St. Michaels Middle/High School, MD homes for sale & real estate

95 homes

Sort:

Recommended

ABOUT THIS HOME
St. Michaels Middle/High School, MD Homes for Sale
Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and dining room combination with a fireplace , open floorplan and sliding doors opening to the screened porch. There is a one car garage and additional parking space. Martingham offers a waterfront park for residents only , plenty of walking and biking opportunities. Just minutes to historic St M

$385,000

2 beds3 baths1,800 sq ft

9545 Quail Holw #205, Saint Michaels, MD 21663

$226 HOA • Garage • Built 1973

(410) 745-0283

ABOUT THIS HOME
St. Michaels Middle/High School, MD Homes for Sale
Your Eastern Shore paradise awaits! This awesomely updated, meticulously maintained, classic colonial-style home is like a breath of fresh air. Located on a full 2 acre parcel, in the heart of the sought after Deep Harbour Farm community, custom features include a lovely private backyard oasis, designed around an 18’x32’ inground salt-water pool, and surrounded by all new, high-quality fencing, mature landscaping and hardscaped patio with built in fire/grilling pit. Built in 2005, this home boasts an open floor plan and flow that welcomes you the moment you step inside. Rich hardwood floors add an elegant touch to the interior living spaces, which have all been freshly painted t

$765,000

3 beds2.5 baths2,240 sq ft

6660 Reeses Pride Rd, Sherwood, MD 21665

High-quality fencing • Hardscaped patio • Mature landscaping

(410) 714-9166

ABOUT THIS HOME
St. Michaels Middle/High School, MD Homes for Sale
Special Year-End Incentive! Seller is offering a Buyer Credit at settlement toward closing costs or repairs with a ratified contract by 12/31/25. This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shore’s most desirable communities. Welcome to Martingham—home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from the heart of historic St. Michaels. Enjoy world-class dining, boutique shopping, and waterfront charm, all right at your fingertips. Set on 1.13 open acres with a tree-lined backdrop for privacy, this 3BR/2.5BA Colonial offers the space, setting, and lifestyle buyers are searching for. Inside,

$630,000

3 beds2.5 baths2,496 sq ft

24749 Swan Rd, St Michaels, MD 21663

Sizeable deck • Private balcony • Tree lined backyard

(410) 745-0415

ABOUT THIS HOME
St. Michaels Middle/High School, MD Homes for Sale
Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this property deserves. The grounds are improved by a pool, tennis court, covered boat house with deep water, formal gardens, magnificent mature trees and a detached 1,670 sq ft guest house. This is a one-of-a-kind property and a true Talbot County piece of History.

$8,400,000

7 beds7 baths8,001 sq ft

26546 Presquile Dr, Easton, MD 21601

Covered boat house • Tennis court • Two year renovation

(410) 822-6272

ABOUT THIS HOME
St. Michaels Middle/High School, MD Homes for Sale
Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/ dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

$1,250,000

3 beds3 baths3,232 sq ft

6050 Sunset Ln, Tilghman, MD 21671

0.46 acre lot • 2 garage spots • Built 1950

(410) 829-3603

Property at 5440 Ferry Neck Rd, Royal Oak, MD 21662, 5 beds, 5.5 baths

$3,000,000

5 beds5.5 baths4,602 sq ft

5440 Ferry Neck Rd, Royal Oak, MD 21662

(410) 673-3344

Property at 8620 Bozman Neavitt, Saint Michaels, MD 21663, 6 beds, 9 baths

$8,495,000

6 beds9 baths17,402 sq ft

8620 Bozman Neavitt, Saint Michaels, MD 21663

(202) 944-5000

Property at 22349 Cooper Ln, Wittman, MD 21676, 2 beds, 1 bath

$245,000

2 beds1 bath1,270 sq ft

22349 Cooper Ln, Wittman, MD 21676

(410) 822-6665

Property at 6670 Tilghman Island Rd, Sherwood, MD 21665, 3 beds, 3 baths

$1,299,000

3 beds3 baths3,853 sq ft

6670 Tilghman Island Rd, Sherwood, MD 21665

(410) 745-2596

Property at 807 Radcliff Ave, St Michaels, MD 21663, 3 beds, 2.5 baths

$859,900

3 beds2.5 baths2,027 sq ft

807 Radcliff Ave, St Michaels, MD 21663

(301) 945-9010

Property at 7849 Ward Brothers Cir, Easton, MD 21601, 3 beds, 2.5 baths

$489,990

3 beds2.5 baths1,978 sq ft

7849 Ward Brothers Cir, Easton, MD 21601

(240) 375-5074

Property at 7090 Cooper Point Rd, Bozman, MD 21612, 5 beds, 5 baths

$7,500,000

5 beds5 baths10,000 sq ft

7090 Cooper Point Rd, Bozman, MD 21612

(410) 673-3344

Property at 21907 Sherwood Landing Rd, Sherwood, MD 21665, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,336 sq ft

21907 Sherwood Landing Rd, Sherwood, MD 21665

(410) 745-0415

Property at 5520 Leeward Ln, Tilghman, MD 21671, 5 beds, 2.5 baths

$1,200,000

5 beds2.5 baths4,214 sq ft

5520 Leeward Ln, Tilghman, MD 21671

(302) 360-0300

Property at 22381 Cooper Ln, Wittman, MD 21676, 2 beds, 1 bath

$164,900

2 beds1 bath1,540 sq ft

22381 Cooper Ln, Wittman, MD 21676

(410) 823-0033

Property at 6403 Bozman Neavitt Rd, Neavitt, MD 21652, 3 beds, 2 baths

$469,500

3 beds2 baths1,834 sq ft

6403 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 745-2596

Property at 7851 Ward Brothers Cir, Easton, MD 21601, 3 beds, 2 baths

$549,990

3 beds2 baths1,939 sq ft

7851 Ward Brothers Cir, Easton, MD 21601

(240) 375-5074

Property at 6343 Bozman Neavitt Rd, Neavitt, MD 21652, 2 beds, 1 bath

$495,500

2 beds1 bath960 sq ft

6343 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 822-6665

Property at 7651 Main St, Sherwood, MD 21665, 2 beds, 2 baths

$425,000

2 beds2 baths1,776 sq ft

7651 Main St, Sherwood, MD 21665

(410) 745-0283

Property at 22860 Middle Point Rd, Neavitt, MD 21652, 3 beds, 2 baths

$1,150,000

3 beds2 baths2,642 sq ft

22860 Middle Point Rd, Neavitt, MD 21652

(410) 745-0415

Property at 5654 Trafalgar Cir, Tilghman, MD 21671, 3 beds, 2 baths

$499,888

3 beds2 baths1,710 sq ft

5654 Trafalgar Cir, Tilghman, MD 21671

(410) 745-0415

Property at 8062 N Fork Blvd, Easton, MD 21601, 3 beds, 2.5 baths

$729,500

3 beds2.5 baths2,184 sq ft

8062 N Fork Blvd, Easton, MD 21601

Property at 7847 Ward Brothers Cir, Easton, MD 21601, 2 beds, 2 baths

$449,990

2 beds2 baths1,385 sq ft

7847 Ward Brothers Cir, Easton, MD 21601

(240) 375-5074

Property at 25826 Orchard Ter, Royal Oak, MD 21662, 4 beds, 4.5 baths

$3,495,000

4 beds4.5 baths— sq ft

25826 Orchard Ter, Royal Oak, MD 21662

(410) 822-6665

Property at 21477 Island Club Rd, Tilghman, MD 21671, 4 beds, 2.5 baths

$1,200,000

4 beds2.5 baths3,040 sq ft

21477 Island Club Rd, Tilghman, MD 21671

(410) 745-2596

Property at 8034 Bozman Neavitt Rd, Bozman, MD 21612, 2 beds, 1 bath

$179,900

2 beds1 bath1,160 sq ft

8034 Bozman Neavitt Rd, Bozman, MD 21612

(443) 320-1344

Property at 21721 Heavenly Haven Rd, Sherwood, MD 21665, 5 beds, 5.5 baths

$4,750,000

5 beds5.5 baths5,554 sq ft

21721 Heavenly Haven Rd, Sherwood, MD 21665

(410) 829-3603

Property at 11470 Wye Heights Rd, Easton, MD 21601, 8 beds, 8 baths

$3,495,000

8 beds8 baths10,533 sq ft

11470 Wye Heights Rd, Easton, MD 21601

(410) 822-6665

Property at 21749 Camper Cir, Tilghman, MD 21671, 3 beds, 1 bath

$295,000

3 beds1 bath1,224 sq ft

21749 Camper Cir, Tilghman, MD 21671

(410) 714-9166

Property at 6135 Summit St, Tilghman, MD 21671, 2 beds, 1 bath

$365,000

2 beds1 bath864 sq ft

6135 Summit St, Tilghman, MD 21671

(410) 714-9166

Property at 9681 Macks Ln, Mcdaniel, MD 21647, 2 beds, 1 bath

$92,000

2 beds1 bath920 sq ft

9681 Macks Ln, Mcdaniel, MD 21647

(410) 822-2152

Property at 5559 Trafalgar Cir, Tilghman, MD 21671, 5 beds, 3.5 baths

$575,000

5 beds3.5 baths3,404 sq ft

5559 Trafalgar Cir, Tilghman, MD 21671

(410) 224-2200

Property at 7845 Ward Brothers Cir, Easton, MD 21601, 2 beds, 2.5 baths

$649,990

2 beds2.5 baths2,493 sq ft

7845 Ward Brothers Cir, Easton, MD 21601

(240) 375-5074

Property at 21825 Langdon Farm Rd, Sherwood, MD 21665, 3 beds, 3.5 baths

$2,395,000

3 beds3.5 baths3,847 sq ft

21825 Langdon Farm Rd, Sherwood, MD 21665

(410) 745-2596

Property at 5648 Trafalgar Cir, Tilghman, MD 21671, 3 beds, 2 baths

$544,888

3 beds2 baths2,068 sq ft

5648 Trafalgar Cir, Tilghman, MD 21671

(410) 745-0415

Property at 7852 Ward Brothers Cir, Easton, MD 21601, 2 beds, 2 baths

$559,990

2 beds2 baths2,143 sq ft

7852 Ward Brothers Cir, Easton, MD 21601

(240) 375-5074

Property at 6020 Sunset Ln, Tilghman, MD 21671, 6 beds, 5 baths

$1,745,000

6 beds5 baths4,397 sq ft

6020 Sunset Ln, Tilghman, MD 21671

(410) 673-3344

Property at 25832 Turner Ave, Royal Oak, MD 21662, 3 beds, 2.5 baths

$859,900

3 beds2.5 baths2,200 sq ft

25832 Turner Ave, Royal Oak, MD 21662

(410) 822-6665

Property at Lot 16A Meadow St, Saint Michaels, MD 21663, 4 beds, 2.5 baths

$799,000

4 beds2.5 baths— sq ft

Lot 16A Meadow St, Saint Michaels, MD 21663

(410) 729-7700

Property at 25833 Turner Ave, Royal Oak, MD 21662, 3 beds, 2.5 baths

$865,500

3 beds2.5 baths2,200 sq ft

25833 Turner Ave, Royal Oak, MD 21662

(410) 822-6665

Property at 704 Meadow St, St Michaels, MD 21663, 4 beds, 3.5 baths

$889,800

4 beds3.5 baths3,100 sq ft

704 Meadow St, St Michaels, MD 21663

(410) 729-7700

Viewing page 2 of 3

More to explore in St. Michaels Middle/High School, MD

How to buy a house in St. Michaels Middle/High School, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.