Real Estate Investment Properties for Sale in Middleton, MA

Looking for investment property in Middleton, MA with high ROI ?

Explore a variety of short-term homes & houses in Middleton, MA. Invest wisely with VRBO & Middleton, MA 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 Middleton, MA

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 Wennerberg Road Middleton, MA Excellent Opportunity Awaits for this conveniently located property in desirable Middleton...	3 beds \| 2 baths \| 1,854 sq.ft.	$629,900	Airbnb cash on cash: 1.5% Traditional cash on cash: 4.41% Airbnb Rental Income: $2980 Traditional Rental Income: $4008 Airbnb ROI: 1.5% Traditional ROI: 4.41%
12 Couture Way Middleton, MA 12 Couture Way, Middleton, MA 01949 \| Single Family Residential	4 beds \| 4 baths \| 6,910 sq.ft.	$2,295,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.47% Airbnb Rental Income: $null Traditional Rental Income: $5821 Airbnb ROI: N/A Traditional ROI: 0.47%
11 James Coffin Way #11 Middleton, MA 11 James Coffin Way #11, Middleton, MA 01949 \| Townhouse	3 beds \| 3 baths \| 2,701 sq.ft.	$799,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 2.72% Airbnb Rental Income: $2980 Traditional Rental Income: $4279 Airbnb ROI: 0.06% Traditional ROI: 2.72%
38 Village Rd #515 Middleton, MA 38 Village Rd #515, Middleton, MA 01949 \| Condo/Coop	2 beds \| 2 baths \| 1,258 sq.ft.	$639,900	Airbnb cash on cash: -1.93% Traditional cash on cash: 1.57% Airbnb Rental Income: $1450 Traditional Rental Income: $3106 Airbnb ROI: -1.93% Traditional ROI: 1.57%
40 Village Rd #1006 Middleton, MA 40 Village Rd #1006, Middleton, MA 01949 \| Condo/Coop	2 beds \| 2 baths \| 1,513 sq.ft.	$565,000	Airbnb cash on cash: -2.58% Traditional cash on cash: 0.49% Airbnb Rental Income: $1450 Traditional Rental Income: $2639 Airbnb ROI: -2.58% Traditional ROI: 0.49%
15 Hilldale Ave Middleton, MA 15 Hilldale Ave, Middleton, MA 01949 \| Single Family Residential	2 beds \| 2 baths \| 1,408 sq.ft.	$749,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.42% Airbnb Rental Income: $1450 Traditional Rental Income: $2639 Airbnb ROI: -0.9% Traditional ROI: 1.42%
40 Village Rd #910 Middleton, MA 40 Village Rd #910, Middleton, MA 01949 \| Condo/Coop	2 beds \| 2 baths \| 1,531 sq.ft.	$589,900	Airbnb cash on cash: -2.59% Traditional cash on cash: 1.33% Airbnb Rental Income: $1450 Traditional Rental Income: $3182 Airbnb ROI: -2.59% Traditional ROI: 1.33%
13 Highland Rd Middleton, MA 13 Highland Rd, Middleton, MA 01949 \| Single Family Residential	3 beds \| 1 baths \| 1,295 sq.ft.	$699,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.51% Airbnb Rental Income: $2980 Traditional Rental Income: $3175 Airbnb ROI: 1.16% Traditional ROI: 2.51%
40 Village Rd #602 Middleton, MA 40 Village Rd #602, Middleton, MA 01949 \| Condo/Coop	2 beds \| 2 baths \| 1,765 sq.ft.	$675,000	Airbnb cash on cash: -2.81% Traditional cash on cash: 0.5% Airbnb Rental Income: $1450 Traditional Rental Income: $3102 Airbnb ROI: -2.81% Traditional ROI: 0.5%
13 James Coffin Way #13 Middleton, MA 13 James Coffin Way #13, Middleton, MA 01949 \| Townhouse	4 beds \| 3 baths \| 2,989 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $4881 Airbnb ROI: N/A Traditional ROI: 2.83%
63 Rowell Ln Middleton, MA 63 Rowell Ln, Middleton, MA 01949 \| Single Family Residential	2 beds \| 3 baths \| 3,565 sq.ft.	$1,295,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.11% Airbnb Rental Income: $1450 Traditional Rental Income: $2639 Airbnb ROI: -1.45% Traditional ROI: -0.11%
4 Shipley Ct Middleton, MA 4 Shipley Ct, Middleton, MA 01949 \| Single Family Residential	4 beds \| 4 baths \| 4,961 sq.ft.	$2,160,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.57% Airbnb Rental Income: $null Traditional Rental Income: $5692 Airbnb ROI: N/A Traditional ROI: 0.57%
14 Dansereau Pl #14 Middleton, MA 14 Dansereau Pl #14, Middleton, MA 01949 \| Condo/Coop	3 beds \| 3 baths \| 2,973 sq.ft.	$899,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.7% Airbnb Rental Income: $2980 Traditional Rental Income: $4379 Airbnb ROI: -0.79% Traditional ROI: 1.7%
16 Couture Way Middleton, MA 16 Couture Way, Middleton, MA 01949 \| Single Family Residential	4 beds \| 3 baths \| 3,972 sq.ft.	$1,849,999	Airbnb cash on cash: N/A Traditional cash on cash: 0.58% Airbnb Rental Income: $null Traditional Rental Income: $4916 Airbnb ROI: N/A Traditional ROI: 0.58%
63 Rowell Ln #63 Middleton, MA 63 Rowell Ln #63, Middleton, MA 01949 \| Townhouse	2 beds \| 3 baths \| 3,565 sq.ft.	$1,295,000	Airbnb cash on cash: -2.22% Traditional cash on cash: 0.21% Airbnb Rental Income: $1450 Traditional Rental Income: $3936 Airbnb ROI: -2.22% Traditional ROI: 0.21%
141 Essex St #141 Middleton, MA 141 Essex St #141, Middleton, MA 01949 \| Single Family Residential	3 beds \| 2 baths \| 2,073 sq.ft.	$1,100,022	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.32% Airbnb Rental Income: $2980 Traditional Rental Income: $3719 Airbnb ROI: -0.07% Traditional ROI: 1.32%
10 White Cedar Dr #10 Middleton, MA 10 White Cedar Dr #10, Middleton, MA 01949 \| Townhouse	3 beds \| 2 baths \| 2,691 sq.ft.	$914,999	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.07% Airbnb Rental Income: $2980 Traditional Rental Income: $3627 Airbnb ROI: -0.5% Traditional ROI: 1.07%
139 Essex St #139 Middleton, MA 139 Essex St #139, Middleton, MA 01949 \| Townhouse	3 beds \| 2 baths \| 2,073 sq.ft.	$1,200,024	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.5% Airbnb Rental Income: $2980 Traditional Rental Income: $3688 Airbnb ROI: -0.75% Traditional ROI: 0.5%
133 Essex St #133 Middleton, MA 133 Essex St #133, Middleton, MA 01949 \| Townhouse	3 beds \| 2 baths \| 2,154 sq.ft.	$1,200,024	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.04% Airbnb Rental Income: $2980 Traditional Rental Income: $3175 Airbnb ROI: -0.75% Traditional ROI: 0.04%
135 Essex St #135 Middleton, MA 135 Essex St #135, Middleton, MA 01949 \| Townhouse	3 beds \| 2 baths \| 2,059 sq.ft.	$1,200,024	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.04% Airbnb Rental Income: $2980 Traditional Rental Income: $3175 Airbnb ROI: -0.75% Traditional ROI: 0.04%
137 Essex St #~ Middleton, MA 137 Essex St #~, Middleton, MA 01949 \| Townhouse	3 beds \| 2 baths \| 2,067 sq.ft.	$1,200,024	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.5% Airbnb Rental Income: $2980 Traditional Rental Income: $3688 Airbnb ROI: -0.75% Traditional ROI: 0.5%
lot 12 39 East Meadow Ln Middleton, MA lot 12 39 East Meadow Ln, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$949,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.05% Airbnb Rental Income: $1761 Traditional Rental Income: $2103 Airbnb ROI: -0.88% Traditional ROI: 0.05%
lot 10 42 East Meadow Ln Middleton, MA lot 10 42 East Meadow Ln, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$869,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.28% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.76% Traditional ROI: -0.28%
lot 7 19 Simcha Rd Middleton, MA lot 7 19 Simcha Rd, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$849,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.24% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.72% Traditional ROI: -0.24%
lot 11 38 East Meadow Ln Middleton, MA lot 11 38 East Meadow Ln, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$849,000	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.24% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.72% Traditional ROI: -0.24%
lot 19 30 Simcha Rd Middleton, MA lot 19 30 Simcha Rd, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$965,000	Airbnb cash on cash: -0.9% Traditional cash on cash: -0.48% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.9% Traditional ROI: -0.48%
lot 13 35 Simcha Rd Middleton, MA lot 13 35 Simcha Rd, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$939,000	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.43% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.87% Traditional ROI: -0.43%
lot 9 31 Simcha Rd Middleton, MA lot 9 31 Simcha Rd, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$899,000	Airbnb cash on cash: -0.81% Traditional cash on cash: -0.35% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.81% Traditional ROI: -0.35%
lot 8 29 Simcha Rd Middleton, MA lot 8 29 Simcha Rd, Middleton, MA 01949 \| Other	N/A beds \| N/A baths \| N/A	$889,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.33% Airbnb Rental Income: $1761 Traditional Rental Income: $1662 Airbnb ROI: -0.79% Traditional ROI: -0.33%

Real Estate investment in Middleton, MA

There are 31 properties for sale in the city of Middleton . The median list price in Middleton is $814,513 and the average price per square foot is $336. In August 2026, the average monthly cash on cash return in Middleton is N/A%. The average monthly rental income in Middleton is $3,175.

Middleton, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 31 investment properties available for sale in Middleton.

In 2026, the best neighborhood to buy investment property is Middleton.

The ROI for Long-Term is higher than the Short-Term in Middleton with average rental income of $3,175.

Your search for investment property begins and ends here

Investment Property for Sale in Middleton, MA

5 Wennerberg Road

Middleton, MA

3 beds | 2 baths | 1,854 sq.ft.

$629,900

Airbnb cash on cash: 1.5%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $2980

Traditional Rental Income: $4008

Airbnb ROI: 1.5%

Traditional ROI: 4.41%

12 Couture Way

Middleton, MA

4 beds | 4 baths | 6,910 sq.ft.

$2,295,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.47%

Airbnb Rental Income: $null

Traditional Rental Income: $5821

Airbnb ROI: N/A

Traditional ROI: 0.47%

11 James Coffin Way #11

Middleton, MA

3 beds | 3 baths | 2,701 sq.ft.

$799,000

Airbnb cash on cash: 0.06%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $2980

Traditional Rental Income: $4279

Airbnb ROI: 0.06%

Traditional ROI: 2.72%

38 Village Rd #515

Middleton, MA

2 beds | 2 baths | 1,258 sq.ft.

$639,900

Airbnb cash on cash: -1.93%

Traditional cash on cash: 1.57%

Airbnb Rental Income: $1450

Traditional Rental Income: $3106

Airbnb ROI: -1.93%

Traditional ROI: 1.57%

40 Village Rd #1006

Middleton, MA

2 beds | 2 baths | 1,513 sq.ft.

$565,000

Airbnb cash on cash: -2.58%

Traditional cash on cash: 0.49%

Airbnb Rental Income: $1450

Traditional Rental Income: $2639

Airbnb ROI: -2.58%

Traditional ROI: 0.49%

15 Hilldale Ave

Middleton, MA

2 beds | 2 baths | 1,408 sq.ft.

$749,900

Airbnb cash on cash: -0.9%

Traditional cash on cash: 1.42%

Airbnb Rental Income: $1450

Traditional Rental Income: $2639

Airbnb ROI: -0.9%

Traditional ROI: 1.42%

40 Village Rd #910

Middleton, MA

2 beds | 2 baths | 1,531 sq.ft.

$589,900

Airbnb cash on cash: -2.59%

Traditional cash on cash: 1.33%

Airbnb Rental Income: $1450

Traditional Rental Income: $3182

Airbnb ROI: -2.59%

Traditional ROI: 1.33%

13 Highland Rd

Middleton, MA

3 beds | 1 baths | 1,295 sq.ft.

$699,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $2980

Traditional Rental Income: $3175

Airbnb ROI: 1.16%