Homes for Sale near Highland Academy

• 

  

  

  /60

  $725,000

  • 3 Beds
  • 3 Baths
  • 2,589 Sq Ft

  526 W Boiling Springs Rd, Portland, TN 37148

  Welcome to 526 Boiling Springs Rd — a lovely all-brick basement home brimming with character and ready for your personal touch! With 7.29 beautiful acres, this property offers a peaceful country setting with mature trees, vibrant landscaping, and plenty of open space. All just a short drive from downtown Portland and easy access to I-65 for commuting to Nashville or Bowling Green.Inside,

  Julie Davis Benchmark Realty, LLC

  526 W Boiling Springs Rd, Portland, TN 37148
• 

  

  

  /39

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,447 Sq Ft

  104 Colbyn Pvt Ln, Portland, TN 37148

  Imagine living in your Brand New home on a Private Lane with NO HOA! Charming 3-Bedroom, 2-Bath Home on a beautiful country setting with Modern Finishes! Welcome to this beautiful 3-bedroom, 2-bathroom home sitting on one acre. Perfectly blending comfort and style, this home features modern finishes throughout. Enjoy an open-concept living area with sleek flooring, contemporary light fixtures,

  Ruby Barnes Platinum Realty Partners, LLC

  104 Colbyn Pvt Ln, Portland, TN 37148
• 

  

  

  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  1812 Tennessee 52, Portland, TN 37148

  Discover your dream retreat on this breathtaking 5-acre oasis, enveloped by lush trees! This manufactured home boasts an open concept layout, seamlessly blending a kitchen, cozy breakfast nook and inviting den with a wood burning fireplace. The private primary suite offers a serene escape, thoughtfully separated from two additional bedrooms by a formal dining room, second den, and versatile study

  Angela Hoover The Realty Association

  1812 Tennessee 52, Portland, TN 37148
• 

  

  

  /66

  $999,000

  • 4 Beds
  • 2.5 Baths
  • 3,266 Sq Ft

  290 Dink Rut Rd, Portland, TN 37148

  Tucked away on 5.06 pristine, level acres in the highly sought-after Oakmont/White House school district, this stunning custom-built luxury estate perfectly blends elegance, functionality, and peace. (Listed as a 4-bedroom but lives like 5 — Percs for 4.)The sellers, who have cherished every inch of this home, are relocating to be closer to their aging family — creating a rare opportunity

  Nik Shewmaker Real Broker LLC, DBA Real Broker

  290 Dink Rut Rd, Portland, TN 37148
• 

  

  

  /58

  $829,000

  • 3 Beds
  • 2.5 Baths
  • 2,025 Sq Ft

  304 Moore Link Rd, Portland, TN 37148

  Tennessee Country Living at Its Finest — on Over 4 Acres! Enjoy the charm of this modern cabin, complete with a wrap-around covered porch, screened room, and private balcony—perfect for soaking in peaceful country views. Inside, you'll find quality finishes including spray foam insulation, a tankless water heater, stainless steel appliances, granite countertops, wood flooring, and tile in wet

  Brian Wiggins Benchmark Realty, LLC

  304 Moore Link Rd, Portland, TN 37148
• 

  

  /11

  $349,900

  • Land
  • 20 Acres
  • $17,627 per Acre

  0 Keytown Rd, Portland, TN 37148

  Secluded 19.85 acre Wooded Retreat with Creek Frontage. City Water and Septic approved for 5 bar home. Discover your private slice of TN paradise on this beautiful 19 acres nestled in the heart of Sumner County. Mostly wooded and rich with natural beauty, this land offers the perfect balance of peace, privacy, and potential. Rolling terrain, mature trees, and a picturesque creek winding through

  Ray Carman Priority ONE Real Estate and Auction

  0 Keytown Rd, Portland, TN 37148
• 

  

  /4

  $177,000

  • 2 Beds
  • 1 Bath
  • 612 Sq Ft

  216 Strawberry St, Portland, TN 37148

  Great location, convenient to town, stores and restaurants. Great rental property. Already has renters established. Bathroom tub/shower & plumbing & flooring was replaced in 2023. Main plumbing line from street replaced in 2025 just a couple of months ago

  Lynn Rich Exit Realty Garden Gate Team

  216 Strawberry St, Portland, TN 37148
• 

  

  /26

  $214,000

  • Land
  • 2.37 Acres
  • $90,295 per Acre

  512 N Happy Hollow Rd, Portland, TN 37148

  Spectacular 2.37-Acre Retreat with Mature Trees...Discover the perfect canvas for your dream home on this expansive 2.37-acre property. Surrounded by mature trees, this serene lot offers both privacy and natural beauty, creating an idyllic setting for a custom residence. Enjoy 2.37 acres of versatile land, ideal for building your personalized oasis. Established trees provide natural shade,

  Mike & April Walls Benchmark Realty, LLC

  512 N Happy Hollow Rd, Portland, TN 37148
• 

  

  /7

  $157,000

  • Land
  • 1.53 Acres
  • $102,614 per Acre

  101 Riggs Rd, Portland, TN 37148

  Corner Lot – 1.53 Acres – Perked for 4BR – Country Setting with City Convenience Build your dream home on this 1.53-acre corner lot offering level land and a peaceful country feel just minutes from town. Soils approved for a 4-bedroom septic system. Restrictions require a minimum of 2,200 sq ft of living space and a 2-car garage, helping maintain a quality neighborhood standard. White House

  Mike & April Walls Benchmark Realty, LLC

  101 Riggs Rd, Portland, TN 37148
• 

  

  /12

  $155,000

  • Land
  • 1.60 Acres
  • $96,875 per Acre

  105 Riggs Rd, Portland, TN 37148

  Build Your Dream Home in the Country—With City Convenience! This beautiful level lot offers the perfect blend of peaceful country living and nearby modern amenities. Located just a short drive from town, this property is ready for your custom home, with White House Water available at the road and soils approved for a 4-bedroom septic system. This 1.5 acre lot is restricted to a minimum of 2,200

  Mike & April Walls Benchmark Realty, LLC

  105 Riggs Rd, Portland, TN 37148
• 

  /2

  $95,500

  • Land
  • 0.13 Acre
  • $734,615 per Acre

  305 Church St, Portland, TN 37148

  Corner lot-Excellent location

  Michelle Gilliam Wally Gilliam Realty & Auction

  305 Church St, Portland, TN 37148
• 

  /2

  $95,500

  • Land
  • 0.13 Acre
  • $734,615 per Acre

  301 Church St, Portland, TN 37148

  Corner lot-Excellent location

  Michelle Gilliam Wally Gilliam Realty & Auction

  301 Church St, Portland, TN 37148
• 

  

  /3

  $89,900

  • Land
  • 0.20 Acre
  • $449,500 per Acre

  124 Sandye Ave, Portland, TN 37148

  Corner building lot-Excellent location-City water and sewer

  Michelle Gilliam Wally Gilliam Realty & Auction

  124 Sandye Ave, Portland, TN 37148
• 

  

  /24

  $250,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  426 Dorris Rd, Portland, TN 37148

  Discover this charming cottage on a peaceful 1-acre lot in Portland, TN. This inviting one-level home offers 2 bedrooms, 1 bath, and 1,008 square feet of living space. Enjoy an oversized eat-in kitchen with ample counter space and plenty of cabinet storage, perfect for home cooking. Relax on the rocking chair front porch or unwind on the back patio shaded by mature trees. Located just off Hwy 76,

  Courtney Brock Mark Spain Real Estate

  426 Dorris Rd, Portland, TN 37148
• 

  

  /4

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,550 Sq Ft

  260 Ranch Rd, Portland, TN 37148

  INVESTORS!! Beautiful Property on Highly-Desirable Ranch Rd in Portland. 3 bed/ 1 bath Home has been occupied until very recently, but needs full remodel. Will not go FHA/VA/USDA etc.. Conventional or cash. Selling property AS-IS with Pass/Fail inspection only.

  Brian Harbin Wally Gilliam Realty & Auction

  260 Ranch Rd, Portland, TN 37148
• 

  

  /21

  $119,999

  • Land
  • 1.40 Acres
  • $85,714 per Acre

  3011 Highway 76, Portland, TN 37148

  Discover 1.4 acres of opportunity in the heart of Sumner County! This spacious lot is ideal for your future homesite or investment project. The property includes a 440 sq. ft. pole barn and a 504 sq. ft. manufactured home—both being sold as-is, at land value only. Zoned RR (Rural Residential), it features a scenic creek and is safely outside of any flood zones. With generous road frontage along

  Gary Ashton The Ashton Real Estate Group of RE/MAX Advantage

  3011 Highway 76, Portland, TN 37148
• 

  

  /46

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,270 Sq Ft

  202 Fowler Ford Rd, Portland, TN 37148

  This 3-bedroom, 2-bathroom gem has been completely remodeled from top to bottom, offering a fresh start and contemporary comfort. Step inside to discover a modern, open-concept layout with gleaming hardwood floors and abundant natural light pouring through brand-new windows. The kitchen is a chef's delight, boasting sleek new cabinets, dazzling stainless steel appliances, and ample counter space.

  Michael Harrison simpliHOM

  202 Fowler Ford Rd, Portland, TN 37148
• 

  

  /17

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft

  397 W Mcglothlin St, Portland, TN 37148

  Meticulously maintained by the original owners, this charming 3-bedroom, 2-bathroom home boasts a desirable corner lot with beautiful landscaping. Step inside to discover an inviting open-concept layout seamlessly connecting the kitchen (with remaining table and chairs), dining area, and living room – perfect for entertaining. Enjoy year-round relaxation in the peaceful screened-in porch, and

  Donald Rush VAM

  397 W Mcglothlin St, Portland, TN 37148
• 

  

  /42

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,225 Sq Ft

  113 Kala Cir, Portland, TN 37148

  Lovely home with covered front porch and fenced back yard! Home offers an split floor plan and a large primary suite with vaulted ceilings. Heated tile floor in owners bath. New roof and gas tankless water heater. Storage building will remain.

  Terri Jaynes Compass

  113 Kala Cir, Portland, TN 37148
• 

  

  /26

  $499,900

  • 3 Beds
  • 2 Baths
  • 2,008 Sq Ft

  154 Dorris Ln, Portland, TN 37148

  Custom Finishes w/ 1 acre of land Minutes from Gallatin, Portland, Hendersonville, and White House. Custom ceilings, cabinets, tiles, trims throughout this open concept w/ 16ft ceilings and huge Bonus room. Custom Master Suite w/ exquisite trims, custom tile shower, and custom closet shelving. Reduced to Sell!

  Joshua Russell Wally Gilliam Realty & Auction

  154 Dorris Ln, Portland, TN 37148
• 

  

  /51

  $529,900

  • 4 Beds
  • 3.5 Baths
  • 3,005 Sq Ft

  202 College St, Portland, TN 37148

  Step into a lifestyle where charm and convenience meet in the heart of Portland. This beautifully newer construction home offers the perfect blend of historic character and modern comfort. With spacious rooms, tall ceilings, well appointed kitchens and bathrooms and warm natural light, every corner invites you to relax and feel at home. Imagine sipping coffee on your front porch before strolling

  Matthew Eden Real Broker

  202 College St, Portland, TN 37148
• 

  

  /19

  $280,000

  • 3 Beds
  • 1 Bath
  • 2,158 Sq Ft

  820 Highway 52 E, Portland, TN 37148

  Opportunity knocks in the growing town of Portland! Built in 1900, this home at 820 Highway 52E is ready for a full renovation and is the perfect canvas for investors or buyers looking to bring new life to a property with history and charm. Nestled just minutes from downtown Portland, you'll enjoy easy access to local restaurants, coffee shops, schools, parks, and seasonal events like the annual

  Sergio Otalora Mark Spain Real Estate

  820 Highway 52 E, Portland, TN 37148
• 

  

  /10

  $219,900

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft

  103 Oak St, Portland, TN 37148

  This absolute dollhouse in the heart of Portland is full of charm and ready for you to call home or potentially bring your business vision to life. Zoned for commercial use but currently utilized as a residence, this 2-bedroom, 1-bathroom home has been thoughtfully updated and well-maintained, including a new roof in 2022. Situated on a large lot with a concrete driveway, it offers ample outdoor

  Jess Birdwell Exit Realty Garden Gate Team

  103 Oak St, Portland, TN 37148
• 

  

  /54

  $559,900

  • 3 Beds
  • 2 Baths
  • 2,363 Sq Ft

  264 Dink Rut Rd, Portland, TN 37148

  RATE BUYDOWN OR OWNER FINANCING for qualified buyers! Make your offer on this slice of Tennessee charm nestled in between the serene area of Cottontown, White House & Portland. This 3-bedroom, 2-bathroom home is the epitome of country living with the convenience of city proximity, sitting proudly on a generous 1.15-acre lot. The covered front and back porches invite you to enjoy tranquil mornings

  Lana Murphy White House Realtors

  264 Dink Rut Rd, Portland, TN 37148
• 

  

  /43

  $564,900

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft

  729 Fowler Ford Rd, Portland, TN 37148

  Set back on 4.1 wooded acres, this 4-bedroom, 3-bath home offers privacy, space, and a long list of updates. The home was completely taken down to the studs and rebuilt in 2006 with new wiring, plumbing, insulation, and more.Recent improvements include a new roof (Aug. 2023), new HVAC (Feb. 2025), plus updated carpet, paint, lighting, appliances, granite countertops, tile backsplash, and

  Eric Hester Lighthouse Realty

  729 Fowler Ford Rd, Portland, TN 37148
• 

  

  /6

  $159,900

  • Land
  • 1.10 Acres
  • $145,364 per Acre

  1171 Highway 52 W, Portland, TN 37148

  Beautiful and build-ready 1.1-acre lot just minutes from Portland and I-65, approximately 45 minutes north of Nashville. City sewer and water approvals secured. TDOT driveway approval in place. Gently sloped terrain ideal for a daylight basement with northern exposure. Permitting underway for a 2,100 sq ft 1 level home—lock in current pricing before value increases post-approval.Turn Key

  Gary Rabideau Crye-Leike, Inc., REALTORS

  1171 Highway 52 W, Portland, TN 37148
• 

  

  /28

  $544,999

  • 3 Beds
  • 2 Baths
  • 2,284 Sq Ft

  205 College St, Portland, TN 37148

  Charming 1920s Income-Producing Property – Turnkey Investment OpportunityStep into timeless elegance with this beautifully restored 1920s gem, currently operating as a successful income-producing short-term rental. This historic home blends vintage character with modern updates, offering guests a unique and memorable stay—and providing you with a steady revenue stream from day

  Kevin Sindorf Benchmark Realty, LLC

  205 College St, Portland, TN 37148
• 

  

  /25

  $310,000 Open Sun 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  112 High St, Portland, TN 37148

  Save up to 1% of your loan amount as a closing cost credit when you use seller's suggested lender! $3k paint credit towards closing! This beautifully redecorated home features brand new flooring, kitchen, HVAC, bathrooms, roof and windows, paint and fixtures and more! Walking distance from restaurants, grocery stores, and food carts. Covered patio with large yard and plenty of space. No HOA.

  Wes Postlethwaite Keller Williams Realty Nashville/Franklin

  112 High St, Portland, TN 37148
• 

  

  /30

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  3177 Tennessee 76, Portland, TN 37148

  Welcome to this stunning custom-built home, constructed in 2019 and meticulously maintained by its original owner. Nestled on 5.39 private acres, this 3-bedroom, 2.5-bath home offers the perfect blend of comfort, function, and natural beauty with 2,181 sq ft of living space. Inside, you'll find a thoughtfully designed floor plan with 9-foot ceilings that enhance the sense of openness and light

  Matt Engesath ListingSpark

  3177 Tennessee 76, Portland, TN 37148
• 

  

  /5

  $272,500

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  106 Tyler Dr, Portland, TN 37148

  Charming great starter home just waiting for new owners. The homes, roof & HVAC were both replaced about 8 years ago. The home has only had two owners. the chicken coop will not convey but the raised bed will remain..Sellers are motivated as they have found their forever home. Seller will remove the carpet in the third bedroom and replace with flooring to match the rest of the home.

  Lynn Rich Exit Realty Garden Gate Team

  106 Tyler Dr, Portland, TN 37148
• 

  

  /41

  $1,175,000

  • 4 Beds
  • 1 Bath
  • 3,432 Sq Ft

  1804 Highway 52 E, Portland, TN 37148

  Step into a timeless masterpiece with this 1945 handcrafted farmhouse, built with rich, authentic wood harvested directly from the farm itself. Nestled in history, this home exudes warmth and charm at every turn. Imagine cozy evenings in the den, surrounded by intricately crafted wood walls and gathered around a stunning red brick fireplace, its elegant wooden hearth framing the glow of gas logs.

  Angela Hoover The Realty Association

  1804 Highway 52 E, Portland, TN 37148
• 

  

  /29

  $825,000

  • 4 Beds
  • 1 Bath
  • 3,432 Sq Ft

  1804 Highway 52 E, Portland, TN 37148

  Step into a timeless masterpiece with this 1945 handcrafted farmhouse, built with rich, authentic wood harvested directly from the farm itself. Nestled in history, this home exudes warmth and charm at every turn. Imagine cozy evenings in the den, surrounded by intricately crafted wood walls and gathered around a stunning red brick fireplace, its elegant wooden hearth framing the glow of gas logs.

  Angela Hoover The Realty Association

  1804 Highway 52 E, Portland, TN 37148
• 

  

  /36

  $994,999

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  300 N Happy Hollow Rd, Portland, TN 37148

  See virtual tour link below. Less than 10 min to I-65 and less than 20 min to 386 in Gallatin. Very well Maintained 4 bed 3 1/2 bath with extra rooms to use to fit your needs. Office, bonus room, lots of closet space. Peaceful surroundings, farm land all around. Commercial grade gas stove and sub zero fridge, under cabinet ice maker all make this kitchen any cook would love.Central Vacuum.

  Nathan Civils Lighthouse Realty

  300 N Happy Hollow Rd, Portland, TN 37148
• 

  

  /45

  $375,000

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  3172 Highway 76, Portland, TN 37148

  PRICE REDUCTION! Charming Custom Rustic Log Cabin on 2.3 Acres - 2BR, 2.5BA, Loft Suite with Bunkbeds, Incredible Country Views, & More!Escape to this stunning custom-built log cabin nestled on 2.3 acres of peaceful rolling terrain, just 30 minutes from Nashville and Bowling Green. Offering 1,500 square feet of rustic elegance, this 2-bedroom, 2.5-bathroom home blends cozy charm with

  Randy Lawyer Benchmark Realty, LLC

  3172 Highway 76, Portland, TN 37148
• 

  

  /3

  $100,000

  • Land
  • 2.17 Acres
  • $46,083 per Acre

  3172 Highway 76, Portland, TN 37148

  Charming 2.17-Acre Building Lot with Scenic Views – Perfect for Your Dream Home!Nestled in a tranquil setting with gently sloping hills, this 2.17-acre property offers the ideal canvas for your country retreat. Located just a short 30-minute drive from both Nashville, TN and Bowling Green, KY, you’ll enjoy the perfect balance of peaceful countryside living and proximity to all modern

  Randy Lawyer Benchmark Realty, LLC

  3172 Highway 76, Portland, TN 37148
• 

  

  /49

  $475,000

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  3172 Highway 76, Portland, TN 37148

  PRICE REDUCTION! Charming Custom Rustic Log Cabin on 4.4 Acres - 2BR, 2.5BA, Loft Suite with Bunkbeds, Incredible Country Views, & More!Escape to this stunning custom-built log cabin nestled on 4.4 acres of peaceful rolling terrain, just 30 minutes from Nashville and Bowling Green. Offering 1,500 square feet of rustic elegance, this 2-bedroom, 2.5-bathroom home blends cozy charm with

  Randy Lawyer Benchmark Realty, LLC

  3172 Highway 76, Portland, TN 37148
• 

  

  /30

  $775,000

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  3177 Highway 76, Portland, TN 37148

  Welcome to this stunning custom-built home, constructed in 2019 and meticulously maintained by its original owner. Nestled on 5.39 private acres, this 3-bedroom, 2.5-bath home offers the perfect blend of comfort, function, and natural beauty with 2,181 sq ft of living space. Inside, you’ll find a thoughtfully designed floor plan with 9-foot ceilings that enhance the sense of openness and light

  Matthew Engesath ListingSpark

  3177 Highway 76, Portland, TN 37148
• 

  

  /25

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,955 Sq Ft

  208 S Russell St, Portland, TN 37148

  Discover the timeless charm of this 1920 Victorian cottage, perfectly nestled in the heart of Portland, TN. This 3-bedroom, 1-bathroom home is filled with character and offers endless possibilities for investors, first-time buyers, or those looking to restore a piece of history. Situated on a sizable lot with mature trees and plenty of room for landscaping or potential expansion. The home is

  Renee Cochran Spicer Benchmark Realty, LLC

  208 S Russell St, Portland, TN 37148
• 

  

  /35

  $499,777

  • 3 Beds
  • 3.5 Baths
  • 2,507 Sq Ft

  1347 Highway 52 E, Portland, TN 37148

  Welcome to this all brick home offering generous square footage with large room sizes and flexibility for any lifestyle. Permitted for 3 bedroom septic system, but can be used as 4 bedrooms—or 3 bedrooms plus a bonus room. This home sits on a large lot, perfect for outdoor living and entertaining. Lots of flexibility in this floor plan whether you need office space, bedrooms, den, etc.

  Shelly Gregory EXIT Realty Refined

  1347 Highway 52 E, Portland, TN 37148
• 

  

  /12

  $379,900

  • 4 Beds
  • 2 Baths
  • 2,009 Sq Ft

  324 Airport Rd, Portland, TN 37148

  Enjoy your new home with all the benefits for summer grilling and chilling!! This beautiful home has it all. Three bedroom, two full baths with a bonus room, attached garage. Nice large fenced in backyard with a spacious pool deck and built in grill area. You won’t need to leave home for summer vacation.

  Tiffany Thomerson Exit Realty Garden Gate Team

  324 Airport Rd, Portland, TN 37148

Showing Results 41 - 80, Page 2 of 4