Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
444 MACUM CREEK DR CHESTER, MD PLEASE CLICK ON VIRTUAL TOUR ICON FOR INTERACTIVE FLOOR PLAN Welcome to 444 Macum Cre...	3 beds \| 3 baths \| N/A	$850,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 1.68% Airbnb Rental Income: $6279 Traditional Rental Income: $2751 Airbnb ROI: 4.58% Traditional ROI: 1.68%
34-E QUEEN ANNE Way CHESTER, MD Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water...	2 beds \| 3 baths \| 1,104 sq.ft.	$469,000	Airbnb cash on cash: 6% Traditional cash on cash: 4.56% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 6% Traditional ROI: 4.56%
312 BLENNY Lane CHESTER, MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 4 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 4.77% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 9.44% Traditional ROI: 4.77%
1870 HARBOR Drive CHESTER, MD OPEN House this Saturday Oct. 18 9:30-11:30am. Discover this charming 2-bedroom, 1-bath ho...	2 beds \| 1 baths \| 832 sq.ft.	$332,500	Airbnb cash on cash: 9.9% Traditional cash on cash: 4.14% Airbnb Rental Income: $4662 Traditional Rental Income: $1895 Airbnb ROI: 9.9% Traditional ROI: 4.14%
1401 CALVERT Road CHESTER, MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED...	2 beds \| 2 baths \| 1,444 sq.ft.	$469,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 3.44% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.53% Traditional ROI: 3.44%
141 SWITCHGRASS Way unit: 34 #34 CHESTER, MD ** NICE VIEWS OF THE CHESTER RIVER * LOWEST PRICED SEVERN MODEL** K Hovnanian'...	3 beds \| 3 baths \| 2,600 sq.ft.	$684,950	Airbnb cash on cash: 5.57% Traditional cash on cash: 2.44% Airbnb Rental Income: $6279 Traditional Rental Income: $3044 Airbnb ROI: 5.57% Traditional ROI: 2.44%
170 HARRIER WAY #34 CHESTER, MD Just reduced by $55,000 to $740,000 with immediate availability. Open House this Sunday 9/...	3 beds \| 3 baths \| N/A	$740,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.47% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.46% Traditional ROI: 2.47%
170 HARRIER Way unit: 11 #11 CHESTER, MD Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bed...	2 beds \| 3 baths \| 2,003 sq.ft.	$499,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.02% Airbnb Rental Income: $4662 Traditional Rental Income: $3099 Airbnb ROI: 5.3% Traditional ROI: 4.02%
190 HARRIER Way unit: 11 #11 CHESTER, MD Luxury 55+ Living at Four Seasons on Kent Island - Move-In Ready & Priced to Sell! Welcome...	2 beds \| 3 baths \| 2,003 sq.ft.	$540,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.17% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 4.83% Traditional ROI: 2.17%
1000 HERONS NEST Way unit: 32 #32 CHESTER, MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 5.26% Traditional ROI: 2.75%
154 HARRIER WAY CHESTER, MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* Price Reduced! Better th...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,545	Airbnb cash on cash: 3.75% Traditional cash on cash: 1.13% Airbnb Rental Income: $4662 Traditional Rental Income: $2132 Airbnb ROI: 3.75% Traditional ROI: 1.13%
47-D QUEEN ANNE Way CHESTER, MD New Price- Owner has relocated & says sell it! Enjoy resort style living every day in the ...	2 beds \| 3 baths \| 1,550 sq.ft.	$555,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 2.23% Airbnb Rental Income: $4662 Traditional Rental Income: $2059 Airbnb ROI: 5.39% Traditional ROI: 2.23%
2865 COX NECK RD CHESTER, MD An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront resi...	4 beds \| 4 baths \| N/A	$2,259,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -0.02% Airbnb Rental Income: $5802 Traditional Rental Income: $3777 Airbnb ROI: 0.39% Traditional ROI: -0.02%
1340 QUEEN ANNE Drive CHESTER, MD Discover the charm of this fully updated ranch in a serene, water-privileged community! Wi...	3 beds \| 2 baths \| 1,248 sq.ft.	$464,900	Airbnb cash on cash: 9.84% Traditional cash on cash: 3.75% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.84% Traditional ROI: 3.75%
114 ADDISON Court CHESTER, MD REDUCED "Shiny and new" might be the best way to describe the feel of this lovely 3 be...	3 beds \| 3 baths \| 2,342 sq.ft.	$549,900	Airbnb cash on cash: 7.82% Traditional cash on cash: 4.06% Airbnb Rental Income: $6279 Traditional Rental Income: $3111 Airbnb ROI: 7.82% Traditional ROI: 4.06%
132 CLAIBORNE Street CHESTER, MD Set on a rare, level, oversized lot in sought-after Gibson's Grant, this inviting front-po...	3 beds \| 4 baths \| 2,400 sq.ft.	$697,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 2.48% Airbnb Rental Income: $6279 Traditional Rental Income: $3180 Airbnb ROI: 5.35% Traditional ROI: 2.48%
1000 HERONS NEST Way unit: 22 #22 CHESTER, MD Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum C...	2 beds \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.47% Airbnb Rental Income: $4662 Traditional Rental Income: $3249 Airbnb ROI: 5.44% Traditional ROI: 4.47%
108 BODYS NECK Road CHESTER, MD Experience Autumn Serenity on the Waterfront Discover the perfect blend of coastal charm a...	3 beds \| 3 baths \| 1,791 sq.ft.	$499,900	Airbnb cash on cash: 8.88% Traditional cash on cash: 4.8% Airbnb Rental Income: $6279 Traditional Rental Income: $3136 Airbnb ROI: 8.88% Traditional ROI: 4.8%
807 AUCKLAND Way CHESTER, MD PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and ...	3 beds \| 4 baths \| 2,100 sq.ft.	$455,000	Airbnb cash on cash: 9.84% Traditional cash on cash: 6.18% Airbnb Rental Income: $6279 Traditional Rental Income: $3486 Airbnb ROI: 9.84% Traditional ROI: 6.18%
2723 COX NECK RD CHESTER, MD Rates are coming down, time to buy! - 100% Financing is Available!!! This newly construct...	4 beds \| 3 baths \| N/A	$447,500	Airbnb cash on cash: 9.56% Traditional cash on cash: 5.32% Airbnb Rental Income: $5802 Traditional Rental Income: $2870 Airbnb ROI: 9.56% Traditional ROI: 5.32%
224 BAYBERRY Drive CHESTER, MD Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, st...	2 beds \| 2 baths \| 1,913 sq.ft.	$599,900	Airbnb cash on cash: 4.64% Traditional cash on cash: 2.78% Airbnb Rental Income: $4662 Traditional Rental Income: $2652 Airbnb ROI: 4.64% Traditional ROI: 2.78%
315 CROSS CREEK CT CHESTER, MD You are going to love this bright and spacious home providing almost 2400 feet of living s...	4 beds \| 3 baths \| N/A	$569,900	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.16% Airbnb Rental Income: $5802 Traditional Rental Income: $3208 Airbnb ROI: 6.87% Traditional ROI: 4.16%
104 WOODS Road CHESTER, MD PERFECT MULTI GENERATIONAL HOME!!!! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PAC...	5 beds \| 4 baths \| 3,065 sq.ft.	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $4174 Airbnb ROI: N/A Traditional ROI: 3.85%
124 NAUSET Lane CHESTER, MD 10K price reduction!!! Better Than New - $175K+ in Upgrades and Lifestyle Ready Now Four S...	3 beds \| 3 baths \| 2,583 sq.ft.	$837,500	Airbnb cash on cash: 4.23% Traditional cash on cash: 1.78% Airbnb Rental Income: $6279 Traditional Rental Income: $3129 Airbnb ROI: 4.23% Traditional ROI: 1.78%
30-C QUEEN MARY Court CHESTER, MD Enjoy low-maintenance living in the desirable waterfront community of Queen's Landing, off...	2 beds \| 3 baths \| 1,440 sq.ft.	$339,900	Airbnb cash on cash: 9.59% Traditional cash on cash: 5.9% Airbnb Rental Income: $4662 Traditional Rental Income: $2518 Airbnb ROI: 9.59% Traditional ROI: 5.9%
306 SKIPPER Lane CHESTER, MD Move-in ready and full of upgrades, this thoughtfully designed home offers a bright, open ...	4 beds \| 3 baths \| 2,610 sq.ft.	$569,000	Airbnb cash on cash: 6.86% Traditional cash on cash: 4.29% Airbnb Rental Income: $5802 Traditional Rental Income: $3279 Airbnb ROI: 6.86% Traditional ROI: 4.29%
26-L QUEEN ANNE Way CHESTER, MD Charming Waterfront Condo with Resort-Style Living. Enjoy vacation vibes every day in this...	2 beds \| 2 baths \| 1,104 sq.ft.	$395,000	Airbnb cash on cash: 8.31% Traditional cash on cash: 4.38% Airbnb Rental Income: $4662 Traditional Rental Income: $2239 Airbnb ROI: 8.31% Traditional ROI: 4.38%
141 SWITCHGRASS Way unit: 23 #23 CHESTER, MD Professional pictures coming! Move-In Ready Luxury in Four Seasons on Kent Island - No Nee...	2 beds \| 3 baths \| 1,821 sq.ft.	$550,000	Airbnb cash on cash: 5.19% Traditional cash on cash: 3.97% Airbnb Rental Income: $4662 Traditional Rental Income: $3069 Airbnb ROI: 5.19% Traditional ROI: 3.97%

Real Estate investment in Chester, MD

There are 28 properties for sale in the city of Chester . The median list price in Chester is $499,000 and the average price per square foot is $271. In October 2025, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,870.

Chester, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 28 investment properties available for sale in Chester.

In 2025, the best neighborhood to buy investment property is CHESTER.

The ROI for Short-Term is higher than the Long-Term in Chester with average rental income of $5,802.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, MD

444 MACUM CREEK DR

CHESTER, MD

3 beds | 3 baths | N/A

$850,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $6279

Traditional Rental Income: $2751

Airbnb ROI: 4.58%

Traditional ROI: 1.68%

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,104 sq.ft.

$469,000

Airbnb cash on cash: 6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 6%

Traditional ROI: 4.56%

312 BLENNY Lane

CHESTER, MD

3 beds | 4 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 9.44%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 9.44%

Traditional ROI: 4.77%

1870 HARBOR Drive

CHESTER, MD

2 beds | 1 baths | 832 sq.ft.

$332,500

Airbnb cash on cash: 9.9%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $4662

Traditional Rental Income: $1895

Airbnb ROI: 9.9%

Traditional ROI: 4.14%

1401 CALVERT Road

CHESTER, MD

2 beds | 2 baths | 1,444 sq.ft.

$469,000

Airbnb cash on cash: 6.53%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.53%

Traditional ROI: 3.44%

141 SWITCHGRASS Way unit: 34 #34

CHESTER, MD

3 beds | 3 baths | 2,600 sq.ft.

$684,950

Airbnb cash on cash: 5.57%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $6279

Traditional Rental Income: $3044

Airbnb ROI: 5.57%

Traditional ROI: 2.44%

170 HARRIER WAY #34

CHESTER, MD

3 beds | 3 baths | N/A

$740,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.46%

Traditional ROI: 2.47%

170 HARRIER Way unit: 11 #11

CHESTER, MD

2 beds | 3 baths | 2,003 sq.ft.

$499,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $3099

Airbnb ROI: 5.3%