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Browse All Properties for Sale Near Rolling Knolls

584 Wayward Ct, Annapolis image
584 Wayward Ct, Annapolis $544,000

Nestled in the serene community of Rolling Knolls, this exquisite split foyer home offers a harmonious blend of modern luxury and timeless comfort. With a major renovatio...

  • 4 Beds
  • 2 Baths
  • MDAA2159396 MLS
2801 Autumn Chase Cir, Annapolis image
2801 Autumn Chase Cir, Annapolis $875,000 ▼

Welcome to 2801 Autumn Chase Circle, Beautifully appointed Annapolis home offering generous living space and timeless style, with an exceptional location ,just a short d...

  • 4 Beds
  • 4 Baths
  • MDAA2155840 MLS
1739 Vineyard Trl, Annapolis image
1739 Vineyard Trl, Annapolis $1,650,000

Waterfront living with a private pier in Annapolis at an exceptional price in gated Epping Forest! Mid-century modern waterfront sanctuary rises above Saltworks Creek on ...

  • 4 Beds
  • 3 Baths
  • MDAA2157874 MLS
2161 Scotts Crossing Ct Unit 302, Annapolis image
2161 Scotts Crossing Ct Unit 302, Annapolis — Scott's Crossing Condo $355,000 ▼

Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s Crossing Condominiums, offering over 1,320 square feet and a prime locati...

  • 3 Beds
  • 2 Baths
  • MDAA2155556 MLS
  • Scott's Crossing Condo Bldg.
2175 Glencrest Cir, Annapolis image
2175 Glencrest Cir, Annapolis $925,000 ▼

Newly and beautifully built in 2026, this stone-accented detached Calvert Model by Dorsey Family Homes offers 3,081 finished square feet and is ideally positioned on a qu...

  • 5 Beds
  • 4 Baths
  • MDAA2156130 MLS
640 Sean Dr, Annapolis image
640 Sean Dr, Annapolis $945,000 ▼

$100,000 Under 2026 Appraised Value!! Welcome to 640 Sean Drive, an impressive brick Colonial set on 1.67 acres in Annapolis, where generous living spaces, distinctive ar...

  • 4 Beds
  • 4 Baths
  • MDAA2155314 MLS
912 Plattner Ct, Annapolis image
912 Plattner Ct, Annapolis $1,200,000 ▼

Welcome to 912 Plattner Court in Annapolis’s Overlook at Broad Creek neighborhood, an elegant stone-front Colonial offering 5 bedrooms, 4.5 baths, and approximately 4,400...

  • 5 Beds
  • 5 Baths
  • MDAA2155286 MLS
2915 South Ct, Annapolis image
2915 South Ct, Annapolis $1,195,000 ▼

Experience the Annapolis waterfront lifestyle from this charming A-frame cottage, where days on the water begin just steps from your door. Designed for relaxed coastal li...

  • 2 Beds
  • 2 Baths
  • MDAA2155152 MLS
206 Bowen Ct, Annapolis image
206 Bowen Ct, Annapolis $950,000 ▼

Don’t miss this opportunity to own a stunning Colonial in the highly sought-after Bowen Manor community of Annapolis. Offering over 4,500 square feet of beautifully appoi...

  • 5 Beds
  • 4 Baths
  • MDAA2154248 MLS
1070 Foxcroft Run, Annapolis image
1070 Foxcroft Run, Annapolis $819,999 ▼

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

*SELLER FINANCING AVAILABLE*. There are waterfront homes...and then there are waterfront estates that redefine luxury. Welcome to 1486 Downham Market, an extraordinary d...

  • 5 Beds
  • 5 Baths
  • MDAA2152082 MLS
903 Scupper Ct, Annapolis image
903 Scupper Ct, Annapolis $1,030,000

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 $345,000

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 $575,000 ▼

New opportunity to own a beautifully renovated split-level home in a sought-after Annapolis community! Move-in ready and thoughtfully updated, this 3-bedroom home offers ...

  • 3 Beds
  • 2 Baths
  • MDAA2151236 MLS
2159 Scotts Crossing Ct Unit 1, Annapolis image
2159 Scotts Crossing Ct Unit 1, Annapolis — Scott's Crossing Condo $330,000 ▲

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 strai...

  • 2 Beds
  • 2 Baths
  • MDAA2150886 MLS
  • Scott's Crossing Condo Bldg.
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
355 Broadview Ln, Annapolis image
355 Broadview Ln, 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
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 $660,000

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 $955,000

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
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
852 Woodmont Rd, Annapolis image
852 Woodmont Rd, Annapolis $703,000

BEAUTIFULLY RENOVATED ONE-LEVEL RANCHER IN HERITAGE HARBOUR Welcome to this beautifully renovated one-level rancher in the sought-after 55+ community of Heritage Harbour...

  • 3 Beds
  • 2 Baths
  • MDAA2146498 MLS
214 Wesley Brown Ln, Annapolis image
214 Wesley Brown Ln, 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
1689 Alice Ct, Annapolis image
1689 Alice Ct, 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
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
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
1588 Eaton Way, Annapolis image
1588 Eaton Way, Annapolis $2,700,000

Welcome to 1588 Eaton Way, an extraordinary, waterfront Chesapeake Bay retreat offering the very best of Annapolis living. Located in the highly coveted Downs on the Seve...

  • 6 Beds
  • 5 Baths
  • MDAA2140638 MLS
130 Summer Village Dr, Annapolis image
130 Summer Village Dr, 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
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
2977 Southaven Dr, Annapolis image
2977 Southaven Dr, 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
603 Admiral Dr Unit 307, Annapolis image
603 Admiral Dr 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.
617 Admiral Dr Unit 403, Annapolis image
617 Admiral Dr 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
86 Harbour Heights Dr, Annapolis image
86 Harbour Heights Dr, 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
322 Clopston Hl, Annapolis image
322 Clopston Hl, 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
property 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
2006 Monticello Dr, Annapolis image
2006 Monticello Dr, Annapolis $990,000

Welcome to this stunning 5/6 bedroom, 5-full-bath brick front Colonial in the highly sought-after Monticello neighborhood. Perfectly situated on a fenced corner lot, this...

  • 5 Beds
  • 5 Baths
  • MDAA2110378 MLS
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1815 Labrott Ln, Annapolis $645,000

Welcome to your slice of paradise! This delightful ranch-style home is a true gem, tucked away in a tranquil cul-de-sac. Boasting three spacious bedrooms, two and a half ...

  • 3 Beds
  • 3 Baths
  • MDAA2081546 MLS
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650 Sean Dr, Annapolis $1,275,000

This home has it all! Generously renovated and impeccably maintained home nestled on a large private 1.65 acre lot in Annapolis. A truly unique property - just minutes fr...

  • 5 Beds
  • 5 Baths
  • MDAA2080878 MLS
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2933 Winters Chase Way, Annapolis $555,550

ANNAPOLIS – Located near all the major commuting areas is the lovely community of Riva Trace situated on the banks of Gingerville Creek flowing into the South River. Ste...

  • 3 Beds
  • 3 Baths
  • MDAA2080036 MLS
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1679 Brickhouse Bar Ct, Annapolis $821,000

**OFFER DEADLINE has been set for Monday, March 25th at 9pm. Please present your highest and best offer by that time. Offers will be evaluated on Tuesday and we will ge...

  • 4 Beds
  • 3 Baths
  • MDAA2079844 MLS
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949 Shadewater Way, Annapolis $640,000

ALL OFFERS DUE BY MONDAY, 4/8/2024, AT 4;00 PM. Welcome to this stunning and well maintained 3 BR, 2 BA home located on a private cul-de-sac in the highly sought after ...

  • 3 Beds
  • 2 Baths
  • MDAA2079566 MLS
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867 Clubhouse Village Vw, Annapolis $680,000

MULTIPLE OFFERS RECEIVED. OFFERS BEING PRESENTED TO SELLER AT 5PM MONDAY, MARCH 11TH. SHOWINGS BY APPOINTMENT ONLY; CALL LISTING AGENT FOR MORE INFORMATION.

  • 3 Beds
  • 2 Baths
  • MDAA2079320 MLS
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603 Admiral Dr Unit 7, Annapolis $346,000

Welcome to this meticulously maintained and upgraded 2 bedroom, 2 bathroom condo nestled in the heart of Annapolis. Effortlessly blending comfort and style, this ground-l...

  • 2 Beds
  • 2 Baths
  • MDAA2078638 MLS
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463 Hoenereng Trl, Annapolis $1,812,000

Dreaming of living on the water and enjoying the Annapolitan lifestyle, in one of the sought after communities in Annapolis?? Now is your chance to escape to your very ow...

  • 4 Beds
  • 3 Baths
  • MDAA2077966 MLS
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833 Coachway, Annapolis $2,100,000

Exquisite Contemporary Colonial home in the highly coveted Downs on the Severn community! This stunning residence is situated on a premium 1 acre lot with captivating wat...

  • 4 Beds
  • 5 Baths
  • MDAA2077844 MLS
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940 Astern Way Unit 506, Annapolis — The Reserve @ Heritage Harbour $525,000

Step into the welcoming embrace of 940 Astern Way #506, a delightful residence situated in the vibrant 55+ amenity-rich community at The Reserve at Heritage Harbour in An...

  • 2 Beds
  • 2 Baths
  • MDAA2075524 MLS
  • The Reserve @ Heritage Harbour Bldg.
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2703 Yeomans Lantern Ct, Annapolis $414,075

We've had a facelift! If you haven't made my acquaintance I encourage you to come on over! If you have taken a tour I welcome you to come see my new look! Welcome to 2703...

  • 2 Beds
  • 3 Baths
  • MDAA2075152 MLS
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946 Riversedge Cir, Annapolis $420,000

This warm Heritage Harbour 2-bedroom, 2-bathroom END UNIT villa has ADDED WINDOWS, a unique OPEN FLOORPLAN, a lovely KITCHEN ISLAND and HARDWOOD floors. No townhouse is ...

  • 2 Beds
  • 2 Baths
  • MDAA2075114 MLS
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320 Severn Rd, Annapolis $2,550,000

Magnificent views of the Severn River from this stunning home in sought-after Epping Forest Community. Enjoy sunrises and sunsets from every room in this open floor pla...

  • 3 Beds
  • 4 Baths
  • MDAA2075040 MLS
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1982 Valley Rd, Annapolis $625,000

This charming home is deceptively spacious and boasts an abundance of character. It showcases an Owner's/inlaw suite and a remodeled kitchen featuring sleek stainless st...

  • 5 Beds
  • 3 Baths
  • MDAA2074998 MLS

Annapolis Real Estate & Homes Near Rolling Knolls

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