55

Middletown, DE Homes for Sale under $500,000

Section Image Section Image Section Image
  • 38 N Cummings Dr, Middletown, DE 19709
    38 N Cummings Dr, Middletown, DE 19709
    38 N Cummings Dr, Middletown, DE 19709
    /43

    $419,900

    • 4 Beds
    • 3.5 Baths
    • 1,750 Sq Ft

    38 N Cummings Dr, Middletown, DE 19709

    Welcome to this beautifully upgraded 4-bedroom, 3.5-bath semi-detached townhome in the desirable Middletown Crossing community of Middletown, DE. From the moment you step inside, you’ll notice the attention to detail, with rich hardwood flooring and custom wood trim flowing seamlessly throughout the entire home.The main level offers a perfect blend of comfort and functionality, featuring an

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    (302) 262-1304

    38 N Cummings Dr, Middletown, DE 19709
  • 1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
    /12

    $499,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft

    Asheville Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Modern kitchen with large island, walk-in pantry, & Looks interior options. Covered front porch & back deck, to welcome guests and unwind in the fresh air. Impressive great room with vaulted ceiling. Luxurious primary suite with triple windows and tray ceiling. Relaxing primary bath with dual sinks, walk-in closet, & optional freestanding tub.

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
  • 79 Lattice Ln, Middletown, DE 19709
    79 Lattice Ln, Middletown, DE 19709
    79 Lattice Ln, Middletown, DE 19709
    /80

    $495,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 2,275 Sq Ft

    79 Lattice Ln, Middletown, DE 19709

    Welcome to 79 Lattice Lane, a beautifully maintained detached ranch home in the highly desirable 55+ community of Spring Arbor in Middletown. Offering the ease of one-level living with the added bonus of an expansive finished basement, this home combines comfort, functionality, and low-maintenance living in one of the area’s most sought-after active adult communities. Inside, you’ll find a bright

    Renee Edge Keller Williams Realty

    79 Lattice Ln, Middletown, DE 19709
  • 137 Silver Maple Rd, Middletown, DE 19709
    137 Silver Maple Rd, Middletown, DE 19709
    137 Silver Maple Rd, Middletown, DE 19709
    /21

    $499,900

    • 3 Beds
    • 2 Baths
    • 1,625 Sq Ft

    137 Silver Maple Rd, Middletown, DE 19709

    This is your opportunity to move into Silver Maple, one of the area’s most desirable 55+ communities, known for its exceptional amenities and active lifestyle. From the moment you enter this 3BR, 2BA, 2-car garage home, you’ll notice the beautiful hardwood floors that flow from the foyer through the main living areas. The open-concept floor plan seamlessly connects the living room, featuring

    Delcollo & Salva Team Patterson-Schwartz-Hockessin

    137 Silver Maple Rd, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
    /23

    $459,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft

    Taylor Plan at Venue at Winchelsea 55+ - Winchelsea Towns, Middletown, DE 19709

    This new two-story townhome is designed to promote low-maintenance living with a sophisticated twist. On the first floor is everything you need day-to-day, featuring a private owner’s suite, a convenient study and an open-concept layout shared among the kitchen, dining room and spacious family room. The top floor presents a loft and two versatile bedrooms to customize as homeowners see fit.

    Lennar Builder
    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
  • 1511 Lesterfield Way, Middletown, DE 19709
    1511 Lesterfield Way, Middletown, DE 19709
    1511 Lesterfield Way, Middletown, DE 19709
    /34

    $499,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,811 Sq Ft

    1511 Lesterfield Way, Middletown, DE 19709

    The Asheville - with over 2,800 finished sq. ft. - delivers modern design and comfortable living with spaces made for both entertaining and everyday relaxation. The contemporary kitchen is the heart of the home, featuring a large island, walk-in pantry, and designer Looks interior selections that elevate the space. A covered front porch and rear deck invite you to welcome guests or unwind

    Barbara Heilman Delaware Homes Inc

    1511 Lesterfield Way, Middletown, DE 19709
  • 409 Galway Ct, Middletown, DE 19709
    409 Galway Ct, Middletown, DE 19709
    409 Galway Ct, Middletown, DE 19709
    /55

    $450,000

    • 3 Beds
    • 3.5 Baths
    • 1,700 Sq Ft

    409 Galway Ct, Middletown, DE 19709

    Welcome to 409 Galway Court in the Popular Community of Hyetts Crossing. Conveniently located with quick access to Rt's 1 & 301. This Home is the Spacious Chesterfield Model Carriage House with a Main Level Owners Suite. Designed for Open Concept Living the Main Level has a Great Room with a Break Away Ceiling (2 Story High) with 2 Walls of Windows allowing in ample sunlight. There is a Gourmet

    Jack Keating RE/MAX Elite

    409 Galway Ct, Middletown, DE 19709
  • 15 Golden Raintree Ct, Middletown, DE 19709
    15 Golden Raintree Ct, Middletown, DE 19709
    15 Golden Raintree Ct, Middletown, DE 19709
    /25

    $499,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,780 Sq Ft

    15 Golden Raintree Ct, Middletown, DE 19709

    This is a To-Be-Built Home. The Eastwood is a beautifully designed one-story floorplan offering 2 bedrooms, 2 bathrooms, and a 2-car garage, thoughtfully created for comfortable and convenient living. An elegant foyer entry welcomes friends and family into the home and leads into a bright, open living space. Generous ceiling heights throughout enhance the sense of openness and allow for an

    Barbara Heilman Delaware Homes Inc

    15 Golden Raintree Ct, Middletown, DE 19709
  • 7 Lesh Ct, Middletown, DE 19709
    7 Lesh Ct, Middletown, DE 19709
    7 Lesh Ct, Middletown, DE 19709
    /19

    $474,900

    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft

    7 Lesh Ct, Middletown, DE 19709

    Located in the Cricklewood Community in a cul-de-sac. Open space as soon as you walk in, 3 bedrooms upstairs, a large master bedroom with a walk-in closet. This home shows lots of updates, roof 2024, heating and air conditioner 2024, new windows 2024, and water heater 2025. Outside has a new deck in 2025, with a private view. The basement has a cedar closet and is partially finished with an

    ANA VASQUEZ RE/MAX Advantage Realty

    7 Lesh Ct, Middletown, DE 19709
  • 1325 Carrick Ct, Middletown, DE 19709
    1325 Carrick Ct, Middletown, DE 19709
    1325 Carrick Ct, Middletown, DE 19709
    /35

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,575 Sq Ft

    1325 Carrick Ct, Middletown, DE 19709

    Welcome to the desirable community of Ponds of Odessa, where you’ll find this beautifully maintained and spacious carriage home. This property offers 3 bedrooms, 2 full bathrooms, and 1 half bathroom, with additional potential for a fourth bedroom or private office on the main level perfect for flexible living. As you enter, you’re greeted by a welcoming foyer that leads to a spacious eat-in

    Kieara Simmons BHHS Fox & Roach-Concord

    1325 Carrick Ct, Middletown, DE 19709
  • 0 Levels Rd & Grears Corner Rd Unit 40352125, Middletown, DE 19709
    0 Levels Rd & Grears Corner Rd Unit 40352125, Middletown, DE 19709
    0 Levels Rd & Grears Corner Rd Unit 40352125, Middletown, DE 19709
    /22

    $449,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,361 Sq Ft

    Harley Plan at Freestone Village - Townhomes, Middletown, DE 19709

    This new two-story home showcases a modern, open-concept layout shared among the main living spaces, ideal for seamless multitasking and daily activities. It includes a sunny Great Room, a well-equipped kitchen and a lovely dining area complemented by a deck for indoor-outdoor gatherings. Situated on the top floor are all three bedrooms, while on the lower level is a sprawling recreation room for

    Lennar Builder
    0 Levels Rd & Grears Corner Rd Unit 40352125, Middletown, DE 19709
  • 248 Ann Dr, Middletown, DE 19709
    248 Ann Dr, Middletown, DE 19709
    248 Ann Dr, Middletown, DE 19709
    /53

    $479,900

    • 4 Beds
    • 4 Baths
    • 1,900 Sq Ft

    248 Ann Dr, Middletown, DE 19709

    Price improvement!!!!Great opportunity to own in the Crossland at Canal at a new value! This beautifully maintained 15 year old 4 bedroom 2.2 bathrooms home offers the perfect blend of comfort, space, and convenience. Step inside to find a bright and inviting layout with generous living areas, ideal for both everyday living and entertaining. The kitchen features ample cabinetry and workspace,

    Priscilla Aidoo Yeboah Tesla Realty Group, LLC

    248 Ann Dr, Middletown, DE 19709
  • 314 Charolais St Unit ASHTON, Middletown, DE 19709
    314 Charolais St Unit ASHTON, Middletown, DE 19709
    314 Charolais St Unit ASHTON, Middletown, DE 19709
    /25

    $456,000 Open Fri 7AM - 8PM

    • 2 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    314 Charolais St Unit ASHTON, Middletown, DE 19709

    Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This home is an end unit has a first-floor owner's bedroom w/ full ensuite bath and walk-in closets, second floor has the 2nd bedroom, loft and an additional full bath. Standard 2-car garage, and additional finished upgrades can be purchased to your taste and budget. Community offers in ground pool w/lounge

    Lindsay Shaffer RE/MAX Elite

    314 Charolais St Unit ASHTON, Middletown, DE 19709
  • 2311 Winchelsea Pkwy, Middletown, DE 19709
    2311 Winchelsea Pkwy, Middletown, DE 19709
    2311 Winchelsea Pkwy, Middletown, DE 19709
    /22

    $449,409 New Construction

    • 3 Beds
    • 2 Baths
    • 2,443 Sq Ft

    2311 Winchelsea Pkwy, Middletown, DE 19709

    The Taylor is a brand-new two-story townhome that is designed to promote low maintenance living with a sophisticated twist. As you enter, you are greeted by an open flex room, perfect for a home office or formal dining space, as well as a first-floor laundry room with Whirlpool washer and dryer included. The well-equipped gourmet-style kitchen features modern stainless-steel appliances, sleek

    Lennar Builder
    2311 Winchelsea Pkwy, Middletown, DE 19709
  • 27 Springmill Dr, Middletown, DE 19709
    27 Springmill Dr, Middletown, DE 19709
    27 Springmill Dr, Middletown, DE 19709
    /24

    $420,000

    • 2 Beds
    • 2 Baths
    • 2,275 Sq Ft

    27 Springmill Dr, Middletown, DE 19709

    Enjoy easy main-level living in this beautifully designed home featuring 2 bedrooms, 2 bathrooms, and a 2-car garage in the sought-after Springmill 55+ resort-style community. The inviting layout offers a living room with a gas fireplace, plus a sitting room and dining room at the front of the home for added flexibility and charm. The spacious kitchen is well-equipped with a center island,

    Michael McKee Long & Foster Real Estate, Inc.

    27 Springmill Dr, Middletown, DE 19709
  • 6028 Freestone Blvd, Middletown, DE 19709
    6028 Freestone Blvd, Middletown, DE 19709
    6028 Freestone Blvd, Middletown, DE 19709
    /22

    $483,920 New Construction

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft

    6028 Freestone Blvd, Middletown, DE 19709

    This new two-story home features a spacious and inviting open-concept layout on the first level, perfect for family gatherings and entertaining. A deck provides seamless indoor-outdoor entertainment, enhancing the living experience. On the second floor, a versatile loft offers convenient shared living, along with two secondary bedrooms and a luxurious owner’s suite with a spa-inspired bathroom.

    Lennar Builder
    6028 Freestone Blvd, Middletown, DE 19709
  • 148 Gazebo Ln, Middletown, DE 19709
    148 Gazebo Ln, Middletown, DE 19709
    148 Gazebo Ln, Middletown, DE 19709
    /37

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    148 Gazebo Ln, Middletown, DE 19709

    WOW! Simply Gorgeous! This popular Kipling model offers open floor plan, foyer with 11 FT ceiling, wainscoting and gleaming hardwoods extending from foyer thru living room, dining room and kitchen. Well appointed kitchen has granite counters including island with seating for 3, stainless steel appliances, recessed & upgraded lighting. Dining area has sliders to upgraded & enlarged paver patio,

    Mary Lynch Patterson-Schwartz-Middletown

    148 Gazebo Ln, Middletown, DE 19709
  • 452 Rederick Ln, Middletown, DE 19709
    452 Rederick Ln, Middletown, DE 19709
    /2

    $489,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    452 Rederick Ln, Middletown, DE 19709

    Massey Elite Townhome at Ponds of Odessa End Unit This 3-bedroom, 2.5-bath end unit townhome offers 2,380 square feet of thoughtfully designed space. Highlights include a two-car garage, a 12' x 10' deck, and a striking two-story bay bump-out that adds natural light and character. The entire second floor features luxury vinyl plank flooring, blending durability with modern style.

    Benchmark Builders Builder
    452 Rederick Ln, Middletown, DE 19709
  • 204 Baldy Ln Unit ALRICH, Middletown, DE 19709
    204 Baldy Ln Unit ALRICH, Middletown, DE 19709
    204 Baldy Ln Unit ALRICH, Middletown, DE 19709
    /29

    $425,000 Open Fri 11AM - 5PM

    • 2 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    204 Baldy Ln Unit ALRICH, Middletown, DE 19709

    Welcome to the 55+ community of Traditions at Whitehall - Alrich Carriage Town Home. This home is available as an interior or end unit & has a first-floor owner's bedroom w/ensuite bath and walk-in closets, second floor has a 2nd bedroom, loft and an additional full bath. Standard 1-car rear load attached garage but can be upgraded for a 2-car garage, and additional finished upgrades can be

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit ALRICH, Middletown, DE 19709
  • 204 Baldy Ln Unit 39052080, Middletown, DE 19709
    204 Baldy Ln Unit 39052080, Middletown, DE 19709
    204 Baldy Ln Unit 39052080, Middletown, DE 19709
    /38

    $425,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,761 Sq Ft

    Alrich Carriage Plan at Traditions at Whitehall - 55+ Active Adult - Carriage Homes, Middletown, DE 19709

    This stunning carriage home offers the perfect blend of elegance and functionality! Step inside and be greeted by a spacious foyer leading to the great room and open-concept kitchen/dining room - perfect for entertaining guests. The large first-floor owner's suite boasts a private bath and walk-in closet. Upstairs, you'll find a versatile loft area, a second bedroom, and another full bath. Below,

    Benchmark Builders Builder
    204 Baldy Ln Unit 39052080, Middletown, DE 19709
  • 442 Rederick Ln Unit MASSEY ELITE LOT 70, Middletown, DE 19709
    442 Rederick Ln Unit MASSEY ELITE LOT 70, Middletown, DE 19709
    442 Rederick Ln Unit MASSEY ELITE LOT 70, Middletown, DE 19709
    /16

    $498,053 Open Fri 11AM - 4:30PM

    • 3 Beds
    • 4 Baths
    • 2,333 Sq Ft

    442 Rederick Ln Unit MASSEY ELITE LOT 70, Middletown, DE 19709

    MASSEY ELITE END UNIT- Late Spring Move-In! 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2380 SF! 12x10 Deck. This home features a Finished den, 42" cabinets in kitchen, island, stainless gas range, dishwasher, microwave, LVP flooring and recessed lighting in Kitchen. LVP floor and Tile Shower surround in master bath. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan!

    Lindsay Shaffer RE/MAX Elite

    442 Rederick Ln Unit MASSEY ELITE LOT 70, Middletown, DE 19709
  • 204 Baldy Ln Unit 39052085, Middletown, DE 19709
    204 Baldy Ln Unit 39052085, Middletown, DE 19709
    204 Baldy Ln Unit 39052085, Middletown, DE 19709
    /24

    $456,000 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,794 Sq Ft

    Ashton Carriage Plan at Traditions at Whitehall - 55+ Active Adult - Carriage Homes, Middletown, DE 19709

    Ashton Carriage End-Unit Comfort with Flexible Space The Ashton Carriage offers 1,794 sq. ft. of thoughtfully designed living with the added privacy of an end-unit layout. Enjoy a convenient first-floor owners suite, open-concept living spaces, and a welcoming front porch for relaxed mornings or friendly chats. Upstairs, a spacious loft, second bedroom, and full bath give guests or hobbies their

    Benchmark Builders Builder
    204 Baldy Ln Unit 39052085, Middletown, DE 19709
  • 441 Rederick Ln, Middletown, DE 19709
    441 Rederick Ln, Middletown, DE 19709
    /2

    $479,260 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,377 Sq Ft

    441 Rederick Ln, Middletown, DE 19709

    Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    441 Rederick Ln, Middletown, DE 19709
  • 550 Lewes Landing Rd, Middletown, DE 19709
    550 Lewes Landing Rd, Middletown, DE 19709
    550 Lewes Landing Rd, Middletown, DE 19709
    /38

    $469,000

    • 3 Beds
    • 2.5 Baths
    • 2,425 Sq Ft

    550 Lewes Landing Rd, Middletown, DE 19709

    Immaculate 3BR/2.5BA Townhome located in Brighton in the desirable Appoquinimink School District. The Schubert model features an open concept floor plan with over 2400 square feet of living space. A pristine white kitchen with 10-foot island and granite counters is centrally located on the main level and includes a walk-in pantry, like new GE stainless steel appliances, and subway tile

    Michael Lenoir Keller Williams Realty Central-Delaware

    550 Lewes Landing Rd, Middletown, DE 19709
  • 435 Rederick Ln, Middletown, DE 19709
    435 Rederick Ln, Middletown, DE 19709
    /2

    $489,624 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,377 Sq Ft

    435 Rederick Ln, Middletown, DE 19709

    Illustrations are artists' concepts and may vary in detail from the actual plans and specifications.

    Benchmark Builders Builder
    435 Rederick Ln, Middletown, DE 19709
  • 2247 Winchelsea Pkwy, Middletown, DE 19709
    2247 Winchelsea Pkwy, Middletown, DE 19709
    2247 Winchelsea Pkwy, Middletown, DE 19709
    /22

    $464,509 New Construction

    • 3 Beds
    • 2 Baths
    • 2,443 Sq Ft

    2247 Winchelsea Pkwy, Middletown, DE 19709

    This new two-story townhome is designed to promote low-maintenance living with a sophisticated twist. On the first floor is everything you need day-to-day, featuring a private owner’s suite, a convenient study and an open-concept layout shared among the kitchen, dining room and spacious family room. The top floor presents a loft and two versatile bedrooms to customize as homeowners see fit.

    Lennar Builder
    2247 Winchelsea Pkwy, Middletown, DE 19709
  • 446 Rederick Ln Unit MASSEY LOT 68, Middletown, DE 19709
    446 Rederick Ln Unit MASSEY LOT 68, Middletown, DE 19709
    446 Rederick Ln Unit MASSEY LOT 68, Middletown, DE 19709
    /18

    $427,056 New Construction

    • 3 Beds
    • 2 Baths
    • 2,001 Sq Ft

    446 Rederick Ln Unit MASSEY LOT 68, Middletown, DE 19709

    ** WORKFORCE HOUSING-BUYER MUST QUALIFY FOR THE NEW CASTLE COUNTY PROGRAM TOPURCHASE -MASSEY INTERIOR UNIT- 3 bedrooms, 2.5 baths, 1 car garage. Approx. 2001 SF! This home features a Finished den, 12x10 DECK, 42" cabinets in kitchen, island, stainless steel appliances, gas range, dishwasher, microwave and recessed lighting in Kitchen. LVP flooring upgrades. 3 pc rough in walk out basement.

    Lindsay Shaffer RE/MAX Elite

    446 Rederick Ln Unit MASSEY LOT 68, Middletown, DE 19709
  • 2511 E Dali Dr, Middletown, DE 19709
    2511 E Dali Dr, Middletown, DE 19709
    2511 E Dali Dr, Middletown, DE 19709
    /55

    $464,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    2511 E Dali Dr, Middletown, DE 19709

    Welcome to 2511 E. Dali Drive, a beautifully maintained 3-bedroom, 2.5-bath twin home in the sought-after Village of Bayberry—available only due to relocation. Featuring the popular Bainbridge open floor plan, the main level is designed for modern living and effortless entertaining. Highlights include maple hardwood plank flooring, upgraded quartz countertops, 42" soft-close cabinetry, stainless

    Judy Chen BHHS Fox & Roach - Hockessin

    2511 E Dali Dr, Middletown, DE 19709
  • 1583 E Matisse Dr, Middletown, DE 19709
    1583 E Matisse Dr, Middletown, DE 19709
    /2

    $415,000 Open Sun 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    1583 E Matisse Dr, Middletown, DE 19709

    Welcome to this beautifully maintained 3-level end-unit townhome in the heart of Middletown; where space, layout, and natural light come together in all the right ways. As you step inside, the first level greets you with a versatile finished space that can easily flex to fit your lifestyle; think second living room, game room, home office, or gym. With direct access to the backyard through

    Kristina Rice Real Broker LLC

    1583 E Matisse Dr, Middletown, DE 19709
  • 6607 Harko Dr, Middletown, DE 19709
    6607 Harko Dr, Middletown, DE 19709
    6607 Harko Dr, Middletown, DE 19709
    /21

    $459,585 New Construction

    • 3 Beds
    • 2 Baths
    • 2,361 Sq Ft

    6607 Harko Dr, Middletown, DE 19709

    This new three-story home showcases a modern, open-concept layout shared among the main living spaces, ideal for seamless multitasking and daily activities. It includes a sunny Great Room, a well-equipped kitchen and a lovely dining area complemented by a deck for indoor-outdoor gatherings. Situated on the top floor are all three bedrooms, while on the lower level is a sprawling recreation room

    Lennar Builder
    6607 Harko Dr, Middletown, DE 19709
  • 554 Lewes Landing Rd, Middletown, DE 19709
    554 Lewes Landing Rd, Middletown, DE 19709
    554 Lewes Landing Rd, Middletown, DE 19709
    /30

    $495,000

    • 4 Beds
    • 3.5 Baths
    • 2,425 Sq Ft

    554 Lewes Landing Rd, Middletown, DE 19709

    Step into this stunning 4 bedroom, 3.5 bath interior townhome in the heart of Brighton, where contemporary design meets effortless functionality. Just three years young, this home is bright, modern, and thoughtfully designed to suit a variety of lifestyles. The first floor boasts a private bedroom with a full bath, making it perfect for multi-generational living, a guest suite, or even a private

    Lauren Janes Compass

    554 Lewes Landing Rd, Middletown, DE 19709
  • 452 Rederick Ln Unit MASSEY ELITE LOT 65, Middletown, DE 19709
    452 Rederick Ln Unit MASSEY ELITE LOT 65, Middletown, DE 19709
    452 Rederick Ln Unit MASSEY ELITE LOT 65, Middletown, DE 19709
    /15

    $489,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,380 Sq Ft

    452 Rederick Ln Unit MASSEY ELITE LOT 65, Middletown, DE 19709

    MASSEY ELITE END UNIT- 3 bedrooms, 2.5 baths, 2 car garage. Approx. 2380 SF! 12x10 Deck. This home features a Finished den, 42" cabinets in kitchen, island, stainless gas range, dishwasher, microwave, LVP flooring and recessed lighting in Kitchen. LVP floor and Tile Shower surround in master bath. 3 pc rough in walk out basement. Don't miss out on this spectacular floor plan! Builder Splits

    Lindsay Shaffer RE/MAX Elite

    452 Rederick Ln Unit MASSEY ELITE LOT 65, Middletown, DE 19709
  • 1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
    /19

    $416,000 Open Sat 11AM - 4:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709

    BASE PRICE LISTING - MODEL HOME IS NOT FOR SALE. Welcome to a stylish and spacious 3-storytownhome that offers 1 or 2 garages, square footage ranging from 2,001-2,333 & contemporary living at its finest. With 3 bedrooms, 2.5 baths, and a finished den on the first level with rough in plumbing for a future bathroom, this home is designed to provide both comfort and versatility. As you step

    Lindsay Shaffer RE/MAX Elite

    1300 Carrick Ct Unit MASSEY ELITE MODEL, Middletown, DE 19709
  • 0 Levels Rd & Grears Corner Rd Unit 40352128, Middletown, DE 19709
    0 Levels Rd & Grears Corner Rd Unit 40352128, Middletown, DE 19709
    0 Levels Rd & Grears Corner Rd Unit 40352128, Middletown, DE 19709
    /24

    $474,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,858 Sq Ft

    Avery Plan at Freestone Village - Carriages, Middletown, DE 19709

    This new two-story home features a spacious and inviting open-concept layout on the first level, perfect for family gatherings and entertaining. A deck provides seamless indoor-outdoor entertainment, enhancing the living experience. On the second floor, a versatile loft offers convenient shared living, along with two secondary bedrooms and a luxurious owner’s suite with a spa-inspired bathroom.

    Lennar Builder
    0 Levels Rd & Grears Corner Rd Unit 40352128, Middletown, DE 19709
  • 2243 Winchelsea Pkwy, Middletown, DE 19709
    2243 Winchelsea Pkwy, Middletown, DE 19709
    2243 Winchelsea Pkwy, Middletown, DE 19709
    /22

    $458,109 New Construction

    • 3 Beds
    • 2 Baths
    • 2,443 Sq Ft

    2243 Winchelsea Pkwy, Middletown, DE 19709

    The Taylor is a brand-new two-story townhome that is designed to promote low maintenance living with a sophisticated twist. As you enter, you are greeted by an open flex room, perfect for a home office or formal dining space, as well as a first-floor laundry room with Whirlpool washer and dryer included. The well-equipped gourmet-style kitchen features modern stainless-steel appliances, sleek

    Lennar Builder
    2243 Winchelsea Pkwy, Middletown, DE 19709
  • 160 Pine Valley Dr, Middletown, DE 19709
    160 Pine Valley Dr, Middletown, DE 19709
    160 Pine Valley Dr, Middletown, DE 19709
    /85

    $500,000

    • 5 Beds
    • 3 Baths
    • 2,900 Sq Ft

    160 Pine Valley Dr, Middletown, DE 19709

    WHY SUCH A DRASTIC PRICE REDUCTION? Every seller wants to obviously get the most for their home. It is their biggest investment after all, and in this case the seller wanted to go above my suggested listing price and see what the results would be. We are now priced aggressively for the neighborhood AND this lovely home has sooooo much to offer!! Welcome to this spacious 5-bedroom, 3-bath ranch,

    Von Guerrero Tesla Realty Group, LLC

    160 Pine Valley Dr, Middletown, DE 19709
  • 860 Lissicasey Loop, Middletown, DE 19709
    860 Lissicasey Loop, Middletown, DE 19709
    860 Lissicasey Loop, Middletown, DE 19709
    /61

    $410,000

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    860 Lissicasey Loop, Middletown, DE 19709

    Welcome to 860 Lissicasey Loop, an end-unit opportunity in Hyett's Crossing that checks every box buyers are searching for... and then some. Homes like this, with space, upgrades, and a prime location in Middletown do not last, and this one is no exception. From the moment you arrive, the curb appeal and added privacy of an end unit set this home apart. Out back, the fully fenced yard, expansive

    Megan Aitken Keller Williams Realty

    860 Lissicasey Loop, Middletown, DE 19709
  • 264 Trellis Ln, Middletown, DE 19709
    264 Trellis Ln, Middletown, DE 19709
    264 Trellis Ln, Middletown, DE 19709
    /34

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    264 Trellis Ln, Middletown, DE 19709

    Fantastic Clean, Cozy Townhome in THE 55+ Community of the Middletown area, SPRING ARBOR. Location, Location, Location! Nestled in the charming Spring Arbor community, conveniently close to all Middletown has to offer, this delightful twin/semi-detached residence offers a serene retreat designed for those seeking a vibrant yet peaceful lifestyle. Built in 2007, this home boasts a spacious 1,800

    Sam Stanton BHHS Fox & Roach - Hockessin

    264 Trellis Ln, Middletown, DE 19709
  • 365 Andrew Ct, Middletown, DE 19709
    365 Andrew Ct, Middletown, DE 19709
    365 Andrew Ct, Middletown, DE 19709
    /32

    $477,000

    • 3 Beds
    • 4 Baths

    365 Andrew Ct, Middletown, DE 19709

    Welcome to 365 Andrew Ct! This beautifully maintained, like-new home offers all the advantages of new construction without the wait. Nestled within the highly acclaimed Appoquinimink School District, this stunning end-unit townhome combines luxury with convenience. Featuring an expansive open-concept floor plan, this home is tailored for modern living. With 3 bedrooms, 2 full baths, 2 half baths,

    Amy Hurley Foraker Realty Co.

    365 Andrew Ct, Middletown, DE 19709

Showing Results 1 - 40, Page 1 of 2

Delaware New Castle County Middletown

Real Estate & Homes in Middletown, DE under $500,000

Home Trends in Middletown, DE

On average, homes in Middletown, DE sell after 200 days on the market compared to the national average of 56 days. The median sale price for homes in Middletown, DE over the last 12 months is $535,550, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$535,550
Median Single Family Sale Price
$583,775
Median Townhouse Sale Price
$440,000
Median 2 Bedroom Sale Price
$265,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
256
Last 12 months Home Sales
696
Months of Supply
4.40
Median List Price
$562,990
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
How to Buy a Home How to Finance a Home How to Sell a Home

In Middletown, you'll encounter a variety of homes and houses for sale priced under $500,000, providing affordable options for potential buyers. With 55 listings available, there's a wide selection to explore, from charming bungalows to contemporary townhouses. These properties offer an opportunity to enter the real estate market or diversify your investment portfolio without exceeding your budget. Discover the range of homes for sale under 500k in Middletown, DE and find the perfect fit for your homeownership goals.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group