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9529 Quail Holw Unit 504, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

Cozy Waterview Townhome Discover serene living in this charming townhome located in the peaceful Cove View Condominium Community. Enjoy breathtaking waterfront views and exclusive access to the community pier, ideal for boating enthusiasts. Situated on a tranquil street, this residence offers the perfect blend of quiet privacy and convenient proximity to local attractions. Inside, you’ll find hardwood flooring on the first level, with a first-floor waterview bedroom or office/den, plus a tiled bathroom. Upstairs features carpeted floors and an additional tiled bathroom. On cooler evenings, cozy up by the wood-burning fireplace to relax in comfort. The unit needs some TLC and is being sold as-is, offering a great opportunity for those looking to customize their home. Additional features include: A convenient first-floor laundry room, a single-car garage for secure parking, and a recently replaced roof for added peace of mind. The condo fee covers hazard insurance (owners are responsible for contents insurance), lawn maintenance, and a contribution to the capital reserve. Experience living at its finest in this charming St. Michaels townhome at Cove View—your gateway to tranquility and outdoor enjoyment.

3 Beds ⋅ 2 Baths

Cozy Waterview Townhome Discover serene living in this charming townhome located in the peaceful Cove View Condominium Community. Enjoy breathtaking waterfront views and exclusive access to the community pier, ideal for boating enthusiasts. Situated on a tranquil street, this residence offers the perfect blend of quiet privacy and convenient proximity to local attractions. Inside, you’ll find hardwood flooring on the first level, with a first-floor waterview bedroom or office/den, plus a tiled bathroom. Upstairs features carpeted floors and an additional tiled bathroom. On cooler evenings, cozy up by the wood-burning fireplace to relax in comfort. The unit needs some TLC and is being sold as-is, offering a great opportunity for those looking to customize their home. Additional features include: A convenient first-floor laundry room, a single-car garage for secure parking, and a recently replaced roof for added peace of mind. The condo fee covers hazard insurance (owners are responsible for contents insurance), lawn maintenance, and a contribution to the capital reserve. Experience living at its finest in this charming St. Michaels townhome at Cove View—your gateway to tranquility and outdoor enjoyment.

314 Cove Vw Unit 5B, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Benson & Mangold, LLC.

$426,000

Nestled in the historic, waterfront town of Saint Michaels, this charming colonial with one-car garage built in 2001, offers comfortable living on a private street! Lovely, level lot for quiet enjoyment surrounded by trees! Lots of nice features throughout! Brand-new carpet on upper level! Engineered hardwood floors! Large living room with lots of natural light! Kitchen with light oak cabinets, granite-look counters and all appliances! Breakfast area with sliders to a large concrete patio, fenced, rear yard and oversized, storage shed! Cozy family room! Additional half bath and huge closet on main level! Upstairs has a great layout with three bedrooms and a full bath featuring well-proportioned rooms that are perfect for everyday living! Gutter guards! Floored attic and much more! A wonderful place to call home! A small, glimpse of water in the winter between houses from back yard!

3 Beds ⋅ 2 Baths

Nestled in the historic, waterfront town of Saint Michaels, this charming colonial with one-car garage built in 2001, offers comfortable living on a private street! Lovely, level lot for quiet enjoyment surrounded by trees! Lots of nice features throughout! Brand-new carpet on upper level! Engineered hardwood floors! Large living room with lots of natural light! Kitchen with light oak cabinets, granite-look counters and all appliances! Breakfast area with sliders to a large concrete patio, fenced, rear yard and oversized, storage shed! Cozy family room! Additional half bath and huge closet on main level! Upstairs has a great layout with three bedrooms and a full bath featuring well-proportioned rooms that are perfect for everyday living! Gutter guards! Floored attic and much more! A wonderful place to call home! A small, glimpse of water in the winter between houses from back yard!

926 Calvert, Saint Michaels

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Bayside Realty.

$425,000

This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.

4 Beds ⋅ 4 Baths

This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.

1206 Washington Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$425,000

Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, including attractive luxury vinyl floors throughout, spacious kitchen w/all-new stainless Whirlpool appliances (range; refrigerator w/ice; dishwasher; built-in microwave oven), separate laundry room w/stacked washer/dryer, powder room, full bath, living room, dining/family room and two bedrooms with good closet space...all on one level! The house is attractive, comfortable and bright inside. Sliding glass doors off the family room lead to a new deck, overlooking the private back yard, where you will see a substantial renovated shed, approximately 20' x 15'...perfect for use as a "He-Shed/She-Shed," workshop and/or garden shed and storage area. "Move-in Ready!"

2 Beds ⋅ 2 Baths

Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, including attractive luxury vinyl floors throughout, spacious kitchen w/all-new stainless Whirlpool appliances (range; refrigerator w/ice; dishwasher; built-in microwave oven), separate laundry room w/stacked washer/dryer, powder room, full bath, living room, dining/family room and two bedrooms with good closet space...all on one level! The house is attractive, comfortable and bright inside. Sliding glass doors off the family room lead to a new deck, overlooking the private back yard, where you will see a substantial renovated shed, approximately 20' x 15'...perfect for use as a "He-Shed/She-Shed," workshop and/or garden shed and storage area. "Move-in Ready!"

111 Gloria, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$418,000

Welcome to 24345 Widgeon Place #25, a premier end-unit townhome in the waterfront community of Martingham, located just a mile from historic St. Michaels and adjacent to the Inn at Perry Cabin Links golf course. This light-filled home features three bedrooms and three full baths, including a rare first-floor bedroom with an ensuite. The open-concept main level offers hardwood floors, a wood-burning fireplace, and a kitchen with stainless steel appliances and seaglass countertops that flows into a sunroom and private patio. Upstairs, you will find two additional ensuites, including a primary suite with a private balcony. This unit uniquely offers direct garage access, abundant storage, and ample outdoor space, perfectly capturing the best of Eastern Shore living. Professional photos to be uploaded shortly.

3 Beds ⋅ 3 Baths

Welcome to 24345 Widgeon Place #25, a premier end-unit townhome in the waterfront community of Martingham, located just a mile from historic St. Michaels and adjacent to the Inn at Perry Cabin Links golf course. This light-filled home features three bedrooms and three full baths, including a rare first-floor bedroom with an ensuite. The open-concept main level offers hardwood floors, a wood-burning fireplace, and a kitchen with stainless steel appliances and seaglass countertops that flows into a sunroom and private patio. Upstairs, you will find two additional ensuites, including a primary suite with a private balcony. This unit uniquely offers direct garage access, abundant storage, and ample outdoor space, perfectly capturing the best of Eastern Shore living. Professional photos to be uploaded shortly.

24345 Widgeon, Unit 25, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

$410,000

MUST SEE THIS CHARMING COTTAGE IN SAINT MICHAELS! Welcome Home to this Adorable Cottage perfectly situated in the desirable and walkable Historic Waterfront Town of Saint Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. A sizable .25 Acre lot with mature trees to include a pecan and walnut tree, mature flower gardens, zoysia grass and an inground pool potential are rare commodities with "in-town" living! Step inside to find a welcoming living room with original restored hardwood floors and a wood-burning brick fireplace, ideal for relaxing evenings. A light filled Sunroom provides the perfect spot for a home office, reading nook, or studio. Large eat-in kitchen with newer oven and refrigerator. Updated bathroom features new ceramic tiled floors, new toilet, sink and a beautifully tiled shower. Peace of mind comes with having all new Anderson Windows all styled up with custom Hunter Douglas blinds! Recent exterior upgrades include a newer metal roof, new gutters, leaf guards and downspouts. The property also offers a rare commodity of off street parking, 1 car garage and a garden shed for additional storage. A fully floored 35' x 17' Attic with nearly 6' of headroom allows for tons of storage and potential expansion! This is a wonderful opportunity to enjoy the Best of Saint Michaels living! Walk to all of the Shops, Boutiques, Restaurants, Cafe's, Markets, Coffee Shops, Post Office, Churches, Waterfront Parks, Marinas, Maritime Museum, Nature Trail, Waterfront fun and so much more! Hit the greens at The Inn at Perry's Cabin or take a quick trip to Easton, Annapolis, DC and Baltimore. Escape the hustle and bustle and come live the Dream Life!

2 Beds ⋅ 1 Baths

MUST SEE THIS CHARMING COTTAGE IN SAINT MICHAELS! Welcome Home to this Adorable Cottage perfectly situated in the desirable and walkable Historic Waterfront Town of Saint Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. A sizable .25 Acre lot with mature trees to include a pecan and walnut tree, mature flower gardens, zoysia grass and an inground pool potential are rare commodities with "in-town" living! Step inside to find a welcoming living room with original restored hardwood floors and a wood-burning brick fireplace, ideal for relaxing evenings. A light filled Sunroom provides the perfect spot for a home office, reading nook, or studio. Large eat-in kitchen with newer oven and refrigerator. Updated bathroom features new ceramic tiled floors, new toilet, sink and a beautifully tiled shower. Peace of mind comes with having all new Anderson Windows all styled up with custom Hunter Douglas blinds! Recent exterior upgrades include a newer metal roof, new gutters, leaf guards and downspouts. The property also offers a rare commodity of off street parking, 1 car garage and a garden shed for additional storage. A fully floored 35' x 17' Attic with nearly 6' of headroom allows for tons of storage and potential expansion! This is a wonderful opportunity to enjoy the Best of Saint Michaels living! Walk to all of the Shops, Boutiques, Restaurants, Cafe's, Markets, Coffee Shops, Post Office, Churches, Waterfront Parks, Marinas, Maritime Museum, Nature Trail, Waterfront fun and so much more! Hit the greens at The Inn at Perry's Cabin or take a quick trip to Easton, Annapolis, DC and Baltimore. Escape the hustle and bustle and come live the Dream Life!

105 Seymour Ave, Saint Michaels

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Shoreline Realty.

$399,000

New Price! Transformative renovation in Martingham! This beautifully updated 2-bedroom, 2-bath single-level Gull Wing Villa overlooks the 6th fairway at Links at Perry Cabin, offering a serene golf course setting just minutes from the heart of St. Michaels. Thoughtfully redesigned, the home features new flooring throughout, a fully renovated kitchen and baths, and a reimagined layout that enhances both flow and functionality. The kitchen now opens seamlessly to the living area—ideal for modern living and entertaining. The primary bath has been expanded and now includes a large vanity. The smart design choices resulted in the addition of a generous extra closet in the primary suite. Additional updates include a new roof (2025), providing peace of mind for years to come. Located in the desirable Martingham community, residents enjoy access to a waterfront park with beach which is only about a 15 minute walk away. All of this is just moments from St. Michaels’ renowned shops, restaurants, and harbor.

2 Beds ⋅ 2 Baths

New Price! Transformative renovation in Martingham! This beautifully updated 2-bedroom, 2-bath single-level Gull Wing Villa overlooks the 6th fairway at Links at Perry Cabin, offering a serene golf course setting just minutes from the heart of St. Michaels. Thoughtfully redesigned, the home features new flooring throughout, a fully renovated kitchen and baths, and a reimagined layout that enhances both flow and functionality. The kitchen now opens seamlessly to the living area—ideal for modern living and entertaining. The primary bath has been expanded and now includes a large vanity. The smart design choices resulted in the addition of a generous extra closet in the primary suite. Additional updates include a new roof (2025), providing peace of mind for years to come. Located in the desirable Martingham community, residents enjoy access to a waterfront park with beach which is only about a 15 minute walk away. All of this is just moments from St. Michaels’ renowned shops, restaurants, and harbor.

24580 Deepwater Pt, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Paul Wesley Real Estate.

$395,000

Seller will offer a 10K credit for a storage shed with full price offer! Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

3 Beds ⋅ 2 Baths

Seller will offer a 10K credit for a storage shed with full price offer! Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

101 Brooks Ln, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

9539 Quail Holw Unit 303, Saint Michaels

$360,000

Located in the desirable Martingham Quail Hollow Community and nestled alongside the prestigious *Links at Perry Cabin* golf course, this well-maintained 1,800 sq. ft. townhouse has been freshly painted throughout. The home welcomes you with a foyer featuring laminate wood floors that flow into the kitchen and dining area. The spacious living room offers a wood-burning fireplace and room to create a formal dining space. Just beyond, a bright sunroom overlooks the park like backyard. Upstairs, the primary suite boasts an attached bath, walk-in closet and sliding glass doors leading to a balcony with views of the community and the 3rd green. The guest suite includes its own bath and a large closet. A detached one-car garage offers ample space for your vehicle and extra space for storage or workshop needs. The community features a waterfront park with a gazebo, sandy beach area, and sweeping views of the Miles River. This townhome is conveniently located within 2 miles of downtown St. Michaels, where you’ll find boutique shops, waterfront parks and vibrant dining. Optional membership at the *Links at Perry Cabin* offers access to one of the Eastern Shore’s finest golfing experiences.

2 Beds ⋅ 3 Baths

Located in the desirable Martingham Quail Hollow Community and nestled alongside the prestigious *Links at Perry Cabin* golf course, this well-maintained 1,800 sq. ft. townhouse has been freshly painted throughout. The home welcomes you with a foyer featuring laminate wood floors that flow into the kitchen and dining area. The spacious living room offers a wood-burning fireplace and room to create a formal dining space. Just beyond, a bright sunroom overlooks the park like backyard. Upstairs, the primary suite boasts an attached bath, walk-in closet and sliding glass doors leading to a balcony with views of the community and the 3rd green. The guest suite includes its own bath and a large closet. A detached one-car garage offers ample space for your vehicle and extra space for storage or workshop needs. The community features a waterfront park with a gazebo, sandy beach area, and sweeping views of the Miles River. This townhome is conveniently located within 2 miles of downtown St. Michaels, where you’ll find boutique shops, waterfront parks and vibrant dining. Optional membership at the *Links at Perry Cabin* offers access to one of the Eastern Shore’s finest golfing experiences.

9539 Quail Holw Unit 303, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Bright MLS.

24700 Deepwater Point Dr Unit 1, Saint Michaels

$350,000

Price improvement! Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home has been recently painted, professionally cleaned, and includes a new roof for added peace of mind, while a new Trex deck offers an ideal place to relax and enjoy the park-like, scenic setting. The home is turnkey, with the HOA maintaining the beautifully kept grounds, allowing for low-maintenance living. Ideally located just minutes from downtown St. Michaels, with shops, dining, and waterfront attractions nearby. An excellent opportunity as a primary residence, weekend retreat, or investment property. Check out the NEW Virtual Staging photography and video... to envision making this home your own!

2 Beds ⋅ 3 Baths

Price improvement! Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home has been recently painted, professionally cleaned, and includes a new roof for added peace of mind, while a new Trex deck offers an ideal place to relax and enjoy the park-like, scenic setting. The home is turnkey, with the HOA maintaining the beautifully kept grounds, allowing for low-maintenance living. Ideally located just minutes from downtown St. Michaels, with shops, dining, and waterfront attractions nearby. An excellent opportunity as a primary residence, weekend retreat, or investment property. Check out the NEW Virtual Staging photography and video... to envision making this home your own!

24700 Deepwater Point Dr Unit 1, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

9545 Quail Holw Unit 205, Saint Michaels

$350,000

REDUCED CLEAN UNIT ... CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort, and scenic beauty. Enjoy stunning golf course views from the second floor, while the first-floor living spaces benefit from a private, landscaped setting. The thoughtfully designed open floor plan seamlessly connects the living and dining areas, highlighted by a cozy fireplace and sliding glass doors that open to the screened porch—an ideal space for relaxing or entertaining. The well-appointed kitchen features granite countertops and a dedicated breakfast area, while the bathrooms also showcase attractive granite finishes. A one-car garage and an additional designated parking space provide convenience and practicality. Residents of Martingham enjoy exclusive access to a private waterfront park, along with abundant opportunities for walking, biking, and enjoying the area's natural beauty. Located just minutes from the charming waterfront town of St. Michaels, this remarkable home offers the perfect combination of luxury, recreation, and Eastern Shore living.

2 Beds ⋅ 3 Baths

REDUCED CLEAN UNIT ... CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort, and scenic beauty. Enjoy stunning golf course views from the second floor, while the first-floor living spaces benefit from a private, landscaped setting. The thoughtfully designed open floor plan seamlessly connects the living and dining areas, highlighted by a cozy fireplace and sliding glass doors that open to the screened porch—an ideal space for relaxing or entertaining. The well-appointed kitchen features granite countertops and a dedicated breakfast area, while the bathrooms also showcase attractive granite finishes. A one-car garage and an additional designated parking space provide convenience and practicality. Residents of Martingham enjoy exclusive access to a private waterfront park, along with abundant opportunities for walking, biking, and enjoying the area's natural beauty. Located just minutes from the charming waterfront town of St. Michaels, this remarkable home offers the perfect combination of luxury, recreation, and Eastern Shore living.

9545 Quail Holw Unit 205, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Chesapeake Bay Real Estate Plus, LLC.

$345,000

Widgeon Place is a charming townhome enclave within the desirable Martingham community, offering effortless comfort and nearly maintenance-free living. Just minutes from the historic waterfront town of St. Michaels, this home is ideally suited for year-round living, a relaxing weekend retreat, or a smart investment opportunity. Martingham overlooks the renowned Links at Perry Cabin Golf Course—originally designed by Pete Dye Sr. and thoughtfully reimagined by Pete Dye Jr.—providing a picturesque and prestigious setting and this location is one of the few buildings overlooking the golf course. Inside the residence features hardwood floors throughout the entry, living, dining, and sunroom areas and ceramic tile in the entry, half-bath and kitchen. The upper level offers two en-suite bedrooms, including a spacious primary suite with a private deck. A rear patio extends from the sunroom, creating additional outdoor living space, and a convenient half bath is located on the main level. Each unit also includes a one-car garage with additional storage space for the homeowner. With its serene setting overlooking a pond on the golf course, this is a great opportunity for those looking to enjoy the best of St. Michaels.

2 Beds ⋅ 3 Baths

Widgeon Place is a charming townhome enclave within the desirable Martingham community, offering effortless comfort and nearly maintenance-free living. Just minutes from the historic waterfront town of St. Michaels, this home is ideally suited for year-round living, a relaxing weekend retreat, or a smart investment opportunity. Martingham overlooks the renowned Links at Perry Cabin Golf Course—originally designed by Pete Dye Sr. and thoughtfully reimagined by Pete Dye Jr.—providing a picturesque and prestigious setting and this location is one of the few buildings overlooking the golf course. Inside the residence features hardwood floors throughout the entry, living, dining, and sunroom areas and ceramic tile in the entry, half-bath and kitchen. The upper level offers two en-suite bedrooms, including a spacious primary suite with a private deck. A rear patio extends from the sunroom, creating additional outdoor living space, and a convenient half bath is located on the main level. Each unit also includes a one-car garage with additional storage space for the homeowner. With its serene setting overlooking a pond on the golf course, this is a great opportunity for those looking to enjoy the best of St. Michaels.

24354 Widgeon Unit 20, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Benson & Mangold, LLC.

24560 Deepwater Pt Unit 1, Saint Michaels

$339,000

Two bedroom, two bath home overlooking the Links at Perry Cabin. The spacious unit offers a living room with brick hearth fireplace, kitchen with table space and separate dining area. Relax on the rear patio overlooking a scenic community area and golf course. Minutes from downtown St. Michaels with boutique shops and restaurants.

2 Beds ⋅ 2 Baths

Two bedroom, two bath home overlooking the Links at Perry Cabin. The spacious unit offers a living room with brick hearth fireplace, kitchen with table space and separate dining area. Relax on the rear patio overlooking a scenic community area and golf course. Minutes from downtown St. Michaels with boutique shops and restaurants.

24560 Deepwater Pt Unit 1, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: EXP Realty, LLC.

$338,000

All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered by peaceful woods,an ideal setting for relaxing or entertaining. Upstairs, two spacious ensuite bedrooms are thoughtfully positioned at opposite ends of the home, providing added privacy for owners and guests alike. Newly installed flooring adds warmth and a fresh, stylish appeal throughout the home. Beautifully cared for and move-in ready, this charming Widgeon Place townhome is a wonderful opportunity to enjoy low-maintenance living in a serene setting.

2 Beds ⋅ 2 Baths

All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered by peaceful woods,an ideal setting for relaxing or entertaining. Upstairs, two spacious ensuite bedrooms are thoughtfully positioned at opposite ends of the home, providing added privacy for owners and guests alike. Newly installed flooring adds warmth and a fresh, stylish appeal throughout the home. Beautifully cared for and move-in ready, this charming Widgeon Place townhome is a wonderful opportunity to enjoy low-maintenance living in a serene setting.

24362 Widgeon Pl Unit 5, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Coldwell Banker Waterman Realty.

24700 Deepwater Pt Unit 23, Saint Michaels

$335,000

Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept layout with a galley kitchen, dining area, and spacious living room. Sliding doors open to a balcony spanning the entire rear of the home, creating the perfect setting for indoor-outdoor living, entertaining, or simply enjoying the abundance of natural light. The main level offers two well-appointed bedrooms, two full baths, and a convenient laundry area. Whether you are seeking a primary residence, second home, first-time purchase, or investment property, this versatile townhome presents an exceptional opportunity. Residents enjoy convenient access to golf (membership available), scenic walking and biking trails, and a nearby waterfront park, all just moments from home. Numerous recent improvements enhance the property's value and appeal, including a new roof, updated bathrooms, new flooring, a new HVAC system, professional landscaping improvements, and fresh interior paint. In addition, the community association is currently completing exterior siding repairs and repainting throughout the community, further enhancing the property's appearance and long-term maintenance. Move-in ready and thoughtfully updated, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Some photographs have been virtually staged. **SELLER OPEN TO CONCESSIONS FOR BUYER CLOSING COST**

2 Beds ⋅ 3 Baths

Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept layout with a galley kitchen, dining area, and spacious living room. Sliding doors open to a balcony spanning the entire rear of the home, creating the perfect setting for indoor-outdoor living, entertaining, or simply enjoying the abundance of natural light. The main level offers two well-appointed bedrooms, two full baths, and a convenient laundry area. Whether you are seeking a primary residence, second home, first-time purchase, or investment property, this versatile townhome presents an exceptional opportunity. Residents enjoy convenient access to golf (membership available), scenic walking and biking trails, and a nearby waterfront park, all just moments from home. Numerous recent improvements enhance the property's value and appeal, including a new roof, updated bathrooms, new flooring, a new HVAC system, professional landscaping improvements, and fresh interior paint. In addition, the community association is currently completing exterior siding repairs and repainting throughout the community, further enhancing the property's appearance and long-term maintenance. Move-in ready and thoughtfully updated, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Some photographs have been virtually staged. **SELLER OPEN TO CONCESSIONS FOR BUYER CLOSING COST**

24700 Deepwater Pt Unit 23, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Redfin Corp.

$330,000

Welcome to Martingham, a premier golf course and waterfront community located just a mile from historic St. Michaels. This Widgeon Place condo offers two en-suite bedrooms and a half bath, with a thoughtful two-level layout designed for comfort and convenience. The main level features a kitchen with a charming breakfast nook, hardwood floors, a gas fireplace, and an open-concept living area. A bright sunroom opens to a private patio, ideal for relaxing or entertaining. Upstairs, the spacious primary suite includes a walk-out balcony, while the second bedroom is complemented by an en-suite bath. A second-floor laundry adds everyday ease. Perfectly situated in a sought-after location, this home combines style, function, and the best of Eastern Shore living.

2 Beds ⋅ 3 Baths

Welcome to Martingham, a premier golf course and waterfront community located just a mile from historic St. Michaels. This Widgeon Place condo offers two en-suite bedrooms and a half bath, with a thoughtful two-level layout designed for comfort and convenience. The main level features a kitchen with a charming breakfast nook, hardwood floors, a gas fireplace, and an open-concept living area. A bright sunroom opens to a private patio, ideal for relaxing or entertaining. Upstairs, the spacious primary suite includes a walk-out balcony, while the second bedroom is complemented by an en-suite bath. A second-floor laundry adds everyday ease. Perfectly situated in a sought-after location, this home combines style, function, and the best of Eastern Shore living.

24362 Widgeon Pl Unit 4, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Unrepresented Buyer Office.

Pea Neck Rd Map 32 Parcel 76, Saint Michaels

$250,000

Incredible opportunity to build just minutes from downtown Saint Michaels. Public Sewer hookup is available. Buyer will be responsible for paying for hookup This property was just sub divided and recorded. The property is 7841 Pea Neck Rd tax Map 32 Parcel 76 Lot 2. 2 acre lot. Public sewer hookup is available. One acre of the property is in forest conservation. Plat is available.

Pea Neck Rd Map 32 Parcel 76, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Meredith Fine Properties.

$249,000

ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY. IT IS SURROUNDED BY BEAUTIFUL HOMES MINUTES TO HISTORIC ST MICHAELS WITH ITS SHOPS, RESTAURANTS, MUSEUM, YACHTCLUB AND WATERFRONT PARKS. THE LOT BACKS UP TO COMMON SPACE THAT IS A NATURAL HABITAT FOR ULTIMATE PRIVACY AND WILDLIFE.

Deepwater Point, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

$245,000

Own a piece of history in the heart of St. Michaels. Believed to be one of the oldest commercial buildings in town, this charming storefront offers a rare opportunity along iconic South Talbot Street. Rich in character and perfectly scaled for boutique retail, gallery space, studio, professional office or specialty business. High visibility in one of the Eastern Shore’s most visited destinations, surrounded by shops, restaurants, the harbor and year-round tourism. A distinctive investment or owner-user opportunity with timeless appeal in historic St. Michaels.

214 Talbot, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Reverie Residential.

$240,000

This is one of the loveliest lots in St. Michaels on a gorgeous residential street surrounded by charming homes. It is conveniently located in the heart of town just one block from restaurants and shopping on S Talbot Street, along with a wonderful trail and waterfront park.

Grace, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$236,000

Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all St Michaels has to offer.

2 Beds ⋅ 1 Baths

Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all St Michaels has to offer.

209 Webb Ln, Saint Michaels

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Meredith Fine Properties.

$165,000

End of non through street. <> 3 -4 blocks from historic district stores, restaurants, etc. Convenience and the quiet of seclusion in town.....As of yet no sign.

117 Chesapeake Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Bayside Realty.

$135,000

New price!...Great opportunity to own a buildable lot in one of Maryland's most charming waterfront towns. This spacious and level parcel offers the perfect canvas for your Eastern shore home. Nestled just blocks from the harbor, shops, restaurants, parks, marinas, and the Chesapeake Bay Maritime Museum. Walk to downtown restaurants and shops! The property combines small-town walkability with relaxed coastal living. The lot is ready for development with public water and sewer. Purchaser/builder will need to do their own due diligence for verify future plans with Talbot County. Don't miss this chance to build in beautiful St. Michaels — where history, charm, and the Chesapeake Bay lifestyle come together.

300 Perry St, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Benson & Mangold, LLC.

$99,500

Great opportunity to own an in-town lot in the historic waterfront town of St. Michaels. This lot is just minutes from the shops, restaurants, harbor and Chesapeake Bay Maritime Museum. Come design and build your home without historic restrictions. The street sign for this lot is Glory, but the tax record has Gloria Avenue.

102 Glory, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Unrepresented Buyer Office.

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How much is your home worth?