Middletown Homes for Sale

Middletown Homes for Sale

Welcome to Middletown, a charming gem nestled in the heart of the United States! This vibrant city offers a delightful blend of small-town warmth and modern conveniences, making it an ideal place to call home. With its rich history, friendly community, and beautiful parks, Middletown is perfect for families, professionals, and retirees alike.

Middletown boasts a variety of homes for sale, catering to diverse lifestyles and preferences. Whether you’re looking for a cozy bungalow, a spacious family home, or a contemporary townhouse, you’ll find an array of options that fit your needs. Many properties feature beautiful landscaping, updated interiors, and easy access to local amenities. The real estate market here is thriving, offering opportunities for first-time buyers and seasoned investors alike.

The city is known for its excellent schools, making it a top choice for families seeking quality education for their children. Outdoor enthusiasts will love the numerous parks and recreational areas that offer trails for hiking, biking, and picnicking. Additionally, Middletown's vibrant downtown area is filled with charming shops, restaurants, and cultural attractions, providing a lively atmosphere for residents to enjoy.

With its welcoming community spirit and a wide range of housing options, Middletown truly has something for everyone. If you’re considering a move to this delightful city, now is the perfect time to explore the homes for sale and discover your dream home in Middletown. Let the adventure begin!

Newest Middletown Homes for Sale

$825,000
6 Beds ⋅ 4 Baths ⋅ VAWR2015102 MLS
Discover a rare opportunity to own an exceptional custom residence where timeless craftsmanship, refined comfort, and peaceful natural surroundings come together. Nestled on five picturesque wooded acres within an exclusive lake community in Middletown, this remarkable estate offers over 4,700 square feet of beautifully designed living space, creating the perfect balance of luxury, privacy, and everyday functionality. Thoughtfully designed, the home features six bedrooms and three-and-a-half bathrooms, providing exceptional flexibility. A dedicated office on the main level creates an elegant work-from-home space, while an expansive loft offers endless possibilities as a library, media lounge, or additional gathering area. The spacious primary suite is conveniently located on the first floor, featuring access to the deck, a stone fireplace and private ensuite bathroom. At the heart of the home, the chef-inspired kitchen is equipped with newer appliances—all less than five years old—and seamlessly flows into generous living and dining spaces designed for effortless entertaining. The walk-out lower level is partially finished and already plumbed for a future full bath, offering exceptional potential to create a luxury guest suite, fitness studio, wine cellar, home theater, or recreation space tailored to your vision. Step outside to experience the home's true sanctuary. A custom multi-level deck overlooks the wooded landscape, providing multiple outdoor living spaces for entertaining or quiet relaxation. A reinforced section has already been engineered to accommodate a hot tub, creating the perfect setting for enjoying peaceful evenings beneath the stars. Exceptional features continue with an oversized two-car garage and the added confidence of a whole-home gas generator, ensuring comfort and peace of mind in every season. Residents enjoy access to the community's private lake, offering opportunities for fishing, kayaking, and embracing the beauty of the surrounding countryside. Despite its serene setting, the property remains conveniently located near commuter routes, historic Middletown, wineries, outdoor recreation, and all that the Shenandoah Valley has to offer. Offering an extraordinary combination of luxury, privacy, and room to grow, this distinguished estate is more than a home—it's a lifestyle.

816 Great Lake Dr, Middletown
$664,900
5 Beds ⋅ 4 Baths ⋅ DENC2108390 MLS ⋅ D.R. Horton BLDG.
This move-in ready, 3-year-old D.R. Horton home is a spacious two-story with five bedrooms, three and a half bathrooms. It also includes a game room with a wet bar, a media room, a workshop or exercise room, a full bathroom, and plenty of storage space in the basement, as well as a two-car garage and an oversized deck. The foyer features a coat closet and creates a welcoming flow for greeting guests. The front room is filled with natural light and is large enough to accommodate both a living and dining area. The spacious kitchen boasts beautiful birch cabinetry, granite countertops, stainless steel appliances, a pantry, and an island with seating. It opens to both the breakfast area and a sizable family room. A convenient powder room is located on the first floor, and the stairs to the second floor are tucked away in the family room, which also includes a cozy fireplace. Upstairs, the owner’s suite offers a large bedroom, two walk-in closets, and an oversized ensuite bathroom. The four additional generously sized bedrooms and a hall bathroom provide ample space for everyone. The first-floor laundry room is conveniently located near the garage, along with an additional coat closet. The property is vacant and ready to move in for the holiday.

1245 Pimpernell Path, Middletown
$339,900
3 Beds ⋅ 4 Baths ⋅ PADA2062508 MLS
Notable Middletown historical home with a history that begins in 1822 located within walking distance to Penn State Middletown Campus and just minutes from HIA and Amtrak Commuter rail station. Large rooms, high ceilings and stunning lighting fixtures that are true to the home’s era. Beautiful thermal windows that bring an abundance of natural light that will invigorate you, spacious living room-dining room combination that will accommodate your largest pieces of furniture, two large living room fireplaces with gas inserts, walls that are in pristine condition, and room layout that is versatile. High efficiency three zone gas heating, central air-conditioning, paved driveway, off-street parking for multiple vehicles with one car carport and a park like rear fenced yard, mature landscaping, majestic trees and wide variety of perennials all throughout the grounds. From the front of home there is a privacy fence with secure gate to a sidewalk way that leads to a peaceful courtyard with brick patio and sunshade that delivers quietness and a great place for outdoor entertaining with an adjacent summer kitchen that has been converted to a storage shed for lawn furniture storage and garden equipment. Kitchen with Corian counters, brick fireplace, and second rear staircase that presently serves as a pantry. Half bath, rear foyer off kitchen with exterior access to courtyard and a hallway that leads to an open staircase to second and third floors. Second floor bath with large soaking whirlpool tub and aerator, pedestal sink and gorgeous tile floor. There are two large bedrooms plus a primary bedroom suite with fireplace, adjacent office with access to a balcony and primary bath with walk-in shower and stone epoxy floor. Middle bedroom is currently used as large dressing area with numerous wardrobe closets that are included in sale. Third floor walk up attic for storage and houses mechanicals for AC system. Block basement foundation was constructed in 1972 and partially set up to be an efficiency which is perfect for an in-law suit or rental unit. Basement already has a full bath with walk in shower, separate heating zone, separate side entrance and windows that face rear yard that provide natural light. This home is packed with personality yet updated to provide efficiency and comfort. It is best to see this home in person and feel the ambiance of a time when everyone talked with their neighbors and enjoyed spending time at home. You will not be disappointed!

535 N Spring St, Middletown
$380,000
3 Beds ⋅ 2 Baths ⋅ DENC2108436 MLS
Back on the market! Don't miss your second chance to step into a storybook at 8 Crawford Street, where history, charm, and modern luxury intertwine in the beloved “Schreitz House,” circa 1879. From the moment you arrive, the freshly painted exterior, cheerful green shutters, and a welcoming front porch complete with a classic porch swing set the tone for something truly special. It’s the kind of home that feels like it belongs in a novel, yet lives beautifully in the present. Surrounding the home, thoughtfully curated gardens burst with native greenery and vibrant blooms, creating a picturesque, low-maintenance landscape that evolves with the seasons. Whether you’re entertaining, unwinding, or simply taking it all in, every inch of this property feels intentional, peaceful, and alive. Inside, the original hardwood floors carry the legacy of the home through the formal living and dining rooms, spaces that feel both timeless and inviting. Just beyond, the heart of the home reveals itself in a stunningly renovated kitchen, where luxury meets craftsmanship. Outfitted with exquisite cabinetry, marble countertops, a classic subway tile backsplash, professional-grade appliances, an apron-front sink, and a beautifully centered island, this space was designed to gather, create, and impress. Tucked just off the kitchen, a convenient half bath and laundry area blend seamlessly into daily life, while the sunroom addition steals the show. Bathed in natural light from oversized windows, it offers the perfect place to sip your morning coffee, dive into a good book, or simply admire the lush backyard beyond. Outside, the magic continues with a thoughtfully designed retreat featuring a patio, fire pit, two sheds (one with an incredible workshop,) and a charming playhouse, each element adding to the home’s enchanting personality. Upstairs, the story continues with more original hardwood flooring, three uniquely styled bedrooms, and a beautifully appointed full bath featuring detailed tile work, rich wood trim, and an antique vanity that feels like a piece of art. A walk-up attic offers additional storage and a whimsical dressing space tucked within, another nod to the home’s character and charm. All of this, perfectly positioned in the heart of Middletown, just moments from local favorites like Silver Lake Park, Appoquinimink Community Library, dining along West Main Street Middletown, and convenient access to Rt. 1 and Rt. 301 for effortless commuting. This is more than a home - it’s a feeling, a piece of history, and a place where everyday life feels just a little more magical. Looking for a business location? This home is zoned C-2, with opportunity for multiple uses. If you’ve been waiting for something that speaks to you - something rare, soulful, and unforgettable... this is your moment. Take the leap, homes like this don’t wait for long.

8 Crawford St, Middletown
$659,900
4 Beds ⋅ 4 Baths ⋅ DENC2107754 MLS
Discover exceptional value in this beautifully crafted custom home by Desabatino Construction, ideally located in the highly sought-after Westside Hunt community within the award-winning Appoquinimink School District. Offering 4900 square feet of thoughtfully designed living space, this home combines timeless craftsmanship with everyday comfort. A beautiful stone façade and welcoming covered front porch set the stage for what awaits inside, where you'll find original finished on-site hardwood floors, 9-foot first-floor ceilings, and spacious, light-filled living areas. The inviting family room with a cozy gas fireplace flows seamlessly into the ample kitchen featuring a center island, large pantry, newer stainless steel appliances, and a sunny breakfast nook overlooking the deck and fully fenced backyard and the spacious living and dining rooms complete the first floor. The impressive two-story foyer with a handsome oak staircase leads to four comfortable bedrooms, three full baths, and a versatile 20' x 24' bonus room with private back staircase that can easily serve as a fifth bedroom, nursery, sitting room, or home office. The luxurious primary suite offers a spa-like bath with a huge soaking tub, walk-in shower, and double vanity, while the private guest suite includes its own full bath with a relaxing jetted tub. The massive finished lower level with a built-in bar provides endless possibilities for entertaining, a media or game room, fitness area, or hobby space. Additional features include a two-car garage with set up for an EV charging plug, convenient mudroom, new water heater, new carpet, newer HVAC, and durable 50-year shingles installed when constructed. Situated on a beautifully sized 0.8-acre lot in peaceful West Middletown, this exceptional home offers convenient access to restaurants, shopping, parks, marinas, the YMCA, schools, outdoor recreation, and Routes 301 and 1 for an easy commute north or south. This is a rare opportunity to own a spacious, quality-built home in one of the area's most desirable communities.

103 Westside Ln, Middletown
$235,000
3 Beds ⋅ 2 Baths ⋅ MDFR2086498 MLS
Don’t miss this opportunity to own a home in the heart of Middletown! This livable fixer-upper is the perfect canvas for an investor, first-time buyer, or anyone looking to create their dream home while building valuable sweat equity. Enjoy a charming front porch, a fully fenced backyard, and LVP flooring already installed throughout much of the home. Whether you’re planning light cosmetic updates or a full renovation over time, this property offers incredible potential in a convenient location close to local shops, restaurants, and everyday amenities.

108 S Jefferson St, Middletown
$699,900
4 Beds ⋅ 4 Baths ⋅ DENC2107552 MLS
Elegant, Bright and Spacious and situated in the sought-after community of Dove Run, this grand estate home boasts of 4-bedrooms, 3.5 bathrooms with over 4,200 square feet of above ground living space and a stately full brick front facade. The kitchen is open and it has a lot of features cabinetry with quartz countertops. Of the kitchen is the breakfast room with plenty of sunshine. The family room is impressive with the soaring 2-story ceiling, oversized windows overlooking the private, tree-lined backyard. Between the living room and the family room is a two-sided fireplace. The main level also features a formal dining room, dining room, a private office, and additional living space. The upper level is equally impressive with the expansive owner’s suite featuring two walk-in closets, a sitting room, and a luxurious en-suite bath. This estate home has two separate staircases providing convenient access to the second floor. Relax yourself outside in the custom paver patio. On the lower level is the expansive full unfinished basement. It presents potentials for more space and entertainment areas. This home is conveniently located near stoppings and restaurants, major highways, award-winning schools, and much more. Upgrades on major items: Newer roof (2018), Newer furnace and A/C (2019), Newer water heater (2020). Schedule your tour today. No showings through August 9th. Open house on Sunday, August 9th 1:00-3:00pm.

226 Bucktail Dr, Middletown
$235,000
3 Beds ⋅ 1 Baths ⋅ PADA2061082 MLS
Welcome home to this charming 3-bedroom Cape Cod nestled in the heart of Middletown! From the moment you arrive, you'll appreciate the care and updates that make this home truly special. The beautifully refreshed kitchen features tile flooring, updated cabinetry, modern countertops, a stylish tile backsplash, and newer appliances (2021), creating a warm and inviting space for everyday living and entertaining. The cozy living room offers durable laminate flooring and plenty of natural light, while the convenient first-floor primary bedroom provides easy one-floor living. A flexible laundry room can also serve as a home office, hobby room, or additional living space to fit your needs. Thoughtful updates provide peace of mind, including a new roof, efficient gas furnace and central air system (2020), and a gas water heater, water softener, and water filtration system (2017). Step outside to enjoy the fully fenced backyard—perfect for pets, gardening, gatherings, or simply relaxing. Two storage sheds offer plenty of room for tools, while the attached carport and driveway provide ample off-street parking. Conveniently located close to shopping, dining, schools, and major commuter routes, this delightful home offers comfort, character, and modern updates all in one package. Come see all it has to offer and imagine yourself at home!

115 Catalpa St, Middletown
$575,000
4 Beds ⋅ 3 Baths ⋅ DENC2105110 MLS
Welcome to this spacious and inviting Colonial offering a bright, open floor plan designed for both everyday living and entertaining. Step inside the impressive two-story foyer with soaring ceilings and beautiful hardwood flooring that extends throughout the entire main level. Just off the foyer, you'll find an exceptionally large front room that offers incredible flexibility. Whether used as a formal dining room, a sitting room, a family room, or a combination of spaces, this oversized room can easily adapt to your lifestyle. The heart of the home is the expansive kitchen and family room, where the open layout creates the perfect gathering place. The kitchen features white cabinetry, stainless steel appliances, a pantry, generous counter space, and a breakfast bar with seating for several. It overlooks the sunny breakfast area, surrounded by windows and offering sliding glass doors that lead to the backyard. The adjoining family room is warm and welcoming, highlighted by a cozy gas fireplace and seamless flow from the kitchen, making it ideal for entertaining or relaxing with family and friends. Upstairs, the spacious primary suite features elegant double-door entry, a vaulted ceiling, abundant natural light, generous closet space, and an en-suite bath with a soaking tub, separate shower, and dual vanities. The additional bedrooms are all comfortably sized, providing plenty of room for family, guests, or a home office. Outside, the level backyard offers a blank canvas for outdoor living, gardening, or play. Ideally situated within the sought-after Village of Bayberry North, this home is part of the highly regarded Appoquinimink School District and offers convenient access to parks, shopping, dining, and major commuting routes. (Square footage is estimated and should be independently verified.) Be sure to view the virtual tour and schedule your showing today!

615 Socrates St, Middletown
$1,349,900
4 Beds ⋅ 4 Baths ⋅ MDFR2086162 MLS
To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

7453 Heritage Oak Ter, Middletown
$649,000
7 Beds ⋅ 7 Baths ⋅ VAFV2043696 MLS
Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7760 Main St, Middletown
$1,719,900
5 Beds ⋅ 8 Baths ⋅ MDFR2086198 MLS
To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 7 beautiful acres, 3150 Bidle Rd (Lot 3E) is a gorgeous build-ready homesite with a 5BR septic approval and high yield 10gpm well already installed. Advertised is the ACL5 plan which features over 6,000 finished sqft, 5 bedrooms (including dual owner's suites), 4 full baths and 3 half baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, parlor/enterainment room, formal dining room, morning room, upper level bonus room, primary suites on both main and upper levels, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3150 Bidle Rd, Middletown
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