Holly Oaks Real Estate, Homes, Condos for Sale in Caroline, VA

3 Beds ⋅ 4 Baths ⋅ MDHR2059848 MLS

**SIGN & SETTLE: Own a New Townhome Near Riverside with No Money Due at Closing** 100% financing available through participating lender plus up to $15,000 toward closing costs for qualified buyers. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with 2- 1st floor bedrooms (optional) and addtl laundry- Bring the Family! This 4 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price.

756 Bur Oak Ct, Aberdeen

$418,152

3 Beds ⋅ 4 Baths ⋅ MDHR2059846 MLS

**SIGN & SETTLE: Own a New Townhome Near Riverside with No Money Due at Closing** 100% financing available through participating lender plus up to $15,000 toward closing costs for qualified buyers. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price.

740 Bur Oak Ct, Aberdeen

$359,918

3 Beds ⋅ 4 Baths ⋅ MDHR2059792 MLS

Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. **The price IS the incentive on this particular property, no additional incentives will be honored on this property.**

742 Bur Oak Ct, Aberdeen

$415,310

4 Beds ⋅ 4 Baths ⋅ MDHR2059608 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with 2- 1st floor bedrooms (optional) and addtl laundry- Bring the Family! This 4 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

760 Bur Oak Ct, Aberdeen

$414,935

4 Beds ⋅ 4 Baths ⋅ MDHR2059606 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with 2- 1st floor bedrooms (optional) and addtl laundry- Bring the Family! This 4 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

754 Bur Oak Ct, Aberdeen

$402,517

4 Beds ⋅ 4 Baths ⋅ MDHR2059600 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with 2- 1st floor bedrooms (optional) and addtl laundry- Bring the Family! This 4 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

758 Bur Oak Ct, Aberdeen

$401,589

3 Beds ⋅ 4 Baths ⋅ MDHR2059598 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

718 Bur Oak Ct, Aberdeen

$399,862

3 Beds ⋅ 4 Baths ⋅ MDHR2059596 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

716 Bur Oak Ct, Aberdeen

$397,864

3 Beds ⋅ 4 Baths ⋅ MDHR2059594 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

712 Bur Oak Ct, Aberdeen

$395,801

3 Beds ⋅ 4 Baths ⋅ MDHR2059592 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

720 Bur Oak Ct, Aberdeen

$410,000

3 Beds ⋅ 3 Baths ⋅ VACV2010882 MLS

Welcome to 14377 Farmer Drive, a beautifully maintained three-level Colonial situated on 1.07 private wooded acres in the Holly Oaks community of Woodford, Virginia. Offering 3 bedrooms, 2 full bathrooms, 1 half bathroom, approximately 2,496 finished square feet, a partially finished walkout basement, 2-car garage, and a brand-new HVAC system installed in 2026, this home delivers the space, privacy, and flexibility today’s buyers are searching for. Step inside to a bright and inviting main level designed for comfortable everyday living and entertaining. The kitchen features beautiful granite countertops and opens to a light-filled morning room/eat-in area, creating the perfect spot for casual meals and morning coffee. A formal dining room offers space for holidays and gatherings, while the spacious living room provides plenty of room to relax and entertain. Patio doors lead directly from the kitchen to a large rear deck overlooking the expansive backyard and mature trees. With more than an acre to enjoy, the outdoor space offers a peaceful, private setting with room for entertaining, gardening, recreation, or simply unwinding and enjoying the surrounding nature. The partially finished walkout basement adds valuable living space and versatility. Create a recreation room, home office, fitness area, media room, or hobby space to fit your lifestyle. The unfinished portion provides additional storage and features a dedicated workshop area—ideal for tools, projects, and DIY enthusiasts. Direct backyard access adds even more functionality to this level. Upstairs, you’ll find three generously sized bedrooms and two full bathrooms, including a spacious primary suite offering a comfortable retreat at the end of the day. Additional highlights include a 2-car garage, approximately 2,496 finished square feet across three levels, and the peace of mind of a new HVAC system installed in 2026. Tucked away in Holly Oaks in Woodford, VA, this home offers a hard-to-find combination of over an acre of land, a private wooded setting, generous indoor and outdoor living space, a walkout basement, workshop, two-car garage, and thoughtful updates. 14377 Farmer Dr offers room to spread out, space to make your own, and a peaceful place to call home.

14377 Farmer Dr, Woodford

$418,152

3 Beds ⋅ 4 Baths ⋅ MDHR2057712 MLS

*SIGN & SETTLE: 100% financing plus up to $15,000 toward closing for qualified buyers! Offer expires 10/31/2026. Welcome Home in the Final Phase of Holly Oaks! These Townhomes, owned as Condominium style, offer you low/no maintenance living with a 1st floor bedroom- Bring the Family! This 3 bed 3.5 bath offers ample room to spread out while having a nice open flow. On the main living level, a gorgeous kitchen greets you with an oversized island, staggered upgraded cabinets, quartz countertops, stainless appliances. All the way up, you'll enjoy the final 2 spacious bedrooms- 1 being the owners suite with tray ceilings and an impressive ensuite with dual vanity, quartz countertops and a glass enclosed ceramic tile shower. This home is perfectly positioned only minutes from the APG gates as well as minutes off I95 for the commuters. This is an awesome opportunity worth checking out! Schedule your private tour today! Photos shown are of a model home or similar floor plan and are for illustrative purposes only. Actual home, finishes, features, and selections may vary. Photos may include optional upgrades not included in the purchase price. *Incentive available on select homes and requires use of builder's preferred lender and title company. Offer subject to change or withdrawal without notice. Restrictions apply. Contact Builder for full terms.

722 Bur Oak Ct, Aberdeen

$395,390

4 Beds ⋅ 4 Baths ⋅ MDHR2045622 MLS

New Construction Alert…Pre-model pricing available now. Welcome to Holly Oaks, a new townhome community in Aberdeen, MD. This newly constructed Craftsman-style townhome features first-floor bedrooms and a second washer/dryer location, making it ideal for multi-generational living. These homes offer 3–4 bedrooms and 3.5 bathrooms. Home features include a primary bedroom with tray ceilings, a walk-in closet, and gorgeous glass shower doors to complement the double sink vanity with a quartz countertop, offering a luxurious en-suite bath. The kitchen is amazing with 42” staggered upgraded cabinets with five color choices, large island, quartz countertops, and stainless-steel appliances. Many more features were included for you to see—an open floor plan with a spacious feel. Enjoy the convenience of APG and I-95 for commuting to New Jersey, Pennsylvania, Delaware, and Baltimore. Outdoor living includes Pickleball Courts, RV Parking, a Dog Park, and community sidewalks that stretch for miles. Enjoy lower tax payments being outside of Aberdeen City Limits. This home not only blends comfort, convenience, and style, but it dares you to Live Different. Contact Joy for directions and access

703 Bur Oak Court, Unit 123, Aberdeen

$402,000

3 Beds ⋅ 2 Baths ⋅ MDSM2025880 MLS

Back on market at a new price — the buyer’s loss is your gain! This is one of only five single-family homes in Leonardtown currently listed under $500,000 — and it’s move-in ready with major updates already done. Renovated just 3 years ago, this charming 3-bedroom, 2-bath rambler sits on a spacious half-acre lot with a walk-out basement and no HOA, giving you flexibility to bring your vision to life — whether that’s a detached garage, outdoor entertaining space, or even a future pool. The home features modern upgrades throughout, including a newer roof (2022 roof certification available), windows, siding, gutters, furnace, LVP flooring, and recessed lighting. The bright and open kitchen is perfect for entertaining with quartz countertops, tile backsplash, a center island, and a gas range — ideal for home chefs. The circular driveway provides plenty of parking, and the carport adds covered convenience. Downstairs, the walk-out basement adds bonus space for a rec room, home gym, or additional living space. The large backyard is ready for gatherings, pets, or simply relaxing in the peaceful setting. Schedule your showing today — this one won’t last long (again)!

23730 Hicks Dr, Leonardtown

$372,000

3 Beds ⋅ 2 Baths ⋅ MDSM2015712 MLS

Enjoy privacy and tranquility in a country setting with NO HOA! Fascinating renovated rambler with exquisite finishes meticulously designed to cater to the most discerning tastes. This home boasts a host of impressive enhancements that redefine country living! Experience the perfect blend of comfort and convenience of an upgraded kitchen with elegant two tone cabinetry, granite countertops and stainless steel appliances. Deck off of kitchen to enjoy your morning coffee, watch the sunrise or plenty of room for a gathering! Bathrooms have been transformed with dazzling tiled updates that are one of a kind! Recess lighting and light fixtures add a touch of charm creating an inviting and elegant ambiance. Entire home has been freshly painted along with brand new flooring providing durability for many years ahead! No need to worry about parking when you have a oversized driveway and large detached garage! This beauty also features a new deep well, new roof and new Hvac and furnace! Schedule your appointment right away while inventory is low because this gem will be gone in no time!

23745 Hicks Dr, Leonardtown

$360,000

3 Beds ⋅ 2 Baths ⋅ VACV2006032 MLS

Beautiful 3 Bed 2 Bath Single Family Home. New Carpet, Fresh Paint, Hardwood Floors, Upgraded Counter Tops, Primary Bath, Walk in Closet on a Large, Level One Acre Lot. Must See!

14445 Farmer Dr, Woodford

$406,000

3 Beds ⋅ 2 Baths ⋅ MDSM2023732 MLS

Welcome to 23745 Hicks Drive, a thoughtfully updated rambler on over half an acre in the quiet Holly Oaks neighborhood of Leonardtown. With a spacious detached garage, a finished basement, and recent renovations throughout, this home offers comfort, functionality, and a great location—all with no HOA. Inside, you’ll find a bright and open layout featuring wide plank flooring, recessed lighting, and an upgraded kitchen with granite countertops, stainless steel appliances, and stylish two tone cabinetry. Just off the kitchen, a back deck overlooks the large, fully fenced yard—perfect for relaxing, entertaining, or letting pets roam freely. The main level offers three bedrooms and two full bathrooms, both updated with bold, modern tile and clean finishes. Downstairs, the walk-out basement adds nearly 800 square feet of flexible space for a rec room, home gym, playroom, or storage. One of the standout features of this property is the oversized detached garage with room for four vehicles, tools, or workshop space. Additional recent upgrades include a new roof, new HVAC system, and a new deep well. Located just minutes from downtown Leonardtown, this home is close to local shops, restaurants, waterfront parks, and community events. Known for its small-town charm and strong sense of community, Leonardtown offers a relaxed lifestyle with easy access to everything Southern Maryland has to offer. This property also qualifies for special financing through the Maryland Mortgage Program. For more information, contact Natalie Miller with the Gary Pierpont & Team at First Home Mortgage.

23745 Hicks Dr, Leonardtown

$625,000

4 Beds ⋅ 3 Baths ⋅ CVR-2420969 MLS

This gorgeous 4 bedroom, 3 full bath home w/ a detached in-law suite sits on an incredible 3.23 acre lot! Upgrades abound in the completely updated/renovated main home: it offers gorgeous walnut flooring & plantation shutters throughout. The downstairs has great living spaces to include: an exquisite dining room, a large living room, & even a private office! The stunning kitchen boasts quartz countertops, custom cabinetry, stainless steel appliances, & an oversized pantry. The kitchen opens to a great room w/ gas fireplace. Two sunrooms are located off of the first floor. Upstairs are four spacious bedrooms to include an amazing primary suite that boasts a relaxing spa/steam shower & a large walk in closet. There is a 1269 square foot unfinished basement. The in-law suite is located over the detached garage & it has a living room, full bath, and bedroom. It can be accessed via the main home or via private drive off of Chriscoe Lane. Need storage space? This home has it all - it offers a 2 car attached garage, a huge detached garage with HVAC and electric, plus a massive carport!

9300 Marlfield Road, Gloucester

$275,000

3 Beds ⋅ 2 Baths ⋅ CVR-2329330 MLS

This 3 level Cape Cod style home is on .7 of an acre & was COMPLETELY renovated in June, July and August of 2023. Improvements: new architectural charcoal color shingle roofing, new siding, fresh paint, new light fixtures, new kitchen appliances, 5 new windows, new 50 gallon electric hot water heater, added GFI outlets in kitchen, new bathroom vanity, new HVAC (installed a new Bosch 16.5 seer 3.0 to r-410 variable speed outdoor heat pump, matched indoor air handler and 10KW back up heater & new touchscreen thermostat, added new return and plenum was installed w/ a new condensate pump condensate tubing also installed as well as easy float switch. And installed a heavy duty plastic pad at outdoor condenser with 6 inch snow legs, surge protector was added to outdoor electrical disconnect - 5 year warranty on parts/one year warranty on labor), basement waterproofing w/ sump pump, septic repair. New steps off the family room to a brick side yard patio and enjoy the mature landscaping with hydrangeas, magnolias, and a variety of perennials. 2 brs on the top level and one br on the main level. The basement has a door to the outside; there are stairs that take you up to side yard. NO HOA!

16223 Melville Lane, Bowling Green

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