Real Estate Investment Properties for Sale in Oakland, TN

Looking for investment property in Oakland, TN with high ROI ?

Explore a variety of short-term homes & houses in Oakland, TN. Invest wisely with VRBO & Oakland, TN Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Oakland, TN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
20 CHESNUT RIDGE Oakland, TN Model home in Waters of Hidden Springs, a Regency Homebuilders community. This Presley II ...	5 beds \| 3 baths \| N/A	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $2831 Airbnb ROI: N/A Traditional ROI: 4.84%
270 OAK HAVEN Oakland, TN Sloane Floor Plan - Model Home (not for sale)! Executive Series features include 8 ft tall...	3 beds \| 2 baths \| N/A	$502,595	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $1776 Airbnb ROI: N/A Traditional ROI: 2.57%
40 LAUREL WOOD Oakland, TN This home is READY NOW!! Fairway Village: A Regency Homebuilders community in Oakland. Th...	4 beds \| 3 baths \| N/A	$444,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $2740 Airbnb ROI: N/A Traditional ROI: 4.65%
130 VALLEYVIEW Oakland, TN $10k BUILDER BONUS! Fabulous Belvedere floor plan by Grant Homes! QUALIFIES FOR USDA! Offe...	4 beds \| 3 baths \| N/A	$434,950	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $2754 Airbnb ROI: N/A Traditional ROI: 5.11%
15 HUGHETTA Oakland, TN Step into the model home AND design center at Carrington Estates where you can tour 44 hom...	5 beds \| 3 baths \| N/A	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3009 Airbnb ROI: N/A Traditional ROI: 3.51%
60 LIVE OAK Oakland, TN 4.99% PERMANENT INTEREST RATE AVAILABLE! CALL FOR DETAILS! The Washington B plan feature...	3 beds \| 2 baths \| N/A	$359,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $2157 Airbnb ROI: N/A Traditional ROI: 4.4%
60 SUGALINA VALLEY Oakland, TN $10K Builder Bonus! Qualifies for USDA! Canterbury Floorplan by Grant Homes! Featuring ove...	4 beds \| 3 baths \| N/A	$439,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $2752 Airbnb ROI: N/A Traditional ROI: 4.75%
50 SUGALINA VALLEY Oakland, TN $10K BUILDER BONUS! New construction by Grant Homes! Valleybrook Subdivision in Oakland -...	4 beds \| 3 baths \| N/A	$439,950	Airbnb cash on cash: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $2752 Airbnb ROI: N/A Traditional ROI: 4.75%
105 DOWNY BIRCH Oakland, TN This home is READY NOW!!! Gardens of Hidden Springs: A Regency Homebuilders community in O...	3 beds \| 2 baths \| N/A	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $2007 Airbnb ROI: N/A Traditional ROI: 3.66%
327 ST ANDREWS Oakland, TN This home is READY NOW!! Villas at Fair Oaks: A Regency Homebuilders community in Oakland....	3 beds \| 3 baths \| N/A	$384,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.24% Airbnb Rental Income: $null Traditional Rental Income: $2365 Airbnb ROI: N/A Traditional ROI: 5.24%
195 HUGHETTA Oakland, TN **Builder offering $10,000 flexible concession for the buyer. Blinds, Gas Range Stove, Ca...	4 beds \| 3 baths \| N/A	$409,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.13% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 5.13%
135 LIVE OAK Oakland, TN 4.99% PERMANENT INTEREST RATE AVAILABLE! CALL FOR DETAILS! MOVE-IN READY HOME IN Twin Oa...	3 beds \| 2 baths \| N/A	$384,950	Airbnb cash on cash: N/A Traditional cash on cash: 3.91% Airbnb Rental Income: $null Traditional Rental Income: $2120 Airbnb ROI: N/A Traditional ROI: 3.91%
365 GREEN WILLOW Oakland, TN Welcome to Gardens of Hidden Springs: A Regency Homebuilders community in Oakland. This As...	3 beds \| 2 baths \| N/A	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.89% Airbnb Rental Income: $null Traditional Rental Income: $2011 Airbnb ROI: N/A Traditional ROI: 3.89%
330 CHESNUT RIDGE Oakland, TN Contact the listing agent to learn about the special September promo! Now available in W...	3 beds \| 2 baths \| N/A	$394,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.47% Airbnb Rental Income: $null Traditional Rental Income: $2011 Airbnb ROI: N/A Traditional ROI: 3.47%
90 HILLSIDE Oakland, TN This home is READY NOW!! Welcome to Waters of Hidden Springs: A Regency Homebuilders commu...	3 beds \| 2 baths \| N/A	$394,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $2049 Airbnb ROI: N/A Traditional ROI: 3.58%
95 MISTY RIDGE Oakland, TN This home is READY NOW!! Fairway Village: A Regency Homebuilders community in Oakland. Th...	5 beds \| 3 baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.9% Airbnb Rental Income: $null Traditional Rental Income: $2875 Airbnb ROI: N/A Traditional ROI: 4.9%
325 ST ANDREWS Oakland, TN This home is READY NOW!! Villas at Fair Oaks: A Regency Homebuilders community in Oakland....	3 beds \| 3 baths \| N/A	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $2417 Airbnb ROI: N/A Traditional ROI: 4.65%
50 SANDY Oakland, TN Wonderful home with an open floor plan. It features 9' ceilings, 4 bedrooms, and 2 full ba...	4 beds \| 2 baths \| N/A	$334,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2289 Airbnb ROI: N/A Traditional ROI: 5.27%
255 HIGHLAND PARK Oakland, TN Back on market due to no fault of seller or home. This GORGEOUS practically LIKE NEW 4BR/2...	4 beds \| 2 baths \| N/A	$446,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.12% Airbnb Rental Income: $null Traditional Rental Income: $2374 Airbnb ROI: N/A Traditional ROI: 4.12%
75 LAUREL WOOD Oakland, TN NEW PRICE! This 2022 Regency built home is like new! Impeccably maintained interior, ful...	4 beds \| 3 baths \| N/A	$445,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.19% Airbnb Rental Income: $null Traditional Rental Income: $2390 Airbnb ROI: N/A Traditional ROI: 4.19%
210 HIGHLAND PARK Oakland, TN Wow! Are you looking for a fantastic home that backs up to common open space with no neigh...	3 beds \| 2 baths \| N/A	$398,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.42% Airbnb Rental Income: $null Traditional Rental Income: $2009 Airbnb ROI: N/A Traditional ROI: 3.42%
350 GREEN WILLOW Oakland, TN *Contact the listing agent to learn about the special promotion on this home for the month...	3 beds \| 2 baths \| N/A	$364,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $1974 Airbnb ROI: N/A Traditional ROI: 3.79%
195 SUGALINA VALLEY Oakland, TN Valleybrook: A Regency Homebuilders community in Oakland. This Presley II floor plan is a ...	5 beds \| 3 baths \| N/A	$494,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2881 Airbnb ROI: N/A Traditional ROI: 4.32%
185 VALLEYVIEW Oakland, TN FABULOUS HENDERSON FLOOR PLAN BUILT BY GRANT HOMES, LLC! $5K BUILDER BONUS AND UNDER 400K!...	4 beds \| 3 baths \| N/A	$394,950	Airbnb cash on cash: N/A Traditional cash on cash: 5.93% Airbnb Rental Income: $null Traditional Rental Income: $2693 Airbnb ROI: N/A Traditional ROI: 5.93%
175 VALLEYVIEW Oakland, TN $5k BUILDER BONUS - QUALIFIES FOR USDA - Canterbury Floor Plan built by Grant Homes, LLC. ...	4 beds \| 3 baths \| N/A	$439,950	Airbnb cash on cash: N/A Traditional cash on cash: 5.23% Airbnb Rental Income: $null Traditional Rental Income: $2693 Airbnb ROI: N/A Traditional ROI: 5.23%
60 MISTY MEADOW Oakland, TN Welcome to this like new home located in Fairway Village. This 2631 sqft Carlisle plan by ...	4 beds \| 3 baths \| N/A	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.26% Airbnb Rental Income: $null Traditional Rental Income: $2365 Airbnb ROI: N/A Traditional ROI: 4.26%
125 ST ANDREWS Oakland, TN This home is READY NOW!! Villas at Fair Oaks: A Regency Homebuilders community in Oakland....	3 beds \| 3 baths \| N/A	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $2329 Airbnb ROI: N/A Traditional ROI: 4.41%
195 CHICKASAW TRACE Oakland, TN Move-in ready and thoughtfully designed, this home combines comfort and modern living with...	4 beds \| 3 baths \| N/A	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.44% Airbnb Rental Income: $null Traditional Rental Income: $2837 Airbnb ROI: N/A Traditional ROI: 6.44%
110 COLE CREEK Oakland, TN Why wait to build when this 2021 home already has the upgrades, space, and charm youâve ...	4 beds \| 3 baths \| N/A	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.2% Airbnb Rental Income: $null Traditional Rental Income: $2725 Airbnb ROI: N/A Traditional ROI: 5.2%
300 ST ANDREWS Oakland, TN Priced to Sell at 369,900! Golfers Paradise! Just a year old and overlooking Fair Oaks gol...	4 beds \| 3 baths \| N/A	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.39% Airbnb Rental Income: $null Traditional Rental Income: $2781 Airbnb ROI: N/A Traditional ROI: 6.39%
100 PINE VALLEY Oakland, TN BACK ON MARKET- BUYERS FAULTED ON DAY OF CLOSING. This beautifully updated home offers 5 b...	5 beds \| 3 baths \| N/A	$488,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.47% Airbnb Rental Income: $null Traditional Rental Income: $2782 Airbnb ROI: N/A Traditional ROI: 4.47%
40 CHESNUT SPRING Oakland, TN Welcome to 40 Chesnut Springs in Oakland, TN! This beautiful 4-bedroom, 2-bathroom homeâ...	4 beds \| 2 baths \| N/A	$354,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.77% Airbnb Rental Income: $null Traditional Rental Income: $2469 Airbnb ROI: N/A Traditional ROI: 5.77%
35 WHISPERING CREEK Oakland, TN Nestled in a quiet cove with lush landscaping and a 2-car garage, this beautiful home welc...	4 beds \| 2 baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.08% Airbnb Rental Income: $null Traditional Rental Income: $2212 Airbnb ROI: N/A Traditional ROI: 5.08%
230 DRIFTWOOD Oakland, TN Welcome Home to this charming 4 bedroom 2 bath home in the Village Park subdivision featur...	4 beds \| 2 baths \| N/A	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.2% Airbnb Rental Income: $null Traditional Rental Income: $2250 Airbnb ROI: N/A Traditional ROI: 5.2%
95 PINEHURST Oakland, TN Experience Golf Course Living in this stunning 3 bedroom 2 bathroom sanctuary. All on one ...	3 beds \| 2 baths \| N/A	$349,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2306 Airbnb ROI: N/A Traditional ROI: 5.4%
200 HUGHETTA Oakland, TN Welcome to the Dove F. Open concept. Expansive Great room bathed in natural light. Electr...	5 beds \| 3 baths \| N/A	$409,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.81% Airbnb Rental Income: $null Traditional Rental Income: $2982 Airbnb ROI: N/A Traditional ROI: 5.81%
100 TOMMIE VALLEY Oakland, TN Welcome to the beautifully designed Presley II floor plan, offering 2,650 square feet of t...	5 beds \| 3 baths \| N/A	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $2629 Airbnb ROI: N/A Traditional ROI: 4.35%
430 GARDEN SPRINGS Oakland, TN Back on the Market, contract fell through - no fault of the Seller. Home is PRICED UNDER A...	3 beds \| 2 baths \| N/A	$309,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $1886 Airbnb ROI: N/A Traditional ROI: 4.86%
95 DOGWOOD SPRING Oakland, TN Built in 2022, this 4-bedroom, 3 full bath home features a split, open-concept floor plan ...	4 beds \| 3 baths \| N/A	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $2435 Airbnb ROI: N/A Traditional ROI: 5.22%
240 LAUREL WOOD Oakland, TN Fairway Village: A Regency Homebuilders community in Oakland. This Carlisle floor plan is ...	4 beds \| 3 baths \| N/A	$464,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2693 Airbnb ROI: N/A Traditional ROI: 4.27%

Real Estate investment in Oakland, TN

There are 88 properties for sale in the city of Oakland . The median list price in Oakland is $394,925 and the average price per square foot is $165. In September 2025, the average monthly cash on cash return in Oakland is 5.00%. The average monthly rental income in Oakland is $2,442.

Oakland, TN Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 88 investment properties available for sale in Oakland.

The ROI for Short-Term is higher than the Long-Term in Oakland with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Oakland, TN

20 CHESNUT RIDGE

Oakland, TN

5 beds | 3 baths | N/A

$479,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2831

Airbnb ROI: N/A

Traditional ROI: 4.84%

270 OAK HAVEN

Oakland, TN

3 beds | 2 baths | N/A

$502,595

Airbnb cash on cash: N/A

Traditional cash on cash: 2.57%

Airbnb Rental Income: $null

Traditional Rental Income: $1776

Airbnb ROI: N/A

Traditional ROI: 2.57%

40 LAUREL WOOD

Oakland, TN

4 beds | 3 baths | N/A

$444,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.65%

Airbnb Rental Income: $null

Traditional Rental Income: $2740

Airbnb ROI: N/A

Traditional ROI: 4.65%

130 VALLEYVIEW

Oakland, TN

4 beds | 3 baths | N/A

$434,950

Airbnb cash on cash: N/A

Traditional cash on cash: 5.11%

Airbnb Rental Income: $null

Traditional Rental Income: $2754

Airbnb ROI: N/A

Traditional ROI: 5.11%

15 HUGHETTA

Oakland, TN

5 beds | 3 baths | N/A

$599,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.51%

Airbnb Rental Income: $null

Traditional Rental Income: $3009

Airbnb ROI: N/A

Traditional ROI: 3.51%

60 LIVE OAK

Oakland, TN

3 beds | 2 baths | N/A

$359,950

Airbnb cash on cash: N/A

Traditional cash on cash: 4.4%

Airbnb Rental Income: $null

Traditional Rental Income: $2157

Airbnb ROI: N/A

Traditional ROI: 4.4%

60 SUGALINA VALLEY

Oakland, TN

4 beds | 3 baths | N/A

$439,950

Airbnb cash on cash: N/A

Traditional cash on cash: 4.75%

Airbnb Rental Income: $null

Traditional Rental Income: $2752

Airbnb ROI: N/A

Traditional ROI: 4.75%

50 SUGALINA VALLEY

Oakland, TN

4 beds | 3 baths | N/A

$439,950

Airbnb cash on cash: N/A

Traditional cash on cash: 4.75%

Airbnb Rental Income: $null

Traditional Rental Income: $2752

Airbnb ROI: N/A