short-term rental, primary residence, or vacation getaway. Showings coordinated between guest stays. Contact listing agent for questions and financials.

476 Deer Lick Trail, Monteagle

$349,000

1 Beds ⋅ 1 Baths ⋅ 3520267 MLS ⋅ ACTIVE Status ⋅ 1.34 Acres ⋅ 37356 Zip Code

Welcome to Little Lodge Retreat, a turnkey mountain getaway and established short-term rental with a proven history of cash flow. Sold fully furnished with the hot tub included, this property is ready for its next owner to continue as an investment or enjoy as a private mountain retreat. Set on just under 1.4 acres, this is one of the larger lots in the area, offering privacy and space rarely found with a tiny home. The property backs to trees and features a fenced yard and private hot tub. The home includes 1 bedroom, 1 bathroom, a full kitchen, twin bunk beds, and a loft with two additional beds, comfortably sleeping up to six as currently configured. There may be potential to add a second tiny home to the property, creating an opportunity for additional income. Buyer to verify zoning, restrictions, utilities, and feasibility. Enjoy direct access to community trails from the back of the property, including a trail leading to a waterfall within the community. Nearby attractions include hiking, waterfalls, local restaurants, ziplining, The Caverns concert venue, Sewanee: The University of the South, and more. This growing area continues to attract visitors seeking outdoor adventure and a peaceful mountain escape. Whether you're looking for a cash-flowing STR, weekend getaway, or full-time residence, Little Lodge Retreat offers the perfect combination of income potential, privacy, and mountain living. *washer/dryer set is brand new.

162 Mountain Laurel Lane, Monteagle

$348,800

3 Beds ⋅ 3 Baths ⋅ 3500811 MLS ⋅ ACTIVE Status ⋅ 0.6 Acres ⋅ 37356 Zip Code

**3.99% interest rate!! OR 100% USDA FINANCING AVAILABLE!! OR first time buyer $35,000 incentive*** SEE ATTACHED!*** Victorian-Inspired New Construction in Historic Monteagle! This distinctive 3 bedroom, 2.5 bath new home offers 1,703 square feet of thoughtfully designed living space, highlighted by an oversized, handcrafted Victorian-inspired front porch, 22 windows, 9 foot ceilings, continuous luxury vinyl plank flooring, and numerous above builder-grade upgrades. The kitchen features quartz countertops, a Zellige-style tile backsplash, stainless steel appliances, and two spacious pantries. Enjoy peaceful wooded views, a private rear deck, and an upstairs primary suite with a custom walk-in closet, double vanity, and tiled walk-in shower with glass enclosure. Energy conscious construction and economical natural gas heating provide lasting comfort and efficiency. Conveniently located near I-24, Sewanee, hiking trails, waterfalls, and state parks. A limited number of additional individually designed new homes are also available in Monteagle. Each home is offered separately. Schedule your private showing today!

58 Laurels Trails Rd, Monteagle

$239,900

2 Beds ⋅ 1 Baths ⋅ 3320402 MLS ⋅ ACTIVE Status ⋅ 1 Acres ⋅ 37356 Zip Code

Owner financing options available! Welcome to The Retreat At Deer Lick! You don't want to miss this amazing opportunity to own your own vacation get away. ~ Two homes available that are nestled beautifully in the woods with a short walk to the waterfall or hiking trails ~ Currently being rented through the Deer Lick rental site ~ Firepit ~ Playground ~ Private primary bedroom ~ The Monteagle area has so much to offer, tucked in the lush forests on the mountains between Nashville and Chattanooga ~ The Retreat at Deer Lick Falls was the first premier tiny home community ~ The area features abundance of hiking trails leading to the roaring falls ~ Guests can enjoy a concert at the Caverns for a truly unique experience. Second possible build site! Call us for more information about the build site.

75A Deer Lick Trail, Monteagle

$230,000

2 Beds ⋅ 1 Baths ⋅ 3305091 MLS ⋅ ACTIVE Status ⋅ 0.68 Acres ⋅ 37356 Zip Code

Don't let the size fool you, this adorable tiny home is overflowing with charm, personality, and opportunity. Whether you're searching for a proven income-producing investment, the perfect weekend mountain getaway, or a cozy place to simplify life as a full-time residence, this turnkey retreat checks every box. One of the newest and best-maintained homes in the community, this charming cottage stands out from the rest with its exceptional condition, thoughtful design, and undeniable curb appeal. It is being sold fully furnished making it completely move-in or rental ready from day one. With a successful short-term rental history already established, this is an investment you can begin enjoying immediately. Inside, you'll be welcomed by a fireplace in the cozy living room. The surprisingly spacious kitchen features elegant black granite countertops, stainless steel appliances, and plenty of room for entertaining family and friends. Just off the bedroom and bathroom, you'll find the convenience of a washer and dryer, while the loft provides additional sleeping space for guests. Step outside and you'll quickly discover what truly makes this property special. A charming covered front porch, oversized yard, beautiful stone patio, firepit gathering area, and enchanting café lights create the perfect outdoor oasis for relaxing after a day of adventure. Rinse off in the outdoor shower after hiking the nearby trails, then unwind under the stars around the fire with family and friends. Cute, cozy, and full of character, this tiny home offers a lifestyle that's anything but small. With its unbeatable location, proven rental history, turnkey furnishings, and exceptional condition, this mountain retreat is truly one of the most desirable opportunities available on Monteagle Mountain. Located in The Retreat at Deer Lick Phase Two on Monteagle Mountain, just minutes from South Cumberland State Park, Fiery Gizzard Trail, The Caverns, the Mountain Goat Trail, and Sewanee.

25 White Oak Trail, Monteagle

$299,900

2 Beds ⋅ 1 Baths ⋅ 3301747 MLS ⋅ ACTIVE Status ⋅ 0.34 Acres ⋅ 37356 Zip Code

Turnkey Tiny Home Investment in Sunset Bluff — Airbnb Approved, Room to Grow Welcome to Eagle's Escape, a like-new tiny home in the Sunset Bluff Tiny Home Community of Monteagle, TN, on the South Cumberland Plateau, minutes from restaurants, shops, waterfalls, and hiking. Sunset Bluff is home to a mix of full-time residents and short-term rentals, and Airbnb use is welcomed here, making this a rare investment opportunity, not just a getaway. Why This One Stands Out: Brand new build — minimal wear, no deferred maintenance, ready to rent from day one Short-term rental & Airbnb approved — start generating income immediately One of only two 2-bedroom septic systems in the entire community, allowing higher occupancy and nightly rates than most neighboring units Lot sized to accommodate a second structure — add another rental unit, bunkhouse, or owner's cabin to potentially double your income on a single parcel The Home: 2 bedrooms, one of which is the loft, 1 bath, sleeps up to 6 — queen master, loft with two twins, and a pullout sofa in the living room. Cozy electric fireplace, covered deck, and an outdoor fire pit with string lights for evenings under the stars. Central heat/air, full kitchen, in-unit laundry, and keypad entry make this a low-maintenance, guest-ready package. The Opportunity: Whether expanding a short-term rental portfolio or making your first move into the Cumberland Plateau vacation market, Eagle's Escape delivers immediate rental income plus a rare path to expand on-site. With a strong base of full-time residents alongside Airbnb-friendly zoning already secured, and one of the community's few dual-bedroom septic allowances in hand, this lot is built for buyers who want to grow, not just buy.

32 Mossy Rock Ln, Monteagle

$315,000

3 Beds ⋅ 2 Baths ⋅ 3298356 MLS ⋅ ACTIVE Status ⋅ 2 Acres ⋅ 37356 Zip Code

Welcome home to this charming property nestled in a quiet subdivision offering both comfort and space. Situated on approx. 2 acres on a corner lot featuring a spacious 2 car garage with a breezeway, 3 porches and a sun room. Outside you'll also find two additional storage sheds with electric, heat and air, offering plenty of room for storage or hobbies. The home has a new hvac unit and water heater as of 2025. With ample acreage and layout potential this property presents a great investment opportunity with room to add another home or additional structures. Enjoy this peaceful neighborhood while being conveniently located in town. Whether you're looking for a place to call home, or an investment opportunity, or both this property offers the perfect blend of functionality, privacy and future potential.

23 Treeline Court, Monteagle

$279,000

3 Beds ⋅ 2 Baths ⋅ 3272263 MLS ⋅ ACTIVE Status ⋅ 1.5 Acres ⋅ 37356 Zip Code

This charming home is nestled in a peaceful setting on 1.5 acres and offers the convenience of being just minutes from town and I-24. The spacious living room provides a warm and inviting gathering space, while the well-appointed kitchen is large and has a nice pantry for ample storage. Primary suite with a relaxing soaking tub, separate shower and a generous walk-in closet. Enjoy your morning coffee on the welcoming covered front porch or unwind on the back deck. This 3 bedroom, 2 bath home with recently added large detached 2 car garage offers the perfect blend of country living and convenience.

398 Armory Rd, Monteagle

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