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1233 Oliver Dr, Monteagle
$729,900
3 Beds ⋅ 2 Baths ⋅ 3183456 MLS ⋅ ACTIVE Status ⋅ 7.19 Acres ⋅ 37356 Zip Code
Discover the ultimate mountain sanctuary in this hidden Monteagle gem, perfectly perched on over 7 acres of pristine bluff-top woods. This rare retreat strikes the perfect balance between rustic charm and modern sophistication, offering a private escape where the only neighbors are the soaring views and mature hardwoods. Whether you envision a serene permanent residence, a peaceful weekend getaway, or a high-performing short-term rental investment, this property delivers unparalleled privacy and breathtaking scenery. Don’t miss your chance to own a piece of Tennessee paradise where total seclusion meets effortless luxury all just minutes from the heart of Monteagle. The sale includes the primary property and three (3) adjacent parcels, totaling approximately 7.19 acres across all four (4) parcels.

1233 Oliver Dr, Monteagle

232 Hollingsworth Cove Rd, Monteagle
$3,200,000
4 Beds ⋅ 5 Baths ⋅ 3176190 MLS ⋅ ACTIVE Status ⋅ 7 Acres ⋅ 37356 Zip Code
Discover this rare 7-acre secluded property on Monteagle Mountain! Purchased in 2001 by the current owner, a small home was lovingly expanded and renovated into an extraordinary family retreat. Lovely stone steps create a curved path to the unique glass tower entry with Kolbe glass windows and where one immediately sees the breathtaking views that expand the width of the home. The Family room has mahogany framed glass doors opening to your choice of decks and a central stone fireplace with a two sided opening which is shared with the Kitchen and Dining areas and an additional Sitting room. The primary bedroom suite has Nana Wall glass folding doors which open to a covered porch and Kolbe windows allowing additional unique views. Three additional bedrooms and two sleeping lofts work well for large families and guests. One of the bedrooms includes a separate entrance and is plumbed for a kitchenette. Many lovely architectural antiques, such as 19th C walnut doors and both bronze and iron gates are featured throughout. In addition to the decks, nature lovers will enjoy the outdoor firepit which is located at the entrance to a trail that leads down to the river stream. Beautiful shrubs, plants and mountain laurel surround this home. Hikers will enjoy the South Cumberland State Park, Fiery Gizzard Trail, Mountain Goat Trail and more. Nearby is the University of the South campus at Sewanee, dining, bookstores and shops, as well as many more scenic views! A new separate guest house is currently under construction!

232 Hollingsworth Cove Rd, Monteagle

73 Twilight Pt, Monteagle
$116,900
3167953 MLS ⋅ ACTIVE Status ⋅ 0.87 Acres ⋅ 37356 Zip Code
The Retreat at Sunset Bluff, Lot #41. Experience refined tiny home living in the heart of the mountains in Monteagle, TN. This ready-to-build homesite offers privacy and natural beauty, complete with a 2-bedroom perc, creating the perfect setting for your personal retreat. As an owner within The Retreat, enjoy access to thoughtfully designed amenities including scenic walking trails, fire pits and gathering spaces, a serene lake, waterfall features, and breathtaking bluff views. Whether you’re envisioning a private getaway, an income-producing short-term rental, or a full-time residence, this community offers the flexibility to match your lifestyle. For additional details on the community and available build options through the developer, please contact the listing agent.

73 Twilight Pt, Monteagle

72 Lady Slipper Ln, Monteagle
$77,900
3149172 MLS ⋅ ACTIVE Status ⋅ 0.52 Acres ⋅ 37356 Zip Code
First click on brochure in Documents below for detailed description!!! Spring Price Improvement!!! Take advantage of this rare opportunity to secure one of Phase 2’s most desirable flat, corner homesites nestled beside a natural stream and protected green space, flowing toward the hiking access, private waterfall. Summer Fall 2026 — BUILD-READY MOUNTAIN PARCEL IN GATED DEERLICK TINY HOME COMMUNITY Check the Links below in this listing for comprehensive overview of property and area!! Lot 85 in DeerLick Falls Phase 2 offers a rare opportunity to step directly into mountain living and short term rental income without waiting on future development. Located in a gated, short-term-rental-approved tiny home community, this heavily wooded and ultra-private parcel is already positioned for immediate use and enjoyment. Anchored by a serene stream flowing toward a natural waterfall and bordered by protected green space and a quiet walking path, the property offers lasting privacy with no future building behind you — just nature, water, and peace. Mature trees, moss-covered stones, and the sound of moving water create a setting that feels established and complete, not speculative. Whether you plan to build a personal mountain retreat or create a thoughtfully designed short-term rental, this lot allows you to move forward now. Owners may partner with Retreat Management and select from a curated offering of Clayton prefab tiny homes or bring a custom design, with added listing advantages available once built. Close proximity to The Caverns music venue and Sewanee University for your Airbnb clients. DeerLick Falls provides access to scenic trails, shared common areas, nearby waterfalls, and easy proximity to local music venues, hiking, and outdoor recreation.

72 Lady Slipper Ln, Monteagle

1629 Clifftops Ave, Monteagle
$859,900
5 Beds ⋅ 4 Baths ⋅ 3130428 MLS ⋅ ACTIVE Status ⋅ 5.49 Acres ⋅ 37356 Zip Code
Beautiful 5 bedroom 4 bath Clifftops home. Extremely low maintenance which could serve as a full time residence, 2nd home or potential Air BB. Real hardwood floors. Wood sixteen foot tall great room ceiling seamlessly flows into the kitchen, dining area and screened porch. Honed granite countertops are taken all the way up the wall in the kitchen which has a large island, stainless appliances and a commercial gas range. A 600 sq/ft bedroom with its own en-suite bath could easily be utilized as a media room/flex space. A circular drive as well as a 3 car garage provide plenty of parking. An added bonus is the attached 900 square foot studio apartment with a full kitchen and bath which can be utilized as a separate Air BB, rental or the perfect guest suite. Clifftops is a highly sought after gated community with a minimum 5 acre lot size on top of Sewanee Mountain next to the University. Clifftops has miles of maintained trails, a lake, pool, two clubhouses, active/daily pickleball and tennis courts.

1629 Clifftops Ave, Monteagle

222 Sunset Bluff Way, Monteagle
$69,000
3128427 MLS ⋅ ACTIVE Status ⋅ 1 Acres ⋅ 37356 Zip Code
HUGE PRICE DROP!!!! SELLERS SAY FIND OUR BUYER!!!! This 2 Bedroom Perc site--The Retreat at Sunset Bluff, Lot #25. Prime luxury tiny home living in a Gated Community! Lot size is .43 of an acre. This community is nestled in the mountains of Monteagle, TN & your personal tiny home retreat awaits on this prime location lot! Enjoy privacy and woods on this ready to build lot. As a Retreat owner, experience everything the two Retreat sister communities in the area (Deer Lick Falls for Hiking Trails and Water's Edge for a lake access) have to offer, i.e., walking trails, fire pits & gazebos, a serene 95-acre lake, Kayaking, Deer Lick Falls is one of TN's largest waterfalls, and so much more! Manage your own property or Oakstone has rental managers to help! Bring a Buyer!!!

222 Sunset Bluff Way, Monteagle

Bridal Veil S, Monteagle
$239,900
3122478 MLS ⋅ ACTIVE Status ⋅ 6.04 Acres ⋅ 37356 Zip Code
Welcome to Grotto Falls! Incredible 6.04-acre bluff lot with over 400 feet of bluff rim view, seasonal stream running through the property with waterfall. Multiple building sites, potential pond location and beautiful rolling terrain transitioning from pines to hardwoods and mountain laurel. Unique “Grotto Falls” feature drops from the upper bluff to a secondary bluff, a rare natural focal point you won’t find elsewhere. Ideal for a primary residence, vacation property, or investment build. A true blend of scenery, privacy, and natural beauty. Features include underground utilities and access to the entire Bridal Veil 600 acre wilderness preserve with extensive amenities including Monteagle Falls, Wilderness Lake, streams, hiking trails, caves, waterfalls, archeological sites, protected wildlife and rare flora species. Nearby attractions include Sewanee University, The Caverns music venue, Savage Gulf State Park, Stone Door, Fiery Gizzard Trailhead, half way between Nashville and Chattanooga! One of the most striking lots in the development. APPOINTMENT WITH AGENT REQUIRED - GATED.

Bridal Veil S, Monteagle

213 Sunset Bluff Way, Monteagle
$63,000
3079058 MLS ⋅ ACTIVE Status ⋅ 0.86 Acres ⋅ 37356 Zip Code
Change In HOA Rules Allow For More Flexibility On What Can Be Built! EXTREMELY MOTIVATED SELLERS & A SIGNIFICANT PRICE ADJUSTMENT MEANS RARE OPPORTUNITY To Own In The Highly Sought-After Retreat At Sunset Bluff, A LUXURY TINY HOME COMMUNITY Nestled In The Mountains Of Monteagle, TN. Due To Personal Circumstances, The Current Owners Are Unable To Build Their Dream Home And Are Ready To Sell This 0.86 Acre Parcel, Creating An Exceptional Opportunity To Secure Lot #45, One Of The Largest And Most Desirable Lots In The Community. This Private, Wooded Lot Offers Peaceful Seclusion With Stunning Views Of Rolling Tennessee Hills. At The Edge Of The Property Just Below The Bluff, Enjoy A Scenic Hiking Trail That Winds Along A Serene, Flowing Creek, Creating A True Nature-Forward Living Experience. The Lot Is Ideal For A Primary Residence, Vacation Retreat, Or Income-Producing Rental. NOO STR Approved Community. Enjoy Access To Extensive Amenities Throughout The Retreat Sister Communities, Including Walking Trails, Fire Pits, Gazebos, A Tranquil 95-Acre Lake Perfect For Fishing And Kayaking, And One Of Tennessee’s Largest Waterfalls. Amenities Are Shared With The Retreat At Deer Lick Falls And The Retreat At Water’s Edge, Offering A Resort-Style Lifestyle Surrounded By Nature. If You Are Looking To Take A Day Trip, You Are Perfectly Located Between Nashville (90 mins) And Chattanooga (60 mins). This Is Truly A Unique Opportunity To Own In A Premier Tiny Home Community Offering Privacy, Natural Beauty, And Flexibility Of Use. All Potential Buyers And Buyer Agents To Verify All Pertinent Information.

213 Sunset Bluff Way, Monteagle

Eagle Rock Rd, Monteagle
$63,000
3050760 MLS ⋅ ACTIVE Status ⋅ 3.21 Acres ⋅ 37356 Zip Code
PRICED BELOW APPRAISAL; INSTANT EQUITY! Experience mountain living at its finest with this 3.21± acre wooded lot with a 4-bed perc test on file, located in the prestigious, gated community of Eagle Bluff Estates. Nestled atop the scenic Cumberland Plateau, this property offers mature hardwoods and the privacy and security of a well-maintained subdivision. Enjoy easy access to some of Tennessee’s most breathtaking parks—Fall Creek Falls, Foster Falls, Savage Gulf, and Franklin State Forest—all just a short drive away. From hiking and climbing to serene nature walks, outdoor recreation is right at your doorstep. Ideally situated just minutes from the charming town of Monteagle and the historic University of the South at Sewanee, this homesite offers both tranquility and convenience. With water, electric, and gig-speed internet available at the road, your dream retreat is ready to take shape in one of the Plateau’s most desirable communities.

Eagle Rock Rd, Monteagle

42 Chickory Ln, Monteagle
$275,000
2999978 MLS ⋅ ACTIVE Status ⋅ 13.7 Acres ⋅ 37356 Zip Code
This 13.7 acre property features beautiful mature hardwoods and several good building sites and could be easily divided into lots for sale and or development. Approved for Campground/RV development. Walking distance to Laurel Lake, to the west of the property, for fishing, swimming, kayaking, canoeing, and water activities. Half mile to Mountain Goat Trail, 5 miles to University of the South at Sewanee, Half mile to Mountain Goat Market, 1 mile to Smoke House Patio Grill with Live Music, and many other restaurants and attractions in a short driving distance. This is a Great family retreat, or VRBO Investment property, weekend getaway retreat, glamping development, camping, RV's. Located in Monteagle only one mile from Mountain Goat Market, in the middle of the South Cumberland Mountains of Adventure, featuring 3 Tennessee State Parks (Fiery Gizzard, Savage Gulf, Head of the Crow) with numerous waterfalls, swimming, caving, camping, hiking trails, Big Foot zip line, rock climbing, road biking, mountain biking, Coalmont off-road vehicle park with trails, and mountain vistas; a great overnight lodging generator. Only 15 minutes from The Caverns, one of the few music venues in the world that is performed in an underground cave; a world renowned destination for live music and a beautiful natural setting above and below ground, offering over 100 shows featuring acclaimed artists every year, February thru December. A great overnight lodging generator. Visit MountainsOfAdventure.com for more information. The property is zoned R – 3, and has been approved by the Monteagle planning commission for Camp Ground RV development. R-3 zoning allows high density residential development; apartments, condos, and Patio homes. There is a city forced main sewer line that runs down the north side of this property, so connection to the city waste water system is possible.

42 Chickory Ln, Monteagle

51 Mossy Rock Ln, Monteagle
$89,000
2988001 MLS ⋅ ACTIVE Status ⋅ 1.7 Acres ⋅ 37356 Zip Code
Discover your private sanctuary on this stunning 1.7-acre lot in the gated Retreat at Sunset Bluff. This homesite offers the perfect canvas for your vision, whether it's two charming tiny homes or a spacious 2-bedroom retreat. Surrounded by natural beauty and mature trees, this property provides the ultimate escape while maintaining easy access to modern conveniences. Just 45 minutes from vibrant Chattanooga, this lot combines the serenity of mountain living with the practicality of being near a major city. The generous acreage ensures privacy and room to create your ideal outdoor living space. Perfect for either a peaceful full-time residence or a potentially profitable short-term rental investment, this property presents a rare opportunity to own a piece of one of Monteagle's sought-after gated community at an attractive price point.

51 Mossy Rock Ln, Monteagle

Timberwood Trce, Monteagle
$135,000
2775759 MLS ⋅ ACTIVE Status ⋅ 12.38 Acres ⋅ 37356 Zip Code
12.38 Wooded Acres for Sale in Monteagle, TN – Private Homesite in Timberwood Trace If you’ve been searching for wooded acreage in Monteagle, TN, a private homesite on the Cumberland Plateau, or land for sale near South Cumberland State Park, 0 Timberwood Trace Lot 43 is a standout opportunity. Located in Timberwood Subdivision, this 12.38-acre residential tract in Grundy County offers privacy, mature timber, scenic natural features, and the kind of setting buyers look for when building a custom Tennessee retreat. Tucked into the peaceful landscape of Monteagle, Tennessee, this property features a beautiful wooded setting with usable terrain, a scenic creek system, and road frontage with utilities available at the road. Whether you’re planning a custom home, vacation retreat, second home, or private estate, this tract offers the space and natural beauty to bring your vision to life. A major advantage for buyers is that the seller will complete a 4-bedroom perc test with an acceptable offer, giving you a valuable head start on the building process. A survey is also included, helping provide clarity and confidence as you plan your future homesite. This Monteagle land for sale is ideally positioned for both privacy and convenience. You’ll be just minutes from some of Tennessee’s best outdoor destinations, including the Fiery Gizzard Trail, South Cumberland State Park, and the natural beauty that makes the Cumberland Plateau such a sought-after place to own land. The property also offers convenient access to I-24, making travel to Chattanooga, Nashville, Sewanee, and surrounding Middle Tennessee communities far more accessible than many mountain properties. For buyers searching for buildable land in Monteagle TN, acreage near Sewanee, or a private lot with creek features and utilities available, Lot 43 Timberwood Trace deserves a closer look. 0 Timberwood Trace Lot 43 | Monteagle, TN 37356 $135,000 | 12.38 Acres

Timberwood Trce, Monteagle

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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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