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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
54 QUEEN CAROLINE COURT CHESTER, MD Price Improvement...End Unit in Sought-After Queens Landing A Waterfront Lifestyle Awaits!...	2 beds \| 3 baths \| 1,280 sq.ft.	$415,000	Airbnb cash on cash: 7.85% Traditional cash on cash: 4.52% Airbnb Rental Income: $4662 Traditional Rental Income: $2400 Airbnb ROI: 7.85% Traditional ROI: 4.52%
444 MACUM CREEK DR CHESTER, MD Welcome to 444 Macum Creek DriveEnjoy the Water Views from the Main Level Porch, Upper...	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 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%
49 QUEEN GUINEVERE WAY CHESTER, MD Welcome to Queens Landing, where resort-style living meets the comfort of home. This beaut...	2 beds \| 3 baths \| 1,600 sq.ft.	$529,250	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.44% Airbnb Rental Income: $4662 Traditional Rental Income: $3064 Airbnb ROI: 5.71% Traditional ROI: 4.44%
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%
203 BARREN RIDGE ROAD CHESTER, MD Priced to Sell- VERY motivated sellers!!! Nestled in the tranquil community of Chester, Ma...	3 beds \| 2 baths \| 2,072 sq.ft.	$475,000	Airbnb cash on cash: 9.36% Traditional cash on cash: 3.97% Airbnb Rental Income: $6279 Traditional Rental Income: $2647 Airbnb ROI: 9.36% Traditional ROI: 3.97%
1401 CALVERT ROAD CHESTER, MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - All on one le...	2 beds \| 2 baths \| 1,444 sq.ft.	$485,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 3.29% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.29% Traditional ROI: 3.29%
208 RINGNECK CT CHESTER, MD 208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom G...	2 beds \| 3 baths \| N/A	$339,900	Airbnb cash on cash: 9.08% Traditional cash on cash: 6.02% Airbnb Rental Income: $4662 Traditional Rental Income: $2721 Airbnb ROI: 9.08% Traditional ROI: 6.02%
170 HARRIER WAY #34 CHESTER, MD Open House this Sunday 8/24 from 12-2. New improved price of $795,000 and immediate occupa...	3 beds \| 3 baths \| N/A	$795,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 2.23% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.02% Traditional ROI: 2.23%
170 HARRIER WAY #11 CHESTER, MD *Redfin powered by Rocket Mortgage Preferred Pricing* Enjoy with a 1% lower interest r...	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 #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 #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* The Donegal model is a s...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,500	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 QUEEN ANNE WAY CHESTER, MD Enjoy resort style living every day in the gorgeous waterfront condo. 42' boat slip w/ wat...	2 beds \| 3 baths \| 1,440 sq.ft.	$598,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 2% Airbnb Rental Income: $4662 Traditional Rental Income: $2059 Airbnb ROI: 4.93% Traditional ROI: 2%
15 QUEEN ANNE WAY #E CHESTER, MD The BIGGEST price drop yet!! Wake up to shimmering Chester River views and let every day f...	2 beds \| 3 baths \| 1,680 sq.ft.	$499,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 4.57% Airbnb Rental Income: $4662 Traditional Rental Income: $2997 Airbnb ROI: 6.07% Traditional ROI: 4.57%
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.	$469,900	Airbnb cash on cash: 9.72% Traditional cash on cash: 3.7% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.72% Traditional ROI: 3.7%
170 HARRIER WAY #33 CHESTER, MD This Chester model has scenic views of the river, beautiful sunrises, and an incredible di...	2 beds \| 3 baths \| 1,900 sq.ft.	$499,950	Airbnb cash on cash: 5.25% Traditional cash on cash: 3.45% Airbnb Rental Income: $4662 Traditional Rental Income: $2853 Airbnb ROI: 5.25% Traditional ROI: 3.45%
114 ADDISON COURT CHESTER, MD REDUCED "Shiny and new" might be the best way to describe the feel of this lovely 3 ...	3 beds \| 3 baths \| 2,342 sq.ft.	$575,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 3.84% Airbnb Rental Income: $6279 Traditional Rental Income: $3111 Airbnb ROI: 7.44% Traditional ROI: 3.84%
132 CLAIBORNE STREET CHESTER, MD Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Communi...	3 beds \| 4 baths \| 2,400 sq.ft.	$725,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 2.35% Airbnb Rental Income: $6279 Traditional Rental Income: $3180 Airbnb ROI: 5.1% Traditional ROI: 2.35%
1000 HERONS NEST WAY #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%
307 SKIPPER LANE CHESTER, MD Welcome to Your Refreshing New Home with First-Floor Living! This beautifully updated resi...	3 beds \| 2 baths \| 2,180 sq.ft.	$525,000	Airbnb cash on cash: 8.46% Traditional cash on cash: 3.46% Airbnb Rental Income: $6279 Traditional Rental Income: $2587 Airbnb ROI: 8.46% Traditional ROI: 3.46%
205 ANCHOR LANE CHESTER, MD Price Improvement! Need more room? This expansive home is ready to welcome your whole fami...	5 beds \| 3 baths \| 3,500 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $4019 Airbnb ROI: N/A Traditional ROI: 5.94%
35-F QUEEN ANNE WAY CHESTER, MD Welcome to 35F Queen Anne Way in Queens Landing! This lakefront updated home offers 2 bedr...	2 beds \| 3 baths \| N/A	$354,900	Airbnb cash on cash: 9.1% Traditional cash on cash: 6% Airbnb Rental Income: $4662 Traditional Rental Income: $2662 Airbnb ROI: 9.1% Traditional ROI: 6%
108 BODYS NECK ROAD CHESTER, MD Coming Soon in Bayside on Kent Island Resort-Style Island Living with Unmatched Water View...	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 an...	3 beds \| 4 baths \| 2,100 sq.ft.	$482,090	Airbnb cash on cash: 9.24% Traditional cash on cash: 5.78% Airbnb Rental Income: $6279 Traditional Rental Income: $3486 Airbnb ROI: 9.24% Traditional ROI: 5.78%
1872 HARBOR DRIVE CHESTER, MD Harbor View Community \| Corner Lot \| Renovated Rancher with Room to Grow Welcome to 1872 H...	3 beds \| 2 baths \| 1,486 sq.ft.	$495,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 3.9% Airbnb Rental Income: $6279 Traditional Rental Income: $2614 Airbnb ROI: 9.14% Traditional ROI: 3.9%
2723 COX NECK RD CHESTER, MD Harbor View - 100% Financing is Available!!!This newly constructed home features 4 bedroom...	4 beds \| 3 baths \| N/A	$473,900	Airbnb cash on cash: 8.98% Traditional cash on cash: 4.97% Airbnb Rental Income: $5802 Traditional Rental Income: $2870 Airbnb ROI: 8.98% Traditional ROI: 4.97%
224 BAYBERRY DRIVE CHESTER, MD Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, s...	2 beds \| 2 baths \| 1,913 sq.ft.	$624,900	Airbnb cash on cash: 4.42% Traditional cash on cash: 2.63% Airbnb Rental Income: $4662 Traditional Rental Income: $2652 Airbnb ROI: 4.42% Traditional ROI: 2.63%
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	$585,000	Airbnb cash on cash: 6.66% Traditional cash on cash: 4.03% Airbnb Rental Income: $5802 Traditional Rental Income: $3208 Airbnb ROI: 6.66% Traditional ROI: 4.03%
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.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $4174 Airbnb ROI: N/A Traditional ROI: 3.82%
124 NAUSET LANE CHESTER, MD NEW UPDATED PHOTOS!! Take another look! Turnkey Luxury with Over $175K in Upgrades Four Se...	3 beds \| 3 baths \| 2,583 sq.ft.	$847,500	Airbnb cash on cash: 4.17% Traditional cash on cash: 1.74% Airbnb Rental Income: $6279 Traditional Rental Income: $3129 Airbnb ROI: 4.17% Traditional ROI: 1.74%

Real Estate investment in Chester, MD

There are 31 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 $268. In September 2025, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,853.

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

There are 31 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

54 QUEEN CAROLINE COURT

CHESTER, MD

2 beds | 3 baths | 1,280 sq.ft.

$415,000

Airbnb cash on cash: 7.85%

Traditional cash on cash: 4.52%

Airbnb Rental Income: $4662

Traditional Rental Income: $2400

Airbnb ROI: 7.85%

Traditional ROI: 4.52%

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 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%

49 QUEEN GUINEVERE WAY

CHESTER, MD

2 beds | 3 baths | 1,600 sq.ft.

$529,250

Airbnb cash on cash: 5.71%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $4662

Traditional Rental Income: $3064

Airbnb ROI: 5.71%

Traditional ROI: 4.44%

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%

203 BARREN RIDGE ROAD

CHESTER, MD

3 beds | 2 baths | 2,072 sq.ft.

$475,000

Airbnb cash on cash: 9.36%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $6279

Traditional Rental Income: $2647

Airbnb ROI: 9.36%

Traditional ROI: 3.97%

1401 CALVERT ROAD

CHESTER, MD

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

$485,000

Airbnb cash on cash: 6.29%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.29%

Traditional ROI: 3.29%

208 RINGNECK CT

CHESTER, MD

2 beds | 3 baths | N/A

$339,900

Airbnb cash on cash: 9.08%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $2721

Airbnb ROI: 9.08%