Vintage homes for sale & real estate in 37027, TN

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ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Welcome to 5566 Hill Rd, an exceptional Brentwood estate offering nearly 7,000 sq ft of refined living space on 2 private, flat acres. Thoughtfully designed for both everyday living and grand-scale entertaining, this gated property features a heated pool and spa by Waterscapes, a tiki bar, and a fully equipped pool house with kitchen and guest suite. Inside the main home, you'll find four bedrooms, a chef’s kitchen with breakfast nook, a dedicated office, media room, and a stunning upstairs bonus with wet bar and attic storage. The detached guest apartment offers a private retreat with kitchenette and full bath, while a 1,000 sq ft barn adds flexible space for hobbies, gym, or storage

$3,350,000

6 beds7 baths6,947 sq ft

5566 Hill Rd, Brentwood, TN 37027

Upstairs bonus • Tiki bar • Dedicated office

Listing provided by REALTRACS as Distributed by MLS Grid

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Beautifully restored 1935 log home on 3.59 private acres in Brentwood. This 3BR/3BA retreat blends historic charm with modern updates, featuring original log details, updated kitchen with double ovens and large island, spacious living areas with two fireplaces, and a primary suite with walk-in closet, spa-like bath, laundry, and private hot tub patio. A detached workshop/garage, 600-amp service, and serene creekside setting complete this one-of-a-kind property just minutes from shopping, dining, and conveniences. Up to 1% lender credit on the loan amount when buyer uses Seller's Preferred Lender.

$2,100,000

3 beds3 baths2,863 sq ft

711 Hill Rd, Brentwood, TN 37027

Restored log home • Large island • Updated kitchen

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Isola Bella, originally built in 1840, sits on a fully fenced 9 acres in the heart of Brentwood! This estate has a rich history and is listed on the National Register of Historic Sites. The main house and two additional houses comprise a total of 13,025 square feet. The original kitchen for this estate stands separately just a few feet from the back of the main house. A 6-stall barn stands ready for horses to return to this beautiful land. Isola Bella, a once in a generation opportunity, is now ready for a complete renovation allowing its new owner to write the next chapter in the history books for this grand estate. This property is a world class home for one very fortunate family. It may

$9,750,000

10 beds10 baths13,025 sq ft

1112 Franklin Rd, Brentwood, TN 37027

Fully fenced 9 acres • 6 stall barn • Original kitchen

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Charming 1942 Cottage with Flexible Space in Prime Brentwood Location! Full of character and thoughtful updates, this beautifully maintained cottage offers a rare blend of vintage charm and modern convenience in one of Brentwood’s most accessible areas. Inside, you’ll find original hardwood floors, updated interiors, and multiple flexible living areas. Formerly used as both a residence and a wellness studio (via limited-use variance), the layout adapts easily for a range of lifestyles—whether that’s home office, art studio, music room, or simply additional living space. The attached bonus room is currently used as a bedroom, and a third flex room—with a closet

$945,000

2 beds1.5 baths2,437 sq ft

1307 Old Hickory Blvd, Brentwood, TN 37027

Third flex room • Brentwood location • Updated interiors

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Discover an Exceptional Opportunity to own 5.96 acres of Pristine Land in the highly sought-after Brentwood, Tennessee. Nestled in a Prestigious & Peaceful setting! This Property offers the perfect blend of Privacy, Natural Beauty, & convenience. Prime location! Situated in one of Brentwood's most desirable areas, offering easy access to Nashville, Franklin & Cool Springs!. Perfect for a Custom Estate, Equestrian Property, or Future Development! Whether you Envision a Luxury Home, Mini Farm, or Investment opportunity, this land provides endless potential. Enjoy mature trees, open spaces, and breathtaking views, creating a tranquil retreat while still being close to City Ame

$1,000,000

3 beds1 bath1,152 sq ft

1529 Hyde Ln, Brentwood, TN 37027

5.96 acres • Pristine land • Privacy

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 5709 Cloverland Dr Unit A, Brentwood, TN 37027, 6 beds, 7 baths

$3,999,900

6 beds7 baths6,000 sq ft

5709 Cloverland Dr Unit A, Brentwood, TN 37027

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 9580 Crockett Rd, Brentwood, TN 37027, 5 beds, 4 baths

$2,490,000

5 beds4 baths4,585 sq ft

9580 Crockett Rd, Brentwood, TN 37027

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 5709 Cloverland Dr, Brentwood, TN 37027

$749,900

— beds— baths— sq ft

5709 Cloverland Dr, Brentwood, TN 37027

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1108 Waller Rd, Brentwood, TN 37027

$662,500

— beds— baths— sq ft

1108 Waller Rd, Brentwood, TN 37027

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1110 Waller Rd, Brentwood, TN 37027

$1,987,500

— beds— baths— sq ft

1110 Waller Rd, Brentwood, TN 37027

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 9227 Old Smyrna Rd Lot 1, Brentwood, TN 37027

$2,250,000

— beds— baths— sq ft

9227 Old Smyrna Rd Lot 1, Brentwood, TN 37027

Listing provided by REALTRACS as Distributed by MLS Grid

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ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Newly renovated all brick home in the desired Caldwell-Abbay Hall neighborhood! Step inside and you'll find a beautiful covered front porch patio right off the front entrance. The main level of the home has 3 bedrooms & 1 full bath with LVP flooring throughout and Tile in the bathrooms. The kitchen is newly remodeled with white shaker cabinets, beautiful quartz countertops and sleek backsplash design! The basement is fully finished, with a 4th bedroom & a huge walk in closet, a 2nd full bathroom and 2 additional recreation/hobby rooms! Use the lower level as an in-law-suite or potential Airbnb (per city approval). Do not miss this one!

$670,000

4 beds2 baths2,349 sq ft

428 Coventry Dr, Nashville, TN 37211

0.68 acre lot • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

NEW

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Don’t miss the opportunity to own this rare 9.44-acre property, nestled in the highly coveted Estate Section of Forest Hills. Ideally located between Belle Meade Blvd and Percy Warner Park, this stunning lot offers the perfect setting for enjoying sunny days and capturing the essence of Nashville living. With lush, expansive greenery and an abundance of natural foliage, the property is a true sanctuary. Whether you're looking to move into an existing home or build your dream residence on a blank canvas, this remarkable lot promises to exceed expectations.

$6,500,000

5 beds5.5 baths5,750 sq ft

1416 Chickering Rd, Nashville, TN 37215

9.44 acre lot • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Make This Your New Home for Thanksgiving! Welcome to this charming and beautifully updated ranch in the heart of Crieve Hall, one of Nashville's most desirable neighborhoods. Experience true neighborhood living with tree-lined streets, friendly neighbors, and the convenience of being zoned for sought-after Crieve Hall Elementary. This 3-bedroom, 2-bath home has been thoughtfully updated throughout. The garage has been converted into a spacious primary suite, complete with a private bath and laundry room. Enjoy a full kitchen renovation featuring modern finishes, stylish cabinetry, and a pantry- perfect for cooking and entertaining. The expansive 20 x 20 screened porch just off the family r

$699,000

3 beds2 baths1,674 sq ft

604 Rochelle Dr, Nashville, TN 37220

0.35 acre lot • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
* Ranch Home on Corner Lot of Dead-End Street * Ample Natural Light * Updated Kitchen * Hardwood & Tile Floors * Stainless Steel Appliances, Granite Countertops, & Subway Tile Backsplash in Kitchen * Updated Bathrooms with Shiplap & Tile * Office/Living Room * Fenced Backyard with Open Deck, Large Shade Tree, & Storage Shed * Roof is 4 Years Old * Firepit/Garden Bed * Close to Shopping and Restaurants off Nolensville Rd * Walking Distance to Schools *

$460,000

3 beds2 baths1,282 sq ft

498 Whispering Hills Dr, Nashville, TN 37211

0.41 acre lot • Somewhat walkable

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Remodeled home with inground pool, and in law suite with separate entrance! This is a perfect option for a family compound, multi generational living, or savvy investor looking to house hack. This fully updated home sits on almost an acre lot with plenty of space to entertain. Covered deck has beautiful sunsets, and very large back yard. Great master bedroom, and plenty of storage

$559,000

4 beds3 baths2,195 sq ft

505 Northcrest Dr, Nashville, TN 37211

0.81 acre lot • Pool • Somewhat walkable

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Vintage Home for sale in 37027, TN:
Beautiful cottage on amazing fenced lawn. The home has beautiful hardwoods through out, updated bathrooms and kitchen with stainless steel appliances, ample cabinets and Corian counter tops. The downstairs features an incredible living space with two full baths, den with electric fireplace, and primary en-suite, a small kitchen/laundry room. The outdoor spaces are incredible with amazing landscaping and a generous deck off the upstairs kitchen, downstairs screened-in porch leads to another hardscaped patio with gas firepit and lush fully fenced and private backyard. Perfect for entertaining. Covered parking leading into the back yard and lower entrance of the home. MOTIVATED SELLER!!!! SELL

$640,000

4 beds3 baths2,050 sq ft

629 Watsonwood Dr, Nashville, TN 37211

0.36 acre lot • 2 garage spots • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 361 Tusculum Rd, Nashville, TN 37211, 3 beds, 2 baths

$410,000

3 beds2 baths1,924 sq ft

361 Tusculum Rd, Nashville, TN 37211

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 849 Forest Acres Dr, Nashville, TN 37220, 5 beds, 3.5 baths

$2,790,000

5 beds3.5 baths4,134 sq ft

849 Forest Acres Dr, Nashville, TN 37220

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 3815 Barlow Dr, Nashville, TN 37211, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths1,499 sq ft

3815 Barlow Dr, Nashville, TN 37211

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 908 W Main St, Franklin, TN 37064, 5 beds, 3.5 baths

$3,350,000

5 beds3.5 baths6,651 sq ft

908 W Main St, Franklin, TN 37064

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 4911 Packard Dr, Nashville, TN 37211, 2 beds, 1 bath

$324,900

2 beds1 bath1,010 sq ft

4911 Packard Dr, Nashville, TN 37211

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 334 Dade Dr, Nashville, TN 37211, 3 beds, 2 baths

$499,999

3 beds2 baths1,400 sq ft

334 Dade Dr, Nashville, TN 37211

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 877 Hillhaven Ct, Nashville, TN 37220, 3 beds, 2.5 baths

$1,375,000

3 beds2.5 baths4,187 sq ft

877 Hillhaven Ct, Nashville, TN 37220

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 819 Forest Acres Dr, Nashville, TN 37220, 4 beds, 2 baths

$1,150,000

4 beds2 baths2,242 sq ft

819 Forest Acres Dr, Nashville, TN 37220

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 961 Glass St, Franklin, TN 37064, 3 beds, 2.5 baths

$599,000

3 beds2.5 baths1,422 sq ft

961 Glass St, Franklin, TN 37064

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 505 Oakley Dr, Nashville, TN 37220, 3 beds, 3 baths

$924,900

3 beds3 baths2,414 sq ft

505 Oakley Dr, Nashville, TN 37220

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 4165 Clovercroft Rd, Franklin, TN 37067, 3 beds, 2 baths

$1,000,000

3 beds2 baths2,474 sq ft

4165 Clovercroft Rd, Franklin, TN 37067

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 504 N Petway St, Franklin, TN 37064, 3 beds, 2 baths

$749,900

3 beds2 baths1,282 sq ft

504 N Petway St, Franklin, TN 37064

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 928 Glass St, Franklin, TN 37064, 4 beds, 2 baths

$569,000

4 beds2 baths1,400 sq ft

928 Glass St, Franklin, TN 37064

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 516 Franklin Limestone Rd, Nashville, TN 37217

$2,000,000

— beds— baths— sq ft

516 Franklin Limestone Rd, Nashville, TN 37217

Listing provided by REALTRACS as Distributed by MLS Grid

Vintage Homes for Sale in 37027

There are currently 11 vintage homes for sale in 37027 at a median listing price of $1.43M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 37027 stay on the market for 80 days and receive 1 offers. This map is refreshed with the newest listings in 37027 every 15 minutes.

In the past month, 76 homes have been sold in 37027. In addition to houses in 37027, there were also 28 condos, 64 townhouses, and 1 multi-family unit for sale in 37027 last month. Find your dream home in 37027 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 37027 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 37027. If you're looking to sell your home in the 37027 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 37027 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Based on information submitted to the MLS GRID as of Mon Oct 20 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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