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Step into timeless charm without leaving behind today's comforts. This distinctive Painted Lady captures the character, craftsmanship, and gracious proportions that make a home truly memorable, right in the heart of Middletown. Set well back from historic Main Street behind an expansive front lawn, the home has an impressive presence, with a wide wraparound porch inviting you to sit awhile and enjoy the rhythm of small-town living. Located within the sought-after Middletown school district, this is a home that feels a part of the town’s story. Offering over 3,000 finished square feet above grade, the home has been lovingly cared for by the same owners since 1997. Natural light and tall ceilings on every level create a remarkably open and airy feel, while fresh paint complements the beautiful architectural details throughout. An impressive entry foyer sets the tone with original millwork and wood floors, fireplace mantels, pocket doors, a built-in bookcase, and a distinctive split staircase. Stacked bay windows on separate levels feature diamond-pattern divided-light upper sashes and clear glass below—one of the many details that makes this home so special. The spacious front living room features custom built-ins, a fireplace, and pocket doors connecting both the foyer and dining room. The large dining room is ready for holidays, celebrations, and everyday dinners, with a side door opening directly onto the wraparound porch. The updated kitchen blends classic character with modern function, featuring a large center island, wall oven, cooktop, built-in cabinetry, and a charming original pass-through cupboard. A mudroom provides a practical everyday entrance and access to the covered rear porch, while a main-level half bath adds convenience. Upstairs are three generously sized bedrooms, including a spacious primary suite with a private full bath, plus an additional hall bath. An open loft area provides flexible space for an office, study, reading nook, or sitting area. The completely remodeled finished third floor adds another exceptional level of living space, with tall ceilings, abundant natural light, a large recreation room, separate den, and laundry area. Use it as an office, studio, exercise space, media room, hobby room, or private retreat. A unique glass-floor feature allows light to pass through and adds an unexpected architectural element. Outside, there is room to breathe—something increasingly difficult to find right in the heart of town. The large, level property stretches from Main Street to Green Street with access from both streets, offering an expansive front lawn and spacious backyard. A detached one-car garage adds convenience, while eligibility for future subdivision through the Town of Middletown adds another unique dimension. Additional features include air conditioning, radiator heat, updated electrical, a clean unfinished basement for utility and storage, and eligibility for a one-year home warranty. Perhaps what makes this home most memorable is simply the feeling of it—the sunlight, tall ceilings, warmth of the wood floors, beautiful architectural details, and the ability to step onto that wonderful wraparound porch and watch Main Street go by. Filled with charm and personality, yet offering the light, space, and functionality for the way we live today, this gracious Painted Lady is ready for its next chapter.

305 E Main St, Middletown

Listing courtesy of RE/MAX Results. Contact:

Selling Office: RE/MAX Results.

$670,000

Selling Office: Unrepresented.

3032 Barber Ln, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact:

$651,000

Some homes simply have a soul—and this beautifully preserved 1920's Craftsman bungalow is one of them. Situated on a rare lot and a half in the heart of historic Middletown, this contributing home to both the National and Frederick Historic Registers has been lovingly cared for by just two families throughout its history. From the moment you arrive, you’ll notice the timeless character that sets this home apart. Tall original windows frame mature trees, gardens, and changing seasonal views from nearly every room, filling the home with natural light and creating a peaceful connection to the outdoors. Original wood floors, handcrafted trim work, pocket doors, custom storm windows, and historic architectural details blend seamlessly with thoughtful modern updates. The sellers have always appreciated the home’s solid clay block construction, which provides a remarkably quiet, comfortable feel and exceptional insulation rarely found in homes of this era. At the heart of the home is a beautifully renovated kitchen that has served as the gathering place for everything from weeknight dinners to holiday celebrations. A spacious island welcomes family and friends, while the thoughtful layout offers the perfect balance of openness and functionality. Upstairs, generously sized bedrooms, second-floor laundry, and an updated bath provide modern convenience while honoring the home’s historic roots. Outside, the property unfolds into a collection of extraordinary outdoor living spaces. Enjoy sunrise views from the backyard, summer sunsets from the welcoming front porch, abundant gardens, mature trees, a kitchen garden, and a private backyard retreat complete with a pergola and gas firepit. Every outdoor space offers its own unique experience, creating a rare sense of privacy and connection to nature in the heart of town. Major improvements include a renovated kitchen and baths, NTI combi-boiler, roof, insulation, updated electrical, propane installation, custom storm windows, and asbestos remediation. Perhaps most special of all are the home’s original handcrafted windows and custom-built storm windows—an increasingly rare treasure that has been lovingly maintained and thoughtfully restored. Throughout their stewardship, the sellers viewed themselves less as owners and more as caretakers of something truly special, dedicated to preserving the integrity and craftsmanship the original builders intended. The result is a home that honors its past while offering the comfort, beauty, and functionality today’s buyers desire. A rare opportunity to own a piece of Middletown history—where historic craftsmanship, thoughtful updates, beautiful gardens, and small-town charm come together to create something truly exceptional. Showings to begin August 1st, not before.

Some homes simply have a soul—and this beautifully preserved 1920's Craftsman bungalow is one of them. Situated on a rare lot and a half in the heart of historic Middletown, this contributing home to both the National and Frederick Historic Registers has been lovingly cared for by just two families throughout its history. From the moment you arrive, you’ll notice the timeless character that sets this home apart. Tall original windows frame mature trees, gardens, and changing seasonal views from nearly every room, filling the home with natural light and creating a peaceful connection to the outdoors. Original wood floors, handcrafted trim work, pocket doors, custom storm windows, and historic architectural details blend seamlessly with thoughtful modern updates. The sellers have always appreciated the home’s solid clay block construction, which provides a remarkably quiet, comfortable feel and exceptional insulation rarely found in homes of this era. At the heart of the home is a beautifully renovated kitchen that has served as the gathering place for everything from weeknight dinners to holiday celebrations. A spacious island welcomes family and friends, while the thoughtful layout offers the perfect balance of openness and functionality. Upstairs, generously sized bedrooms, second-floor laundry, and an updated bath provide modern convenience while honoring the home’s historic roots. Outside, the property unfolds into a collection of extraordinary outdoor living spaces. Enjoy sunrise views from the backyard, summer sunsets from the welcoming front porch, abundant gardens, mature trees, a kitchen garden, and a private backyard retreat complete with a pergola and gas firepit. Every outdoor space offers its own unique experience, creating a rare sense of privacy and connection to nature in the heart of town. Major improvements include a renovated kitchen and baths, NTI combi-boiler, roof, insulation, updated electrical, propane installation, custom storm windows, and asbestos remediation. Perhaps most special of all are the home’s original handcrafted windows and custom-built storm windows—an increasingly rare treasure that has been lovingly maintained and thoughtfully restored. Throughout their stewardship, the sellers viewed themselves less as owners and more as caretakers of something truly special, dedicated to preserving the integrity and craftsmanship the original builders intended. The result is a home that honors its past while offering the comfort, beauty, and functionality today’s buyers desire. A rare opportunity to own a piece of Middletown history—where historic craftsmanship, thoughtful updates, beautiful gardens, and small-town charm come together to create something truly exceptional. Showings to begin August 1st, not before.

106 Prospect St, Middletown

Listing courtesy of RE/MAX Results. Contact:

Selling Office: Redfin Corp.

$624,955

Selling Office: Blenheim Marketing LLC.

2844 Bernstein Cir, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact:

$585,000

Charming Victorian Home offers the perfect blend of historic character and modern upgrades in the heart of Middletown. Vehicle access from both Beautiful Main Street and Convenient Broad Street, this home provides excellent accessibility and curb appeal. Beautiful Hard Wood Floors, Wainscoting, Crown Molding throughout. Main Level Features Separate Living Room, Dining Room w/Pocket Doors, Family Room, Kitchen, Updated Full Bath. Kitchen includes Center Island w/Seating, Gas Cook-top, and Pantry. (2024: New Refrigerator, New Gas Cooktop, New Kitchen Disposal). Upper Level Features 3 Nice Size Bedrooms. Updated Full Bath with Heated Floor, Large Glass Front Shower, Custom Cabinets, Makeup Vanity, and Jetted Claw Foot Tub. An Oversized 2nd Floor Laundry Room with a Pocket Door features a second kitchenette area including upper and lower cabinets and countertop space. New Washer and Dryer in 2022. Access to Attic and a Small room with view overlooking back yard. Property also includes a Large/Tall Detached 2 Car Garage w/Tesla EV Charger. Attached to the Garage is a Large Shop/General Use Space. Home includes a Large Rear Deck off the Kitchen. A Whole-House Backup Power Generator w/New Battery in 2026. 2 Whole-House Surge Protectors, 2 Outdoor A/C unit Surge Protectors installed 2025. 4 Propane Tanks. This Listing also includes an Attached Additional Lot of Record w/Temp Restrictions. Conveniently located near schools, shopping, dining, parks, and easy access to major highways. This well-cared-for Victorian on Main Street is truly special.

Charming Victorian Home offers the perfect blend of historic character and modern upgrades in the heart of Middletown. Vehicle access from both Beautiful Main Street and Convenient Broad Street, this home provides excellent accessibility and curb appeal. Beautiful Hard Wood Floors, Wainscoting, Crown Molding throughout. Main Level Features Separate Living Room, Dining Room w/Pocket Doors, Family Room, Kitchen, Updated Full Bath. Kitchen includes Center Island w/Seating, Gas Cook-top, and Pantry. (2024: New Refrigerator, New Gas Cooktop, New Kitchen Disposal). Upper Level Features 3 Nice Size Bedrooms. Updated Full Bath with Heated Floor, Large Glass Front Shower, Custom Cabinets, Makeup Vanity, and Jetted Claw Foot Tub. An Oversized 2nd Floor Laundry Room with a Pocket Door features a second kitchenette area including upper and lower cabinets and countertop space. New Washer and Dryer in 2022. Access to Attic and a Small room with view overlooking back yard. Property also includes a Large/Tall Detached 2 Car Garage w/Tesla EV Charger. Attached to the Garage is a Large Shop/General Use Space. Home includes a Large Rear Deck off the Kitchen. A Whole-House Backup Power Generator w/New Battery in 2026. 2 Whole-House Surge Protectors, 2 Outdoor A/C unit Surge Protectors installed 2025. 4 Propane Tanks. This Listing also includes an Attached Additional Lot of Record w/Temp Restrictions. Conveniently located near schools, shopping, dining, parks, and easy access to major highways. This well-cared-for Victorian on Main Street is truly special.

124 E Main St, Middletown

Listing courtesy of Real Estate Teams, LLC. Contact:

Selling Office: Epique Realty.

$575,000

Very unusual historic home in the heart of Middletown. Just blocks from new YMCA. Home was assembled in 1944-1948 from parts of multiple historic homes being demolished to make room for post war housing. The front facade and much of the brick exterior were transported and re-assembled on site, proudly boasting 1736 construction. Add various plank floors, beamed ceiling, fireplaces with Mable surround or beautiful delft tiles, decorative moldings, beautiful wood doors.... You may think you can visualize how beautiful this house is, but it will still surprise you, now add recent kitchen, a first floor primary suite with spacious en-suite, large closets and room for washer and dryer. Wait there's more!! Recent HVAC (2 zone) a large Amish built workshop shed , a carriage house/pool house with full bathroom. Ornate gardens and landscaping, a koi pond, brick walkways encased with privacy fencing , yet walking distance to schools, stores , dining and entertainment. A Must see to imagine. Book your private tour as soon as possible.

4 Beds ⋅ 3 Baths

Very unusual historic home in the heart of Middletown. Just blocks from new YMCA. Home was assembled in 1944-1948 from parts of multiple historic homes being demolished to make room for post war housing. The front facade and much of the brick exterior were transported and re-assembled on site, proudly boasting 1736 construction. Add various plank floors, beamed ceiling, fireplaces with Mable surround or beautiful delft tiles, decorative moldings, beautiful wood doors.... You may think you can visualize how beautiful this house is, but it will still surprise you, now add recent kitchen, a first floor primary suite with spacious en-suite, large closets and room for washer and dryer. Wait there's more!! Recent HVAC (2 zone) a large Amish built workshop shed , a carriage house/pool house with full bathroom. Ornate gardens and landscaping, a koi pond, brick walkways encased with privacy fencing , yet walking distance to schools, stores , dining and entertainment. A Must see to imagine. Book your private tour as soon as possible.

12 E Cochran St, Middletown

Listing courtesy of BHHS Fox & Roach-Christiana. Contact:

Selling Office: BHHS Fox & Roach-Greenville.

$560,000

This well built, all brick rancher sits on a corner lot and is in excellent condition. It has 4 generous sized bedrooms and 3 full bathrooms (every bedroom has direct access to a full bath) and an in-law suite with 2 separate entrances. Gas fireplace on main level and wood burning fireplace in finished basement. Beautiful hardwood floors in the foyer, hallway, dining room, living room and 3 bedrooms. Huge finished walk-out basement with large storage area. Floors in basement (rec room and basement bedroom) were recently replaced. Circular driveway and 2 car garage with a hot tub!

4 Beds ⋅ 3 Baths

This well built, all brick rancher sits on a corner lot and is in excellent condition. It has 4 generous sized bedrooms and 3 full bathrooms (every bedroom has direct access to a full bath) and an in-law suite with 2 separate entrances. Gas fireplace on main level and wood burning fireplace in finished basement. Beautiful hardwood floors in the foyer, hallway, dining room, living room and 3 bedrooms. Huge finished walk-out basement with large storage area. Floors in basement (rec room and basement bedroom) were recently replaced. Circular driveway and 2 car garage with a hot tub!

215 Broad St, Middletown

Listing courtesy of RE/MAX Results. Contact:

Selling Office: Real Estate Teams, LLC.

$530,000

Welcome home to this beautifully maintained custom-built 3-bedroom duplex in the heart of highly sought-after Middletown, Maryland. Designed with quality and efficiency in mind, this exceptional home features durable 2x6 exterior wall construction, higher R-value insulation, a 2025 installed heat pump and air conditioning system, and a long-lasting 40-year roof. Enjoy the charm of small-town living from the inviting covered front porch or relax on the rear patio complete with a sunshade awning—perfect for entertaining or enjoying quiet evenings outdoors. Inside, you’ll find thoughtful upgrades throughout, including custom cherry kitchen cabinetry, hardwood flooring, tile-surround showers, recessed lighting, ceiling fans, crown molding, and an elegant tray ceiling. Bay windows fill the home with natural light, while entry-level bedrooms and laundry provide convenient one-level living options. The location is truly unmatched. Situated within walking distance of Middletown Elementary, Middle, and High Schools, Middletown Park, the brand-new public library, and the shops and restaurants of downtown Middletown, you’ll enjoy easy access to everything the community has to offer. Leave the parking worries behind and stroll to Heritage Days celebrations, holiday parades, local events, and evenings out on the town. Combining quality construction, modern efficiency, and an unbeatable walkable location, this home offers the perfect blend of comfort, convenience, and timeless appeal.

Welcome home to this beautifully maintained custom-built 3-bedroom duplex in the heart of highly sought-after Middletown, Maryland. Designed with quality and efficiency in mind, this exceptional home features durable 2x6 exterior wall construction, higher R-value insulation, a 2025 installed heat pump and air conditioning system, and a long-lasting 40-year roof. Enjoy the charm of small-town living from the inviting covered front porch or relax on the rear patio complete with a sunshade awning—perfect for entertaining or enjoying quiet evenings outdoors. Inside, you’ll find thoughtful upgrades throughout, including custom cherry kitchen cabinetry, hardwood flooring, tile-surround showers, recessed lighting, ceiling fans, crown molding, and an elegant tray ceiling. Bay windows fill the home with natural light, while entry-level bedrooms and laundry provide convenient one-level living options. The location is truly unmatched. Situated within walking distance of Middletown Elementary, Middle, and High Schools, Middletown Park, the brand-new public library, and the shops and restaurants of downtown Middletown, you’ll enjoy easy access to everything the community has to offer. Leave the parking worries behind and stroll to Heritage Days celebrations, holiday parades, local events, and evenings out on the town. Combining quality construction, modern efficiency, and an unbeatable walkable location, this home offers the perfect blend of comfort, convenience, and timeless appeal.

22 E Green St, Middletown

Listing courtesy of EXP Realty, LLC. Contact:

Welcome Home to 8209 Old Hagerstown a beautifully updated and spacious 5-bedroom, 3-bathroom home located in the highly sought-after Middletown, MD. This move-in ready property features modern upgrades throughout, offering the perfect blend of style, comfort, and functionality. Enjoy generous living spaces, an updated kitchen featuring SS Appliances, white shaker cabinets, quartz counters and MORE! Well-appointed bedrooms ideal for both everyday living and entertaining. Fully finished basement offers so much space for entertaining. Large deck great for relaxation! Private off street parking in driveway and SO MUCH MORE! Situated in a desirable location close to commuter routes and many attractions —this is a home you won’t want to miss! All new Siding, New Gutters, New Roof, Freshly painted interior of Garage, New Well Pump and SO MUCH MORE!!

$499,900

5 Beds ⋅ 3 Baths

Welcome Home to 8209 Old Hagerstown a beautifully updated and spacious 5-bedroom, 3-bathroom home located in the highly sought-after Middletown, MD. This move-in ready property features modern upgrades throughout, offering the perfect blend of style, comfort, and functionality. Enjoy generous living spaces, an updated kitchen featuring SS Appliances, white shaker cabinets, quartz counters and MORE! Well-appointed bedrooms ideal for both everyday living and entertaining. Fully finished basement offers so much space for entertaining. Large deck great for relaxation! Private off street parking in driveway and SO MUCH MORE! Situated in a desirable location close to commuter routes and many attractions —this is a home you won’t want to miss! All new Siding, New Gutters, New Roof, Freshly painted interior of Garage, New Well Pump and SO MUCH MORE!!

8209 Old Hagerstown Rd, Middletown

Listing courtesy of Alberti Realty, LLC. Contact:

Renovated oversized farmhouse nestled in the heart of Middletown Valley, where timeless character meets modern comfort. This charming 3-bedroom, 2-full-bath home is truly move-in ready and filled with warmth and natural light. On the main floor you will find a spacious open concept living area with custom fireplace, while the updated kitchen showcases SS appliances/quartz countertops/white shaker cabinets/ a custom tiled backsplash and lots of countertop space for entertaining. On the 2nd floor there are 3 large bedrooms, a laundry room, a large full bath with custom tile work and owners suite with a access to a private rear balcony as well as access to the full walk up attic! Outside you can relax on the covered front porch and take in the peaceful surroundings, or entertain in the generous yard framed by scenic valley views. A standout feature is the two-story “man cave” with a workshop below and an upper-level living space—ideal for conversion into a private studio, home office, or creative retreat. On top of all this there is a brand new roof, new furnace and new AC!

$444,900

Renovated oversized farmhouse nestled in the heart of Middletown Valley, where timeless character meets modern comfort. This charming 3-bedroom, 2-full-bath home is truly move-in ready and filled with warmth and natural light. On the main floor you will find a spacious open concept living area with custom fireplace, while the updated kitchen showcases SS appliances/quartz countertops/white shaker cabinets/ a custom tiled backsplash and lots of countertop space for entertaining. On the 2nd floor there are 3 large bedrooms, a laundry room, a large full bath with custom tile work and owners suite with a access to a private rear balcony as well as access to the full walk up attic! Outside you can relax on the covered front porch and take in the peaceful surroundings, or entertain in the generous yard framed by scenic valley views. A standout feature is the two-story “man cave” with a workshop below and an upper-level living space—ideal for conversion into a private studio, home office, or creative retreat. On top of all this there is a brand new roof, new furnace and new AC!

8109 Old Hagerstown Rd, Middletown

Listing courtesy of Hyatt & Company Real Estate LLC. Contact:

TAKING BACK UP OFFERS - SHAKY FINANING - Welcome to 304 Washington Street, a charming Cape Cod nestled in the heart of Middletown, Maryland—where natural light, character, and walkability take center stage. Built by Lancaster Homes, this residence is tucked on a quiet cul-de-sac and set on approximately 0.18 acres, offering 1,229 square feet above grade with a thoughtful and inviting layout. The main level features a first-floor primary bedroom with a full bath, along with a light-filled family room, kitchen, and convenient half bath designed for everyday living. Recent updates create a fresh, move-in-ready feel, including new luxury vinyl plank flooring throughout the main level, brand-new carpet upstairs, and a freshly painted exterior that enhances curb appeal. All three bedrooms offer walk-in closets, with the upstairs bedrooms featuring separate sinks within the shared Jack and Jill full bath for added functionality. The unfinished basement provides excellent storage with built-in shelving, while additional storage continues in the attached one-car garage, complete with a rear door for easy access to both the patio and front of the home. From the front porch, a bird’s-eye perspective reveals a more level setting, leading to a flatter, walkable backyard that adds to the home’s everyday ease. The yard is thoughtfully maintained with trees and plantings and offers beautiful sunset views stretching toward the mountains—a truly special feature. A small rear patio creates the perfect spot to relax and enjoy the outdoor space. Located in a quiet, friendly neighborhood just moments from Middletown’s Historic Main Street, shops, dining, parks, schools, and library, this home offers the charm of in-town living with the ease of a truly walkable lifestyle.

$428,000

TAKING BACK UP OFFERS - SHAKY FINANING - Welcome to 304 Washington Street, a charming Cape Cod nestled in the heart of Middletown, Maryland—where natural light, character, and walkability take center stage. Built by Lancaster Homes, this residence is tucked on a quiet cul-de-sac and set on approximately 0.18 acres, offering 1,229 square feet above grade with a thoughtful and inviting layout. The main level features a first-floor primary bedroom with a full bath, along with a light-filled family room, kitchen, and convenient half bath designed for everyday living. Recent updates create a fresh, move-in-ready feel, including new luxury vinyl plank flooring throughout the main level, brand-new carpet upstairs, and a freshly painted exterior that enhances curb appeal. All three bedrooms offer walk-in closets, with the upstairs bedrooms featuring separate sinks within the shared Jack and Jill full bath for added functionality. The unfinished basement provides excellent storage with built-in shelving, while additional storage continues in the attached one-car garage, complete with a rear door for easy access to both the patio and front of the home. From the front porch, a bird’s-eye perspective reveals a more level setting, leading to a flatter, walkable backyard that adds to the home’s everyday ease. The yard is thoughtfully maintained with trees and plantings and offers beautiful sunset views stretching toward the mountains—a truly special feature. A small rear patio creates the perfect spot to relax and enjoy the outdoor space. Located in a quiet, friendly neighborhood just moments from Middletown’s Historic Main Street, shops, dining, parks, schools, and library, this home offers the charm of in-town living with the ease of a truly walkable lifestyle.

304 Washington St, Middletown

Listing courtesy of RE/MAX Results. Contact:

Selling Office: Signature Home Realty LLC.

$417,000

Welcome to your dream home, located in the heart of Middletown! Where you can walk or ride your bike to the new county library, Silver Lake Park, the new YMCA, and Historic downtown with its charming restaurants and shops. In the highly sought after Appoquinimick school district, the Niche A rated Silver Lake Elementary school is right at the end of the block! This gorgeous three bedroom two full bath Ranch home, with a full finished basement, has been lovingly renovated. Where to even begin?? This home is a combination of modern and charming. Gorgeous hardwood floors , the kitchen has been given a beautiful upgrade with new kitchen cabinets, stunning quartz countertops , new appliances and a large stainless steel Kraus sink ( 2022/23). Off the kitchen is a large light filled sunporch where you can spend your days and nights relaxing and enjoying the view of your .24 acre lot with upgraded landscaping and your cedar raised bed garden (2024). Both full bathrooms have been done , and done well! All new sinks, vanities, toilets , light fixtures... Nothing was missed! This stunner features over 1800 sq ft with main floor living, and the added bonus of a large beautifully finished basement. No detail was missed in upgrading this lower space. All new drywall, and foam board insulation to replace the dated looking paneling , flooring upgraded to beautiful LVP's, full renovated bathroom, and new drop ceiling. This gorgeous space has unlimited possibilities. This home is a real showstopper . Highlights include: New recessed lighting and ceiling fans, New interior doors, new windows and trim, new Mitsubishi heat pump/ ceiling cassette mini splits for heat and cooling (three total, each can control the temperature separately for zone heating/cooling), new washer and dryer, new exterior shutters, new electric water heater and so much more!

Welcome to your dream home, located in the heart of Middletown! Where you can walk or ride your bike to the new county library, Silver Lake Park, the new YMCA, and Historic downtown with its charming restaurants and shops. In the highly sought after Appoquinimick school district, the Niche A rated Silver Lake Elementary school is right at the end of the block! This gorgeous three bedroom two full bath Ranch home, with a full finished basement, has been lovingly renovated. Where to even begin?? This home is a combination of modern and charming. Gorgeous hardwood floors , the kitchen has been given a beautiful upgrade with new kitchen cabinets, stunning quartz countertops , new appliances and a large stainless steel Kraus sink ( 2022/23). Off the kitchen is a large light filled sunporch where you can spend your days and nights relaxing and enjoying the view of your .24 acre lot with upgraded landscaping and your cedar raised bed garden (2024). Both full bathrooms have been done , and done well! All new sinks, vanities, toilets , light fixtures... Nothing was missed! This stunner features over 1800 sq ft with main floor living, and the added bonus of a large beautifully finished basement. No detail was missed in upgrading this lower space. All new drywall, and foam board insulation to replace the dated looking paneling , flooring upgraded to beautiful LVP's, full renovated bathroom, and new drop ceiling. This gorgeous space has unlimited possibilities. This home is a real showstopper . Highlights include: New recessed lighting and ceiling fans, New interior doors, new windows and trim, new Mitsubishi heat pump/ ceiling cassette mini splits for heat and cooling (three total, each can control the temperature separately for zone heating/cooling), new washer and dryer, new exterior shutters, new electric water heater and so much more!

102 E Redding St, Middletown

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

Selling Office: Compass.

$399,999

Welcome to this inviting rancher tucked into the heart of Middletown where you can enjoy scenic views and walk for ice cream all in a few steps. This one screams for ice cream. Just kidding. It screams LOCATION, LOCATION, LOCATION! No HOA and under $400K. That should be a headline! Inside, you'll find three bedrooms, three baths and an easy, open layout designed for everyday living. Neutral paint, LVP flooring and stainless appliances make the upper level shine bright-like a diamond. A newly built breezeway that connects the oversized single car garage is charming and will keep you dry! A cute little backyard to get creative with. Bring the chickens or a play set. It's open space, waiting for you. The lower level is finished and screams movie room and let's hang out! Flex space and plenty of storage. Did I mention Middletown schools? This district is known for its school spirit and community. GO Knights! Views, Updates, space, NO HOA and BRAND NEW HVAC!!! THIS one checks all the boxes. YOU ARE HOME!!

Welcome to this inviting rancher tucked into the heart of Middletown where you can enjoy scenic views and walk for ice cream all in a few steps. This one screams for ice cream. Just kidding. It screams LOCATION, LOCATION, LOCATION! No HOA and under $400K. That should be a headline! Inside, you'll find three bedrooms, three baths and an easy, open layout designed for everyday living. Neutral paint, LVP flooring and stainless appliances make the upper level shine bright-like a diamond. A newly built breezeway that connects the oversized single car garage is charming and will keep you dry! A cute little backyard to get creative with. Bring the chickens or a play set. It's open space, waiting for you. The lower level is finished and screams movie room and let's hang out! Flex space and plenty of storage. Did I mention Middletown schools? This district is known for its school spirit and community. GO Knights! Views, Updates, space, NO HOA and BRAND NEW HVAC!!! THIS one checks all the boxes. YOU ARE HOME!!

98 Summers Dr, Middletown

Listing courtesy of Century 21 Redwood Realty. Contact:

Selling Office: Real Estate Teams, LLC.

$375,000

Welcome home to this beautifully updated home where timeless charm meets modern comfort! Be prepared to Fall In Love! From the inviting front porch to the stylish finishes throughout, this move-in-ready property offers the perfect blend of character, functionality, and outdoor living. Step inside to discover a bright and spacious living room that flows seamlessly into the generous dining room—an ideal space for holiday gatherings, dinner parties, or everyday meals. The beautifully updated kitchen features ample cabinetry, modern finishes, and direct access to the charming screened porch, creating the perfect spot to enjoy your morning coffee, unwind with an evening drink, or dine outdoors while overlooking the backyard. Upstairs, you'll find three generously sized bedrooms, including a spacious 19'2" x 11'7" primary bedroom with plenty of room for a king-sized bed and additional furniture. Two additional bedrooms measure 12'7" x 11'2" and 12'3" x 9'8", offering comfortable accommodations for family, guests, or a home office. A walk-up attic provides exceptional storage or future expansion potential, while the full basement offers even more storage and workspace opportunities. The backyard is truly an extension of the home, featuring a beautifully designed paver patio that's perfect for entertaining, grilling, or relaxing around a fire pit. The fenced yard provides privacy and space for pets, gardening, or outdoor play, while the detached garage is currently divided into 2 areas- a workshop and a recreation room. This would be perfect for an art studio, home business, and many other options. The long driveway offers abundant parking and storage. Ideally located within walking distance to local schools, parks, and downtown Middletown amenities, this home combines classic charm with thoughtful modern updates in a location that's hard to beat. Don't miss your opportunity to own this beautifully maintained property that offers space, style, and exceptional indoor-outdoor living!

Welcome home to this beautifully updated home where timeless charm meets modern comfort! Be prepared to Fall In Love! From the inviting front porch to the stylish finishes throughout, this move-in-ready property offers the perfect blend of character, functionality, and outdoor living. Step inside to discover a bright and spacious living room that flows seamlessly into the generous dining room—an ideal space for holiday gatherings, dinner parties, or everyday meals. The beautifully updated kitchen features ample cabinetry, modern finishes, and direct access to the charming screened porch, creating the perfect spot to enjoy your morning coffee, unwind with an evening drink, or dine outdoors while overlooking the backyard. Upstairs, you'll find three generously sized bedrooms, including a spacious 19'2" x 11'7" primary bedroom with plenty of room for a king-sized bed and additional furniture. Two additional bedrooms measure 12'7" x 11'2" and 12'3" x 9'8", offering comfortable accommodations for family, guests, or a home office. A walk-up attic provides exceptional storage or future expansion potential, while the full basement offers even more storage and workspace opportunities. The backyard is truly an extension of the home, featuring a beautifully designed paver patio that's perfect for entertaining, grilling, or relaxing around a fire pit. The fenced yard provides privacy and space for pets, gardening, or outdoor play, while the detached garage is currently divided into 2 areas- a workshop and a recreation room. This would be perfect for an art studio, home business, and many other options. The long driveway offers abundant parking and storage. Ideally located within walking distance to local schools, parks, and downtown Middletown amenities, this home combines classic charm with thoughtful modern updates in a location that's hard to beat. Don't miss your opportunity to own this beautifully maintained property that offers space, style, and exceptional indoor-outdoor living!

408 S Cass St, Middletown

Listing courtesy of Century 21 Gold Key Realty. Contact:

Selling Office: Century 21 Gold Key Realty.

$369,000

This 3/4 Bedroom home has 2 Full Baths and sits in a country setting. It has been completely remodeled inside and out. New siding, new roof, new windows and landscaping on the outside. The inside has been freshly painted, all new flooring, kitchen has new stainless steel appliances and new cabinets. The eat-in kitchen also has new counter tops, beautiful backsplash and top of the line kitchen sink. The basement family room has built in book shelves and a full bath off of it. The office/ 4th bedroom has built in book shelves as well. There is plenty of storage and the laundry room in the basement too. Large rear yard! Convenient to shopping, schools, travel and historic sites.

This 3/4 Bedroom home has 2 Full Baths and sits in a country setting. It has been completely remodeled inside and out. New siding, new roof, new windows and landscaping on the outside. The inside has been freshly painted, all new flooring, kitchen has new stainless steel appliances and new cabinets. The eat-in kitchen also has new counter tops, beautiful backsplash and top of the line kitchen sink. The basement family room has built in book shelves and a full bath off of it. The office/ 4th bedroom has built in book shelves as well. There is plenty of storage and the laundry room in the basement too. Large rear yard! Convenient to shopping, schools, travel and historic sites.

323 S Jefferson St S, Middletown

Listing courtesy of Mackintosh , Inc.. Contact:

Selling Office: Kelley Real Estate Professionals.

$360,000

Rare Opportunity: Own 2 Units for the Price of 1 in Historic Middletown! Discover this exceptional multi-unit property in the heart of charming, historic Middletown—perfectly positioned for a lifestyle of convenience, character, and potential. Stroll to your favorite restaurants, boutique shopping on vibrant Main Street, and scenic local parks featuring jogging trails, streams, and lush green spaces. Immerse yourself in the rich history and timeless beauty this community has to offer! The main residence is a classic Historic Victorian boasting 3 bedrooms and 1.5 baths, rich with the architectural elegance and original details you’d expect: ornate moldings, grand proportions, and old-world charm. This diamond in the rough offers incredible potential for the visionary buyer or investor—Investor Alert! The primary residence requires renovation and will not qualify for standard financing options (such as FHA 203(b), Conventional, VA, or USDA) due to the lack of operational heat and other needed repairs. Bring your creativity and contractor to restore this beauty to its former glory. Complementing the main home is a spacious detached 3-bedroom, 1-bath apartment with its own entrance, located at the rear of the property. This unit is in excellent, move-in ready condition and includes a 3-car garage—an incredible bonus for parking, storage, or hobbies. Versatile Living Options: Occupy the apartment while renovating the main Victorian at your own pace or possible rental /Airbnb for strong income potential. Ideal for extended family, guests, or generating passive revenue in a highly desirable historic district. This rare package combines historic appeal, modern practicality, and strong investment upside in one of Middletown’s most walkable locations. Don’t miss your chance to own a piece of history with immediate income or living flexibility! Schedule your private showing today—properties like this don’t last long.

6 Beds ⋅ 4 Baths

Rare Opportunity: Own 2 Units for the Price of 1 in Historic Middletown! Discover this exceptional multi-unit property in the heart of charming, historic Middletown—perfectly positioned for a lifestyle of convenience, character, and potential. Stroll to your favorite restaurants, boutique shopping on vibrant Main Street, and scenic local parks featuring jogging trails, streams, and lush green spaces. Immerse yourself in the rich history and timeless beauty this community has to offer! The main residence is a classic Historic Victorian boasting 3 bedrooms and 1.5 baths, rich with the architectural elegance and original details you’d expect: ornate moldings, grand proportions, and old-world charm. This diamond in the rough offers incredible potential for the visionary buyer or investor—Investor Alert! The primary residence requires renovation and will not qualify for standard financing options (such as FHA 203(b), Conventional, VA, or USDA) due to the lack of operational heat and other needed repairs. Bring your creativity and contractor to restore this beauty to its former glory. Complementing the main home is a spacious detached 3-bedroom, 1-bath apartment with its own entrance, located at the rear of the property. This unit is in excellent, move-in ready condition and includes a 3-car garage—an incredible bonus for parking, storage, or hobbies. Versatile Living Options: Occupy the apartment while renovating the main Victorian at your own pace or possible rental /Airbnb for strong income potential. Ideal for extended family, guests, or generating passive revenue in a highly desirable historic district. This rare package combines historic appeal, modern practicality, and strong investment upside in one of Middletown’s most walkable locations. Don’t miss your chance to own a piece of history with immediate income or living flexibility! Schedule your private showing today—properties like this don’t last long.

33 E Main St, Middletown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: Keller Williams Realty Centre.

$345,000

Charming, completely remodeled 3 bedroom, 1 1/2 bath twin home in downtown Middletown within walking distance to shopping and dining! The current owners have lovingly improved this home over the past three years. The welcoming covered front porch invites you into the main level which was completely opened up to provide a true open concept design. The kitchen was completely remodeled with white cabinets, large island, butcher block countertops and stainless appliances. The main level also has a half bath, all new overhead lighting, fresh paint and beautiful maple flooring! Door from the kitchen leads to the covered rear deck looking over the very large rear yard with gardens filled with native plants, vegetable garden and flowers. Upstairs are three generously sized bedrooms with good closet space, plus a bonus room off of one bedroom that could be a nursery, a small office or large walk-in closet. The full bath was also remodeled with tile floor and double vanity. Walk up attic for additional storage. Unfinished basement with updated electric and plumbing. Hurry to schedule your private tour today!

Charming, completely remodeled 3 bedroom, 1 1/2 bath twin home in downtown Middletown within walking distance to shopping and dining! The current owners have lovingly improved this home over the past three years. The welcoming covered front porch invites you into the main level which was completely opened up to provide a true open concept design. The kitchen was completely remodeled with white cabinets, large island, butcher block countertops and stainless appliances. The main level also has a half bath, all new overhead lighting, fresh paint and beautiful maple flooring! Door from the kitchen leads to the covered rear deck looking over the very large rear yard with gardens filled with native plants, vegetable garden and flowers. Upstairs are three generously sized bedrooms with good closet space, plus a bonus room off of one bedroom that could be a nursery, a small office or large walk-in closet. The full bath was also remodeled with tile floor and double vanity. Walk up attic for additional storage. Unfinished basement with updated electric and plumbing. Hurry to schedule your private tour today!

311 S Cass St, Middletown

Listing courtesy of Patterson-Schwartz-Newark. Contact:

Selling Office: Patterson-Schwartz-Hockessin.

$330,000

Welcome to 108 E Cochran Avenue in the heart of Middletown, Delaware. This cute house has it all - including location. The moment you arrive you will pull up in the driveway and feel like you belong here. The covered porch is wonderful and adds to the curb appeal and style of hte home. Inside, the kitchen is open and spacious. There are plenty of cabinets along with ample counter space. The living room is wide open with large windows and tons of natural light. The rear of the home has a enclosed three-season room where the windows are amazing. There are three ample bedrooms ensuring everyone has a place to call their own. Downstairs the full basement is perfect for extra storage space. The back yard is flat and perfect for spending time outdoors during those summer barbecues with family and friends. Come see this one today!.

3 Beds ⋅ 1 Baths

Welcome to 108 E Cochran Avenue in the heart of Middletown, Delaware. This cute house has it all - including location. The moment you arrive you will pull up in the driveway and feel like you belong here. The covered porch is wonderful and adds to the curb appeal and style of hte home. Inside, the kitchen is open and spacious. There are plenty of cabinets along with ample counter space. The living room is wide open with large windows and tons of natural light. The rear of the home has a enclosed three-season room where the windows are amazing. There are three ample bedrooms ensuring everyone has a place to call their own. Downstairs the full basement is perfect for extra storage space. The back yard is flat and perfect for spending time outdoors during those summer barbecues with family and friends. Come see this one today!.

108 E Cochran St, Middletown

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

Selling Office: Empower Real Estate, LLC.

$310,000

Easy Middletown Living on a Rare .39-Acre Lot! Welcome to this thoughtfully updated ranch home located in the highly sought-after Appoquinimink School District, right in the heart of Middletown. Set on a rare 0.39-acre lot, this home offers the perfect blend of space, convenience, and walkability—just moments from Middletown’s shops, restaurants, and everyday amenities. Lovingly maintained, the home has been refreshed with a clean, modern feel while keeping its original charm. Bedrooms feature new drywall, fresh paint, 6" baseboards, and updated 6-panel doors with modern hardware, along with updated lighting, switches, and outlets throughout. The fully renovated bathroom offers an accessible shower and updated electrical. The kitchen includes updated flooring and backsplash, with room for the next owner to personalize further over time. Major improvements provide peace of mind, including a new roof (2026), new water heater, basement waterproofing (Drylock), partial French drain, sump pump, new basement windows, gutter guards, and popup drains. The basement has also been partially finished with drywall and updated laundry plumbing. Outside, enjoy a repaired screened porch, rebuilt rear steps, a freshly paved double-wide driveway with ample parking, and a spacious yard enhanced by recent tree removal—offering plenty of room to relax, entertain, or garden. This is a home where the heavy lifting has already been done, offering a solid, move-in ready opportunity with room to grow in one of Middletown’s most convenient locations. Private showings will begin after the Open House on Sunday, March 22nd.

3 Beds ⋅ 1 Baths

Easy Middletown Living on a Rare .39-Acre Lot! Welcome to this thoughtfully updated ranch home located in the highly sought-after Appoquinimink School District, right in the heart of Middletown. Set on a rare 0.39-acre lot, this home offers the perfect blend of space, convenience, and walkability—just moments from Middletown’s shops, restaurants, and everyday amenities. Lovingly maintained, the home has been refreshed with a clean, modern feel while keeping its original charm. Bedrooms feature new drywall, fresh paint, 6" baseboards, and updated 6-panel doors with modern hardware, along with updated lighting, switches, and outlets throughout. The fully renovated bathroom offers an accessible shower and updated electrical. The kitchen includes updated flooring and backsplash, with room for the next owner to personalize further over time. Major improvements provide peace of mind, including a new roof (2026), new water heater, basement waterproofing (Drylock), partial French drain, sump pump, new basement windows, gutter guards, and popup drains. The basement has also been partially finished with drywall and updated laundry plumbing. Outside, enjoy a repaired screened porch, rebuilt rear steps, a freshly paved double-wide driveway with ample parking, and a spacious yard enhanced by recent tree removal—offering plenty of room to relax, entertain, or garden. This is a home where the heavy lifting has already been done, offering a solid, move-in ready opportunity with room to grow in one of Middletown’s most convenient locations. Private showings will begin after the Open House on Sunday, March 22nd.

403 New St, Middletown

Listing courtesy of Redfin Corporation. Contact:

Step into timeless charm with a fresh, modern touch at this beautifully renovated 3-bedroom, 1.5-bath Middletown home. From the moment you enter, you're welcomed into a stunning living room with rich woodwork, setting the tone for the character and warmth of the home. Thoughtful updates make the home truly move-in ready, while a brand-new roof and HVAC system, along with refreshed landscaping, enhance curb appeal and provide valuable peace of mind for years to come. The main floor also includes a flexible space ideal for a home office or den. Upstairs are three light-filled bedrooms, including one with access to a private balcony. A walk-out basement provides excellent storage and leads to a fenced-in yard—perfect for pets, gardening, or entertaining. With its blend of classic detail and modern improvements, this home is a standout opportunity you won't want to miss.

$279,300

Step into timeless charm with a fresh, modern touch at this beautifully renovated 3-bedroom, 1.5-bath Middletown home. From the moment you enter, you're welcomed into a stunning living room with rich woodwork, setting the tone for the character and warmth of the home. Thoughtful updates make the home truly move-in ready, while a brand-new roof and HVAC system, along with refreshed landscaping, enhance curb appeal and provide valuable peace of mind for years to come. The main floor also includes a flexible space ideal for a home office or den. Upstairs are three light-filled bedrooms, including one with access to a private balcony. A walk-out basement provides excellent storage and leads to a fenced-in yard—perfect for pets, gardening, or entertaining. With its blend of classic detail and modern improvements, this home is a standout opportunity you won't want to miss.

68 E Water St, Middletown

Listing courtesy of Keller Williams of Central PA. Contact:

Selling Office: RE/MAX Pinnacle.

$260,000

Offer Deadline is Monday, May 11th, at 2pm. Enjoy country living right outside of downtown Middletown. This charming two bedroom, one bathroom home features fresh paint, stylish LVP flooring in the family room, beautiful granite countertops in the kitchen and a fenced in backyard. The hardwood staircase leads you to a small sitting area, full bathroom and two spacious bedrooms. Ample storage can be found in the large basement. Ideally located near scenic Catoctin Creek, this home offers a wonderful blend of comfort, convenience, and natural surroundings. Don’t miss out on your chance to make this house your next home!

2 Beds ⋅ 1 Baths

Offer Deadline is Monday, May 11th, at 2pm. Enjoy country living right outside of downtown Middletown. This charming two bedroom, one bathroom home features fresh paint, stylish LVP flooring in the family room, beautiful granite countertops in the kitchen and a fenced in backyard. The hardwood staircase leads you to a small sitting area, full bathroom and two spacious bedrooms. Ample storage can be found in the large basement. Ideally located near scenic Catoctin Creek, this home offers a wonderful blend of comfort, convenience, and natural surroundings. Don’t miss out on your chance to make this house your next home!

3204 Bidle Rd, Middletown

Listing courtesy of Charis Realty Group. Contact:

Selling Office: Charis Realty Group.

$260,000

Welcome home to this charming two-story townhome in Middletown featuring attractive stone accents and a thoughtfully designed layout perfect for comfortable everyday living. Step inside to a bright and inviting main level that includes a convenient half bath and a spacious living area that flows seamlessly into the kitchen. The kitchen is a standout feature with a custom tile backsplash and a peninsula/island with seating for stools, making it the perfect spot for casual meals, morning coffee, or a place for homework and gathering with friends and family. Upstairs, you’ll find a well-designed second floor with three bedrooms and two full bathrooms. The primary bedroom suite offers a private retreat, while two additional bedrooms share a hallway bathroom—ideal for family, guests, or a home office. Additional highlights include an attached garage and a full basement that offers excellent storage and the potential to be easily finished for additional living space. Step outside to enjoy the beautiful backyard patio, perfect for relaxing or entertaining, with trees lining the property for added privacy. Conveniently located just minutes from Harrisburg International Airport, the Pennsylvania Turnpike, and major commuter routes including Interstate 83, Interstate 81, and Pennsylvania Route 283, this home offers easy access to surrounding areas. The community itself is walkable and welcoming, with a park and lake nearby—perfect for enjoying the outdoors. This home combines style, convenience, and location—don’t miss the opportunity to make it yours!

Welcome home to this charming two-story townhome in Middletown featuring attractive stone accents and a thoughtfully designed layout perfect for comfortable everyday living. Step inside to a bright and inviting main level that includes a convenient half bath and a spacious living area that flows seamlessly into the kitchen. The kitchen is a standout feature with a custom tile backsplash and a peninsula/island with seating for stools, making it the perfect spot for casual meals, morning coffee, or a place for homework and gathering with friends and family. Upstairs, you’ll find a well-designed second floor with three bedrooms and two full bathrooms. The primary bedroom suite offers a private retreat, while two additional bedrooms share a hallway bathroom—ideal for family, guests, or a home office. Additional highlights include an attached garage and a full basement that offers excellent storage and the potential to be easily finished for additional living space. Step outside to enjoy the beautiful backyard patio, perfect for relaxing or entertaining, with trees lining the property for added privacy. Conveniently located just minutes from Harrisburg International Airport, the Pennsylvania Turnpike, and major commuter routes including Interstate 83, Interstate 81, and Pennsylvania Route 283, this home offers easy access to surrounding areas. The community itself is walkable and welcoming, with a park and lake nearby—perfect for enjoying the outdoors. This home combines style, convenience, and location—don’t miss the opportunity to make it yours!

1781 Lakeside Dr, Middletown

Listing courtesy of RE/MAX Realty Associates. Contact:

Selling Office: EXP Realty, LLC.

$240,000

Price Improved and ready for you to make this your new home in 2026 !! Welcome to this delightful 3-bedroom, 1-bath single-family home nestled on Main St. in the heart of historic Middletown. Full of character and timeless appeal, this vintage gem is brimming with potential. Situated on a generous lot, the home boasts a spacious backyard—perfect for outdoor entertaining, gardening, or future expansion. Inside, you'll find original details that speak to the home's heritage, creating a warm and inviting atmosphere that’s ready to be reimagined. Whether you're looking to bring new life to a classic property or create your dream home in a sought-after location, this residence offers the perfect canvas. Attic is fully floored for extra storage, basement is unfinished & is another great storage space. With its unbeatable location in a charming community close to schools, shops, and parks, this is an opportunity you don’t want to miss.

3 Beds ⋅ 1 Baths

Price Improved and ready for you to make this your new home in 2026 !! Welcome to this delightful 3-bedroom, 1-bath single-family home nestled on Main St. in the heart of historic Middletown. Full of character and timeless appeal, this vintage gem is brimming with potential. Situated on a generous lot, the home boasts a spacious backyard—perfect for outdoor entertaining, gardening, or future expansion. Inside, you'll find original details that speak to the home's heritage, creating a warm and inviting atmosphere that’s ready to be reimagined. Whether you're looking to bring new life to a classic property or create your dream home in a sought-after location, this residence offers the perfect canvas. Attic is fully floored for extra storage, basement is unfinished & is another great storage space. With its unbeatable location in a charming community close to schools, shops, and parks, this is an opportunity you don’t want to miss.

417 W Main St, Middletown

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

Selling Office: RE/MAX Realty Group.

$218,800

Property is being sold AS IS. Spacious home in the beautiful town of Middletown with a 2-car garage, large lot, and plenty of square footage. This property offers an opportunity for the right buyer to renovate and make it their own. The home requires significant work and is priced accordingly. Bring your vision and contractor to transform this property into something special!