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CHARLESTOWN

One of the most popular communities provided by Charis Realty

CHARLESTOWN

About CHARLESTOWN

Discover Charlestown, MA Real Estate

Charlestown, Massachusetts is one of Boston’s most storied and sought-after neighborhoods. Nestled just north of downtown Boston, Charlestown blends classic New England charm with modern city conveniences, making it an ideal destination for homebuyers and investors alike.

Why Live in Charlestown?

Charlestown boasts a unique combination of history, waterfront views, and easy access to downtown Boston. The neighborhood is renowned for its:

  • Historic Landmarks: Home to the Bunker Hill Monument, USS Constitution Museum, and centuries-old architecture.
  • Vibrant Community: Enjoy lively local restaurants, coffee shops, and boutique shopping along Main Street and in City Square.
  • Excellent Schools: Top-rated public and private schools serve families in the Charlestown area.
  • Easy Commuting: Direct access to I-93, MBTA Orange Line at Community College Station, and several MBTA bus routes make getting around the city a breeze.
  • Parks & Waterfront: Residents love the scenic Charlestown Navy Yard, Paul Revere Park, and the Boston Harborwalk for outdoor activities.

Real Estate Market Overview

The Charlestown, MA real estate market features a mix of lovingly restored brownstones, modern condominiums, luxury waterfront properties, and single-family homes. Whether you’re looking to buy your first condo or upgrade to a spacious family home, Charlestown offers diverse real estate options.

Types of Properties

  • Historic Townhomes: Classic brick exteriors with original details and updated interiors.
  • Luxury Condos: Amenities like gyms, concierge services, and private parking.
  • Single-Family Homes: Charming, spacious residences ideal for families.
  • Waterfront Apartments: Breathtaking harbor views and direct access to marina life.

Living in Charlestown: Neighborhood Highlights

  • Community Feel: Annual events, farmer’s markets, and neighborhood meetups foster a tight-knit, welcoming environment.
  • Dining & Nightlife: Savor local favorites like Warren Tavern, Brewer’s Fork, and Monument Restaurant & Tavern.
  • Cultural Attractions: Visit historical sites, art galleries, and theaters unique to Charlestown.
  • Recreation: Sail on the harbor, stroll the Freedom Trail, or bike to downtown Boston in minutes.

Invest in Charlestown We Real Estate

Charlestown is consistently rated as one of Boston’s top neighborhoods for real estate investment. With rising property values, strong rental demand, and ongoing revitalization projects, now is the perfect time to explore real estate opportunities in Charlestown, Massachusetts.

Ready to find your dream home in Charlestown? Contact a local Charlestown real estate expert today!

Explore the historic charm and modern convenience of Charlestown, MA—your ideal Boston neighborhood for real estate and community living.

One of the most popular communities provided by Charis Realty
150
# of Listings
3
Avg # of Bedrooms
$230
Avg. $ / Sq.Ft.
$523,836
Med. List Price

Browse CHARLESTOWN Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

27 Properties Found. Page 2 of 2.

**Stunning Former Model Home – Where Elegance Meets Functionality!** Discover this breathtaking former model home, meticulously designed with a perfect balance of style and practicality. Nestled on a beautifully manicured corner lot, this residence offers 9-foot ceilings and nearly 4,500 square feet of sun-drenched, open living space. Step inside to find rich hardwood floors, sophisticated wainscoting, and exquisite crown molding. The heart of the home is the gourmet kitchen, featuring an expansive island with a breakfast bar, pristine white cabinets, stainless steel appliances, a double oven, and a built-in microwave. The adjoining living room, highlighted by a stunning stone fireplace, creates a warm and inviting atmosphere. The main level boasts two spacious bedrooms and two full bathrooms, including a luxurious primary suite. This retreat showcases elegant crown molding, chair rail, wainscoting, a generous walk-in closet, and a spa-like ensuite bathroom with double sinks, granite countertops, a soaking tub, shower stall, and a private water closet. Upstairs, you'll find a third bedroom, a full bathroom, and a sprawling family room — perfect for relaxation or entertainment. The fully finished lower level is a versatile space, offering a massive recreation room, a fourth bedroom, a fourth full bathroom, and a bonus room that could serve as a fifth bedroom, theater, or home office. Outdoor living is equally impressive, with a low-maintenance Trex deck that steps down to a beautiful patio and a vast backyard — ideal for gatherings or quiet moments. Yard maintenance is made easy with the lawn irrigation system. The covered front porch adds an inviting touch, and the two-car garage provides ample storage. Live efficiently and environmentally friendly with green efficient construction, HVAC, lighting, and appliances, as well as moisture control for green indoor air quality and low-flow fixtures & efficient hot water distribution for green water conservation. This highly sought-after community offers exceptional amenities, including a pool, clubhouse, playground, walking trails, and scenic common areas. With easy access to US-340, WV-9, and VA-7, commuting to Northern Virginia is a breeze. Additionally, enjoy the charm of nearby historic Harpers Ferry and the local wine region just minutes away. Don't miss your chance to own this remarkable home — where luxury and convenience unite! This home is also rent.
#WVJF2016484

CHARLES TOWN

18 COURIER DRIVE

4 Beds

4 Baths

4,763 Sq.Ft.

$649,999

MLS#: WVJF2016484

Located in the established Eastland subdivision, this stately brick home combines timeless design with modern updates across 3,200+ square feet and 1.8 landscaped acres. With 4 bedrooms, 3.5 baths, and a layout that balances elegance and function, it offers a lifestyle of both comfort and sophistication. The renovated primary suite creates a private retreat, while the main level offers a formal living and dining room, a den, and a welcoming family room anchored by a propane fireplace. A second fireplace warms the fully finished basement, where the expansive rec room provides 20 grounded outlets—ideal for hobbies, gaming, or creative projects. Outdoor living shines with a screened-in deck, a brick patio, a shaded koi pond witing for your TLC, and peaceful views of the small lake behind the home. A custom pergola and swing, enhanced by an antique gas street light, create a charming setting for quiet reflection or evening conversation. For car enthusiasts or hobbyists, two garages—a standard two-car plus a 45x13 workshop garage—deliver abundant space and flexibility. Updates for peace of mind include a new roof (2018–2019), propane HVAC (2017), a newer upstairs HVAC handler, an owned propane tank, and a water treatment system installed in 2024. With exceptional storage, formal and casual living areas, and serene outdoor spaces, this Eastland property offers the perfect blend of luxury and everyday livability.
#WVJF2019534

CHARLES TOWN

54 CHATHAM COURT

4 Beds

3 Baths

3,204 Sq.Ft.

$635,000

MLS#: WVJF2019534

**Back on the market at no fault of seller** Located in the sought-after Eastland community, this expansive colonial sits on a private cul-de-sac lot and features 5 bedrooms and 5 full bathrooms across a generous and well-planned layout. The main level offers two true bedroom suites with attached full baths, ideal for multi-generational living or guest accommodations. The interior includes a bright living area, formal dining space, and a well-appointed kitchen with quartz counters, double microwave/oven setup, and an adjoining breakfast room with rear yard views. The upper level features three additional bedrooms, each with convenient access to full bathrooms, providing flexibility and privacy for household members or guests. With nearly an acre of usable outdoor space, the lot offers a private setting for outdoor enjoyment. Located within a community known for its paved walking paths and peaceful surroundings, this property blends space, function, and neighborhood appeal in one of Charles Town’s established residential settings.
#WVJF2020084

CHARLES TOWN

98 FOXHALL ROAD

5 Beds

4 Baths

3,944 Sq.Ft.

$629,000

MLS#: WVJF2020084

Nestled in the prestigious Aspen Greens community of Jefferson County WV, this exquisite Executive Colonial residence, built in 2019, epitomizes luxury living. Spanning over 3,500 sf above grade and nearly 1,300 sf finished in the lower level for nearly 5,000 total finished living space, this home boasts four spacious bedrooms and four and a half elegantly appointed bathrooms, each featuring high-end finishes and thoughtful design. Step inside to discover an open floor plan that seamlessly integrates the gourmet kitchen, complete with upgraded countertops, a large island, and top-of-the-line appliances, including a built-in microwave, wall oven, and a down-draft cooktop. The family room, adorned with a stunning stone fireplace, invites warmth and comfort, while the formal dining area, enhanced by crown moldings and chair railings, sets the stage for sophisticated gatherings. Retreat to the primary suite, where two lavish walk-in closets and a spa-like bathroom with a walk-in shower and soaking tub await. One of the four bedrooms is a Princess Suite with attached private full bath and walk in closet. Additional interior highlights include recessed lighting, built-ins, and a convenient upper-floor laundry. The exterior is equally impressive, featuring extensive hardscaping, beautifully landscaped grounds, and inviting patio and porch that provide serene outdoor spaces for relaxation. The property sits on a generous 0.38-acre lot, offering a level, fenced rear yard perfect for entertaining or enjoying peaceful moments. With an attached two-car garage and ample driveway parking, convenience is paramount. The community amenities, including well-maintained sidewalks and jog/walk paths, enhance the exclusive lifestyle this home offers. Experience the perfect blend of luxury, comfort, and modern living in this remarkable property.
#WVJF2020028

CHARLES TOWN

31 WINTERGREEN WAY

4 Beds

4 Baths

5,349 Sq.Ft.

$625,000

MLS#: WVJF2020028

*PENDING RELEASE OF CURRENT CONTRACT* The only community within historic Charles Town with resort style amenities! *UP TO $12,500 CLOSING COST ASSISTANCE AVAILABLE ON SELECT HOMES, FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!* ATTACHED 2 CAR GARAGE INCLUDED!!! Live the Huntfield lifestyle in Charles Town's largest planned community ideally situated along the rolling hills of the Blue Ridge Mountains! Welcome to the Bridgeport II, a place where style meets functionality! This beautifully finished Move-In Ready home features 5 bedrooms, a finished basement including a bedroom and a full bath, a 4 ft. extension, a Morning Room, a 14x10 deck, and many other upgrades! Crossing the threshold, you'll find an open concept layout that includes a bright gathering room with a spacious kitchen with a large island and walk-in pantry, a mudroom, a powder room, and a flex room on the main level. Moving upstairs, you'll discover a private primary suite that comes with a sizable walk-in closet and luxurious bathroom featuring a dual sink vanity, a large tub, and a walk-in shower. Beyond the primary suite, you will find additional bedrooms, a hall bathroom, and a laundry room on the second level. Don't miss out on this rare opportunity for a brand new home without the wait!!
#WVJF2018936

CHARLES TOWN

812 LORD FAIRFAX STREET

5 Beds

3 Baths

3,596 Sq.Ft.

$623,990

MLS#: WVJF2018936

Lot A offers exceptional visibility and access at the southeast ramp of George Street and US Route 340, strategically located within the thriving Norborne Glebe community. Perfect for retail, office, or hospitality, this lot benefits from proximity to major highways, growing residential developments, and Jefferson County’s economic expansion. Zoned for commercial use and equipped with infrastructure access, making development straightforward and cost-effective. Located within the Norborne Glebe residential project and adjacent to key highways like US Route 340, Lot is ideally positioned to capitalize on the growth trends and development priorities outlined in Jefferson County's 2035 and 2045 Comprehensive Plans. The county's focus on creating urbanized hubs, mixed-use areas, and high-density residential zones makes these lots prime for impactful commercial use. Few of the New Residential Housing Development projects around this location: Norborne Gleebe King's Crossing Huntfield Shennandoah Springs President's Pointe Huntwell West Magnolia Springs Red Clover Ryan homes are coming in the area as well in the future. Jefferson County's Comprehensive Growth Plans( In the document) *****Please note this is GC zoned lot, Seller has the updated record. *******
#WVJF2015126

CHARLES TOWN

S GEORGE STREET

None Beds

None Baths

1.62 acres

$615,250

MLS#: WVJF2015126

MOTIVATED SELLER - TOUR AND BRING AN OFFER - ONE LEVEL LIVING WITH MOUNTAIN VIEWS ***Welcome to your dreamy 5-acre farmette, a charming oasis nestled amidst stunning landscapes. This picturesque property features a spacious garage, a versatile shed, and a run-in shed, ideal for housing your horses or other beloved livestock. Dive into summer fun with an inviting in-ground pool and a quaint pool house, perfect for entertaining guests or simply unwinding. Inside, this cozy 3-bedroom, 2-bathroom rancher boasts a fully finished walk-out basement with two additional rooms, offering ample space for guests or hobbies. The spacious family room , new eat-in kitchen with access to covered, screened porch, sunroom offers a tranquil space to relax and soak in the beauty of your surroundings, plus main-level laundry add practical touches to this enchanting home. Discover the perfect blend of comfort and charm—your dream home awaits. Low taxes, high speed internet. no hoa! New roof, hvac, well pump and more ! Exceptional location with multiple routes to and from the property with close proximity to northern Virginia and Maryland. Enjoy the serenity of countryside living with the convenience of nearby local amenities.
#WVJF2017614

CHARLES TOWN

85 KEALA COURT

3 Beds

2 Baths

2,846 Sq.Ft.

$599,000

MLS#: WVJF2017614

*MAJOR PRICE IMPROVEMENT* This exquisite new construction home on original foundation, completed in 2025, embodies the perfect blend of luxury and comfort. Completely rebuilt from the foundation up, you will have peace of mind knowing every detail is brand new, including a brand new septic and 50 year roof. With a traditional architectural style, this detached residence offers an inviting atmosphere that feels like home from the moment you step inside. Spanning over 3.77 unrestricted acres, the property boasts pastoral views and tranquil wooded areas, creating a picturesque backdrop for your everyday life. The expansive circular driveway provides ample parking and enhances the home's curb appeal, welcoming you and your guests. Step inside to discover a thoughtfully designed interior featuring four spacious bedrooms and three full bathrooms. The heart of the home is the gourmet kitchen, equipped with high-end stainless steel appliances and updated finishes. The kitchen island serves as a focal point for gatherings, while upgraded countertops and the eye-catching backsplash adds a touch of sophistication. The primary suite is a true retreat, complete with a luxurious bathroom featuring a gorgeous tiled tub-shower, along with a generous walk-in closet. Each additional bedroom is designed with comfort in mind, ensuring ample space for relaxation and personalization. Two of the upstairs bedrooms have access to the upper level deck where you can relax and enjoy your morning coffee. Luxury vinyl plank flooring flows throughout the home, providing durability and style, while ceiling fans and natural sunlight enhance the inviting ambiance. The entry-level bedroom offers convenience and flexibility, making it ideal for guests or as a private office space. Outside, the property features a charming barn, adding character and potential for various uses, whether for hobbies or storage. The surrounding landscape invites you to unwind and enjoy the beauty of nature right at your doorstep. This home is not just a residence; it's a lifestyle. Experience the tranquility of country living while being just moments away from local amenities. With its impeccable design, high-end features, and stunning views, this property is a rare gem that promises a life of comfort and luxury. Embrace the opportunity to make this exquisite home your own and enjoy the lifestyle it offers. No HOA!
#WVJF2018336

CHARLES TOWN

15990 CHARLES TOWN ROAD

4 Beds

3 Baths

2,964 Sq.Ft.

$589,000

MLS#: WVJF2018336

Welcome to 439 Lord Fairfax Street — a home that truly stands out on a corner lot in one of Charles Town’s most desirable communities. While nearby new construction homes come at a higher price, this 10-year-young property feels like new thanks to numerous thoughtful upgrades and meticulous care that make it show like a model home. From the moment you arrive, the wrap-around porch with its inviting swing sets the tone for a perfect spot to sip morning coffee, chat with neighbors, or unwind at sunset. Around back, a spacious Trex deck with a privacy wall extends the living space outdoors, creating an ideal setting for entertaining or relaxing after a long day. Inside, every detail reflects modern comfort and timeless style. The kitchen gleams with granite countertops and a large island as well as updated appliances to include a gas cooktop. The extended kitchen cabinetry flows into the breakfast area, offering ample room for meal prep, entertaining, and everyday convenience. The primary suite and Jack-and-Jill baths have been beautifully refreshed with quartz countertops, double vanities, tiled finishes and updated faucets. Fresh paint, higher end lighting, and plantation shutters throughout the home give it that “brand-new” sparkle — without the wait or expense of new construction. Major updates add peace of mind as well as value: the roof was replaced in 2018, both HVAC units were replaced in 2021 with surge protection, and the two-car garage is finished with a storage landing, gel-coated floor, and 220V EV outlet. Outside, a custom storage shed, concrete walkway, widened driveway, and newly established oak and magnolia trees enhance the home’s curb appeal. Also, new tile and LVP in the finished areas of the basement. Blending quality craftsmanship, smart upgrades, and everyday comfort, this home offers the best of both worlds — the fresh, like-new feel of new construction at a more approachable price. Schedule your private tour today and experience this exceptional home for yourself!
#WVJF2020218

CHARLES TOWN

439 LORD FAIRFAX STREET

4 Beds

3 Baths

4,548 Sq.Ft.

$585,000

MLS#: WVJF2020218

Our brand new Middleton offers all the features of our modern farmhouse designs, but at an affordable price. Starting in the upper-400’s, with 2140 square feet on 2 levels, the Middleton includes a 1st floor owner’s suite, with 2-3 additional bedrooms on the upper level, as well as a 2-car rear, attached garage, and a gorgeous INCLUDED sky roof terrace on the upper level. Please note that the Middleton priced at $499,900 is built on slab. We are offering only a limited number of these, so reserve yours today and you can be in your new Beallair home within the next 8-9 months!
#WVJF2002530

CHARLES TOWN

73 CLAYMONT HILL STREET

3 Beds

2 Baths

2,142 Sq.Ft.

$584,900

MLS#: WVJF2002530

Welcome to 504 S Church Street — a home where charm and thoughtful updates meet in a rare opportunity. Ideally located near downtown Charles Town, this well-maintained 4-bedroom, 3.5-bathroom residence offers the perfect blend of flexibility and comfort for a variety of living arrangements. Inside, you'll find hardwood floors, solid wood doors, cedar closets, and warm, inviting living spaces. The main level includes a formal dining room, a spacious family room with an electric fireplace insert that provides heat, and access to an upgraded screened-in porch—ideal for relaxing or entertaining. The kitchen features table space for casual dining, and a main level bedroom with a full bath offers convenience for guests or multigenerational living. Upstairs, there are three large bedrooms, each with ceiling fans, and a full bathroom. The finished basement includes a second family room with fireplace, a separate living area with a full kitchen including new appliances, a full bathroom, and an efficiency setup—well-suited for extended family, guests, or income-generating potential. From 2022 to 2025, the home underwent comprehensive updates including electrical wiring and panels, plumbing, bathroom renovations, lighting, switches, outlets, kitchen improvements, a rebuilt basement staircase, a sump pump, smart features like a Nest thermostat and smart locks. Other improvements include a newer roof & siding, and updated shed. Whether you're looking for a beautiful full-time residence or a turnkey business opportunity, this home delivers. With separate entrances and full amenities on both levels, it’s perfectly set up to operate as two distinct short-term rental units—rent the upper level and basement independently, or live in one and rent the other. Set on a thoughtfully designed lot with gorgeous landscaping, new patios, porches and walkways, the outdoor space is as inviting as the interior. Located in the heart of Charles Town, stroll down the road to the Hollywood Casino, restaurant's, shopping, farmers market, entertainment, historic sites. Just a short drive, enjoy Harpers Ferry Historic National Park, biking, hiking, water sports, ghost tours, wineries, breweries. Just a 30-minute drive to Frederick MD, Leesburg VA, Winchester VA. 1 hour to Washington DC, Baltimore MD and Gettysburg PA. Schedule your private tour today!
#WVJF2016982

CHARLES TOWN

504 S CHURCH STREET

4 Beds

3 Baths

3,606 Sq.Ft.

$579,000

MLS#: WVJF2016982

This DRB-built Clemson II model stands tall on a corner lot, combining charm with modern functionality. Offering 4 spacious bedrooms and 3.5 baths across three thoughtfully designed levels, it provides the flexibility today’s families need. The open-concept kitchen is a chef’s dream, featuring a large central island that’s ideal for entertaining or everyday meals. The Owner’s Suite Retreat boasts a walk-in closet, dual-sink vanity, and a seated shower for a spa-like escape. A detached 2-car garage enhances convenience while maintaining the community’s timeless streetscape. Upgrades include a $10,000 fence, $3,000 blinds package, and a $750 EV charger with professional installation—all ready for you to enjoy. With three full levels of living space, this home offers plenty of room for family, guests, or work-from-home options. Welcome to Huntfield – Jefferson County’s Premier Master-Planned Community Huntfield is celebrated for its tree-lined streets, pocket parks, wide boulevards, and scenic walking trails with views of the Blue Ridge Mountains. The architecture blends timeless design with small-town charm, while its location ensures everyday convenience. Just minutes from historic downtown Charles Town, residents enjoy easy access to commuter routes, schools, shopping, dining, and the history-rich surroundings of Harpers Ferry and Shepherdstown. Huntfield is where elegance, community, and convenience come together seamlessly.
#WVJF2019286

CHARLES TOWN

246 NEWBURY STREET

4 Beds

3 Baths

3,281 Sq.Ft.

$515,000

MLS#: WVJF2019286

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