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$1,350,000
5 Beds ⋅ 3 Baths ⋅ 3529358 MLS ⋅ ACTIVE Status ⋅ 2.29 Acres ⋅ 37375 Zip Code
Welcome to 3107 Jackson Point Road, a one-of-a-kind custom estate offering breathtaking views from atop the Cumberland Plateau bluff. Nestled on approximately 2.29 picturesque acres, this fully furnished, multilevel retreat boasts over 4,300 square feet of thoughtfully designed living and entertaining space. Whether envisioned as a luxurious primary residence, an income-producing short-term rental, an intimate wedding venue, or a combination of all three, this exceptional property offers endless possibilities. Currently operating as a short-term rental with future booked dates, the estate has also been utilized as a small wedding venue, creating a unique opportunity for its next owner. Custom details and character can be found throughout the home, complemented by multiple decks on various levels designed to showcase the incredible bluff views. The outdoor amenities are equally impressive, featuring a private pool surrounded by expansive decking with additional entertaining space, string lights, grilling areas, and a hot tub overlooking the beautiful natural surroundings. Inside, enjoy a spacious man cave along with an impressive private home gym that comes complete with exercise equipment and a built-in sauna—creating your own personal wellness retreat without ever leaving home. An additional building offers even more potential and is ready for its next phase, with infrastructure already in place to finish the space as an expanded wedding or event venue, additional guest accommodations, or whatever best suits your vision. Located just minutes the Sewanee Airport, this remarkable estate combines privacy, unforgettable scenery, luxury amenities, and exceptional business potential in one extraordinary property. From quiet mornings overlooking the bluff to weekends filled with guests and celebrations, 3107 Jackson Point Road is more than a home—it is an opportunity to create something truly special.

3107 Jackson Point Rd, Sewanee
$649,000
3 Beds ⋅ 3 Baths ⋅ 3516600 MLS ⋅ ACTIVE Status ⋅ 0.84 Acres ⋅ 37375 Zip Code
Prime Sewanee Property with Income Potential Nestled directly on the historic campus of the University of the South, this meticulously maintained brick home offers an unbeatable location within easy walking distance to the School of Theology, central campus, and downtown. Combining classic charm with incredible versatility, this property is ideal for an owner-occupant, investor, or campus faculty member. The main residence has 3 Bedrooms, 2 Bathrooms: Features timeless interior finishes with all-hardwood, tile, or brick flooring throughout—no carpet. Kitchen appliances updated within the past year. Includes a large, versatile shop space that can easily be transformed into a spacious second master suite or expanded living area. Outdoor Amenities: A paved circle driveway welcomes you home, complemented by two storage sheds and a small greenhouse for gardening enthusiasts. Income-Producing Apartment is fully equipped with its own separate entrance and private porch. 1 Bedroom, 1 Bathroom: Features an open-concept full kitchen and living area, offering comfortable and private living space for tenants or guests. Complete with a new washer and dryer set installed last year. This lease is located in the Sewanee Village Planning Zone. https://new.sewanee.edu/files/resources/updated-sewanee-village-implementation-plan-packet.pdf

161 Kentucky Ave, Sewanee
$499,900
3 Beds ⋅ 2 Baths ⋅ 3509975 MLS ⋅ ACTIVE Status ⋅ 0.6900000000000001 Acres ⋅ 37375 Zip Code
Nestled directly within the iconic grounds of the University of the South, 77 Kentucky Ave offers a rare opportunity to own a piece of Sewanee’s storied landscape. This classic brick ranch combines the ease of single-level living with the unmatched prestige of a campus location, making it a standout find for those who value both tradition and versatility. The main residence spans 1,400 square feet, featuring three comfortable bedrooms and two full bathrooms. Windows invite an abundance of natural light into the living spaces, creating an atmosphere that is both bright and grounded. Outside, the expansive yard provides a lush, open canvas for gardening or hosting gatherings. The true jewel of this property is the detached 660-square-foot guesthouse. Complete with its own full kitchenette and a full bathroom, this secondary dwelling is a flexible space that’s hard to find. Whether you envision it as a sophisticated home office, a creative studio, or a private retreat for visitors, it adds incredible value and functionality to the estate. Living on the mountain means being part of a unique, vibrant community where world-class lectures, scenic trails, and collegiate charm are just beyond your doorstep. Properties on the University leasehold are a rarity; 77 Kentucky Ave is your chance to step into the heart of it all.

77 Kentucky Ave, Sewanee
$1,699,000
4 Beds ⋅ 4 Baths ⋅ 3278136 MLS ⋅ ACTIVE Status ⋅ 14.36 Acres ⋅ 37375 Zip Code
Rare, north facing bluff views!! Find peace and serenity on this amazing bluff compound located on the edge of the Cumberland Plateau near Sewanee and The University of the South, as well as the Franklin-Marion State Forest. Recently renovated, the main house features custom built-ins, updated bathrooms and kitchen, and a full/finished basement that walks out to the backyard and your view of the untouched Mitchell Cove. In the winter, enjoy a full panorama view of the nearly 400' of bluff frontage from your kitchen! With two guest houses (1,500sqft cabin built in 2022, and 576sqft studio renovated in 2022), this is the perfect property for large families, or for anyone looking for immediate income potential! Just minutes from Sewanee and Monteagle, with easy access to South Pittsburg and Chattanooga, this property is perfectly secluded while still being close to all major amenities. Water heater and HVAC replaced in 2025, kitchen and pantry completed in 2020. Property also features a small pond that stays full most of the year and leads to a waterfall that can be heard after heavy rains. There is also a well and pump house located on the property for anyone who wants private water as well as city water. Enjoy the temperate and quiet beauty each season brings, while taking in all the local wildlife right from your back (or front!) door!

569 Haynes Rd, Sewanee
$299,500
3 Beds ⋅ 2 Baths ⋅ 3272098 MLS ⋅ ACTIVE Status ⋅ 3.5300000000000002 Acres ⋅ 37375 Zip Code
Nestled in a beautiful country setting, this home sits on 3.5 fenced acres with a pond. The property features 3 bedrooms, 2 baths, along with a welcoming covered front porch perfect for relaxing and enjoying the peaceful surroundings. If you are looking for country living with room to roam, come see this property.

19314 S Pittsburg Mountain Rd, Sewanee
$350,000
1 Beds ⋅ 1 Baths ⋅ 3251623 MLS ⋅ ACTIVE Status ⋅ 16.61 Acres ⋅ 37375 Zip Code
Escape to the mountains with this unique off-grid retreat nestled in the peaceful woods of Sewanee on Roarks Cove Rd. Designed for self-sufficient living, this property features a well, septic system, solar power system capable of supporting heavy appliances, high-speed internet access, tankless water heater, and propane service. The finished living space is located on the second floor, while the unfinished main level offers excellent potential for additional living area with minimal work required. Situated on a private, cleared, and relatively level homesite surrounded by mostly wooded acreage, the property offers abundant wildlife, privacy, and tranquility just minutes from the University of the South in Sewanee. The sale includes 3.30 acres on one tract plus an adjoining 13.58-acre tract (Tax ID #049 029.00), for a total of approximately 16.88 unrestricted acres. A Conex storage container and propane tank may remain with the property. Property is being sold AS-IS. Due to the off-grid nature of the home, traditional financing is not available; cash purchase only.

1431 Roarks Cove Rd, Sewanee
$309,900
1 Beds ⋅ 1 Baths ⋅ 3246165 MLS ⋅ ACTIVE Status ⋅ 0.43 Acres ⋅ 37375 Zip Code
Tucked right into the heart of the University of the South campus, this charming cottage offers a rare chance to own a piece of Sewanee’s storied landscape. Located on an oversized lot and zoned for commercial mixed use, this home offers many possibilities for creative owners. Additionally the home has an excellent short- and long-term rental history. Completely renovated in 2022, it radiates charm, blending its cozy footprint with the incredible outdoor access that makes Sewanee so special. A large outbuilding outfitted with electricity provides ample storage, potential studio, workshop or office possibilities. It’s not just a property; it’s a front-row seat to the culture, trails, and unique spirit of the Mountain. Step out the back door and you are immediately on the historic Mountain Goat Trail. This paved path winds through the forest, offering miles of scenic beauty for morning jogs or sunset strolls. When it’s time to grab a bite or catch up with friends, you’re just a 10 minute walk to Michelin awarded restaurants Judith's Tavern and Lunch as well as Blue Chair, Shenanigans, local shops and campus.

237 Lake Odonnell Rd, Sewanee
$699,000
3 Beds ⋅ 3 Baths ⋅ 3232492 MLS ⋅ ACTIVE Status ⋅ 12.67 Acres ⋅ 37375 Zip Code
Mountain Living at its Finest: 12+ Acres in Sewanee! Escape to your own mountain paradise with this exceptional property spanning over 12 pristine acres across three parcels. Perfectly set up for homesteading or hobby farming, the acreage features fenced and cross-fenced pastures ready for livestock, a large barn (48x35 with stalls on one side), and a beautiful shared pond. Inside, the spacious home offers over 2,000 sq. ft. of living space featuring 3 comfortable bedrooms and 2.5 bathrooms (half bath has plumbing in place to convert to a full bath), office space & relaxing sunroom. Built to embrace the mountain lifestyle, it comes equipped with a cozy wood-burning backup heating system to keep things warm and efficient year-round. A well offers an additional water source. There a very spacious yard, covered front porch and open deck ready to enjoy! Location & Community Highlights Proximity to Campus: Just a quick 10-minute drive to the historic University of the South. Top-Tier Education: Zoned for Sewanee Elementary, with the prestigious St. Andrew's-Sewanee private school (serving middle and high school) also located just 10 minutes away. Adventure Awaits: Enjoy hiking, golfing, waterfalls, and rock climbing right outside your back door. Culture & Dining: Minutes from local Sewanee eateries, charming boutiques, and a short drive to the world-renowned underground music venue, The Caverns. Whether you are looking for a peaceful mountain retreat, a functional small farm, or a home close to university life, this Sewanee treasure offers the perfect balance of convenience and country living. Schedule your tour today!

18753 S Pittsburg Mountain Rd, Sewanee
$499,000
2 Beds ⋅ 3 Baths ⋅ 3229234 MLS ⋅ ACTIVE Status ⋅ 7.97 Acres ⋅ 37375 Zip Code
5+/- miles to the Domain, the Un of the South. Close to Monteagle and I-24, yet private setting. Great location with almost 8 mostly wooded acres. Two large master suites w/whirlpool tubs, separate showers, and walk-in closets. LR could possibly be converted to a third BR. Mountain stone fireplace with French doors to the screened-in porch with windows for winter use. Stone front porch. Spacious(30x42) insulated and wired workshop/equipment bldg with sink. May have horses. Being sold "As Is."

415 Laurel Branch Trl, Sewanee
$533,000
4 Beds ⋅ 3 Baths ⋅ 3191603 MLS ⋅ ACTIVE Status ⋅ 5.49 Acres ⋅ 37375 Zip Code
Welcome to this beautifully crafted custom home, completed in 2020 and nestled on 5.49 serene acres at 1500 Jackson Point Rd in Sewanee, TN. Designed with both comfort and quality in mind, this thoughtfully built residence offers an open floor plan ideal for modern living, all set against the backdrop of peaceful mountain and rolling countryside. Inside, you'll find true craftsmanship throughout, highlighted by stunning hardwood and tile flooring, two spacious primary suites, and a cozy den anchored by a large stone wood-burning fireplace. The home's galley kitchen is a standout feature--expansive and elegant, with custom Glenrose hickory cabinetry, quartz countertops, a built-in wine rack, gas cooktop stove, and abundant counter space. An eat-in area is complemented by a separate flexible space perfect for formal dining or a home office. Built to last, the home was framed using a double lumber package and includes a recently encapsulated crawlspace for added efficiency and durability. Additional features include fiber optic internet, energy-efficient systems, a two-car garage, and a dedicated laundry room. Step outside to enjoy the natural beauty of the land, complete with a small seasonal creek and gently rolling terrain--ideal for those seeking a homestead lifestyle or simply a quiet retreat. Conveniently located just 10 minutes from Sewanee University, approximately 20 minutes to South Pittsburg/Jasper area, and about 45 minutes to Chattanooga, this property offers both seclusion and accessibility. Experience the perfect blend of comfort, quality, and countryside charm--this is Tennessee living at its finest.

1500 Jackson Point Rd, Sewanee
$950,000
3 Beds ⋅ 4 Baths ⋅ 3181682 MLS ⋅ ACTIVE Status ⋅ 1.6400000000000001 Acres ⋅ 37375 Zip Code
Elevated Living with Unrivaled Panoramic Vistas Experience the pinnacle of mountain living in this stunning bluff-top estate. Perched high above the protected forest, this home offers 180-degree views that redefine "breathtaking." Floor-to-Ceiling Windows: Walls of glass invite the outdoors in. Expansive Decking: Perfect for sunset entertaining or quiet morning coffee. Natural Light: South-facing orientation ensures sun-drenched interiors year-round. Seamless Indoor-Outdoor Flow: Designed for a lifestyle of ease and fresh air. The best sunsets in the county, guaranteed. BLUFF home on 5 wooded ac; 250' of sunset facing bluff; 2-story greatroom with dramatic stone fireplace; main floor master suite & living areas enjoy views; remodeled kitchen & baths; sunroom & large deck views;

3442 Sherwood Rd, Sewanee
$2,245,000
3 Beds ⋅ 3 Baths ⋅ 3164306 MLS ⋅ ACTIVE Status ⋅ 2.27 Acres ⋅ 37375 Zip Code
Step into the timeless charm of this custom Craftsman home at 394 Myers Point Rd in Sewanee, TN. Nestled in the prestigious gated community of Myers Point, this 3-bedroom, 3-bathroom masterpiece offers an unparalleled lakefront lifestyle with breathtaking views and meticulous craftsmanship throughout. From the moment you arrive, you will be captivated by the home’s inviting façade, blending classic architectural details with craftsman warmth. Inside, the open-concept floor plan is bathed in natural light, showcasing rich hardwood floors, custom stone fireplace, vaulted ceilings, and exquisite millwork that pay tribute to true artisanal design. The heart of the home is a chef’s kitchen boasting custom cabinetry, granite/quartz countertops, and stainless steel appliances. Perfectly suited for both grand and intimate gatherings, the adjacent dining and living areas open onto a spacious lakeside deck. You can savor your morning coffee or unwind at sunset, all while soaking up serene water views. Retreat to the luxurious primary bedroom which offers an attached home office overlooking both lake and bluff views, a spacious bathroom complete with a custom tile shower, double vanities, and built in linen closet. Two additional bedrooms offer generous space for family and guests. Outdoors, the property delivers a slice of paradise with a beautifully landscaped yard that gently slopes toward the water’s edge. Whether you’re kayaking, paddle boarding, fishing, or simply relaxing by the lake, this home invites you to embrace the tranquility of nature. Located on the popular Cumberland plateau in Myers Point, this home offers the perfect balance of seclusion and convenience, with easy access to local amenities, the University of the South, and endless outdoor recreation. Don’t miss the chance to own this one-of-a-kind lakefront gem. Schedule your private tour today and fall in love with everything 394 Myers Point Rd has to offer!

394 Myers Point Rd, Sewanee
$85,000
3131482 MLS ⋅ ACTIVE Status ⋅ 5 Acres ⋅ 37383 Zip Code
Public Remarks: This unique property is ready for your personal touch. Originally built by local townsmen for card games with a bluff front view of the valley below. Water and septic were never installed, but could be by new buyers. This is the perfect location for Air BNB or VRBO. The cabin sits between Cowan and Sewanee and is 5 minutes to either town. The Seller has removed all walls, ceilings, insulation, and sheetrock;(the hard part) and it is ready for your new cabin design. Paths have been cleared for walking or 4 wheelers to the back of the 5 acres. There is power run to the cabin with no breaker box, and Seller never had it turned on. AS IS Agent is related to Seller.

10367 Sewanee Hwy, Sewanee
$540,000
4 Beds ⋅ 3 Baths ⋅ 3045257 MLS ⋅ ACTIVE Status ⋅ 18.13 Acres ⋅ 37375 Zip Code
Nestled in the woods this beautiful bluff front home sits on 18.13 Acres, secluded off the main road. Enjoy the drive in and take in all the nature. You might see a deer, two or three. This home offers much: 4 Bedrooms, 2 1/2 Baths, Great Room with fireplace with gas logs that can be easily converted back to wood burning, Living Room, Dining Room and Eat in Kitchen, lots of built ins. Also, a two-car garage with two openers, shed, patio and lots of storage. Property can qualify for Green Belt Tax Exemption. Come check out the park like setting and enjoy the wildlife, especially the deer. Oh, and the view is stunning with ridges, draws and the Valley below (Sweeten's Cove, South Pittsburg), and the other side of mountain on Hwy 156 and the Ridges at Franklin Forrest. So, we are offering a $10,000 flooring allowance/paint or closing allowance. Also, the upstairs central heat and air unit was replaced 8/19/26.

1454 Stage Coach Rd, Sewanee
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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.