Sherwood, TN Homes for Sale

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  /30

  $1,500,000

  $534K PRICE DROP

  • Land
  • 81.34 Acres
  • $18,441 per Acre

  0 Nor-Nan Rd, Decherd, TN 37324

  This absolutely beautiful farmland is only accessible from two side roads but yet is just seconds away from the main strip in Winchester!! You get complete privacy yet the convenience of being right in town!! Talk about prime location!! About 75 +/- acres of the property is currently planted with Soy Beans!! The farming lease is year to year. This lease could be continued or end after this years

  Jimmy Jernigan Century 21 Coffee County Realty & Auction

  0 Nor-Nan Rd, Decherd, TN 37324
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• 

  

  

  /17

  $298,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  383 Strawberry Dr, Winchester, TN 37398

  Welcome to this well-maintained, move in ready, 3 bedroom, 2 full bath home situated on a full one-acre lot, offering space, privacy, and outdoor enjoyment. The fully fenced backyard is perfect for entertaining and everyday living, featuring a swimming pool, fire pit, and play set. Enjoy relaxing or hosting gatherings on the covered concrete patio, ideal for year-round use. There is a 50 amp

  Aubrey Layne Century 21 Coffee County Realty & Auction

  383 Strawberry Dr, Winchester, TN 37398
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  /32

  $349,000

  $36K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,812 Sq Ft

  1445 Georgia Crossing Rd, Winchester, TN 37398

  This stunning Franklin County, Tennessee, country home, originally built in 1912, has undergone a complete modernization while retaining its rustic 1900s charm! The exterior boasts new windows, updated trim, and a new front door, while the interior has been virtually gutted and completely redone with a new HVAC system, flooring, updated ceiling heights, and beautiful wooden staircase accents.

  Brian Whitt Arrowhead Land Company

  1445 Georgia Crossing Rd, Winchester, TN 37398
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  /84

  $1,650,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,900 Sq Ft

  220 Deer View Ln, Winchester, TN 37398

  This stunning Franklin County, Tennessee, farm offers a pristine rural setting for those seeking a beautiful 3 bedroom, 2 bathroom home with acreage! The property includes +/- 50 acres of highly productive tillable land, yielding exceptional row crops, alongside rolling pastures, barns, and gorgeous front porch views. The updated home provides ample space for a growing family or future expansion.

  Brian Whitt Arrowhead Land Company

  220 Deer View Ln, Winchester, TN 37398
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  /49

  $465,000

  New Construction $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,543 Sq Ft

  201 Lookout Dr, Winchester, TN 37398

  Welcome to this meticulously designed new home! The residence features three spacious bedrooms and two bathrooms, along with a supplemental room with a half bath. It includes upscale features like top-of-the-line stainless steel appliances, custom-built expansive wardrobes, and an exquisite coffered ceiling in the main living area. Through precise craftsmanship and the use of premium materials,

  Mena Shaker Dream Homes Realty

  201 Lookout Dr, Winchester, TN 37398
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  /82

  $734,900

  • 4 Beds
  • 5 Baths
  • 3,960 Sq Ft

  323 Ridgecrest Dr, Winchester, TN 37398

  *Seller has an accepted offer with a 48-hour Buyers First Right of Refusal Contingency* BE A PART OF THE FRANKLIN HILLS COMMUNITY! Relax in this stunning 4BR/5BA home in sought after Franklin Hills subdivision, where timeless elegance meets contemporary convenience. Nestled minutes from Tims Ford Lake and the Winchester city park, this home offers unparalleled living, sophisticated design and

  Daryl Welch Freedom Realty Group

  323 Ridgecrest Dr, Winchester, TN 37398
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  /55

  $599,999

  • 4 Beds
  • 3 Baths
  • 2,544 Sq Ft

  88 Norwood Creek Rd, Winchester, TN 37398

  2 story home on 5.4+/- acres. Large garage, 4 bedrooms, 3 baths, 20x40 inground pool.

  Bj Rigsby Lynch Rigsby Realty & Auction, LLC

  88 Norwood Creek Rd, Winchester, TN 37398
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  /98

  $649,000

  $51K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,224 Sq Ft

  154 Barefoot Way, Winchester, TN 37398

  The best value in Barefoot Bay, offering more space, more flexibility, & fully furnished. With 4 bedrooms (sleeps 12) & sold turnkey, this home stands apart from anything else currently available, giving buyers more sleeping capacity, immediate usability, & long-term versatility whether for personal use, second home, or short-term rental. Seller will pay TWO years of HOA dues w/ an acceptable

  Julianne Richard Compass Tennessee, LLC

  154 Barefoot Way, Winchester, TN 37398
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  /70

  $635,000

  $54K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,592 Sq Ft

  65 Pontoon Place, Winchester, TN 37398

  DON'T PASS UP THIS AMAZING OPPORTUNITY!! Lake life is waiting for you! BUYER INCENTIVES: Seller will pay ONE year of HOA dues with an acceptable offer. Home is turnkey ready. Selling fully furnished with all appliances and TVs, and available for immediate possession. Can be used aa your primary home, a fun weekend getaway, or an income-boasting rental. This stunning, excellently cared for home is

  Angela Miller John Smith Jr Realty and Auction LLC

  65 Pontoon Place, Winchester, TN 37398
• 

  

  /30

  $499,900

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,645 Sq Ft

  2607 Old Tullahoma Rd, Winchester, TN 37398

  Let's talk about convenience! This home is located within a few minutes of everything you'll ever need. Winchester, TN is a charming lakeside town offering a blend of outdoor recreation, historic charm, and a historic down town. We have it all boutiques, locally owned restaurants, and a vintage theater. This spacious 3–4 bedroom home with 2 full baths and a half bath, offering primary bedroom on

  Valerie Wilder Century 21 Coffee County Realty & Auction

  2607 Old Tullahoma Rd, Winchester, TN 37398
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  /73

  $689,900

  • 4 Beds
  • 3.5 Baths
  • 3,705 Sq Ft

  356 Ridgecrest Dr, Winchester, TN 37398

  Step into this magnificent 3,705 square foot home, an absolute gem in the highly sought-after Franklin Hills Subdivision. Designed for both grand entertaining and comfortable family living, this residence offers 4 bedrooms and 3.5 baths across two levels.You will immediately notice the architectural elegance, highlighted by premier trim work and stunning tray ceilings. The entryway is graced

  Sean Crabtree Blue Door Realty Group

  356 Ridgecrest Dr, Winchester, TN 37398
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  /54

  $479,900

  New Construction $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,290 Sq Ft

  108 Lookout Dr, Winchester, TN 37398

  Welcome to this beautiful 1.5-level home designed for comfort, convenience, and style! This 3-bedroom home features a zoned primary suite on the main floor, offering privacy and functionality for modern living. The open-concept layout creates an inviting space perfect for entertaining family and friends, while the spacious covered back porch provides the ideal spot to relax and unwind outdoors.

  Mitchell Bowman simpliHOM - The Results Team

  108 Lookout Dr, Winchester, TN 37398
• 

  

  /17

  $442,700

  $6K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,952 Sq Ft

  26 Mimosa Dr, Decherd, TN 37324

  Collins Place model home is now available! This beautifully designed 3-bedroom, 3-bath ranch plan offers spacious main-level living with thoughtful upgrades throughout. Enjoy an epoxy-coated 3-car garage and a very large lot, providing exceptional outdoor space for entertaining, gardening, or future additions. Choose either a 4.99% 30-year fixed rate with payments as low as $2,328 per month using

  Jennifer Lucy Harney Realty, LLC

  26 Mimosa Dr, Decherd, TN 37324
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  /61

  $454,900

  • 4 Beds
  • 2 Baths
  • 1,887 Sq Ft

  25 Lookout Dr, Winchester, TN 37398

  Brand new construction opportunity with early buyer selections available. Construction hasn't begun, giving buyers who secure a contract early the opportunity to personalize select finishes such as paint colors, countertops, cabinetry, and flooring. Qualified buyers who use the preferred lender with an accepted offer may be eligible for rates in the 4s! Welcome to your brand-new dream home in the

  Christopher (Chr Tapp APP Realty

  25 Lookout Dr, Winchester, TN 37398
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  /62

  $459,000

  $21K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,209 Sq Ft

  220 Bryan Dr, Winchester, TN 37398

  Welcome to your new home nestled in a serene lake neighborhood on Tims Ford Lake. This delightful house offers the perfect blend of comfort, privacy and entertaining space, making it ideal for families and those seeking a relaxed lifestyle. The privacy-fenced backyard provides the perfect escape for gatherings or quiet evenings under the stars. The convenient patio is perfect for barbecues,

  Sharon Swafford Swaffords Property Shop

  220 Bryan Dr, Winchester, TN 37398
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  /64

  $475,000

  • 5 Beds
  • 2 Baths
  • 3,922 Sq Ft

  309 2nd Ave NW, Winchester, TN 37398

  Income-producing property just over a block from downtown Winchester, offering a rare opportunity for buyers seeking investment property in Tennessee with immediate rental income and future flexibility. Built in 1917, this historic, commercially zoned 5-bedroom, 2-bath residence generates approximately $2,000/month in rental income and includes approximately 3,922 sq ft on a .34-acre lot in the

  Robert Duncan eXp Realty

  309 2nd Ave NW, Winchester, TN 37398
• 

  

  /54

  $499,000

  • 6 Beds
  • 4 Baths
  • 3,158 Sq Ft

  109 Carter Farris Ln, Winchester, TN 37398

  Nestled on 2.4 enchanting acres, this grand 6-bedroom, 4 bath country estate feels like a storybook come to life. Beneath a canopy of towering shade trees, the home rises with grace and charm, offering space as vast as imagination itself. Inside each room is generous in size. Perfect for gathering with family and friends. Full unfinished basement offers plenty of space for storage, workshop, etc.

  Angela Miller John Smith Jr Realty and Auction LLC

  109 Carter Farris Ln, Winchester, TN 37398
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  /70

  $521,900

  New Construction Open House 6/14 $28K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft

  211 Majestic Dr, Decherd, TN 37324

  New Price on a Brand New Home!! No HOA & Home Warranty Included! Beautiful semi-custom new construction home on 1.18 ac partially wooded lot is located at the end of a quiet cul-de-sac with serene mountain views to the East & underground utilities. This thoughtfully designed residence features an open interior concept with split bedroom floor plan. It has an oversized garage for large trucks or

  Candice Bedwell Epique Realty

  211 Majestic Dr, Decherd, TN 37324
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  /33

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 3,067 Sq Ft

  615 Lakeview Way, Winchester, TN 37398

  This distinguished residence at 615 Lakeview Way offers a rare blend of timeless elegance and everyday comfort within the desirable lakefront subdivision of Winchester. Set on a serene, park-like 1 acre corner lot, the 3,067-square-foot home welcomes you with stained glass windows that bathe the entry in soft, colorful light. Inside, the spacious formal living room invites conversation beneath

  Landon Keller Century 21 Volunteer Realty

  615 Lakeview Way, Winchester, TN 37398
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  /54

  $449,900

  New Construction $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft

  124 Lookout Dr, Winchester, TN 37398

  Welcome to the Winchester Plan—a beautifully designed 1-level, 4-bedroom home offering comfort, style, and functionality! The open living concept creates a warm and inviting atmosphere, perfect for family gatherings and entertaining guests. Enjoy relaxing evenings on the covered back porch, ideal for outdoor dining or simply taking in the peaceful surroundings. Located in a gated, family-friendly

  Mitchell Bowman simpliHOM - The Results Team

  124 Lookout Dr, Winchester, TN 37398
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  /44

  $499,000

  • 3 Beds
  • 2 Baths
  • 2,045 Sq Ft

  1405 Old Estill Springs Rd, Winchester, TN 37398

  Tucked away on over 3 beautiful acres right in the heart of town, this lovely home feels like your own private retreat while still being only minutes from shopping, dining, and the sparkling waters of Tims Ford Lake. From the moment you pull into the driveway, you can feel the warmth and charm this property offers. Step inside and imagine cozy evenings gathered around the stunning

  Angela Miller John Smith Jr Realty and Auction LLC

  1405 Old Estill Springs Rd, Winchester, TN 37398
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  /95

  $449,900

  • 4 Beds
  • 2.5 Baths
  • 4,075 Sq Ft

  162 Grizzell Ln, Winchester, TN 37398

  Endless possibilities await you on this beautiful slice of Tennessee countryside! This classic, estate-style, home has everything you need to make this the property of your dreams. Bathrooms have been recently renovated, along with the cabin in the back of the property. Further updates include HVAC and mini-splits (located in the basement), as well as some electrical and plumbing upgrades.

  Hampton Mauzy Compass

  162 Grizzell Ln, Winchester, TN 37398
• 

  

  /70

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,629 Sq Ft

  314 4th Ave NW, Winchester, TN 37398

  Charming Southern Elegance Awaits You! Step into a world of timeless beauty and modern luxury with this stunning turn-of-the-century home, meticulously renovated to blend classic charm with contemporary comfort. The heart of the home is the spacious kitchen, featuring exquisite quartz and granite countertops that will inspire your culinary adventures. Whether hosting intimate dinners or grand

  Sharon Swafford Swaffords Property Shop

  314 4th Ave NW, Winchester, TN 37398
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  /50

  $424,900

  New Construction $14K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,114 Sq Ft

  106 5th Ave N, Decherd, TN 37324

  Welcome home!! This stunning brand-new home is perfectly situated in the heart of Decherd. Designed with today's lifestyle in mind, this residence combines sleek modern finishes with thoughtful details throughout. The grand open concept floor plan is filled with natural light, soaring ceilings, and luxury flooring that flows seamlessly from room to room. The gourmet kitchen is the centerpiece of

  Angela Miller John Smith Jr Realty and Auction LLC

  106 5th Ave N, Decherd, TN 37324
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  /42

  $465,000

  • 5 Beds
  • 3 Baths
  • 2,420 Sq Ft

  71 David Crockett Hwy, Winchester, TN 37398

  Completely remodeled and move-in ready, this stunning home offers the perfect blend of modern upgrades and functional space. Situated on approximately one acre, this property features 5 bedrooms, an office, a spacious recreation/game room upstairs, and a 2-car garage. Inside, you’ll find beautiful new flooring throughout, custom cabinetry, granite countertops, and stylish finishes at every turn.

  Eberley Holloway Southern Middle Realty

  71 David Crockett Hwy, Winchester, TN 37398
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  /51

  $499,900

  $5K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,229 Sq Ft

  805 N Jefferson St, Winchester, TN 37398

  TURN KEY READY to RENT! FULLY FURNISHED with kitchen items, sheets, towels, etc. Barely lived in. Conveniently located to 3 different boat ramps close by. Twin Creeks Marina ramp, Winchester City ramp, Tim's Ford Lake Park ramp. Restaurants & shopping on the town square. Waterproof LVP flooring throughout. Primary bath features double vanity sinks and oversized shower. Lots of walk in closets and

  Linda Seaton Benchmark Realty, LLC

  805 N Jefferson St, Winchester, TN 37398
• 

  /2

  $275,000

  • 4 Beds
  • 2 Baths
  • 1,930 Sq Ft

  810 N High St, Winchester, TN 37398

  Great duplex in perfect location...convenient to Tims Ford lake, Twin Creeks marina and downtown Winchester! One side had an extensive overhaul in 2025. Both sides are currently rented at 975.00 each. Great return on your money! Allow 24hr showing notice to alert tenants.

  Curtis Benchmark Realty, LLC

  810 N High St, Winchester, TN 37398
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  /29

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,898 Sq Ft

  135 Chickamauga Trail, Winchester, TN 37398

  Nestled in the established Cherokee Estates community of Winchester, this beautifully maintained 3-bedroom, 2-bath home, built in 2017, offers the perfect blend of comfort, functionality, and outdoor enjoyment. A versatile bonus room provides endless possibilities as a home office, playroom, media room, or additional living space. Step inside to an inviting open-concept floor plan designed for

  Linda Mendoza eXp Realty

  135 Chickamauga Trail, Winchester, TN 37398
• 

  

  /45

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  423 Shasteen Bend Dr, Winchester, TN 37398

  Nestled in the exclusive community of Lee Ford Estates, this exceptional lakefront retreat offers breathtaking waterfront living just minutes from downtown Winchester. Designed to maximize the beauty of the lake from every angle, the home features French doors throughout, creating stunning panoramic water views and seamless indoor-outdoor living. This beautiful home offers 3 bedrooms and 2 baths,

  Yvonne Stewart Winton Auction & Realty Co.

  423 Shasteen Bend Dr, Winchester, TN 37398
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  /36

  $349,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  253 Brookfield Cir, Winchester, TN 37398

  Beautiful NEW construction just minutes away from Twin Creeks Marina! This beautifully crafted home features a durable Hardiboard exterior and an inviting open floor plan designed for comfortable everyday living and entertaining. Split bedroom concept, luxury vinyl flooring in main living areas, custom shelving in all closets and pantry, walk in tile shower in primary bathroom, stunning lighting

  Jackson Lynch Lynch Rigsby Realty & Auction, LLC

  253 Brookfield Cir, Winchester, TN 37398
• 

  

  /51

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  1114 N High St, Winchester, TN 37398

  Great opportunity for Lake Life without the Lake front headache! Property is Lake View situated 0.5 mile or less to the Winchester City Park and Boat Ramp. Enjoy Family time at the City Park or Lake. This is a beautifully maintained home with upgrades such as hardwood and tile flooring - new in much of the house. Electrical panel and wiring upgrades - New HVAC installed Jul. 2025; Roof installed

  Donald Golden WEICHERT, REALTORS Joe Orr & Associates

  1114 N High St, Winchester, TN 37398
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  /27

  Call for Price

  • Land
  • 86.9 Acres

  1584 Liberty Rd, Winchester, TN 37398

  ABSOLUTE LIVE/ SIMULCAST REAL ESTATE AUCTION!!! SELLING 86.9 +/- ACRES IN 9 TRACTS ON SATURDAY APRIL 4TH AT 10:00 AM. This land is ABSOLUTELY BEAUTIFUL with stunning Mountain Views!! 10% BUYERS PREMIUM ADDED TO FINAL BID PRICE TO DETERMINE FINAL SALES PRICE. 10% down the day of the sale and balance due in 30 days or less. Tracts 2, 4, & 6 have PERC SITES!!! County water, electricity, & internet

  Van Massey Van Massey Realty & Auction

  1584 Liberty Rd, Winchester, TN 37398
• 

  

  /19

  $224,900

  • 3 Beds
  • 1.5 Baths
  • 1,333 Sq Ft

  205 8th Ave NW, Winchester, TN 37398

  Welcome to this delightful brick home nestled on a generous corner lot surrounded by mature shade trees. Full of character and timeless appeal, this home features gleaming original hardwood floors that add warmth and authenticity throughout. Perfectly situated close to town and just minutes from Tims Ford Lake. This combines peaceful living with everyday convenience. Replacement windows

  Angela Miller John Smith Jr Realty and Auction LLC

  205 8th Ave NW, Winchester, TN 37398
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  /35

  $275,000

  • Land
  • 9.42 Acres
  • $29,193 per Acre

  0 Tullahoma Hwy Unit RTC3171237, Winchester, TN 37398

  PREMIUM and RARE investment opportunity to own 9+ acres on Hwy 41A! Positioned in a high-traffic area with excellent visibility, it’s perfectly suited for future development. Opportunities like this are hard to find—don’t miss your chance!

  Aimee Whitt Freedom Realty Group

  0 Tullahoma Hwy Unit RTC3171237, Winchester, TN 37398
• 

  

  /19

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  404 Heikens Dr, Decherd, TN 37324

  If you're looking for the convenience of in-town living but still want some room to stretch out, look no further then 404 Heikens Drive. Sitting on a mostly level 1.53 acre corner lot that backs up to woods, this handsome and functional single-story brick home has been lovingly maintained and is ready for its next owner. With a new roof, freshly refinished floors, and new paint, you set to move

  Adam Brock Canopy Real Estate

  404 Heikens Dr, Decherd, TN 37324
• 

  

  /26

  $175,000

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  714 N Cedar St, Winchester, TN 37398

  MOVE IN READY! This adorable 2-bedroom, 1.5-bath home featuring an inviting open-concept kitchen and dining area, is perfect for everyday living and entertaining. Tile flooring in the kitchen and wet areas, while beautiful hardwood floors add warmth throughout the remaining living spaces. The home also offers a spacious laundry room, an attached carport, and a full unfinished basement. Step

  Eberley Holloway Southern Middle Realty

  714 N Cedar St, Winchester, TN 37398
• 

  

  /67

  $998,996

  $51K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,521 Sq Ft

  49 Why Worry Ln, Winchester, TN 37398

  Experience elevated lake living in this fully custom residence in sought-after Twin Creeks Village, offering over 3,500 square feet of thoughtfully curated design and exceptional craftsmanship. Created for both grand entertaining and everyday comfort, the expansive open-concept layout is anchored by a true chef’s kitchen featuring a dramatic oversized quartz island with integrated dining, 60”

  Shelia Lunsford Benchmark Realty, LLC

  49 Why Worry Ln, Winchester, TN 37398
• 

  

  /49

  $290,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  367 Carol Cir, Winchester, TN 37398

  Welcome home to this move-in ready 3-bedroom, 2-bath home perfectly situated on a corner lot in a quiet Winchester neighborhood—located outside the city limits and just minutes from Tims Ford Lake and Twin Creeks Marina. Built in 2003, this 1,420 sq. ft. home offers a comfortable, functional layout with an attached two-car garage and thoughtful updates throughout. Inside, you’ll find welcoming

  Paige Morris Southern Middle Realty

  367 Carol Cir, Winchester, TN 37398
• 

  /2

  $95,000

  • Land
  • 5.34 Acres
  • $17,790 per Acre

  0 Haddon Ln Unit RTC3190742, Winchester, TN 37398

  5.34 acres on the desirable Broadview side of Winchester! This beautiful tract is ready to go with a perk site already established—bring your plans and start building. Enjoy the perfect blend of privacy and convenience, located less than 10 minutes from Devil Step boat ramp and Tims Ford Lake. Whether you're looking for a homesite or weekend getaway, this one checks all the boxes! More pictures

  Nathan Smith John Smith Jr Realty and Auction LLC

  0 Haddon Ln Unit RTC3190742, Winchester, TN 37398
• 

  

  /18

  $509,450

  • Land
  • 22.15 Acres
  • $23,000 per Acre

  0 Haddon Ln Unit RTC2946006, Winchester, TN 37398

  TAX ID has not been split off from the original 50 +/- parcel. This parcel has been survey and will be recorded when sold. There is a well on property, and property has been surveyed into tracts/perked. RARE-FIND! Minutes to Tims Ford Lake. Seller selling as a whole, and SOLD AS IS.

  Teresa Miller Century 21 Coffee County Realty & Auction

  0 Haddon Ln Unit RTC2946006, Winchester, TN 37398

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