Refine Search
Sort by
Reliance Road, Middletown
$2,300,000
Large tract of land bordering the Sly Fox Golf Club. 183 wooded acres suitable for subdivision. The seller has created a sketch showing 36 lots for this subdivision that is BY RIGHT SO it cannot be denied! there are 24 1-acre lots; 9 ten-acre lots; 2 - 22 acre lots; and 1 - 20 acre lot & innternal streets that would stem from Reliance Rd. Tax Map #11 13 (55.2704 ac), TM#11 12 (103.00 ac), TM# 11 14 (4.00 ac), and TM#11 8E (20.9187 ac) Totaling 183.1891 acres. All lots will be well & septic; Seller is offering the front 24 one-acre lots with the vdot entrance installed for $700,000; the back lots will be sold as one parcel for 1.6 million or individually! Take on this project and tap into the flux of buyers leaving the DC and NOVA areas for greener pastures. Easy commute to DC and NOVA via I-66. Enjoy local golf clubs, Vineyards, AT hiking, and Skyline Drive, and see why everyone is moving out here! Close to Sly Fox Golf course - in Warren County with Middeltwon address!

Reliance Road, Middletown

Listing courtesy of Sager Real Estate. Contact:

3121 Bidle Rd, Middletown
$1,785,000
5 Beds ⋅ 4 Baths
Lot 3 South at Heritage Oak Estates | To-Be-Built Custom Home by Atlantic Homes. Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including Masonry board exterior siding with stone water table and 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Contact listing agent for available plans, site details, and to explore available homesite options. Start designing your future dream home today at Heritage Oak Estates!

3121 Bidle Rd, Middletown

Listing courtesy of VCRE.CO. Contact:

2802 Bidle Rd, Middletown
$1,375,000
5 Beds ⋅ 5 Baths
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:

3101 Bidle Rd, Middletown
$1,292,500
4 Beds ⋅ 3 Baths
Lot 1 South at Heritage Oak Estates | To-Be-Built Custom Home by Atlantic Homes. Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including Masonry board exterior siding with stone water table and 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Contact listing agent for available plans, site details, and to explore available homesite options. Start designing your future dream home today at Heritage Oak Estates!

3101 Bidle Rd, Middletown

Listing courtesy of VCRE.CO. Contact:

3111 Bidle Rd, Middletown
$1,250,500
3 Beds ⋅ 3 Baths
Lot 2 South at Heritage Oak Estates | To-Be-Built Custom Home by Atlantic Homes. Heritage Oak Estates, an exclusive twelve-lot community by Atlantic Homes, nestled in the heart of the scenic Middletown Valley. Located less than a mile from charming Main Street in Middletown, MD this enclave offers panoramic views of pastoral landscapes and surrounding mountains—all with no HOA restrictions. Choose from a range of fully customizable floor plans or bring your own design. Each home will feature elevated standard finishes throughout, including Masonry board exterior siding with stone water table and 10’ to 12' ceilings on the main level. Lot sizes in the community range from 2 to 7 acres, each offering its own unique views and privacy. Protective covenants ensure architectural integrity and long-term value—vinyl siding is not permitted, and minimum build standards apply. Contact listing agent for available plans, site details, and to explore available homesite options. Start designing your future dream home today at Heritage Oak Estates!

3111 Bidle Rd, Middletown

Listing courtesy of VCRE.CO. Contact:

6346 Zittlestown Rd, Middletown
$1,166,611
4 Beds ⋅ 3 Baths
You may think you’ve seen this quintessential 1920’s Mid-Atlantic Craftsman single family home somewhere on 6th or 7th street in Frederick, Maryland… you might have indeed. Only this new custom home only looks like a period home. A garage has been added to suit the hill upon which this new home will sit. The garage features a rooftop deck for country views and outdoor living. While we follow the historical inspiration on the exterior, we use only maintenance free materials for easy care by the owners. Inside there is to be bedroom-sized mudroom/clutter space and a home office. The rest of the first floor is essentially an open space featuring a gourmet kitchen, two story foyer, and a family room. Upstairs features a large owner's suite and luxury primary bath, 3 more bedrooms, a full bath, and a 2nd laundry.

6346 Zittlestown Rd, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

610 Spring Hollow Dr, Middletown
$929,000
5 Beds ⋅ 4 Baths
NEW PRICE! Welcome to 610 Spring Hollow Drive in the highly desirable community of Parkside. Situated on one of the neighborhood's premier lots, this exceptional Versailles model - one of the most coveted floor plans in the community - offers over 5200 sq ft above grade, expansive living spaces, timeless design, and a backyard setting that is truly second to none. Upgraded engineered hardwood flooring extends throughout the main level, where the thoughtfully designed floor plan perfectly balances open-concept living with defined spaces for both everyday life and formal entertaining. Just off the foyer, the formal living and dining rooms provide an elegant setting for gatherings and celebrations. At the heart of the home, the dramatic two-story family room is flooded with natural light and seamlessly connects to the kitchen, creating an inviting atmosphere for family and guests alike. With 5 bedrooms and 4 full bathrooms, the versatile layout is designed to accommodate a variety of lifestyles. A first-floor bedroom with an adjoining full bath offers exceptional flexibility for guests, multigenerational living, or a private home office. The upper level features generously sized bedrooms and a spacious loft that can easily be transformed into a media room, second family room, playroom, study area, or workspace. The fully finished basement adds yet another level of versatility, providing ample space for recreation, fitness, gaming, entertaining, or whatever best suits your lifestyle. Offering an exceptional combination of one of Parkside's most sought-after floor plans, a premier lot, impressive living space, and a desirable location, this remarkable home is designed to meet the needs of today's discerning buyer while providing room to grow, gather, and create lasting memories. Schedule your tour!

610 Spring Hollow Dr, Middletown

Listing courtesy of Burns & Ellis Realtors. Contact:

126 Green Forest Dr, Middletown
$864,900
4 Beds ⋅ 4 Baths
MODEL HOME FOR SALE. The stunning Houston model home at Rothwell Estates is available for sale. The intricate coffered ceiling in the 2 story great room has been a favorite show piece of anyone that has seen this home, and the fireplace with floor to ceiling stonework tops off the WOW FACTOR of this beautifully designed model home. High end features include the 3 CAR SIDE TURNED GARAGE, craftsman elevation with metal roof and extra stonework, sprinkler system, whole house speakers, mature landscaping, sunroom, gourmet kitchen with double wall oven, wet bar, deck, catwalk, freestanding soaking tub, engineered wood floors throughout most of the home, and custom moldings that you would normally need to hire a high end carpenter to achieve. The finished basement is complete with walk-up access to the back yard, a bar, separate game/exercise room, and a full bath. You won't regret making time this weekend to come take a look at this gorgeous home!

126 Green Forest Dr, Middletown

Listing courtesy of RE/MAX Elite. Contact:

424 Crownleaf Dr, Middletown
$862,000
4 Beds ⋅ 5 Baths
**Long awaited release - only 4 of our final 15 homes now available for purchase!** 424 Crownleaf Drive showcases the popular Aurora floorplan. The grandeur of this home is immediately apparent, with a formal living room and dining room elegantly flanking the wide, two-story foyer. Moving through the home, you have a powder room tucked neatly down the hall. The great room has a show-stopping two story ceiling and features. This space effortlessly moves into the kitchen, featuring stainless steel appliances, upgraded cabinets, modern quartz counter tops and a large walk-in pantry. This particular home features a popular morning room option, allowing natural light to pour through. This space is easily transitional for many uses. This level also includes a mudroom - a perfect drop zone as you come in through your two car side entry garage! Upstairs, you'll find a smart layout - with two large bedrooms sharing a bath. The third bedroom has a large closet and it's own en suite! The primary bedroom is a true retreat, offering a large bathroom with a walk in shower, linen closet, dual sinks and a water closet. Moving past the bathroom is an oversized walk-in closet that makes starting and ending your day a breeze. The laundry room is also found nearby for added convenience. The partial finished basement on this home offers an enormous amount of storage space and/or future living! Come see why so many have decided to call Copperleaf home! Schedule a private or self-guided tour today and make this magnificent home yours, where every detail is designed for your comfort and enjoyment. ** Please Read: Photos are for illustrative purposes only and may include renderings or images of the actual home or similar home/plan. Please see New Home Consultant for final pricing, finishes, and details. Taxes will be assessed after settlement. If you are working with a realtor, buyer representation must be acknowledged during the first interaction with Lennar, and the realtor must accompany the client on their first visit. Visits to Copperleaf are by appointment only. During your visit the sales team can review details, timelines, and current incentives. Financing is available through Lennar Mortgage upon qualification. **

424 Crownleaf Dr, Middletown

Listing courtesy of Atlantic Five Realty. Contact:

507 Ibis Ct, Middletown
$799,900
6 Beds ⋅ 5 Baths
Welcome to 507 Ibis Court, an exceptional 2023-built K. Hovnanian Stavanger offering 6 bedrooms, 4.5 bathrooms, and more than 4,600 square feet of finished living space in Middletown’s desirable Pleasanton community. Thoughtfully upgraded and already complete, this home offers the appeal of newer construction without the wait. Set on a cul-de-sac and backing to the community walking path and woods, the property enjoys a rare combination of privacy, convenience, and a peaceful natural backdrop. A covered front porch welcomes you inside, where 9-foot ceilings and luxury vinyl plank flooring throughout most of the main level create a bright, polished feel. To the left of the foyer, barn doors open to a private office, while the formal dining room sits to the right. At the heart of the home is a dramatic two-story great room anchored by a floor-to-ceiling stone gas fireplace. The adjoining gourmet kitchen is equally impressive, featuring a large center island with breakfast seating, a six-burner gas range, second oven, abundant cabinetry, generous counter space, and a large pantry. Just off the kitchen, the screened deck extends the living space outdoors and offers a comfortable place to relax or entertain while enjoying the wooded setting. The first floor also includes a private Extra Suite with its own full bath, providing valuable flexibility for guests or extended stays. A two-car garage adds everyday convenience, and the interior garage entry opens to a practical drop-zone area for coats, shoes, and bags. A beautiful dark-oak staircase leads to the second floor, where four bedrooms are located. The primary suite features a tray ceiling, a well-appointed private bath with dual sinks, and an exceptionally large walk-in closet just beyond the bath. Three additional bedrooms and convenient upper-level laundry complete this floor. The finished basement adds substantial additional living space for recreation, fitness, entertaining, or work-from-home needs, while a separate unfinished area provides valuable extra storage. Pleasanton offers sidewalks, a community walking path, playground/tot lot, and dog park, with convenient access to Downtown Middletown, shopping, dining, and major commuter routes. Built in 2023, the home may also offer applicable remaining K. Hovnanian builder-warranty coverage, subject to the builder’s terms and transfer requirements. With more than 4,600 finished square feet, an expanded 6-bedroom layout, premium cul-de-sac setting, wooded backdrop, and extensive upgrades already in place, **507 Ibis Court delivers the space, finish, and convenience of newer construction—ready now.**

507 Ibis Ct, Middletown

Listing courtesy of EXP Realty, LLC. Contact:

212 Layla Dr, Middletown
$775,000
4 Beds ⋅ 3 Baths
MOUNTAIN VIEWS, POOLSIDE LIVING & PRIVACY IN MIDDLETOWN. There’s something special about a home that gives you room to breathe, beautiful views, and a backyard that makes staying home feel like a getaway. Set high on a .46-acre corner lot in Foxfield at Middletown, this spacious Admar-built home offers approximately 3,252 square feet above grade, a full unfinished walkout lower level, beautiful views toward Braddock Mountain, and an outdoor setting designed to be enjoyed. LIGHT-FILLED LIVING & ROOM TO GATHER. Step inside to a light-filled floor plan where a dramatic two-story family room creates an impressive gathering space. The main level also offers separate living and dining rooms, a private home office, and a kitchen designed for everyday living and entertaining with quartz countertops, stainless-steel appliances, a center island, and butler’s pantry. Hardwood floors and the staircase were refinished in 2019, wrought-iron pickets add character, and remote-controlled Hunter Douglas blinds bring convenience to the living space. FOUR BEDROOMS & A PRIVATE PRIMARY RETREAT. Upstairs are four spacious bedrooms, including a generous primary suite with a private en-suite bath, soaking tub, and two walk-in closets. Two York HVAC systems separately serve the main and upper levels, while a gas fireplace, main-level laundry, and side-load two-car garage with added overhead storage provide additional comfort and function. YOUR OWN BACKYARD ESCAPE. But it may be outside where this home becomes truly unforgettable. The large composite deck overlooks the fenced backyard and approximately 16’ x 34’ heated gunite saltwater pool, installed by Browning Pools & Spas in 2020. Built-in steps, underwater lighting, and a loveseat tucked into the deep end create your own private place to spend long summer afternoons. SUNSETS, SUMMER NIGHTS & EVEN FIREWORKS. As evening arrives, settle onto the deck and enjoy gorgeous sunsets over the surrounding landscape. And in the fall, there’s an unexpected bonus—you can even catch the nearby pumpkin patch fireworks right from the pool and deck. It’s a backyard designed not simply to look beautiful, but to be lived in and enjoyed. ROOM TO GROW. There’s plenty of room to grow, too. The full unfinished walkout lower level features high ceilings, three full-size windows overlooking the backyard, and a bathroom rough-in, offering tremendous potential for future living space while providing abundant storage today. THOUGHTFULLY MAINTAINED. A new roof was installed in 2021 with a transferable warranty, and the home has been thoughtfully maintained throughout the sellers’ ownership. THE MIDDLETOWN LIFESTYLE. Nearly half an acre, no HOA, Middletown schools, mountain views, gorgeous sunsets, and your own backyard pool—this is the kind of home that makes you want to stay awhile.

212 Layla Dr, Middletown

Listing courtesy of RE/MAX Results. Contact:

202 Stover Ct, Middletown
$770,000
4 Beds ⋅ 3 Baths
Welcome to this exceptional 3,200 sq ft home, perfectly situated on a private wooded lot with beautiful landscaping, outstanding curb appeal, and a professionally manicured lawn. Thoughtfully designed with timeless finishes and an open, light-filled floor plan, this home offers the perfect blend of elegance, comfort, and functionality. The gourmet kitchen is the heart of the home, featuring granite countertops, stainless steel appliances, a cooktop with a stainless vent hood, an oversized center island with seating and an undermount sink, a walk-in pantry, recessed lighting, and a spacious breakfast area. The kitchen flows seamlessly into the dramatic two-story family room, where floor-to-ceiling windows fill the space with natural light and a stunning floor-to-ceiling stone fireplace creates a warm and inviting focal point. Ideal for both everyday living and entertaining, the main level also includes formal living and dining rooms with elegant trim details, as well as a private office/additional bedroom or flex room and a convenient powder room. Upstairs, the luxurious primary suite offers a peaceful retreat with a large walk-in closet and a spa-inspired en-suite bath featuring dual vanities, a custom tiled walk-in shower with dual shower heads, and a relaxing soaking tub. Three additional generously sized bedrooms, a full hall bath, and an upstairs laundry room complete the second floor. The expansive 1,756-square-foot walk-out basement features 9+ foot ceilings and plumbing rough-ins for a future bathroom, providing endless possibilities for additional living space, a home gym, recreation room, or guest suite. Step outside to your own private backyard retreat with a perfect setting for outdoor dining, relaxing, and entertaining while overlooking the peaceful-wooded backdrop. A 10' x 12' storage shed provides ample space for lawn equipment, tools, and outdoor gear. Located in the highly regarded Appoquinimink School District, this beautiful home offers space, style, and an exceptional location. Combining elegant interior finishes with exceptional indoor and outdoor living, this move-in-ready home is a rare opportunity you won't want to miss. **please note some areas of the home have virtual staging and object removal performed**

202 Stover Ct, Middletown

Listing courtesy of Crown Homes Real Estate. Contact:

426 Crownleaf Dr, Middletown
$769,000
4 Beds ⋅ 4 Baths
*Long awaited release - only 4 of our final 15 homes now available for purchase!* Welcome to 426 Crownleaf Drive, the stunning Montgomery floorplan! Come on in and be greeted by a grand double story entry way. This open style floorplan connects the formal dining space to your living room seamlessly. Off your gourmet style kitchen you will find a home office and spacious mudroom with direct access to your two car garage. Moving upstairs you will conveniently find your laundry room as well as four bedrooms and two full baths. This home is complete with a partially finished basement with an additional full bathroom! Copperleaf homes are located in the highly coveted Appoquinimink School district on half acre lots! ** Please Read: Photos are for illustrative purposes only and may include renderings or images of the actual home or similar home/plan. Please see New Home Consultant for final pricing, finishes, and details. Taxes will be assessed after settlement. If you are working with a realtor, buyer representation must be acknowledged during the first interaction with Lennar and the realtor must accompany the client on their first visit. Visits to Copperleaf are by appointment only. During your visit the sales team can review details, timelines, and current incentives. Financing is available through Lennar Mortgage upon qualification.**

426 Crownleaf Dr, Middletown

Listing courtesy of Atlantic Five Realty. Contact:

934 Skimmer St, Middletown
$764,990
4 Beds ⋅ 3 Baths
Welcome to the Macon II—this is your exclusive early look at a beautifully designed home that blends an open-concept layout with timeless Classic-inspired elements. Scheduled for settlement in September 2026, this home offers 4 bedrooms, 3 baths, and a 2-car garage, delivering both style and functionality. The main living area features a cozy fireplace with shiplap, creating a warm and inviting focal point. A finished basement provides additional living space ideal for entertaining, guests, or a private retreat. The screened-in covered deck extends your living area outdoors, perfect for relaxing or hosting gatherings. The kitchen is designed to impress, showcasing statement pendant lighting and elegant Calacatta quartz countertops, combining everyday functionality with elevated style. Laminate flooring flows throughout the main floor, second-floor loft, and primary suite, creating a cohesive and modern look. The bath includes a walk-in shower, offering a clean and contemporary finish. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

934 Skimmer St, Middletown

Listing courtesy of Delaware Homes Inc. Contact:

642 Vivaldi Dr, Middletown
$749,999
4 Beds ⋅ 3 Baths
Welcome to the Village of Bayberry South! Boasting pride of ownership both inside and out, this beautifully maintained home offers the rare opportunity to enjoy a home that feels like new. This home features thoughtful upgrades and established landscaping that makes it feel like your new home. Built in 2018 and beautifully appointed with a neutral interior throughout, it provides the perfect blank canvas for your own creative touches. Situated in the Village of Bayberry South, this exceptional home is set on a premium $30,000 lot that backs to trees and open space beside the property, creating a peaceful setting with a wonderful sense of privacy. An inviting front porch and mature landscaping enhance the home's curb appeal, welcoming you into a property that has been lovingly cared for. Inside, you'll find 4 bedrooms, including a main-level primary suite with a 2-foot extension, upgraded primary bath featuring upgraded hardware, tile flooring, vanity, and shower, plus a spacious walk-in closet. The main level also offers a sunroom extension, recessed lighting, and a family room with a fireplace accented by a granite surround. The designer kitchen is a standout, featuring upgraded appliances, cabinetry with pull-out trays, and upgraded hardware. Beautiful 5-inch Hickory hardwood flooring extends through the foyer, dining room, sunroom, kitchen, and breakfast area, complemented by upgraded carpet throughout the home. Upstairs, the spacious loft includes a separate HVAC zone, along with a fourth bedroom and upgraded bath, offering a wonderful private retreat for guests or additional living space. This home includes an impressive $118,871 in builder options, reflecting the thoughtful upgrades and attention to detail throughout. The Village of Bayberry South is a distinguished 55+ community offering an elegant setting, beautiful homes, and a welcoming atmosphere. With its established streetscapes, attractive surroundings, and impressive amenities, it provides a wonderful place to enjoy the next chapter of life. The impressive clubhouse serves as the heart of the community, offering a spacious gathering room, bar, fitness center, exercise studio, billiards room, meeting room, and a beautiful outdoor patio overlooking a tranquil pond with a fire pit. A vibrant social calendar featuring clubs, events, and activities makes it easy to stay active, meet neighbors, and enjoy the lifestyle you've been looking for. Conveniently located with easy access to the brand-new Bayberry Town Center, you'll enjoy nearby shopping, restaurants, fitness centers and healthcare facilities. Come discover the pride of ownership, exceptional upgrades and stately community setting that make this Village of Bayberry South home such a wonderful place to call your own!

642 Vivaldi Dr, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

883 Merlin Dr, Middletown
$749,990
4 Beds ⋅ 3 Baths
Welcome to the Macon II—this is your exclusive early look at a beautifully designed home that blends an open-concept layout with timeless Classic-inspired elements. Scheduled for settlement in September 2026, this home offers 4 bedrooms, 3 baths, and a 2-car garage, delivering both style and functionality. The main living area features a cozy fireplace with shiplap, creating a warm and inviting focal point. A finished basement provides additional living space ideal for entertaining, guests, or a private retreat. The screened-in covered deck extends your living area outdoors, perfect for relaxing or hosting gatherings. The kitchen is designed to impress, showcasing statement pendant lighting and Arctic White quartz countertops, combining everyday functionality with elevated style. Laminate flooring flows throughout the main floor, creating a seamless and cohesive look. The bath includes a walk-in shower, offering a clean and modern finish. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

883 Merlin Dr, Middletown

Listing courtesy of Delaware Homes Inc. Contact:

104 Marathon Dr, Middletown
$749,900
4 Beds ⋅ 3 Baths
Welcome to this grand 2-story, colonial-style residence nestled in the serene community of Middletown, DE. Set on an expansive .91-acre lot, the property boasts of privacy and tranquility with its 55 Arborvitae trees perfectly lined up across the backyard, creating an exclusive haven. Step into the backyard to discover a professionally maintained, fenced inground pool, accessorized with a new liner, cover, motor/pump, and multi-purpose valve, all updated in 2023 along with a custom pool shed, offering the perfect space for relaxing and entertaining. Inside, the rustic concept immediately greets you with attractive detailing. Experience the feeling of warmth and welcome as you traverse the gleaming hardwood floors that run throughout the house, punctuated by a stunning full-height brick wall that stretches from the formal living room to the dining room. Creating the perfect flow for entertaining, the open concept kitchen features state-of-the-art amenities including a gas cooktop, stainless steel appliances, a wall oven, and beautiful granite countertops. Relax and unwind in the cozy family room, complemented by soaring vaulted ceilings that create an airy feel. As you make your way upstairs, you'll appreciate the option of a stunning double staircase that leads to four generously sized bedrooms on the 2nd floor. The primary bedroom offers added luxury with tiled floors, a comfortable soaking tub, and a double sink, adding to the overall appeal of this well-designed area. The basement is beautifully finished, showcasing rustic accent walls, a wet bar, and durable vinyl flooring, providing additional living and entertainment space. This home also offers peace of mind with a brand new septic system, D-box and dual drain fields that will last one over 40 years. Experience the perfect balance between comfort and efficiency with a central A/C system (3 zone unit) and forced air heating. Add this to your tour today, you won't be disappointed.

104 Marathon Dr, Middletown

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

69 Kirkcaldy Ln, Middletown
$749,900
5 Beds ⋅ 4 Baths
Welcome to this stunning Colonial-style home nestled in Middletown, DE, in the highly desirable community of The Estates at St. Anne’s. Offering 5 bedrooms—including a main-level bedroom—and 3 1/2 bathrooms across three spacious levels, this beautifully appointed home also offers legitimate potential for a 6th bedroom with egress in the finished lower level. Step inside to a bright, open floor plan featuring a formal living room and dining room accented by elegant crown molding and hardwood flooring. The welcoming foyer showcases 24-inch tile flooring that continues through the kitchen and morning room, creating a seamless flow throughout the main living spaces. The gourmet kitchen is truly the heart of the home, featuring upgraded countertops, an enormous yet inviting center island, stainless steel appliances, farmhouse sink, gas range with custom hood, beverage refrigerator, built-in microwave, pantry, and a breakfast area perfect for casual dining and morning gatherings. Just off the kitchen, the cozy family room features a stone-surround wood-burning fireplace, providing the perfect setting for relaxing evenings and holiday gatherings. The main level also includes a spacious bedroom with a full bathroom, offering exceptional flexibility for guests, extended family, or an in-law suite. Upstairs, the luxurious primary suite provides a private retreat with a beautifully appointed bathroom featuring a soaking tub and tiled stall shower. Three closets—including a walk-in closet with custom shelving by Closets by Design—provide excellent storage. Additional bedrooms are generously sized and feature ceiling fans and plush carpeting, with convenient access to the laundry room and another full bathroom with tub/shower combination. The finished lower level expands the living space with a recreation/family room, stylish bar featuring granite countertops, sink, beverage refrigerator and glass-panel cabinetry, table area, and powder room—with room to expand and add a shower. A dedicated home gym offers additional flexibility and could potentially serve as a 6th bedroom due to it having proper egress. Luxury vinyl plank flooring and recessed lighting complete this versatile level. Outside, enjoy relaxing or entertaining on the paver patio with firepit, unwind on the covered front porch, or explore the community walking trails and charming gazebos throughout the neighborhood. Major updates include a new roof and HVAC system in 2021(w/ Humidifier and Air Purifier) and a new water heater in 2025. The home is also equipped with OWNED solar panels, 2 Powerwalls with generator and off grid capability, offering added energy efficiency and peace of mind. The Estates at St. Anne’s offers convenient access to St. Anne’s Club Golf Course, Casa 19 Restaurant, Highlands Whiskey Bar, and the option to join the community pool—providing a refreshing retreat during the warmer months. Beautifully maintained and thoughtfully designed, this exceptional home seamlessly blends comfort, style, flexibility, and modern amenities in one of Middletown’s most desirable communities. This is a must-see!

69 Kirkcaldy Ln, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

2744 Van Cliburn Cir, Middletown
$749,000
4 Beds ⋅ 3 Baths
Stunning property available in the much sought after 55+ community of The Ponds at Bayberry. An opportunity to own this beautiful home for a fraction of new construction costs with upgrades and it is competitively priced for sale. A beautiful premium lot that is professionally landscaped with an underground irrigation system. This lot provides privacy with incredible views to be enjoyed from the screened porch and patio. This expanded ranch offers 4 spacious bedrooms with 3 full upgraded baths. The spacious primary suite is your personal retreat, with an ensuite bath and large walk-in closet. A fabulous gourmet chef's kitchen with a gas cook top, microwave, 2 wall ovens, vented range hood, dishwasher (2026), refrigerator (2022), upgraded cabinetry with soft close drawers, pull out drawers, beautiful granite with counter seating, upgraded stainless appliances. Featuring an open floor plan. A conveniently located mud room with newer washer and dryer leads to a full two-car garage. Full daylight walkout basement with 9ft ceilings. New sump pump (2026) and replaced the garage door cables which have a warranty. There is a whole home surge suppressor, coated concrete on the front and back porches and a whole house humidifier. This 55+ resort-style community offers luxury amenities for a low monthly HOA fee that includes landscaping, snow plowing and trash removal. There is an outdoor heated pool, pickle ball courts, tennis courts, bocce courts, and walking trails. Inside the large 10,000 sq ft clubhouse features a large community room, bar, fitness room, exercise room, billiards room, meeting rooms and a large patio overlooking one of the large outdoor ponds with a fire pit. There is an active social scene full of activities for many interests.

2744 Van Cliburn Cir, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact:

127 Burlina Blvd Unit LOT 86 COTTONWOOD, Middletown
$748,262
3 Beds ⋅ 2 Baths
Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of Traditions at Whitehall. This 3-bedroom home features a generous Owner’s Suite at the front of the home, complete with double walk-in closets leading to a luxurious en-suite bath, offering a privacy water closet and a 5-foot tile shower. At the rear of the home, you will find the kitchen and dining area that opens to a bright and airy great room, perfect for relaxation or entertaining. Step outside to enjoy the peaceful surroundings on the optional deck off the breakfast area, where you can take in views of the trees and open space. With a variety of structural and decorative options available, this home can be customized to suit your style and needs. The Cottonwood Model offers the perfect blend of comfort, size, elegance, and low-maintenance living in a vibrant active adult community. As a resident you will enjoy access to amenities that include a clubhouse, fitness facilities, swimming pools, walking trails, and a full calendar of social events to keep you engaged and connected with neighbors.

127 Burlina Blvd Unit LOT 86 COTTONWOOD, Middletown

Listing courtesy of RE/MAX Elite. Contact:

6023 Freestone Blvd, Middletown
$735,250
5 Beds ⋅ 5 Baths
Welcome to 6023 Freestone Boulevard at Freestone Village, where luxury, space, and thoughtful design come together in one exceptional home. This beautifully upgraded Danbury floorplan offers over 3,800 square feet of living space plus a partially finished basement with its own full bath, making it ideal for growing families, entertaining, or multigenerational living. The open-concept main level is designed for everyday living and hosting alike, featuring a gourmet kitchen, quartz countertops, soft close cabinetry, a spacious island, and a morning room extension that fills the home with natural light. The adjoining great room showcases a cozy fireplace, while a convenient first-floor guest suite with a full bath offers the perfect space for overnight guests or extended family. Upstairs, the luxurious owner's suite provides a relaxing retreat with a tray ceiling, spa-inspired bath with soaking tub, and an oversized walk-in closet. Three additional bedrooms, including a secondary bedroom with its own private en-suite bath, plus a centrally located laundry room completes the second floor. The finished basement adds even more flexible living space with a large recreation room and a full bathroom—perfect for a home theater, fitness area, game room, or additional guest accommodations. Additional premium features include oak stairs with open railing, designer tile selections, stainless-steel appliances including refrigerator, washer, and dryer, and a prime location in the award-winning Appoquinimink School District with easy access to shopping, dining, and major commuter routes. *Pictures are of model home from a sister community and for representational purposes only. There is a sales trailer on-site. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit.

6023 Freestone Blvd, Middletown

Listing courtesy of Atlantic Five Realty. Contact:

248 Wickerberry Dr, Middletown
$735,000
4 Beds ⋅ 3 Baths
Seller's job relocation equates to an opportunity for one lucky buyer. They are motivated to sell. This move-in ready and beautifully updated Parkside home offering exceptional living and entertaining space inside and out. A welcoming front porch leads into a bright, freshly painted interior with refinished hardwood floors and updated lighting. The main level features a flexible office with potential for use as a bedroom, formal living and dining rooms, and a completely renovated kitchen with new cabinetry, countertops, appliances, and a walk-in pantry. The kitchen opens to the spacious family room, where a double-sided fireplace adds warmth and character. French doors lead to the bright sunroom overlooking the backyard. Both the kitchen and sunroom offer sliding-door access to the oversized deck, creating a seamless connection between the indoor and outdoor living spaces. The deck features illuminated post caps, while the private fenced backyard is enhanced with perimeter lighting—perfect for evening entertaining or relaxing outdoors. A newly added built-in drop zone provides convenient organization near the two-car garage, which includes an EV charger and direct backyard access. The enormous unfinished basement with egress offers excellent potential for future finished living space. Upstairs, new carpeting runs throughout. The spacious primary suite features a tray ceiling, sitting area, generous closet space, and an ensuite bath with a soaking tub and separate shower. Each additional bedroom is nicely sized, freshly painted, and features double closets and ceiling fans. The laundry is conveniently located in the hallway for ease of use. Recent updates include a two-year-old roof, newer HVAC system, new tankless water heater, whole-home surge protection, new water manifold valves, and a radon remediation system. An ADT security system is also available for reactivation. Enjoy everything the desirable Parkside community has to offer, including its clubhouse, pool, fitness space, playground, and year-round community activities. This is a home designed to be enjoyed with its beautiful updates and thoughtful design. Which make it ready for its next owner!

248 Wickerberry Dr, Middletown

Listing courtesy of Keller Williams Realty Wilmington. Contact:

645 Greylag Rd, Middletown
$729,999
4 Beds ⋅ 3 Baths
HUGE $100,000 price reduction!!!! A Private 2.74‑Acre Retreat Featuring a Spacious 4BR/3BA Ranch, W/ 2 Car attached garage, In-ground Pool, and a 2,700 SF Heated Detached Garage/Workshop Designed for Real‑World Needs in the heart of northern Middletown, WITH NO DEED RESTRICTIONS!!!!! ** New Septic has been installed**** Welcome to a rare opportunity to enjoy both privacy and practicality on 2.74 peaceful, tree‑lined acres in the heart of Middletown. Located in the award‑winning Appoquinimink School District and just minutes from Routes 1 and 13, this property offers the ideal blend of convenience, comfort, and capability for families and small business owners alike. The home features beautiful hardwood flooring, bright and open living spaces, and an updated kitchen with white cabinetry, granite counter tops, 3 built‑in pantry storage areas, 1st floor laundry and all appliances included. The main level provides comfortable everyday living, while the finished basement adds valuable flexibility — perfect for a guest suite, home office, gym, recreation room, or multi‑generational living. A sunroom overlooking the backyard offers year‑round enjoyment, and the patio and in-ground pool create a welcoming space for gatherings, celebrations, and relaxed family time. Recent upgrades include a new roof in 2025, newer heating and air conditioning systems, an approximately 150‑foot‑deep well, and a brand‑new septic system has been installed, ensuring peace of mind for years to come. This is where the property becomes truly exceptional approximately 2,700‑square‑foot detached garage/workshop — a dream setup for anyone needing serious workspace. Fully equipped with electric, heat, and water, and designed with multiple access points, this building is ideal for contractors, mechanics, hobbyists, collectors, entrepreneurs, or families needing substantial storage for equipment, vehicles, or small business operations. The possibilities are endless. If you've been searching for a home that offers privacy, comfort, and extraordinary workspace-along with the freedom to use the land your way look no further. With parking for more than 20 vehicles, expansive outdoor space, and unmatched versatility, this property supports a lifestyle that blends home, work, and recreation seamlessly. If you’re looking for a place where your family can thrive and your business or hobbies can grow, 645 Greylag Road offers the space and freedom to make it happen

645 Greylag Rd, Middletown

Listing courtesy of Iron Valley Real Estate Premier. Contact:

932 Skimmer St, Middletown
$719,990
4 Beds ⋅ 4 Baths
Welcome to the Omaha—this is your exclusive early look at a beautifully designed home that blends an open-concept layout with charming Farmhouse-inspired elements. Scheduled for settlement in September 2026, this home offers 4 bedrooms, 3.5 baths, and a 2-car garage, delivering both comfort and style. The main living area features a stunning stone fireplace, creating a warm and inviting focal point. A finished basement provides additional living space ideal for entertaining, guests, or a private retreat. The screened-in covered deck extends your living area outdoors, perfect for relaxing or hosting gatherings. The kitchen is designed to impress, showcasing statement pendant lighting and elegant Calacatta quartz countertops, combining everyday functionality with elevated style. Laminate flooring flows throughout the main floor, second-floor loft, and primary suite, creating a seamless and modern look. The bath includes a walk-in shower, offering a clean and contemporary finish. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

932 Skimmer St, Middletown

Listing courtesy of Delaware Homes Inc. Contact:

1620 Jaymes Cir, Middletown
$699,990
3 Beds ⋅ 4 Baths
Brand New 55+ Community in Middletown, DE Welcome to the Carver, a beautifully designed home that combines an open-concept layout with plenty of natural light. Scheduled for settlement in October 2026, this home offers 3 bedrooms, 3.5 baths, and a 2.5-car garage, providing a comfortable blend of style and functionality. A welcoming front porch creates charming curb appeal, while the screened deck offers an inviting space to enjoy the outdoors. Inside, the finished basement provides additional living space, and a fireplace adds warmth and character to the main living area. The spacious kitchen features a huge island and quartz countertops, perfect for cooking, gathering, and entertaining. Laminate flooring throughout the first floor offers a cohesive and stylish finish, while the bathrooms feature a walk-in shower with tile walls. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

1620 Jaymes Cir, Middletown

Listing courtesy of Delaware Homes Inc. Contact:

1703 Jaymes Cir, Middletown
$699,990
2 Beds ⋅ 3 Baths
Brand New 55+ Community in Middletown, DE Welcome to the Morse, a beautifully designed home that blends an open-concept layout with timeless Classic-inspired elements. Scheduled for settlement in October 2026, this home offers 2 bedrooms, 3.5 baths, and a 2.5-car garage, delivering both comfort and thoughtful design throughout. The main living area features a stunning fireplace with shiplap, complemented by elegant crown molding in the great room for a refined and polished finish. A screened deck extends the living space outdoors, creating the perfect setting for relaxing or entertaining, while a finished basement provides additional flexible living space. The kitchen is equipped with a smart cooking suite of appliances and quartz countertops, combining modern convenience with elevated style. Laminate flooring flows throughout the entire first floor, creating a cohesive and durable foundation for everyday living. The bath includes a walk-in shower with a rain shower head, offering a spa-like experience with a clean, modern design. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

1703 Jaymes Cir, Middletown

Listing courtesy of Delaware Homes Inc. Contact:

2419 Quebec School Rd, Middletown
$699,900
5 Beds ⋅ 5 Baths
Welcome to 2419 Quebec School Road, a truly one-of-a-kind property offering nearly 3 acres, multiple living spaces, and incredible versatility in beautiful Middletown, Maryland. Situated on 2.98 acres with scenic mountain views and a brand-new roof on the main house, this property offers an incredibly rare setup for multigenerational living, extended family, guests, or anyone looking for additional space and flexibility. The main home features a split-level layout with beautiful hardwood floors, three bedrooms, and three full bathrooms. The main living level offers a spacious family room, dining room, and kitchen, creating a comfortable and functional space for everyday living. Step outside to the screened-in, covered rear deck overlooking the property. Upstairs, you'll find three bedrooms and two full bathrooms, along with an additional room currently configured as a laundry room with an adjoining full bathroom. This flexible space offers the potential to be converted back into a fourth bedroom, if desired, while providing the convenience of upper-level laundry in its current configuration. The lower level adds even more versatility with a second family room, kitchenette, laundry room, and den/flex room, providing a great setup for an in-law suite, home office, guest space, or additional living area. Continue down another level to find a finished recreation room offering even more room to spread out. But what truly sets this property apart is the detached accessory dwelling unit offering more than 2,100 square feet of additional living space. The ADU features two bedrooms, two full bathrooms, a full kitchen, dining area, multiple family/living spaces, and a dressing room that provides additional flexibility as an office, hobby room, or bonus space. A private deck off the rear of the ADU provides another outdoor space to enjoy the surrounding property. Outside, the professionally landscaped 2.98-acre level lot offers plenty of room to spread out while enjoying beautiful views of the surrounding Middletown landscape and mountains. The property provides even more possibilities for its next owner. Additional improvements include a well pump replaced in 2022 and a well pressure tank replaced in 2018. Between the main residence, lower-level in-law setup, and detached ADU, this property offers three kitchen or kitchenette areas, multiple gathering spaces, five established bedrooms, and an abundance of additional flex space. Whether you're searching for a true multigenerational property, space for extended family, or simply a home that can evolve alongside your needs, 2419 Quebec School Road offers a combination of space, versatility, and setting that is incredibly hard to replicate. Schedule your showing today!

2419 Quebec School Rd, Middletown

Listing courtesy of Charis Realty Group. Contact:

How much is your home worth?

Get instant property value now!