CHARIS REALTY GROUP

Victorian

107 E CHESTNUT

SAINT MICHAELS, MD 21663

MLS#: MDTA2013968

$1,165,000

Status: Active
Listing number: MDTA2013968
Listing provided by: TTR Sotheby's International Realty
Listing agent phone: None
Last update: 15 hours ago
New on site today
Browse Properties
ST. MICHAELS - Residential

Property

Beds

2

Full Baths

2

1/2 Baths

None

Year Built

1880

Sq.Footage

2,024

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

Features & Amenities

Interior

  • Other Interior Features

    Beamed Ceilings

  • Total Bedrooms

    2

  • Bathrooms

    2

  • Above Grade Finished Area

    2024.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Electric

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Electric, Heat Pump

  • Pet friendly

    N/A

Exterior

  • Garage

    No

  • Construction Materials

    Aluminum Siding, Wood Siding

  • Parking

    Driveway

  • Pool

    No

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.08

  • Lot Size(square feet)

    3600.0

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Victorian

Price

  • Sales Price

    $1,165,000

  • Tax Amount

    $6,685

  • Sq. Footage

    2, 024

  • Price/SqFt

    $575

HOA

  • Association

    No

School District

  • Elementary School

    N/A

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • New Construction

    NO

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

TALBOT

Elementary School

Middle School

High School

Listing Courtesy of Monica S Penwell , TTR Sotheby's International Realty

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent Summer Burton

AGENT

Summer Burton

Call Summer today to schedule a private showing.

(443) 952-0034

summer@charisrealty.com


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

107 E CHESTNUT

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Charis Realty Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Related Properties

Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 48" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large custom closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.
#MDTA2013310

SAINT MICHAELS

7865 PEA NECK

4 Beds

3 Baths

3,332 Sq.Ft.

$1,379,800

MLS#: MDTA2013310

Known as the William J. Wrightson House, this distinguished circa 1897 residence in the heart of St. Michaels beautifully blends timeless elegance and refined architectural detail with the comforts and conveniences of modern living. Lovingly restored from top to bottom, the home has undergone extensive renovations and improvements, including all new HVAC systems, tankless hot water system, updated wiring, crawlspace encapsulation, new roof and gutters, recessed lighting, high-end appliances, three fully renovated baths, a custom butler’s pantry, complete interior and exterior painting, and new patio grading and drainage, among many others. A full list of improvements is available. Ideally situated just steps from the waterfront, marinas, boutique shops, waterfront dining, and renowned local restaurants, the property offers an exceptional in-town lifestyle in one of the Eastern Shore’s most beloved waterfront communities. Filled with natural light throughout, the beautiful 3BR/3BA residence showcases heart pine and yellow pine flooring, custom millwork, and thoughtfully renovated living spaces designed for both everyday comfort and effortless entertaining. The welcoming living room, anchored by a new gas fireplace/stove, flows seamlessly into a gracious formal dining room ideal for gatherings with family and friends. The gourmet kitchen features quartz countertops, top-tier appliances, abundant cabinetry, and custom built-ins, effortlessly combining style and functionality. At the rear of the home, a stunning sunroom addition serves as a true focal point, featuring vaulted ceilings, a shiplap accent wall, wet bar and custom butler’s pantry with beverage chiller and bar sink, custom built-ins, a renovated full bath, and French doors opening to the picturesque gardens and brick patio beyond. Upstairs, the comfortable primary suite offers a peaceful retreat, complemented by a luxurious bath with a clawfoot soaking tub, Carrara Bella marble flooring (in shower as well), custom antique vanity, and glass-enclosed walk-in shower. Two additional guest bedrooms and a beautifully renovated bath with marble tile flooring, granite-topped vanity, and Perrin & Rowe fixtures provide inviting accommodations for family and guests. The outdoor spaces are equally enchanting, highlighted by a stunning English garden filled with roses, crepe myrtles, and hydrangeas, all enclosed by a charming French Gothic lattice shadowbox fence, creating a private and storybook setting.
#MDTA2013714

SAINT MICHAELS

202 E CHESTNUT STREET

3 Beds

3 Baths

2,052 Sq.Ft.

$1,275,000

MLS#: MDTA2013714

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual needs, all while maintaining privacy and a connection to the surrounding natural landscape. Restaurants, shops, seasonal events, waterfront parks, and the charm of the historic district are all close at hand, yet the property feels quietly removed. Approximately three times the size of a typical in-town lot, the parcel allows for thoughtful home placement, outdoor living areas, and driveway access from Miles Avenue, Canton Street, or both, depending on the final plan. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.
#MDTA2012368

SAINT MICHAELS

108 MILES AVENUE

3 Beds

2 Baths

N/A

$999,000

MLS#: MDTA2012368

Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.
#MDTA2013116

SAINT MICHAELS

114 W CHESTNUT STREET

4 Beds

4 Baths

3,528 Sq.Ft.

$1,285,000

MLS#: MDTA2013116

This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family room—perfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street—a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.
#MDTA2013980

SAINT MICHAELS

109 W MARENGO STREET

4 Beds

3 Baths

2,250 Sq.Ft.

$1,049,000

MLS#: MDTA2013980

Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.
#MDTA2013022

SAINT MICHAELS

101 MULBERRY STREET

4 Beds

2 Baths

1,500 Sq.Ft.

$1,194,000

MLS#: MDTA2013022

This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.
#MDTA2013438

SAINT MICHAELS

504 SEYMOUR AVENUE

3 Beds

2 Baths

2,200 Sq.Ft.

$1,049,000

MLS#: MDTA2013438

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Charis Realty Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

I agree to receive communications and understand I can unsubscribe at any time.

I agree to be contacted by Charis Realty Group via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service