Middletown, DE Homes for Sale under $500,000

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  $449,500 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

  1104 Highland St, Middletown, DE 19709

  Annandale Carriage Flexible Living with First-Floor EaseThe Annandale Carriage offers 1,699 sq. ft. of comfortable, low-maintenance living designed for 55+ lifestyles. With a first-floor owners suite, an additional bedroom, 2.5 baths, and an open-concept main level, this home makes everyday living effortless. Upstairs, a spacious loft provides the perfect spot for guests, hobbies, or a

  

  Benchmark Builders

  Builder

  1104 Highland St, Middletown, DE 19709
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  $425,331 New Construction

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

  446 Rederick Ln, Middletown, DE 19709

  Massey Townhome at Ponds of OdessaThis 3-bedroom, 3.5-bath townhome offers 2,001 square feet of well-designed living space. Enjoy a one-car garage, a 12' x 10' deck for outdoor gatherings, and a breakfast bar in the upgraded kitchen. A finished den adds flexible space for work, hobbies, or relaxation.Workforce Housing Unit Only. Follow link for more details:

  

  Benchmark Builders

  Builder

  446 Rederick Ln, Middletown, DE 19709
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  $439,311 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,232 Sq Ft

  448 Rederick Ln, Middletown, DE 19709

  Massey Townhome at Ponds of OdessaThis 3-bedroom, 2.5-bath townhome offers 2,232 square feet of comfortable living space. Features include a one-car garage, an upgraded kitchen with a breakfast bar, and a finished den that provides flexible space for work or leisure.

  

  Benchmark Builders

  Builder

  448 Rederick Ln, Middletown, DE 19709
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  $400,800 New Construction

  • 5 Beds
  • 2 Baths
  • 2,669 Sq Ft

  3128 Pett Level Dr, Middletown, DE 19709

  Welcome to Venue at Winchelsea by Lennar — Middletown’s premier active adult (55+) community offering low-maintenance living, spacious designs, and exceptional value. This 2,669 sq. ft. two-story townhome is part of Lennar’s Pathway to Ownership Program -application and income qualification are required for purchase.3128 Pett Level Drive is a Fall move-in home thoughtfully designed for

  David Vasso Atlantic Five Realty

  3128 Pett Level Dr, Middletown, DE 19709
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  $425,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

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

  Annandale Carriage Flexible Living with First-Floor EaseThe Annandale Carriage offers 1,699 sq. ft. of comfortable, low-maintenance living designed for 55+ lifestyles. With a first-floor owners suite, an additional bedroom, 2.5 baths, and an open-concept main level, this home makes everyday living effortless. Upstairs, a spacious loft provides the perfect spot for guests, hobbies, or a

  

  Benchmark Builders

  Builder

  204 Baldy Ln Unit 36447810, Middletown, DE 19709
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  $425,000 New Construction

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

  Alrich Carriage Plan at Traditions at Whitehall - 55+ Active Adult, 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

  

  Benchmark Builders

  Builder

  204 Baldy Ln Unit 36500401, Middletown, DE 19709
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  /22

  $439,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,178 Sq Ft

  Serenade Plan at Crossings at Silver Lake, Middletown, DE 19709

  Crossings at Silver Lake offers the only new homes walkable to Middletown’s Main Street, adjacent to the new library, YMCA & Silver Lake Park. Outdoor living & 2-car garage included. The Serenade offers an updated take on townhome living. Enter through the foyer on the lower level, where a quiet study makes work-from-home easy and an included recreation room is ideal for game day gatherings.

  

  Ryan Homes

  Builder

  303 E Cochran St Unit 36143320, Middletown, DE 19709
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  $440,990 New Construction

  • 2 Beds
  • 2 Baths
  • 1,968 Sq Ft

  Beacon II Plan at Venue at Winchelsea 55+ - Winchelsea Carriages, Middletown, DE 19709

  This two-story home showcases a luxurious and comfortable design, hosting an open-concept floorplan for easy entertaining and two bedrooms on the first level. The expansive owner’s suite is nestled into a back corner for optimal privacy, featuring an en-suite bathroom and walk-in closet. Upstairs, a versatile loft area provides shared living on the second floor, next to a spacious storage room.

  

  Lennar

  Builder

  2405 Greyfriar Loop Unit 36041416, Middletown, DE 19709
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  $499,990 New Construction

  • 2 Beds
  • 2 Baths
  • 1,728 Sq Ft

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

  This new home features a basement offering ample opportunities for recreation and entertainment. An inviting open-concept layout on the first floor combines the kitchen with the living and dining areas, with a convenient flex space located off the foyer. Two bedrooms are tucked away to the side of the home, including the lavish owner’s suite with an en-suite bathroom and dual walk-in closets.

  

  Lennar

  Builder

  2405 Greyfriar Loop Unit 36041426, Middletown, DE 19709
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  $412,800 New Construction

  • 5 Beds
  • 2 Baths
  • 2,669 Sq Ft

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

  The first floor of this new two-story townhome is host to an inviting open-concept floorplan that blends the kitchen, living and dining areas. The luxurious owner’s suite is nestled into a private rear corner, with another bedroom located at the front of the home. On the second floor, three additional bedrooms surround a versatile loft. This plan is part of the Venue at Winchelsea Pathway to

  

  Lennar

  Builder

  2405 Greyfriar Loop Unit 36041420, Middletown, DE 19709
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  $464,990 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
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  $416,000 New Construction

  • 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
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  /22

  $412,800 New Construction

  • 5 Beds
  • 2 Baths
  • 2,669 Sq Ft

  2674 Fairlight Dr, Middletown, DE 19709

  The first floor of this new two-story townhome is host to an inviting open-concept floorplan that blends the kitchen, living and dining areas. The luxurious owner’s suite is nestled into a private rear corner, with another bedroom located at the front of the home. On the second floor, three additional bedrooms surround a versatile loft. This plan is part of the Venue at Winchelsea Pathway to

  

  Lennar

  Builder

  2674 Fairlight Dr, Middletown, DE 19709
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  $465,000 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  527 Swansea Dr, Middletown, DE 19709

  COMING SOON.... worth the wait...professional pictures coming....Welcome to this charming 3-bedroom home with 3.1 bathrooms in The Preserve at Deep Creek located in Middletown, DE just minutes from plenty of dining, shopping, the 301 highway to connect you to all major roads and a great park across the way with walking trails, fishing, 2 large dog parks, an amazing tot lot, gazebo with bbq grills

  Ann Marie Germano Patterson-Schwartz-Middletown

  527 Swansea Dr, Middletown, DE 19709
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  $490,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  13 Brady Cir, Middletown, DE 19709

  Stunning Fully Renovated Home Backing to Protected Nature PreserveWelcome to this beautifully renovated single-family home perfectly situated on a quiet, clear road across from peaceful parkland — and backing to a serene open space and creek that will never be built on. Enjoy privacy, views, and the sounds of nature right from your oversized rear deck.This home features a spacious open

  Katina Geralis EXP Realty, LLC

  13 Brady Cir, Middletown, DE 19709

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