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$475,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Welcome home to 4 Lamar Lane, a beautifully updated Admar-built rancher tucked away at the peaceful back of the highly sought-after Foxfield 55+ community in Middletown. Thoughtfully designed for easy living and filled with warmth and charm, this move-in ready home offers the perfect blend of comfort, convenience, and low-maintenance living. A covered front porch welcomes you home, while the level-access ramp from the two-car garage provides added ease and accessibility. Inside, you’ll find 1,359 finished square feet on the main level featuring two spacious bedrooms, each with its own private ensuite bath, plus main-level laundry for true one-level living. The heart of the home is the beautifully remodeled kitchen, complete with new cabinetry, countertops, and propane-fueled gas cooking. The inviting living room offers a cozy propane-fueled gas fireplace, creating the perfect space to relax or gather with friends and family. Recent updates throughout include a new roof, new HVAC system, refinished hardwood floors, updated bathrooms, fresh paint, and a low-maintenance exterior, allowing you to simply move in and enjoy. Step outside to discover a fenced backyard with two rear decks, providing wonderful spaces for morning coffee, outdoor dining, gardening, or enjoying the peaceful surroundings. An unfinished basement with windows offers abundant storage and endless possibilities for future expansion. Rarely does a home in Foxfield combine this level of updating, accessibility, outdoor living space, and prime location. This is the kind of home that allows you to spend less time maintaining and more time enjoying everything the Middletown Valley has to offer.

4 Lamar Ln, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$625,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Welcome to 7 Derr Lane in the sought-after Villages at Foxfield—Middletown’s premier 55+ community—where Original Owners have meticulously maintained and thoughtfully upgraded this beautiful home, showcasing true pride of ownership everywhere you look. Perfectly positioned within walking distance to Middletown Park and its many amenities, this home also backs to serene woods, walking/jogging paths, and open green space—offering both convenience and some privacy. Enjoy peaceful mornings on the covered front porch or unwind in the backyard retreat featuring a walkout patio, koi pond, and a hidden “secret garden” be sure not to miss. Inside, the home blends comfort and modern updates. The kitchen is a standout with a Corian island, mosaic tile backsplash, stainless steel appliances (replaced 2019), induction downdraft cooktop, double oven, and ceramic flooring—ideal for both everyday living and entertaining. The main level boasts hardwood flooring (2018) and a warm, inviting family room with a propane fireplace and direct access to the newer, enlarged Trex deck (2022, with updated door in 2025). The spacious layout includes vaulted ceilings, a tray ceiling in the primary suite, and a dramatic two-story overlook with loft above. The primary bath was beautifully renovated in 2017, and the upper level features new carpet (2019). Additional updates include leased solar panels for energy efficiency (2018), washer and dryer (2021), vinyl fencing (2022), new roof and ventilation (2024), HVAC (2015), and water heater (2018). The unfinished lower level offers a walkout to the backyard, rough-in for a full bath, and a wide-open layout ready to be customized to your needs. Garage is equipped with a 200 amp 240 volt EV charging circuit and a newer garage door opener (2021). This is a rare opportunity to own a truly move-in-ready home in Middletown’s most desirable active adult communities—combining thoughtful upgrades, natural beauty, and a vibrant lifestyle.

7 Derr Ln, Middletown

Listing courtesy of Corner House Realty. Contact: (443) 499-3839
$699,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status
This home is an absolute MUST SEE. This home has been immaculately maintained and features all of it's original charm. You will fall in love with the beautiful hardwood floors throughout this spacious 5 bedroom, 3 full bath colonial that features 3,200 square feet of living space along with a large 832 square foot basement, with outside entrance. This classic beauty is situated on a large, beautifully landscaped and manicured, corner lot of .64 acres in Middletown's Historic District. You will fall in love with all of the historic charm and craftsmanship that blends seamlessly with modern upgrades such as vinyl siding and replacement windows. There are several bonus areas that provide added charm to this already captivating home. There is a family room that was crafted from a former garage, a second floor sunroom area for relaxing, a bonus room that could be a home office and a sitting area off of the formal dining room. This is a true gem and you will be amazed at the incredible condition.

200 Prospect St, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$499,900
4 Beds ⋅ 2 Baths ⋅ COMING SOON Status
Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm, community character, and a prime Main Street address come together on a generous half acre lot! There is SO MUCH potential to revitalize this home to your most creative imagination. Bathed in natural light throughout, this spacious 4-bedroom, 2-bath home features gleaming hardwood floors and a comfortable, flowing layout. The main level offers a primary bedroom with a private ensuite bath, ideal for single-level living convenience, while the upper-level hosts three additional generously sized bedrooms and a full bath. The expansive lot provides plenty of outdoor space to enjoy, entertain, and make your own. A roof updated in 2025 offers genuine peace of mind, and the home is connected to the public sewer system via a Sanitary Sewer Lift Pump, offering the reliability of public utilities. Middletown offers everything you come here for, a small-town feel with walkability to parks, restaurants, the library, and shopping, including beloved local spots like The Main Cup, Fratelli's Italian & Seafood, and Aleko's Village Cafe just down the road. The 79-acre Middletown Community Park is just minutes away, offering basketball courts, soccer fields, disc golf, fishing, picnic shelters, and walking trails. Commuters will appreciate the easy access to I-70 and Rt. 340, with Downtown Frederick just a short drive away. Don't miss this one!

718 E Main St, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

$419,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status
Beautiful Townhouse in sought after Glenbrook backing to the putting green on Richmond Golf Course with 4 bedrooms, 3.5 baths & a no-maintenance deck. This is the largest model offered, with a full 3 level bump out. Step into a bright and open main level featuring an eat-in kitchen which is located between the two large living spaces ideal for everyday living and entertaining. There is a generous Trex deck overlooking the golf course. Upstairs, the huge primary suite offers a vaulted ceiling, a sitting area, huge walk-in closet, a private ensuite bath and beautiful distant views over the surrounding mountains. There are two addition bedrooms and another full bath on this floor. The lower level offers a fourth bedroom with a fully opening true egress window, another full bath, and an enormous rec room. *** Recent updates * 2026 brand new range and microwave (never used), new carpeting throughout, the entire home freshly painted * 2025 new hot water heater * 2023 new furnace and dishwasher * 2022 new refrigerator *** The deck has steps to a flat back yard with common ground separated from the golf course by a tasteful fence and a tree line. An added bonus is that the community mows both the front and back yards and does snow removal with just the exception of the front steps. Beautiful community and great location. Make this home yours today!!

408 Stone Springs Ln, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

$495,000
3 Beds ⋅ 2 Baths ⋅ COMING SOON Status
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: (301) 698-5005
$439,900
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status
Welcome home to this beautifully updated end-unit townhome in the highly sought-after Glenbrook community, where modern updates, generous living space, and an unbeatable Middletown location come together to create a home you’ll love from the moment you arrive. This spacious three-level home features luxury vinyl plank flooring on all levels, with brand-new carpeting on the staircases (hardwood stairs remain beneath the carpeting, offering future flexibility), fresh paint, and custom blinds. A full three-level bump-out enhances every level, creating an open, airy feel with room to spread out, relax, and entertain. At the heart of the home is the completely renovated kitchen, thoughtfully designed with shaker-style cabinetry, quartz countertops, a spacious center island, gas cooking, and a full suite of Frigidaire Gallery stainless steel appliances. Whether you’re preparing weeknight dinners or hosting holiday gatherings, you’ll love how the kitchen flows seamlessly into the generous dining area and the expanded family room, making it the true gathering place of the home. The main level also offers a welcoming living room and a convenient powder room for guests. Upstairs, you’ll find three spacious bedrooms and two full bathrooms, including an expanded primary suite designed as your own private retreat. The en-suite bath offers a double vanity, soaking tub, separate walk-in shower, and generous space, while a large walk-in closet provides exceptional storage. The finished lower level offers incredible flexibility with a fourth bedroom, an updated full bathroom, a den, a spacious recreation room, and a dedicated laundry and mechanical room—perfect for overnight guests, multigenerational living, a home office, fitness space, or movie nights. Step outside and enjoy one of the many advantages of this end-unit location—a large side and rear yard offering outdoor space that’s hard to find in a townhome community. Two designated parking spaces and additional windows that fill the home with natural light add even more everyday convenience. For added peace of mind, the seller is offering a home warranty. Located in the sought-after Middletown school district, this home is just minutes from charming downtown Middletown, local restaurants, boutique shopping, parks, walking trails, wineries, golf, community events, and convenient commuter routes. With four bedrooms, multiple living areas, and flexible spaces for working from home, entertaining, or hosting guests, this home offers the space and versatility today’s buyers are looking for. Come experience all that Middletown has to offer and discover why this vibrant community is one of Maryland’s most desirable places to call home.

400 Stone Springs Ln, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$499,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and convenience. Step inside to beautiful hardwood floors that flow throughout the main level, creating a warm and inviting atmosphere. The formal living room features a cozy wood-burning fireplace, making it the perfect place to gather on chilly winter evenings. Just beyond, the formal dining room provides an elegant setting for holiday celebrations, dinner parties, and everyday meals. The updated kitchen is designed with both style and functionality in mind, featuring a spacious island perfect for entertaining, ample cabinet storage, and a bright breakfast area where you can enjoy your morning coffee while overlooking the expansive backyard. The main level offers two comfortable bedrooms and a full bathroom, providing flexible living options for guests, family, or a home office. The finished lower level includes two additional generously sized bedrooms, a second full bathroom, and a spacious laundry room with abundant storage. Outdoor living is just as inviting, with a large deck that's perfect for summer barbecues, outdoor dining, and relaxing evenings. The one-car garage offers additional storage, while the oversized backyard provides endless possibilities with plenty of room for play, gardening, pets, or future outdoor entertaining spaces. Located just moments from Middletown's charming shops, restaurants, parks, and top-rated schools, this home offers small-town living with all the conveniences you need. Don't miss your opportunity to make this beautiful Main Street home your own.

708 E Main St, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

$499,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect for everyday living and entertaining. Step outside to enjoy the spacious backyard, offering endless possibilities for outdoor gatherings, recreation, gardening, or simply relaxing while taking in the peaceful surroundings. Enjoy the tranquility of country living while remaining just minutes from downtown Middletown, Frederick, shopping, dining, schools, parks, and major commuter routes. Whether you're looking for your forever home or a quiet retreat with modern comforts, this exceptional property is ready for its new owner. Don't miss this rare opportunity!

9001 Hollow Rd, Middletown

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

$849,000
4 Beds ⋅ 5 Baths ⋅ COMING SOON Status
Coming soon ! Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this exceptional home is also just minutes from the nature center, local restaurants, golf courses, and major commuter routes. Step inside to a welcoming foyer featuring a private home office, then continue past the elegant formal dining room into the spacious living room that seamlessly opens to the bright, eat-in kitchen—perfect for everyday living and entertaining. Entering through the attached 2-car garage, you'll appreciate the thoughtfully designed mudroom with built-in storage, along with an oversized pantry and convenient powder room on the main level. Upstairs offers an ideal layout with an additional loft-style lounge that provides flexible living space. The luxurious primary suite occupies its own private wing and features a sitting area, two walk-in closets, and a spa-like ensuite bath. Two additional bedrooms share a full hall bath, while the opposite wing includes a fourth bedroom with its own ensuite bath and a conveniently located laundry room. The finished walkout basement is an entertainer's dream, featuring a large recreation area, wet bar, full bathroom, and ample storage space. Outside, the beautifully hardscaped backyard offers a low-maintenance setting that's perfect for relaxing or hosting gatherings. Meticulously maintained and truly move-in ready, this thoughtfully upgraded home combines generous living spaces, quality finishes, and an unbeatable location. 5 Dean Lane has everything you've been looking for.

5 Dean Ln, Middletown

Listing courtesy of Real Estate Innovations. Contact:

$599,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 square feet of finished living space and comes with not one, but two parcels totaling approximately 7.63 acres. The home is situated on 5.90 acres and includes an additional 1.73-acre wooded lot located directly behind the property, providing even more privacy and future possibilities. Inside, you'll find beautiful wood flooring throughout the main level and a spacious layout designed for comfortable living. The primary suite features its own private full bath and direct access to a deck overlooking the peaceful surroundings. Two additional bedrooms and a full bath complete the main level. Enjoy the outdoors from the wraparound rear porch or entertain guests on the expansive two-tier deck. During the colder months, cozy up beside one of the home's two wood-burning fireplaces. The lower level offers additional living space along with a third full bath, making it ideal for a recreation room, guest area, or home office. With plenty of driveway parking and a 2-car attached garage, there is ample room for vehicles, equipment, and guests. Conveniently located just minutes from downtown Middletown and within the highly sought-after Middletown School District, this property offers the perfect combination of privacy, acreage, and accessibility.

2748 Bennies Hill Rd, Middletown

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

$1,475,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status
Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman is the perfect option! Like new, only better thanks to an investment of all the things that are a hassle to add to a new home - rear yard fence, plantation shutters and luxury shades, water softener/treatment system, an Amish garden shed and more! Move in now and do nothing but pack your personal belongings! Amazing opportunity in quiet Middletown but just minutes to all of the area's conveniences. Relax and escape to your own private retreat, enjoy sunsets on your covered back porch and find plenty of room to stretch out and play - over 5000 square feet of perfectly curated living space. Dedicated home office, formal dining and gourmet open kitchen with oversized island and eat-in breakfast area. Family room with soaring ceilings and a cozy fireplace - truly the perfect setting with floor to ceiling windows that floods the space with natural light. Smart open layout with primary bedroom suite on main level, complete with massive double-sided walk-in closet, dual vanity spaces, a soaking tub and oversized walk-in shower. Upstairs there are three generously sized secondary bedrooms, one with a private en suite bath and walk-in closet and a second hall bath. Gorgeous cat walk hallway overlooks the family room. On the lower level you have a secondary living level with yet another full bedroom and en suite bath, perfect for a guest suite. Tons of conditioned storage space finishes off the walk-out lower level. Enjoy the outdoors from your covered patio off the eat-in breakfast area/morning room and play down below in the spacious split-rail fenced rear yard. New Amish storage shed has space for all of the lawn equipment. Plenty of room for the furry family members or even a chicken run! Attached two car garage and expanded driveway has plenty of space for guest parking as well. While the peaceful setting can make you feel like you're a world away, this home is just two miles to the heart of downtown Middletown and less than 30 minutes to Downtown Frederick. Tons of great area shopping and dining, but the small town feel you've been yearning for. Don't miss out on this incredible opportunity!

2802 Bidle Rd, Middletown

Listing courtesy of EXP Realty, LLC. Contact: 8333357433
$489,900
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status
Welcome home to 4 Lamar Lane, a beautifully updated Admar-built rancher tucked away at the peaceful back of the highly sought-after Foxfield 55+ community in Middletown. Thoughtfully designed for easy living and filled with warmth and charm, this move-in ready home offers the perfect blend of comfort, convenience, and low-maintenance living. A covered front porch welcomes you home, while the level-access ramp from the two-car garage provides added ease and accessibility. Inside, you’ll find 1,359 finished square feet on the main level featuring two spacious bedrooms, each with its own private ensuite bath, plus main-level laundry for true one-level living. The heart of the home is the beautifully remodeled kitchen, complete with new cabinetry, countertops, and propane-fueled gas cooking. The inviting living room offers a cozy propane-fueled gas fireplace, creating the perfect space to relax or gather with friends and family. Recent updates throughout include a new roof, new HVAC system, refinished hardwood floors, updated bathrooms, fresh paint, and a low-maintenance exterior, allowing you to simply move in and enjoy. Step outside to discover a fenced backyard with two rear decks, providing wonderful spaces for morning coffee, outdoor dining, gardening, or enjoying the peaceful surroundings. An unfinished basement with windows offers abundant storage and endless possibilities for future expansion. Rarely does a home in Foxfield combine this level of updating, accessibility, outdoor living space, and prime location. This is the kind of home that allows you to spend less time maintaining and more time enjoying everything the Middletown Valley has to offer.

4 Lamar Ln, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$150,000
ACTIVE Status
Charming 1/4 acre buildable on E. Green Street. The buyer of 19 E. Main Street will have the right of first refusal on the sale. Additional photos available on the 19 E. Main Street listing MDFR2082574.

Lot 1 E Green St, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$1,150,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status
Carefully reimagined between 2018 and 2021, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Middletown — complete with a secret speakeasy concealed behind a swinging bookshelf, a breathtaking custom kitchen addition, and a covered courtyard entertaining area anchored by a stunning stone fireplace. Rich in history yet thoughtfully transformed for modern luxury living, this extraordinary four-bedroom residence with dedicated office space blends timeless craftsmanship with sophisticated design rarely found in historic homes. Perched above historic Main Street with sunset views toward South Mountain, the home showcases soaring ceilings, original architectural details, custom Mennonite-crafted millwork, designer Circa lighting, and extensive infrastructure updates throughout. At the heart of the home is the stunning kitchen addition featuring exposed historic brick, dramatic steel scissor-beam trusses, handcrafted cabinetry, quartz perimeter counters, granite center island, GE Monogram appliances, farmhouse sink, induction cooktop, and a dramatic picture window overlooking the beautifully landscaped courtyard and covered side porch. The original kitchen was transformed into a spacious dining room, creating exceptional flow for entertaining while preserving the home’s historic character. Outdoor living spaces feel like an extension of the home itself with stamped concrete, custom stone fireplace, a covered entertaining area, integrated storage, and beautifully landscaped gathering spaces designed for both intimate evenings and large-scale entertaining. The front parlor was transformed into a stunning library with built-in shelving, restored historic shutters, statement lighting, and the hidden swinging bookshelf leading to the speakeasy featuring a solid wood bar, wet bar, beverage refrigerator, custom ceiling paneling, and dramatic finishes. The family room was created by opening two original parlors and is crowned by a dramatic bay window that floods the space with natural light. Upstairs, the home offers two primary suites along with spacious secondary bedrooms featuring exceptional flexibility, including a custom Murphy bed/work table system and built-in bay window seating. A dedicated office conceals a hidden opening into an untouched portion of the original home, creating a fascinating preserved time capsule rarely found in homes of this era. A covered upper porch overlooks the courtyard below, while the redesigned laundry room introduces marble countertops, statement lighting, and additional storage. The finished attic was transformed into a truly unique owner’s retreat featuring reclaimed oak flooring, exposed brick chimneys, preserved historic wall surfaces, dressing room, laundry chute, separate staircase access, and a spa-inspired bath with a hidden Japanese-inspired Ofuro soaking tub room. Infrastructure improvements include dedicated high-end Carrier HVAC systems with hospital-grade filtration and smart thermostats, radiant heated floors, replaced electrical systems in 2020, updated copper plumbing, Japanese toilets, hand-tooled standing seam metal roof, replacement gutters, energy-efficient wooden sash windows, composite porch decking, central vacuum, Sonos integration, and extensive custom woodworking throughout. Stretching from Main Street to West Green Street, the property also includes a subdivided, buildable rear lot. The purchaser of 19 E Main Street will have first right of refusal on the lot, which is also available separately, creating a rare opportunity for future expansion or investment in the heart of Middletown. Located on one of Maryland’s historic designated Main Streets, just steps from Middletown’s restaurants, library, shops, parks, & sought-after schools, this extraordinary residence offers a lifestyle as rare as the home itself. Owned by only three families in 100+ years, this one-of-a-kind home blends history, luxury, & craftsmanship.

19 E Main St, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005
$2,500,000
ACTIVE Status
Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$2,500,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status
Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,185,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status
HOME TO BE BUILT - Don't miss the final opportunity to build your custom home! Experience the breathtaking mountain views and modern luxury in this stunning new construction home to be built by Grossnickle Construction, nestled in the heart of Middletown Valley. This thoughtfully designed 4-bedroom, 3.5 bath home offers the perfect blend of elegance, comfort and functionality. Step inside to discover an open concept floor plan featuring spacious living areas, abundant natural light and high-end finishes throughout. The gourmet kitchen will impress with premium cabinetry, quartz countertops, oversized island and seamless flow into the dining and family rooms - perfect for entertaining or everyday living. Conveniently located near charming downtown Middletown, parks and commuter route, this exceptional to be built home offers the rare opportunity to personalize your dream home.

5901 Cloudberry Ct, Middletown

Listing courtesy of Charis Realty Group. Contact: 3018315099
$924,500
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
HOME TO BE BUILT. Nestled on a beautiful, wooded 2.25-acre lot, this to-be-built home by Grossnickle Construction offers the perfect blend of luxury and comfort. The home features 3 spacious bedrooms, including a private primary suite, 2 full bathrooms, and a convenient powder room. This plan also includes 400 sqft rec room in the basement and the option for an upstairs bonus room. Enjoy the peaceful, natural setting with mature trees and scenic surroundings while still having the opportunity to personalize your new home. This featured plan can be built as-is, tweaked to your preferences, or you can choose a completely different custom plan to fit this homesite. Don’t miss this chance to build your dream home in a truly serene location.

Mountain Church Rd, Middletown

Listing courtesy of Real Estate Teams, LLC. Contact: 3016953020
$2,100,000
ACTIVE Status
LOCATION! LOCATION! LOCATION!!! Prime Commercial Property Zoned GC with endless possiblilities, easy access to highways & walkability to downtown/residential development is waiting for your business! Property coonsist of TWO substantial buildings with two entrances! Enormous three story brick containing a plethora of warehouse/storage space, high ceilings, loading doc on first and second level, two restrooms, newly remodeled kitchenette, office area with seperate entence as well as access to entire building. Giant two story block builing also contains a loading doc for each level. Bring your imaginations to life, Call today to schedule a private showing!

106 N Church Street, Middletown

Listing courtesy of RE/MAX Quality Service, Inc.. Contact: (717) 632-5111
$989,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Escape the subdivision life for a residence defined by scale, privacy, and rugged utility. Set on 32.39+/- acres, this cabin-style estate is built for those who want their permanent home to feel like a fortress of solitude without sacrificing modern comforts. The interior features a recently updated kitchen equipped with new appliances and granite countertops. While there is a propane furnace, there is also a classic woodstove that provides a high-efficiency heating source and a focal point for the entertainment area in the basement. The home’s footprint is anchored by an expansive rear deck designed for four-season use; whether you’re hosting or decompressing, the integrated hot tub offers total privacy, screened by a dense canopy of mature timber to create an outdoor living room that feels completely removed from the outside world. This isn't just a woodlot; it's a gateway. The property borders Gambrill State Park, providing exploration and recreational opportunities right out your back door. For the serious outdoorsman or the family seeking an active lifestyle, the land offers endless utility for hiking, scouting, and wildlife management. The long, wooded approach ensures a level of seclusion and security that is increasingly rare, making this an ideal primary residence for those seeking a quiet, secure environment. Practicality meets potential inside and out, with a walkout basement that provides the ideal entertainment area or can be converted into a home office, gym, or additional bedrooms to grow with your needs. An existing shed provides organized storage for ATVs and maintenance equipment, keeping your primary living spaces clutter-free. Shown by appointment only, this is more than a getaway—it is a rare opportunity to own a significant piece of acreage with your ideal mountain retreat on your own recreational land in the Catocin Mountains.

8939 Hawbottom Rd, Middletown

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$699,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status
Price Improvement! This iconic 1937 Brick Tudor Revival residence and adjacent additional structure are being sold together, situated on two separately deeded parcels that share a well and septic system. The Tudor Revival home has been freshly painted and offers timeless character blended with thoughtful updates throughout. The kitchen features stainless steel appliances, a new cooktop, custom cabinetry, and granite countertops. The formal dining room boasts built-in china closets and an oversized bay window, while the inviting living room centers around a classic wood-burning fireplace. The primary suite includes custom wood-paneled walls, an oversized bay window, a walk-in closet plus two additional closets, and a private ensuite bath. A new hot water heater, along with new roofs on both the home and pool house, provides added peace of mind. The finished basement expands the living space with a recreation room, partial kitchen, office, laundry area with shower, and a half bath—ideal for a variety of residential needs. Outside, the oversized fully fenced backyard creates a private retreat, featuring an in-ground pool with a new liner installed in 2022, a brick pool house, and a storage shed—perfect for entertaining or relaxing. The adjacent structure offers substantial additional space and includes notable features such as three-phase 400-amp electrical service, a 4,000-pound jib crane, and existing interior infrastructure. The property is currently zoned R3 and is being sold strictly for residential use. Any future use of the additional structure is subject to zoning regulations, and buyers are encouraged to conduct their own due diligence with the appropriate local authorities.

3213 Old National Pike, Middletown

Listing courtesy of Kelley Real Estate Professionals. Contact: