Real Estate Investment Properties for Sale in Annapolis, MD

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

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

Windcrest Investment Property for Sale in Annapolis, MD

Search for Windcrest Investment Property for Sale in Annapolis, Maryland. Browse all of Mashvisor’s Windcrest Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 310 Windcrest Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 Park Pl #431 Annapolis, MD PLEASE TAKE A LOOK AT EVERY CONDO IN THE BUILDING SOLD IN THE LAST YEAR AND THEN MAKE AN A...	1 beds \| 1 baths \| 839 sq.ft.	$484,950	Airbnb cash on cash: -1.17% Traditional cash on cash: 0.39% Airbnb Rental Income: $1744 Traditional Rental Income: $1969 Airbnb ROI: -1.17% Traditional ROI: 0.39%
5 Park Pl #314 Annapolis, MD Live the Annapolis Lifestyle at the Residence at Park Place. Chic 2 bedroom, 2 bath cond...	2 beds \| 2 baths \| 1,056 sq.ft.	$564,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 0.03% Airbnb Rental Income: $2338 Traditional Rental Income: $2401 Airbnb ROI: -1.19% Traditional ROI: 0.03%
1915 TOWNE CENTRE Boulevard unit: 807 Annapolis, MD FRESH INTERIOR PAINT THROUGHOUT - A PRISTINE, NEUTRAL PALETTE READY FOR YOUR STYLE!! SELLE...	2 beds \| 2 baths \| 1,246 sq.ft.	$545,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.85% Airbnb Rental Income: $2338 Traditional Rental Income: $2694 Airbnb ROI: -0.98% Traditional ROI: 0.85%
1090 BROADVIEW DR Annapolis, MD Welcome home to this cozy four bedroom, two full bath split foyer in sought after Cape St ...	4 beds \| 2 baths \| N/A	$550,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 3.36% Airbnb Rental Income: $3104 Traditional Rental Income: $2771 Airbnb ROI: 2.63% Traditional ROI: 3.36%
1915 Towne Centre Blvd #513 Annapolis, MD Maintenance free living in this 2 bedroom and 2 full bath Condo. Easy access to downtown...	2 beds \| 2 baths \| 1,485 sq.ft.	$549,000	Airbnb cash on cash: -1.39% Traditional cash on cash: -0.59% Airbnb Rental Income: $2338 Traditional Rental Income: $2171 Airbnb ROI: -1.39% Traditional ROI: -0.59%
190 Duke Of Gloucester St Annapolis, MD Historic charm and everyday comfort come together beautifully in this spacious Victorian i...	4 beds \| 3 baths \| 3,393 sq.ft.	$1,500,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.88% Airbnb Rental Income: $3104 Traditional Rental Income: $5080 Airbnb ROI: -0.04% Traditional ROI: 1.88%
2129 Beach Village Ct #101 Annapolis, MD OFFER DEADLINE FOR MONDAY, 3/30 AT NOON. Please submit all highest and best offers by then...	2 beds \| 2 baths \| 1,250 sq.ft.	$699,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 1.48% Airbnb Rental Income: $2338 Traditional Rental Income: $2370 Airbnb ROI: 0.54% Traditional ROI: 1.48%
1 Shipwright Hbr Annapolis, MD Reduced & priced below 3/10/2018 appraisal! One of the finest homes on Spa Creek located o...	3 beds \| 3 baths \| 3,108 sq.ft.	$5,898,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.85% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: -1.01% Traditional ROI: -0.85%
819 Janice Dr Annapolis, MD Beautiful Colonial-Under Construction*9 ft ceilings & Hardwood flrs- Main level 2 Story ...	4 beds \| 3 baths \| 4,043 sq.ft.	$1,195,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.28% Airbnb Rental Income: $3104 Traditional Rental Income: $2722 Airbnb ROI: -0.01% Traditional ROI: 0.28%
2654 Ogleton Rd Annapolis, MD OPEN HOUSE this SUNDAY 7/17 from 1 to 3 PM! A great opportunity to move right in to Annap...	4 beds \| 3 baths \| 3,220 sq.ft.	$899,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.43% Airbnb Rental Income: $3104 Traditional Rental Income: $3450 Airbnb ROI: 1.17% Traditional ROI: 2.43%
52 Primrose Hill Ln Annapolis, MD Modern accents meet classic Georgian design in a downtown Annapolis private enclave of cus...	5 beds \| 4 baths \| 3,978 sq.ft.	$949,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.2% Airbnb Rental Income: $3871 Traditional Rental Income: $5022 Airbnb ROI: 0.95% Traditional ROI: 3.2%
3280 Arundel On The Bay Rd Annapolis, MD Significant Price Improvement!! A rare opportunity! Priced to sell, won't last long. Welco...	5 beds \| 4 baths \| 3,144 sq.ft.	$850,000	Airbnb cash on cash: 1.88% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 1.88% Traditional ROI: N/A
113 Bay Dr Annapolis, MD Stunning Chesapeake Bay views in desirable Bay Ridge neighborhood. Water view home, open f...	3 beds \| 2 baths \| 2,286 sq.ft.	$3,195,000	Airbnb cash on cash: -0.76% Traditional cash on cash: -0.65% Airbnb Rental Income: $2680 Traditional Rental Income: $2358 Airbnb ROI: -0.76% Traditional ROI: -0.65%
1519 Winchester Rd Annapolis, MD Original owners lovingly cared for this water access privileged home in Winchester on the ...	5 beds \| 3 baths \| 2,375 sq.ft.	$849,000	Airbnb cash on cash: 2.13% Traditional cash on cash: N/A Airbnb Rental Income: $3871 Traditional Rental Income: $0 Airbnb ROI: 2.13% Traditional ROI: N/A
1109 Boucher Ave Annapolis, MD Greet neighbors from the front porch or entertain them on the private, fenced rear patio. ...	4 beds \| 4 baths \| 3,779 sq.ft.	$1,545,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.44% Airbnb Rental Income: $3104 Traditional Rental Income: $4864 Airbnb ROI: -0.28% Traditional ROI: 1.44%
2013 Warners Ter S #242 Annapolis, MD Wonderful 2 BR 2 BA Bath Condo in the Rivergate Community. Gorgeous open kitchen with gran...	2 beds \| 2 baths \| 1,062 sq.ft.	$335,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 3.83% Airbnb Rental Income: $2338 Traditional Rental Income: $2171 Airbnb ROI: 2.52% Traditional ROI: 3.83%
905 Scupper Ct Annapolis, MD ...	6 beds \| 4 baths \| 6,238 sq.ft.	$1,100,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 2.61% Airbnb Rental Income: $3871 Traditional Rental Income: $4696 Airbnb ROI: 0.99% Traditional ROI: 2.61%
1576 Saint Margarets Rd Annapolis, MD Welcome to 1576 St. Margaret's Road, a meticulously rebuilt rancher set on a peaceful 1.89...	4 beds \| 2 baths \| 1,792 sq.ft.	$690,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.44% Airbnb Rental Income: $3104 Traditional Rental Income: $2950 Airbnb ROI: 1.58% Traditional ROI: 2.44%
930 Astern Way #304 Annapolis, MD Welcome to 930 Astern Way - a spacious and beautifully updated 1-bedroom, 1 1/2-bath condo...	1 beds \| 1 baths \| 1,152 sq.ft.	$275,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 2.13% Airbnb Rental Income: $1744 Traditional Rental Income: $2070 Airbnb ROI: -0.97% Traditional ROI: 2.13%
1014 Wells Ave Annapolis, MD Welcome Home to Eastport. Walk to the Eastport Shopping center for breakfast or to downtow...	4 beds \| 1 baths \| 880 sq.ft.	$430,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 3.24% Airbnb Rental Income: $3104 Traditional Rental Income: $2363 Airbnb ROI: 3.33% Traditional ROI: 3.24%
1915 Towne Centre Blvd #403 Annapolis, MD Much desired "DAVENPORT" corner unit on the 4th floor with walls of windows bringing in t...	2 beds \| 2 baths \| 1,602 sq.ft.	$695,000	Airbnb cash on cash: -1.51% Traditional cash on cash: -0.88% Airbnb Rental Income: $2338 Traditional Rental Income: $2171 Airbnb ROI: -1.51% Traditional ROI: -0.88%
1703 NIMITZ Drive Annapolis, MD Rarely available colonial in the extremely sought-after, water-privileged community of Adm...	3 beds \| 3 baths \| 2,629 sq.ft.	$795,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 1.77% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: 0.56% Traditional ROI: 1.77%
9 Shipwright St Annapolis, MD Waterfront on Spa Creek in Downtown Annapolis!!! Property features open floor plan, walls ...	3 beds \| 2 baths \| 2,621 sq.ft.	$3,495,000	Airbnb cash on cash: -1.15% Traditional cash on cash: -0.89% Airbnb Rental Income: $2680 Traditional Rental Income: $2887 Airbnb ROI: -1.15% Traditional ROI: -0.89%
310 Giddings Ave Annapolis, MD Welcome to 310 Giddings Avenue, a stunningly re-imagined Craftsman-style home on an expans...	3 beds \| 3 baths \| 3,218 sq.ft.	$1,750,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.17% Airbnb Rental Income: $2680 Traditional Rental Income: $2942 Airbnb ROI: -0.39% Traditional ROI: 0.17%
141 West St #201 Annapolis, MD Welcome to 141 West a boutique building styled after one of Manhattan's most iconic neighb...	1 beds \| 1 baths \| 612 sq.ft.	$482,500	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.49% Airbnb Rental Income: $1744 Traditional Rental Income: $2190 Airbnb ROI: -0.56% Traditional ROI: 1.49%
1553 Star Pine Dr Annapolis, MD UPDATE: NEW ROOF RECENTLY INSTALLED. Discover your new home in this well-maintained duplex...	2 beds \| 1 baths \| 1,060 sq.ft.	$339,990	Airbnb cash on cash: 3.2% Traditional cash on cash: 4.47% Airbnb Rental Income: $2338 Traditional Rental Income: $2165 Airbnb ROI: 3.2% Traditional ROI: 4.47%

Your search for investment property begins and ends here

Windcrest Investment Property for Sale in Annapolis, MD

5 Park Pl #431

Annapolis, MD

1 beds | 1 baths | 839 sq.ft.

$484,950

Airbnb cash on cash: -1.17%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $1744

Traditional Rental Income: $1969

Airbnb ROI: -1.17%

Traditional ROI: 0.39%

5 Park Pl #314

Annapolis, MD

2 beds | 2 baths | 1,056 sq.ft.

$564,000

Airbnb cash on cash: -1.19%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $2338

Traditional Rental Income: $2401

Airbnb ROI: -1.19%

Traditional ROI: 0.03%

1915 TOWNE CENTRE Boulevard unit: 807

Annapolis, MD

2 beds | 2 baths | 1,246 sq.ft.

$545,000

Airbnb cash on cash: -0.98%

Traditional cash on cash: 0.85%

Airbnb Rental Income: $2338

Traditional Rental Income: $2694

Airbnb ROI: -0.98%

Traditional ROI: 0.85%

1090 BROADVIEW DR

Annapolis, MD

4 beds | 2 baths | N/A

$550,000

Airbnb cash on cash: 2.63%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $3104

Traditional Rental Income: $2771

Airbnb ROI: 2.63%

Traditional ROI: 3.36%

1915 Towne Centre Blvd #513

Annapolis, MD

2 beds | 2 baths | 1,485 sq.ft.

$549,000

Airbnb cash on cash: -1.39%

Traditional cash on cash: -0.59%

Airbnb Rental Income: $2338

Traditional Rental Income: $2171

Airbnb ROI: -1.39%

Traditional ROI: -0.59%

190 Duke Of Gloucester St

Annapolis, MD

4 beds | 3 baths | 3,393 sq.ft.

$1,500,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $3104

Traditional Rental Income: $5080

Airbnb ROI: -0.04%

Traditional ROI: 1.88%

2129 Beach Village Ct #101

Annapolis, MD

2 beds | 2 baths | 1,250 sq.ft.

$699,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $2338

Traditional Rental Income: $2370

Airbnb ROI: 0.54%

Traditional ROI: 1.48%

1 Shipwright Hbr

Annapolis, MD

3 beds | 3 baths | 3,108 sq.ft.

$5,898,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $2680

Traditional Rental Income: $2942

Airbnb ROI: -1.01%