Airbnb Properties for Sale in Chester, MD

Looking for a vacation rental investment in Chester, MD with high ROI ?

Explore a range of newly added short-term rental homes in Chester, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Chester, MD

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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 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 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 PRICE IMPROVEMENT!! Welcome to Queens Landing, where resort-style living meets the comfort...	2 beds \| 3 baths \| 1,600 sq.ft.	$519,500	Airbnb cash on cash: 5.84% Traditional cash on cash: 4.54% Airbnb Rental Income: $4662 Traditional Rental Income: $3064 Airbnb ROI: 5.84% Traditional ROI: 4.54%
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%
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%
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%
141 SWITCHGRASS WAY #34 CHESTER, MD K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesape...	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 Open House this Sunday 9/14 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%
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.	$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%
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 Set on a rare, level, oversized lot in sought-after Gibsons Grant, this inviting front-por...	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.	$500,000	Airbnb cash on cash: 8.93% Traditional cash on cash: 3.68% Airbnb Rental Income: $6279 Traditional Rental Income: $2587 Airbnb ROI: 8.93% Traditional ROI: 3.68%
108 BODYS NECK ROAD CHESTER, MD Resort-Style Island Living with Unmatched Water Views! Discover the perfect blend of coas...	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%
2723 COX NECK RD CHESTER, MD Seller Offering Closing HELP - 100% Financing is Available!!! Rates are coming down, time...	4 beds \| 3 baths \| N/A	$469,500	Airbnb cash on cash: 9.07% Traditional cash on cash: 5.03% Airbnb Rental Income: $5802 Traditional Rental Income: $2870 Airbnb ROI: 9.07% Traditional ROI: 5.03%
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.	$610,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.71% Airbnb Rental Income: $4662 Traditional Rental Income: $2652 Airbnb ROI: 4.55% Traditional ROI: 2.71%
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%
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%
130 SUNRISE COURT CHESTER, MD Welcome to Four Seasons at Kent Island, where luxury and comfort meet coastal living. This...	3 beds \| 4 baths \| 3,494 sq.ft.	$949,900	Airbnb cash on cash: 3.54% Traditional cash on cash: 1.82% Airbnb Rental Income: $6279 Traditional Rental Income: $3520 Airbnb ROI: 3.54% Traditional ROI: 1.82%
635 DOMINION ROAD CHESTER, MD Beautiful waterfront property in Chester that is so unique in every way offering five leve...	3 beds \| 5 baths \| 2,818 sq.ft.	$925,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 3.66% Airbnb Rental Income: $6279 Traditional Rental Income: $4785 Airbnb ROI: 3.96% Traditional ROI: 3.66%
1839 HARBOR DRIVE CHESTER, MD Opportunity Knocks! Welcome to Harbor View on Kent Island - Just 7 minutes from the Bay Br...	4 beds \| 2 baths \| 2,035 sq.ft.	$415,000	Airbnb cash on cash: 9.97% Traditional cash on cash: 5.38% Airbnb Rental Income: $5802 Traditional Rental Income: $2862 Airbnb ROI: 9.97% Traditional ROI: 5.38%

Vacation Rentals in Chester

There are 30 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $499,950 and the average price per square foot is $246. The cash on cash return on vacation rentals in Chester is 6.00%. The average monthly short term rental income in Chester is $6,041.

Chester, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 30 Airbnb properties available for sale in Chester.

In 2025, the best neighborhood to buy short term rental property is CHESTER.

In September 2025, the average Airbnb occupancy rate in Chester is 38%.

Airbnb data on vacation rentals in Chester, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Chester, MD market insights, guest information and booking details, seasonality trends and historical Chester, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb 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.

$519,500

Airbnb cash on cash: 5.84%

Traditional cash on cash: 4.54%

Airbnb Rental Income: $4662

Traditional Rental Income: $3064

Airbnb ROI: 5.84%

Traditional ROI: 4.54%

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%

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%

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%

Traditional ROI: 6.02%

141 SWITCHGRASS WAY #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%