Princess Anne Homes under $500,000

Princess Anne Homes under $500,000

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Newest Princess Anne Homes under $500,000

29564 Deal Island Rd W, Princess Anne
$79,990
3 Beds ⋅ 2 Baths
Investor opportunity with plenty of potential! This 3-bedroom, 2-bath home sits on a full acre and features separate front and rear entrances, offering the ability to potentially lock off the property into a 2-bedroom, 1-bath side and a separate 1-bedroom, 1-bath side. With an estimated ARV of approximately $215,000 and projected rents of $1,300/month for the 2-bedroom side and $1,000/month for the 1-bedroom side, the property offers potential combined rental income of $2,300 per month, putting it well above the 1% rule for investors. Whether you're looking for a strong rental opportunity, house-hack potential, or a property with room to add value, this one is worth a look.

29564 Deal Island Rd W, Princess Anne

Listing courtesy of EXP Realty, LLC. Contact:

11856 Drexwood Dr, Princess Anne
$310,000
4 Beds ⋅ 2 Baths
Room to gather, space to unwind, and a wooded backdrop that brings a little more calm to your day. Built in 2021, this four-bedroom, two-bath home in Princess Anne’s Somerset Landing offers single-level living with an open layout that keeps everyone connected. Natural light fills the spacious great room, where evenings on the couch flow easily into dinner with friends or conversation around the kitchen island. White cabinetry, stainless-steel appliances, a pantry, and an island with breakfast-bar seating make the kitchen as practical for busy mornings as it is for weekend entertaining. Set apart from the other bedrooms, the primary suite offers a quiet retreat with a walk-in closet and private bath with a step-in shower. Two bedrooms share a full bath near the front of the home, while the fourth bedroom gives you flexibility for guests, a home office, or a hobby room. A covered front entry, laundry room near the attached two-car garage, and additional garage storage add everyday convenience. Outside, the generous homesite backs to trees, with partial privacy fencing and room to garden, play, or simply enjoy some fresh air. Located just minutes from Route 13 and historic downtown Princess Anne, this home offers an easy drive to Salisbury or Chincoteague, VA, whether you’re heading to work, enjoying dinner out, or spending a day by the water. Closer to home, Somerset County’s boat ramps, fishing and crabbing spots, parks, and wildlife areas offer plenty of ways to enjoy the relaxed pace of life on the Lower Eastern Shore.

11856 Drexwood Dr, Princess Anne

Listing courtesy of Real Broker, LLC - Salisbury. Contact:

30445 Oak St, Princess Anne
$300,000
Turnkey income-producing duplex, walkable to Downtown Princess Anne! This well-maintained property features two units. One is 3-bedroom, 2-bath unit, and the other is a 2-bedroom, 1-bath unit generating $2,320/month in rental income with the potential to easily generate $3,000/ month based on recent market rents. Current Cap Rate 5.77% with Market Potential of 8.08%. Both units are occupied with stable tenants, including one since 2025 and the second since 2020, providing immediate cash flow from day one. A new HVAC system was installed in Unit B in 2025, and in 2019 for Unit A. Unit A has been recently updated. Separately metered electric keeps operating costs low, and the strong local rental market continues to support long-term demand. Conveniently located near UMES, healthcare, county employers, and the US Route 13 corridor, this property attracts workforce and university-affiliated tenants alike. Whether you're adding to your portfolio or purchasing your first multifamily investment, this duplex offers a proven rental history, strong cash flow, and excellent long-term investment potential. **Full Capital Expenditures Report Available Upon Request**

30445 Oak St, Princess Anne

Listing courtesy of Northrop Realty. Contact:

30445 Oak St, Princess Anne
$300,000
5 Beds ⋅ 3 Baths
Turnkey income-producing duplex in the heart of Princess Anne! This well-maintained 5 Bed/ 3 Bath Home, which features two units. One is 3-bedroom, 2-bath unit, and the other is a 2-bedroom, 1-bath unit generating $2,320/month in rental income with the potential to easily generate $3,000/ month based on recent market rents. Current Cap Rate 5.77% with Market Potential of 8.08%. Both units are occupied with stable tenants, including one since 2025 and the second since 2020, providing immediate cash flow from day one. A new HVAC system was installed in Unit B in 2025, and in 2019 for Unit A. Unit A has been recently updated. Separately metered electric keeps operating costs low, and the strong local rental market continues to support long-term demand. Conveniently located near UMES, healthcare, county employers, and the US Route 13 corridor, this property attracts workforce and university-affiliated tenants alike. Whether you're adding to your portfolio or purchasing your first multifamily investment, this duplex offers a proven rental history, strong cash flow, and excellent long-term investment potential. **Full Capital Expenditures Report Available Upon Request**

30445 Oak St, Princess Anne

Listing courtesy of Northrop Realty. Contact:

10908 Brownstone Rd, Princess Anne
$149,000
3 Beds ⋅ 2 Baths
Cash buyers only. Heavy renovation opportunity in Princess Anne, just outside the UMES market with convenient access to Route 13 and Salisbury. Property is being sold strictly as-is and will require a full rehab. Brick construction with detached garage, new shed, and newer hot water heater. Ideal for an experienced investor looking for a rehab or flip opportunity.

10908 Brownstone Rd, Princess Anne

Listing courtesy of Sell Your Home Services. Contact:

11502 Beckford Ave, Princess Anne
$210,000
4 Beds ⋅ 2 Baths
House is currently used as a duplex, with an upstairs unit and downstairs unit. Recent electrical and plumbing updates made. Kitchen, two bedrooms, one bath, and laundry room downstairs. Upstairs are two bedrooms, one bath, and kitchen with access to a large attic. Close to downtown Princess Anne and UMES with off street parking behind the house. Each unit has been renting for $1,150/mo. Easy enough to convert back to a single family home.

11502 Beckford Ave, Princess Anne

Listing courtesy of The Land Group. Contact:

11502 Beckford Ave, Princess Anne
$210,000
Duplex located close to Downtown Princess Anne and UMES. Recent electrical and plumbing updates made. Duplex features a two bedroom one bath apartment downstairs. Upstairs is a two bedroom one bath with access to a large attic. Property has a shared laundry room downstairs and off street parking behind the house. Each unit has been renting for $1,150/mo.

11502 Beckford Ave, Princess Anne

Listing courtesy of The Land Group. Contact:

31901 Mitchell Rd, Princess Anne
$275,000
3 Beds ⋅ 2 Baths
Set on 2.03 acres in a peaceful rural setting, 31901 Mitchell Rd offers a blend of recent updates, functional space, and room to enjoy the property. The home features updated LVP flooring throughout and a newly renovated primary bathroom, adding a fresh, modern feel to the interior. The property also includes a large newly constructed pole building with electric, providing versatile additional space for a workshop, home gym, studio, hobby area, storage, or other recreational and personal-use needs. The acreage extends to state-owned land that is protected from future development, providing a lasting natural backdrop and added privacy to the property. With its combination of updated interior features, substantial acreage, additional outbuilding space, and protected land along the property, this is a unique opportunity to enjoy the flexibility and character of a rural Eastern Shore property. Property is being sold "As-Is"

31901 Mitchell Rd, Princess Anne

Listing courtesy of Worthington Realty Group, LLC. Contact:

31008 Peggy Neck Rd, Princess Anne
$295,000
3 Beds ⋅ 1 Baths
Welcome home!! Come check out what this property has to offer! This property was fully updated in 2024 with new plumbing, roof, siding, and many upgrades all throughout! With over 5 acres of land the possibilities are endless with this property. With the peacefulness of nature all around you and the privacy, it truly could be your own oasis! Property comes with guest home that includes a living area, kitchenette, along with washer and dryer and bathroom! It also comes with a shed for additional storage. This property is in excellent condition and it is waiting to be yours! Come check out what 31008 Peggy Neck Rd has to offer and schedule your tour today!

31008 Peggy Neck Rd, Princess Anne

Listing courtesy of Wilson Realty. Contact:

30566 Skipjack Cir, Princess Anne
$249,900
3 Beds ⋅ 2 Baths
This 3-bedroom, 2-bath rancher offers a bright, open floor plan with beautiful LVP flooring throughout and plenty of natural light. The layout is functional and inviting, with an easy flow between the main living spaces. The spacious primary suite features a private en suite bath with dual vanities, while two additional bedrooms and a separate laundry area complete the functional single-level layout. Located on Skipjack Road in Manokin Village, this home gives you the benefits of new construction in a growing community while still being close to everything Princess Anne has to offer. One of the biggest perks? Public water and sewer with NO city taxes — a rare combination that adds even more value. The home is nearing completion and will be move-in ready in no time! Schedule your private tour today!

30566 Skipjack Cir, Princess Anne

Listing courtesy of Keller Williams Realty Delmarva. Contact:

11552 Beckford Ave, Princess Anne
$299,000
4 Beds ⋅ 3 Baths
FULLY RENOVATED & COMING SOON! This gorgeous 2,335 sq. ft. Victorian has been completely reimagined from the beams up, blending timeless character with the comfort of essentially new construction. Offering 4 spacious bedrooms and 3 full baths, the home features a thoughtful floor plan with a main-level primary suite, upstairs primary suite, multiple walk in closets, and laundry rooms on both levels. Nearly everything is new—including the roof, windows, HVAC system, LVP flooring, new carpet in bedrooms, freshly painted siding, elegant gray shutters, fully renovated kitchen with stainless steel appliances, and completely new and updated bathrooms. Beautiful bay windows and a charming wraparound front porch preserve the home’s Victorian appeal, while a new Trex deck overlooks the huge backyard on over a quarter acre. A wide gravel driveway provides abundant parking. Conveniently located near downtown so that you can enjoy easy access to local restaurants, coffee shops, shopping, UMES, and more!

11552 Beckford Ave, Princess Anne

Listing courtesy of Northrop Realty. Contact:

10590 Rosewood Ct, Princess Anne
$449,900
4 Beds ⋅ 3 Baths
Like-new 4-bedroom, 2.5-bath home in the lovely Rose Hill neighborhood. Completed in 2023, this home has been meticulously maintained and still feels brand new. The main level features a spacious primary suite, offering a private retreat with plenty of room to relax. The open and inviting layout provides comfortable living spaces throughout, with modern finishes and thoughtful details that make this home truly move-in ready.

10590 Rosewood Ct, Princess Anne

Listing courtesy of The Land Group. Contact:

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