195

Middletown, DE Homes for Sale under $800,000

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  • /14

    $759,990

    New Construction $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,772 Sq Ft

    932 Skimmer St, Middletown, DE 19709

    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

    Barbara Heilman Delaware Homes Inc

    932 Skimmer St, Middletown, DE 19709
  • /80

    $694,900

    • 4 Beds
    • 2.5 Baths
    • 3,325 Sq Ft

    107 Sassafras Dr, Middletown, DE 19709

    Welcome to 107 Sassafras Drive in the desirable community of Matapeake in Middletown, Delaware. Situated on over one acre, this property offers space, privacy, and a newly installed 2,160 sq ft pole barn—perfect for storage, hobbies, or workshop use. This spacious home features a grand two-story foyer with a dual staircase, providing access from both the front and rear of the home. The main level

    Daniel Mawn RE/MAX Associates - Newark

    107 Sassafras Dr, Middletown, DE 19709
  • /40

    $629,900

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,250 Sq Ft

    649 Spring Hollow Dr, Middletown, DE 19709

    PRICE IS RIGHT! THE HOME EVERYONE WANTS BUT RARELY FINDS IN MIDDLETOWN! Better than new and in one of Middletown's most sought-after communities. Finished basement, home office, tree-lined street & move-in ready. One-year home warranty being offered by seller + 6 months HOA dues paid by seller! Welcome to this beautifully appointed 4-bedroom, 2.5-bath home nestled along a picturesque tree-lined

    Ben Stentz Iron Valley Real Estate at The Beach

    649 Spring Hollow Dr, Middletown, DE 19709
  • /19

    $749,500

    • 5 Beds
    • 2.5 Baths
    • 3,775 Sq Ft

    362 Neverland Dr, Middletown, DE 19709

    Welcome to 362 Neverland Dr in Middletown, Delaware — a beautifully upgraded home offering space, privacy, flexibility, and lifestyle features in one of Delaware’s most desirable and fast-growing towns. Perfectly positioned on a premium wooded lot with no rear neighbors, this home offers peaceful views, added privacy, and the rare feeling of not looking directly into another backyard. From the

    Ray Dockery LPT Realty, LLC

    362 Neverland Dr, Middletown, DE 19709
  • /31

    $649,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,250 Sq Ft

    224 Tralee Dr, Middletown, DE 19709

    Discover the charm and elegance of this exceptional home in the highly sought-after Wheatland community. Set on a picturesque two-acre lot, this stunning residence offers 3,250 square feet of above-grade living space, five spacious bedrooms, a sparkling pool, and the perfect blend of comfort, style, and functionality.A grand two-story foyer welcomes you into a light-filled interior featuring

    Margaret Poisson Century 21 Gold Key-Dover

    224 Tralee Dr, Middletown, DE 19709
  • /11

    $662,990

    New Construction
    • 5 Beds
    • 3 Baths
    • 2,797 Sq Ft

    Knoxville Plan at Pleasanton, Middletown, DE 19709

    Lovely home office off foyer for working from home. Stylish kitchen with large island overlooking great room. Open great room with tons of windows for sunlight. Extra Suite tucked off great room for overnight guests. Relaxing primary suite with private bath and walk-in closet. Versatile loft on second floor, great for a home theater, gameroom, play room, and more.

    K. Hovnanian Homes Builder
    129 Patterson Ct Unit 36482432, Middletown, DE 19709
  • /50

    $650,000

    • 4 Beds
    • 3.5 Baths
    • 4,475 Sq Ft

    14 Haggis Rd, Middletown, DE 19709

    Welcome to 14 Haggis Road, a magnificent Colonial nestled on a coveted corner lot in the prestigious Estates at St. Anne’s — one of Middletown’s most sought-after golf course communities. Offering nearly 4,800 square feet of living space, 4 bedrooms, 3.5 bathrooms, and room sizes that are simply hard to find at this price point, this is a rare opportunity to own a truly grand home in an

    Devon Smith Crown Homes Real Estate

    14 Haggis Rd, Middletown, DE 19709
  • /23

    $545,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,151 Sq Ft

    Tuscany Luxe Plan at Venue at Winchelsea 55+ - Winchelsea Singles, Middletown, DE 19709

    This new two-story home features an open kitchen, dining room, family room and conveniently located office. At opposite ends of the layout is a secondary bedroom and the spacious owner's suite with a private bathroom and walk-in closet. Rounding out the home is a sprawling upstairs loft for versatile shared entertainment space and a two-car garage for storage room.

    Lennar Builder
    2405 Greyfriar Loop Unit 36041428, Middletown, DE 19709
  • /2

    $539,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 3,800 Sq Ft

    354 Northhampton Way, Middletown, DE 19709

    Professional photos to follow

    Shanika Clark EXP Realty, LLC

    354 Northhampton Way, Middletown, DE 19709
  • /32

    $689,000

    $41K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,675 Sq Ft

    412 Maplewood Dr, Middletown, DE 19709

    Welcome to the highly sought-after community of Lea Eara Farms in Middletown, Delaware, located within the Appoquinimink School District. Rarely does a property like this become available. Situated on a private half-acre lot backing to mature woods, this beautifully maintained 3,675 square foot 4 bedroom, 3.1 bath home offers exceptional space, functionality, and privacy. From the moment you

    Liam O'Neill Compass

    412 Maplewood Dr, Middletown, DE 19709
  • /60

    $659,900

    $35K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 4,936 Sq Ft

    103 Westside Ln, Middletown, DE 19709

    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

    Susan Fitzwater RE/MAX Advantage Realty

    103 Westside Ln, Middletown, DE 19709
  • /17

    $559,250

    New Construction $21K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,778 Sq Ft

    3223 Rye Harbour Way, Middletown, DE 19709

    This new two-story home features an open kitchen, dining room, family room and conveniently located office. At opposite ends of the layout is a secondary bedroom and the spacious owner's suite with a private bathroom and walk-in closet. Rounding out the home is a sprawling upstairs loft for versatile shared entertainment space and a two-car garage for storage room.

    Lennar Builder
    3223 Rye Harbour Way, Middletown, DE 19709
  • /3

    $599,454

    New Construction
    • 4 Beds
    • 2.5 Baths

    304 N Thales Dr, Middletown, DE 19709

    This Astaire Farmhouse elevation quick-delivery home offers homeowners an airy yet cozy open concept floor plan. With a multi-purpose formal space at the front of the home and everyday spaces spanning the entire width of the back of the home, the Astaire provides the perfect balance of necessary separation and cozy connectivity for couples or families engaging in an array of daily activities

    Brittany Stephens Blenheim Marketing LLC

    304 N Thales Dr, Middletown, DE 19709
  • /22

    $549,900

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,441 Sq Ft

    Eastwood Loft Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

    Elegant foyer entry welcoming friends and family. Generous ceiling height for maximum natural light and openness. Open, single-story home design boasting dream kitchen with island. Spacious great room with optional fireplace creating relaxing atmosphere. Secluded owner's suite with oversized closet and private bath. Optional Extra Suite Plus offers privacy for guests and multi-generational living.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36473802, Middletown, DE 19709
  • /4

    $570,500

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,456 Sq Ft

    Chadwick Plan at The Town of Whitehall - Mapleton Village, Middletown, DE 19709

    Open 5 days a week, 11 a.m. 5 p.m. Please call ahead or email lshaffer@benchmarkbuilders.com to check tour availability. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    530 Wheelmen St Unit 36501616, Middletown, DE 19709
  • /41

    $585,000

    • 4 Beds
    • 3.5 Baths
    • 2,650 Sq Ft

    211 Douglas Way, Middletown, DE 19709

    Advantages of this Town House: Advantages of This Townhome: Main-Level In-Law Suite / Spacious Deck / Bright Sunroom / Private Patio / Desirable Corner Lot Location. Welcome to beautiful Townhome 211 Douglas Way Middletown, DE 19709. This beautifully maintained 4-bedroom, 3 and half bath townhome located in the highly desirable Middletown Reserve community of Middletown, Delaware. Built in 2023,

    RAGHU CHITTIBOMMALA Tesla Realty Group, LLC

    211 Douglas Way, Middletown, DE 19709
  • /61

    $675,000

    $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,650 Sq Ft

    871 Sweet Birch Dr, Middletown, DE 19709

    Welcome to 871 Sweet Birch, a great home in the sought-after community of Parkside.... Middletown, DE. As you walk inside this home take in the beautiful hardwood floors that span into the open concept living area. The main floor open living area creates a warm and comfortable setting for all your family and entertaining needs. The kitchen area has newer appliances, granite counter tops and is

    Ann Marie Germano Patterson-Schwartz-Middletown

    871 Sweet Birch Dr, Middletown, DE 19709
  • /4

    $590,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    530 Wheelmen St Unit 6 CHARLESTON, Middletown, DE 19709

    CHARLESTON -TO BE BUILT. This 4 bedroom (OPTIONAL 1ST FLOOR 5TH BEDROOM) open floor plan welcomes homeowners and visitors alike in a space that flows effortlessly from one room to the next. There is a spacious kitchen with hardwood floors, along with 42" maple cabinets, granite countertops, and so much more! Be the first to build this floor plan and get a special incentive off any upgrades. Ask

    Lindsay Shaffer RE/MAX Elite

    530 Wheelmen St Unit 6 CHARLESTON, Middletown, DE 19709
  • /2

    $649,900

    Coming Soon
    • 5 Beds
    • 3.5 Baths
    • 3,825 Sq Ft

    601 Yensid Dr, Middletown, DE 19709

    Coming soon!601 Yensid Drive in Middletown. This beautifully maintained 5 bed, 3.5 bath home offers 3825 square feet of generous living space and a thoughtfully designed layout for everyday comfort located in the desirable Crossland at the Canal, with access to a community pool, and clubhouse. Stay tuned for professional photos, and full details coming soon.

    Linda Chase Compass

    601 Yensid Dr, Middletown, DE 19709
  • /105

    $749,900

    $25K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 5,877 Sq Ft

    138 Green Forest Dr, Middletown, DE 19709

    Welcome to 138 Green Forest Drive, a beautifully appointed 4–5 bedroom home offering generous living spaces, thoughtful design, and exceptional versatility. Designed with an open floor plan ideal for both everyday living and entertaining, this impressive residence combines timeless architectural details with modern functionality. The main level features elegant formal living and dining rooms,

    Michael Wilson BHHS Fox & Roach-Greenville

    138 Green Forest Dr, Middletown, DE 19709
  • /96

    $600,000

    $25K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,575 Sq Ft

    23 Browning Cir, Middletown, DE 19709

    Welcome to 23 Browning Circle, where comfort, privacy, and thoughtful design come together in one of Middletown's most desirable communities. Nestled in the sought-after community of Middletown Crossing and located within the acclaimed Appoquinimink School District, this beautifully maintained home offers the perfect blend of spacious living, modern updates, and a backyard setting that is

    Megan Aitken Keller Williams Realty

    23 Browning Cir, Middletown, DE 19709
  • /33

    $682,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,440 Sq Ft

    Amesbury Plan at Freestone Village - Singles, Middletown, DE 19709

    Upon entry into this new two-story home is a flex space ideal for hosting guests. The partially secluded formal dining room leads to an open-concept main living area, featuring a center fireplace and seamless access to the backyard. In a thoughtful design, all four bedrooms and a spacious loft are tucked away upstairs for privacy. The owner’s suite includes split walk-in closets and a serene

    Lennar Builder
    0 Levels Rd & Grears Corner Rd Unit 40352122, Middletown, DE 19709
  • /5

    $638,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,225 Sq Ft

    Armstrong Plan at Rothwell Estates, Middletown, DE 19709

    Tours by appointment onlyplease call 302-274-0712 to schedule. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    126 Green Forest Dr Unit 36488866, Middletown, DE 19709
  • /16

    $652,990

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,737 Sq Ft

    Cordoba Plan at Pleasanton, Middletown, DE 19709

    Extra Suite with private bath for multi-generational living and guests. Private home office off foyer, to work from home with plenty of space. Striking kitchen with large island and Looks interior options. Impressive great room adjoining the dining area and kitchen, ideal for entertianing. Luxurious primary suite with walk-in closet. Relaxing primary bath with dual sinks.

    K. Hovnanian Homes Builder
    129 Patterson Ct Unit 36449446, Middletown, DE 19709
  • /85

    $665,000

    Open Fri 5PM - 7PM
    • 5 Beds
    • 5 Baths
    • 3,500 Sq Ft

    74 Kirkcaldy Ln, Middletown, DE 19709

    Welcome home to timeless elegance, thoughtful upgrades, and exceptional value in one of Middletown's most desirable communities of Estates at St. Annes. From the moment you arrive, this home makes an unforgettable first impression with its crisp white exterior, freshly painted columns and trim, and beautifully crafted new paver walkway, landing, and steps that create a warm, welcoming entrance.

    Megan Aitken Keller Williams Realty

    74 Kirkcaldy Ln, Middletown, DE 19709
  • /48

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 2,484 Sq Ft

    529 Saint Michael Dr, Middletown, DE 19709

    The beautiful home at 529 St Michael is situated on a hilltop in a private cul-de-sac. It boasts a 3⁄4 acre property (looks like more!) backing to community open space and established woodlands. There is no other homesite that comes close to this beauty! The home itself is a 4 Bedroom, 2 1⁄2 bath with both formal living and dining areas, a huge eat-in kitchen, and central (vaulted) family room

    Michelle D Varner Patterson-Schwartz-Middletown

    529 Saint Michael Dr, Middletown, DE 19709
  • /89

    $675,000

    • 5 Beds
    • 3.5 Baths
    • 4,700 Sq Ft

    50 Haggis Rd, Middletown, DE 19709

    Welcome to 50 Haggis Road, an exceptional opportunity to own a stunning home in the prestigious resort community of St. Anne's, one of Middletown's most sought-after neighborhoods. Perfectly blending elegance, comfort, and functionality, this expansive residence offers 5 bedrooms, 2 full bathrooms, 2 half bathrooms, and a beautifully finished basement, creating the ideal setting for both everyday

    Megan Aitken Keller Williams Realty

    50 Haggis Rd, Middletown, DE 19709
  • /47

    $658,000

    $11K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,475 Sq Ft

    42 Watson Ln, Middletown, DE 19709

    Welcome to 42 Watson Lane—offering the space, layout, and setting you’ve been searching for. With over 3,000 square feet and a prime location backing to the golf course, this well-maintained home is ready for its next owner to make it their own. Step inside to a spacious foyer with a striking double staircase leading to the second level. The main floor features a formal dining room to the left

    Melvin Sarpey Crown Homes Real Estate

    42 Watson Ln, Middletown, DE 19709
  • /89

    $775,000

    • 5 Beds
    • 4.5 Baths
    • 4,225 Sq Ft

    201 Parker Dr, Middletown, DE 19709

    Welcome to 201 Parker Drive, an exceptional residence nestled in the highly sought-after Crossland at the Canal community, where elegant design, luxurious amenities, and energy-efficient living come together in one remarkable home. Offering five bedrooms, four full bathrooms, and one half bath, this beautifully appointed property welcomes you with a bright two-story foyer and hardwood flooring

    Michael Kelczewski Century 21 Emerald

    201 Parker Dr, Middletown, DE 19709
  • /35

    $676,990

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 3,261 Sq Ft

    Adaline Plan at Freestone Village - Singles, Middletown, DE 19709

    This new two-story home enjoys a spacious layout that offers endless possibilities. A serene bedroom suite and flex space are situated along the foyer for versatile needs, while down the hall is an open-concept main living area with a center fireplace. Residing upstairs are four bedrooms centered around an expansive loft, ideal for shared entertainment. In a corner is the sprawling owner’s suite

    Lennar Builder
    0 Levels Rd & Grears Corner Rd Unit 40352124, Middletown, DE 19709
  • /9

    $615,000

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,908 Sq Ft

    602 Corbit Dr, Middletown, DE 19709

    Welcome to this exceptional, turnkey 4-bedroom, 2.5-bath home with a 2-car garage in the highly sought-after Cantwell Ridge community, located in the award-winning Appoquinimink School District and served by Odessa High School. Perfectly situated across the street from a neighborhood park, this beautifully renovated home offers the ideal combination of luxury, comfort, and convenience.The

    Jay Shinn RE/MAX Point Realty

    602 Corbit Dr, Middletown, DE 19709
  • /48

    $789,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,875 Sq Ft

    228 Wickerberry Dr, Middletown, DE 19709

    This Stunning Home built by Anderson Builder is located on the Corner lot in the Parkside Community. This 4 bedroom, 2 1/2 bath home welcomes you as soon as you enter into the home. The 2-story foyer provides an embracing warmth separating the dining and living room. The Large office can be access by the double doors off the living room or by the hall entrance. A butler's pantry connects dining

    Angela Clement EXP Realty, LLC

    228 Wickerberry Dr, Middletown, DE 19709
  • /29

    $751,250

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 2,948 Sq Ft

    6027 Freestone Blvd, Middletown, DE 19709

    Discover exceptional space, style, and flexibility in the Grier at Freestone Village, Middletown's newest premier community.This beautifully appointed home offers over 3,000 square feet of thoughtfully designed living space plus a partially finished basement with its own full bath. From the moment you step inside, you'll appreciate the open-concept layout, designer finishes, and impressive

    Lennar Builder
    6027 Freestone Blvd, Middletown, DE 19709
  • /30

    $647,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft

    Danbury Plan at Freestone Village - Singles, Middletown, DE 19709

    Designed for elevated comfort and entertainment, this new home features two stories of gracious living space. At the heart of the first floor is a welcoming Great Room with a center fireplace and easy access to the kitchen and dining area. It’s complemented by a flex space and an office. Residing upstairs are all four bedrooms, including the tranquil owner’s suite with a private bathroom and

    Lennar Builder
    0 Levels Rd & Grears Corner Rd Unit 40352127, Middletown, DE 19709
  • /4

    $624,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 3,110 Sq Ft

    Bennett Plan at Ponds of Odessa - Single Family Homes, Middletown, DE 19709

    Fabulous home with front & rear staircases and 4 bedrooms. Tours by appointment onlyplease call 302-274-0712 to schedule. Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    400 Rederick Ln Unit 36446342, Middletown, DE 19709

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