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Browse All Properties for Sale Near Rolling Knolls

86 Harbour Heights   Drive, Annapolis image
86 Harbour Heights Drive, Annapolis $410,000

Welcome to 86 Harbour Heights Dr, Annapolis! This bright, move-in ready, 3-bedroom, two-level condo, offers modern comfort and a peaceful wooded view. Freshly painted and...

  • 3 Beds
  • 3 Baths
  • MDAA2140860 MLS
1070 Foxcroft Run, Annapolis image
1070 Foxcroft Run, Annapolis $874,999

Tucked away on a quiet, wooded homesite, this beautiful 4BR/3.5BA single-family home offers the perfect combination of privacy, space, and natural beauty. Sunlight fills ...

  • 4 Beds
  • 4 Baths
  • MDAA2151908 MLS
1486 Downham Market, Annapolis image
1486 Downham Market, Annapolis $2,999,900

There are waterfront homes...and then there are waterfront estates that redefine luxury. Welcome to 1486 Downham Market, an extraordinary deep-water retreat in the prest...

  • 5 Beds
  • 5 Baths
  • MDAA2152082 MLS
130 Summer Village   Drive, Annapolis image
130 Summer Village Drive, Annapolis $600,000

Welcome to 130 Summer Village Drive, a beautifully maintained three-bedroom, two-and-one-half bath townhome located in the highly sought-after Riva Trace community of Ann...

  • 3 Beds
  • 4 Baths
  • MDAA2144804 MLS
355 Broadview   Lane, Annapolis image
355 Broadview Lane, Annapolis $999,999

A rare opportunity for the true history enthusiast, this stunning Keith Anthony reproduction of the iconic Noah Webster Home, originally built in New England circa 1758, ...

  • 4 Beds
  • 3 Baths
  • MDAA2148762 MLS
2568 Glen   Cove, Annapolis image
2568 Glen Cove, Annapolis $465,000

OPEN HOUSE SATURDAY JUNE 6th, 10-12!!! And, HOLY MOLY, look at that NEW, LOW PRICE. Buyer had a change of heart and this fabulous house is now back on the market and c...

  • 3 Beds
  • 3 Baths
  • MDAA2135788 MLS
903 Scupper Ct, Annapolis image
903 Scupper Ct, Annapolis $1,050,000

Luxury living awaits in the highly desirable Broad Creek Landing community! Offering nearly 5,800 finished square feet, this exceptional home combines timeless elegance, ...

  • 4 Beds
  • 5 Baths
  • MDAA2151448 MLS
607 Admiral Dr Unit #101, Annapolis image
607 Admiral Dr Unit #101, Annapolis $354,900

Completely renovated in 2024, this beautifully updated first-floor condominium in the desirable Admirals Reach community offers turnkey living in one of Annapolis' most c...

  • 2 Beds
  • 2 Baths
  • MDAA2151284 MLS
622 Wayward Dr, Annapolis image
622 Wayward Dr, Annapolis $625,000

Welcome home to this beautifully renovated split-level in a sought-after community! Featuring a bright, open floor plan with quality finishes throughout, this move-in rea...

  • 3 Beds
  • 2 Baths
  • MDAA2151236 MLS
2646 Quiet Water   Cove, Annapolis image
2646 Quiet Water Cove, Annapolis $370,000

MASSIVE PRICE DROP! PRICE NOW RELECTS NEED FOR UPDATES. THIS IS THEE LOWEST PRICED SEMI-DETACHED HOME WITH A GARAGE IN HERITAGE HARBOUR IN THE PAST YEAR! Popular, one le...

  • 3 Beds
  • 2 Baths
  • MDAA2139960 MLS
2159 Scotts Crossing Ct Unit #1, Annapolis image
2159 Scotts Crossing Ct Unit #1, Annapolis — Scott's Crossing Condo $320,000 ▼

Enjoy the perfect blend of comfort and convenience in this beautifully updated Annapolis home. This lower-level property offers unique privacy enabling you to walk straig...

  • 2 Beds
  • 2 Baths
  • MDAA2150886 MLS
  • Scott's Crossing Condo Bldg.
1689 Alice   Court, Annapolis image
1689 Alice Court, Annapolis $907,502

ALL OFFERS ARE DUE ON 6/1 BY 9PM. Welcome to 1689 Alice Court, a distinctive Mid-Century Modern Acorn Deck House tucked away on a wooded cul-de-sac in the community of Sa...

  • 3 Beds
  • 3 Baths
  • MDAA2144670 MLS
214 Wesley Brown   Lane, Annapolis image
214 Wesley Brown Lane, Annapolis $580,649

Welcome to this beautifully maintained, original-owner townhome built in 2018 and thoughtfully designed for modern living. Inside, functional design meets comfortable sty...

  • 3 Beds
  • 5 Baths
  • MDAA2146876 MLS
1718 Westminster   Way, Annapolis image
1718 Westminster Way, Annapolis $1,149,000

Nestled on a tranquil private drive in the highly sought-after water access neighborhood, The Downs on the Severn. This stunning stone-front Colonial offers the perfect b...

  • 4 Beds
  • 3 Baths
  • MDAA2143876 MLS
1717 Westminster   Way, Annapolis image
1717 Westminster Way, Annapolis $937,000

Nestled on 1.3 private wooded acres in the sought-after waterfront community of The Downs, this distinctive Deck House offers a rare opportunity to own a home designed to...

  • 3 Beds
  • 2 Baths
  • MDAA2145080 MLS
2977 Southaven   Drive, Annapolis image
2977 Southaven Drive, Annapolis $800,000

Authentic Log Cabin Living in One of Annapolis' Most Desirable Waterfront Communities - A Genuinely Rare Find. Real log construction you simply cannot find in the Annapol...

  • 5 Beds
  • 4 Baths
  • MDAA2144784 MLS
617 Wayward Dr, Annapolis image
617 Wayward Dr, Annapolis $599,000 ▼

Welcome to 617 Wayward Drive in the highly sought-after Rolling Knolls community of Annapolis. Situated on a spacious corner lot, this well-maintained home offers excepti...

  • 3 Beds
  • 2 Baths
  • MDAA2149288 MLS
527 Post Oak Rd, Annapolis image
527 Post Oak Rd, Annapolis $885,075

New listing in the sought-after, water-privileged community of Windfern Forest on Southaven Peninsula! Enjoy private access to fishing, boating, and kayaking on Broad Cre...

  • 4 Beds
  • 3 Baths
  • MDAA2145824 MLS
1602 Locksley Dr, Annapolis image
1602 Locksley Dr, Annapolis $1,175,000

This STUNNINGLY UPDATED brick colonial is set on almost an acre of land on a private cul-de-sac. Move-in ready with 4,000+ square feet on three levels... this sun-filled ...

  • 4 Beds
  • 4 Baths
  • MDAA2148532 MLS
2656 Shadow Cv, Annapolis image
2656 Shadow Cv, Annapolis $655,900

Wonderful opportunity to live in this NON AGE RESTRICTED section of Heritage Harbor and enjoy all the amenities Heritage Harbour has to offer. No initial recreational ...

  • 4 Beds
  • 3 Baths
  • MDAA2148230 MLS
553 Choptank Cove Ct, Annapolis image
553 Choptank Cove Ct, Annapolis $995,995

Tax records are incorrect the house has approximately 4000 square feet of living space. English Tudor featuring large slate patio, flagstone retaining wall and small cove...

  • 4 Beds
  • 4 Baths
  • MDAA2148078 MLS
2804 Pennypond  N Lane N, Annapolis image
2804 Pennypond N Lane N, Annapolis $705,000

Nestled within the sought-after Riva Trace community of Annapolis, this beautifully updated end-unit townhome is surrounded by mature trees, offering a private and tranqu...

  • 3 Beds
  • 4 Baths
  • MDAA2137370 MLS
617 Admiral   Drive Unit #403, Annapolis image
617 Admiral Drive Unit #403, Annapolis $401,108

Welcome to 617 Admiral Drive Unit 403 — a beautifully maintained and move-in ready condo located in the sought-after Admirals Reach community in Annapolis! This spacious ...

  • 2 Beds
  • 2 Baths
  • MDAA2140894 MLS
1074 Foxcroft   Run, Annapolis image
1074 Foxcroft Run, Annapolis $925,000

Nestled in the highly sought-after Carriage Hills community—where opportunities are few and far between—this stately detached Colonial offers exceptional space, privacy, ...

  • 4 Beds
  • 4 Baths
  • MDAA2140310 MLS
603 Admiral   Drive Unit #307, Annapolis image
603 Admiral Drive Unit #307, Annapolis — Admirals Reach $365,000

Coveted penthouse-level condo with a loft in the sought-after Admirals Reach!! Ideally located within the community as well, backing up to the woods for wonderful privac...

  • 2 Beds
  • 2 Baths
  • MDAA2144598 MLS
  • Admirals Reach Bldg.
322 Clopston   Hill, Annapolis image
322 Clopston Hill, Annapolis $1,500,000

Nestled on a hillside overlooking the Severn River, this property presents a rare opportunity in the highly coveted Sherwood Forest community. Set on a private lot, the h...

  • 4 Beds
  • 3 Baths
  • MDAA2142300 MLS
930 Astern   Way Unit #512, Annapolis image
930 Astern Way Unit #512, Annapolis — South River / Heritage Harbour $355,000

Resort-style living awaits in this 1,551 sq ft, 2-bedroom, 2-bath condominium located in the one-of-a-kind South River 55+ Condominium within the highly sought-after comm...

  • 2 Beds
  • 2 Baths
  • MDAA2132540 MLS
  • South River / Heritage Harbour Bldg.
1714 Broadlee Trl, Annapolis image
1714 Broadlee Trl, Annapolis $900,000

Brand new to the market in enchanting Epping Forest—one of Annapolis’ most sought-after gated, waterfront communities. Perched among the higher elevations, this home offe...

  • 3 Beds
  • 3 Baths
  • MDAA2139650 MLS
2762 Bon Haven   Lane, Annapolis image
2762 Bon Haven Lane, Annapolis $1,050,000

OPEN HOUSE, Saturday, April 4, 11am-1pm...HUGE price improvement! Welcome to this lovely, affordable waterfront ranch home and Chalet house w/wrap-around deck at water's...

  • 4 Beds
  • 2 Baths
  • MDAA2134402 MLS
1588 Eaton Way, Annapolis image
1588 Eaton Way, Annapolis $2,950,000 ▲

PRICE REDUCTION 245K! Welcome to 1588 Eaton Way, an extraordinary, waterfront Chesapeake Bay retreat offering the very best of Annapolis living. Located in the highly cov...

  • 6 Beds
  • 5 Baths
  • MDAA2140638 MLS
207 1st   Street, Annapolis image
207 1st Street, Annapolis $480,000

UPDATE: Open House this Saturday from 11-2pm. Seller is offering Seller help of $10,000 for any contract closed on or before 5/13. The update to open house would be sch...

  • 4 Beds
  • 2 Baths
  • MDAA2139948 MLS
2568 Forest   Knoll, Annapolis image
2568 Forest Knoll, Annapolis $725,000

COME SEE HOW BEAUTIFUL LIFE CAN BE! Welcome to easy, elegant living in one of Annapolis' most sought-after active adult communities! This highly desirable, one-level, de...

  • 3 Beds
  • 2 Baths
  • MDAA2137484 MLS
1866 Lynnfield   Drive, Annapolis image
1866 Lynnfield Drive, Annapolis $915,000

Welcome to 1866 Lynnfield Drive—a rare offering that seamlessly balances privacy, space, and convenience. Set on just under 6 serene, wooded acres, this meticulously upda...

  • 5 Beds
  • 3 Baths
  • MDAA2140326 MLS
2019 Valley   Road, Annapolis image
2019 Valley Road, Annapolis $470,000

Welcome to this charming all‑brick rancher in the highly desired Rolling Knolls community! This well‑maintained home offers a warm and inviting layout featuring hardwood ...

  • 2 Beds
  • 3 Baths
  • MDAA2130848 MLS
2321 Hickory   Road, Annapolis image
2321 Hickory Road, Annapolis $950,000

Custom Craftsman Home w/Private In-Law Suite! This custom-built three-level home (2017) in the water-access community of Severn Grove offers timeless architectural charac...

  • 3 Beds
  • 3 Baths
  • MDAA2137040 MLS
704 Roane Hollow   Lane, Annapolis image
704 Roane Hollow Lane, Annapolis $1,245,000

Welcome to 704 Roane Hollow Lane! A covered front porch leads into a beautifully appointed foyer, where custom built-in shelving introduces the home’s thoughtful design a...

  • 5 Beds
  • 4 Baths
  • MDAA2139694 MLS
2729 Poplar   Lane, Annapolis image
2729 Poplar Lane, Annapolis $774,900

Tucked away at the end of a quiet Cul-de-sac, this alpine contemporary home at 2729 Poplar Lane offers privacy, nature, and modern comfort in one of Annapolis’ most seren...

  • 4 Beds
  • 3 Baths
  • MDAA2137480 MLS
992 Riversedge   Circle, Annapolis image
992 Riversedge Circle, Annapolis $410,000

Experience easy living in Annapolis’ premier 55+ community at this charming 2-bedroom, 2-bath villa in Heritage Harbour, perfectly positioned just steps from the communit...

  • 2 Beds
  • 2 Baths
  • MDAA2134066 MLS
1753 Ebling   Trail, Annapolis image
1753 Ebling Trail, Annapolis $1,100,000

This exceptional residence is nestled in the exclusive, gated and water-privileged enclave of Epping Forest on the Severn River, set within a tranquil landscape of mature...

  • 3 Beds
  • 4 Baths
  • MDAA2134304 MLS
900 Coachway, Annapolis image
900 Coachway, Annapolis $910,000

MID-CENTURY MODERN HOME IN THE DOWNS ON THE SEVERN! ALL OFFERS DUE AT 8PM SUNDAY 1/25/26. NO Open House 1/25/26 - Cancelled. Tucked away in an upscale water-access neigh...

  • 3 Beds
  • 3 Baths
  • MDAA2134002 MLS
2175 Glencrest   Circle, Annapolis image
2175 Glencrest Circle, Annapolis $250,000

A rare find. One of the few lots in the community of Rolling Knolls. Public water is available in the community. A septic system would need to be installed. Perc has ...

  • MDAA2114718 MLS
1974 Scotts Crossing   Way Unit #102, Annapolis image
1974 Scotts Crossing Way Unit #102, Annapolis — Scott's Crossing Condo $368,000

>> IMMEDIATE AVAILABILITY << Welcome To 1974 Scotts Crossing #102, A Spacious Annapolis Condo Offering The Perfect Blend Of Comfort And Convenience (Unit Located on Entry...

  • 3 Beds
  • 2 Baths
  • MDAA2129946 MLS
  • Scott's Crossing Condo Bldg.
856 St Edmonds Pl, Annapolis image
856 St Edmonds Pl, Annapolis $2,795,000

**Open House - Sunday June 7th, 11-1 pm** Welcome to 856 St Edmonds Place! Newly positioned $700k below recent appraisal! Have it all with stunning views from nearly eve...

  • 5 Beds
  • 5 Baths
  • MDAA2136468 MLS
847 Woodmont   Road, Annapolis image
847 Woodmont Road, Annapolis $689,000

Welcome Home to Comfort, Convenience & Community Living This well-maintained 2-bedroom, 2-bathroom single-family home offers 1,709 finished square feet of easy, single-s...

  • 2 Beds
  • 2 Baths
  • MDAA2134362 MLS
108 Harbour Heights   Drive, Annapolis image
108 Harbour Heights Drive, Annapolis — Sea Breeze $390,000

Welcome home to the highly sought-after Seabreeze community! This end-unit condo, ideally located in the heart of Annapolis, is sure to impress. Rarely available, this up...

  • 2 Beds
  • 3 Baths
  • MDAA2132432 MLS
  • Sea Breeze Bldg.
1800 Severn Grove   Road, Annapolis image
1800 Severn Grove Road, Annapolis $960,000

Nestled in the serene Dellwood community, this contemporary gem offers an exclusive lifestyle defined by luxury and comfort. Perfect location leaves you minutes from down...

  • 3 Beds
  • 3 Baths
  • MDAA2131896 MLS
940 Astern   Way Unit #604, Annapolis image
940 Astern Way Unit #604, Annapolis — Heritage Harbour $400,000

Sought after top floor (6th) unit with elevator access, you'll love the views from your sunroom and bedrooms! Great room/living room with gas fueled fireplace, spacious d...

  • 2 Beds
  • 2 Baths
  • MDAA2127410 MLS
  • Heritage Harbour Bldg.
39 Oak   Court, Annapolis image
39 Oak Court, Annapolis $440,000

COMMERCIAL AND/OR RESIDENTIAL USE!!Discover the perfect blend of comfort and functionality with this well-maintained property! Offering flexible zoning for residential or...

  • 4 Beds
  • 1 Baths
  • MDAA2129984 MLS
1909 Marconi   Circle, Annapolis image
1909 Marconi Circle, Annapolis $524,900

One-level living with thoughtful design! Experience resort-style living at Heritage Harbour in Annapolis. This spacious and inviting townhome is designed for effortless l...

  • 2 Beds
  • 2 Baths
  • MDAA2129820 MLS
1007 Boom   Court, Annapolis image
1007 Boom Court, Annapolis $497,000

If you are looking to get into the popular, 55+ community of Heritage Harbour in Annapolis, this is a wonderful opportunity! This large, 3 level townhouse won't force you...

  • 3 Beds
  • 4 Baths
  • MDAA2126268 MLS

Annapolis Real Estate & Homes Near Rolling Knolls

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