90

Middletown, DE Homes for Sale with Pool

Section Image Section Image
  • 152 Tywyn Dr, Middletown, DE 19709
    152 Tywyn Dr, Middletown, DE 19709
    152 Tywyn Dr, Middletown, DE 19709
    /25

    $665,000

    • 5 Beds
    • 3.5 Baths
    • 4,797 Sq Ft

    152 Tywyn Dr, Middletown, DE 19709

    Check out this beautiful and well-kept 5-bedroom, 3.5-bath home in the popular Preserves at Deep Creek community. This spacious home sits on a great lot at the end of a quiet street. As you walk in, you'll find a welcoming open hallway that leads to the lovely formal living and dining rooms. The kitchen features a large island that overlooks the great room and a bright morning room, making it

    Tijuana Garvin EXP Realty, LLC

    152 Tywyn Dr, Middletown, DE 19709
  • 830 Sweet Birch Dr, Middletown, DE 19709
    830 Sweet Birch Dr, Middletown, DE 19709
    830 Sweet Birch Dr, Middletown, DE 19709
    /90

    $969,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 5,050 Sq Ft

    830 Sweet Birch Dr, Middletown, DE 19709

    Welcome Home to 830 Sweet Birch Drive, located in the desirable PARKSIDE community in Middletown DE. This stunning home is a KINGFISHER Schell Brothers model has upgrades galore. This home is located on a wooded lot with one of the largest yard that is fully fenced in. A true walkout with a full apartment to welcome the extended family to live with you. Lets go back to the front of this home

    Ann Marie Germano Patterson-Schwartz-Middletown

    830 Sweet Birch Dr, Middletown, DE 19709
  • 810 Ashby Dr, Middletown, DE 19709
    810 Ashby Dr, Middletown, DE 19709
    810 Ashby Dr, Middletown, DE 19709
    /63

    $949,900 Open House 9/14

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

    810 Ashby Dr, Middletown, DE 19709

    Welcome to 810 Ashby Drive, an exquisite estate in the prestigious Ashby’s Place community. This expansive 5-bedroom, 5.5-bathroom Aspen II model by K. Hovnanian offers over 5,000 sq ft of living space, thoughtfully designed for comfort, entertaining, and modern family living.From the moment you step inside, you’re greeted by a dramatic two-story foyer, sweeping hardwood staircase, and rich

    Nakisha Powell-Jones EXP Realty, LLC

    810 Ashby Dr, Middletown, DE 19709
  • 448 Spring Hollow Dr, Middletown, DE 19709
    448 Spring Hollow Dr, Middletown, DE 19709
    448 Spring Hollow Dr, Middletown, DE 19709
    /50

    $999,000

    • 5 Beds
    • 5.5 Baths
    • 6,840 Sq Ft

    448 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 448 Spring Hollow Drive. This well-maintained freshy painted colonial home sits on a lovely corner lot located in the desirable community of Parkside, with an additional 1/2 acre of non-buildable open space behind the property. Being a former model home, this 5 bedroom, 5 1/2 bath home features many well-executed upgrades, 4 fireplaces, stunning trim and lighting upgrades throughout.

    Christopher Carr HomeZu

    448 Spring Hollow Dr, Middletown, DE 19709
  • 525 Contemplation Way, Middletown, DE 19709
    525 Contemplation Way, Middletown, DE 19709
    525 Contemplation Way, Middletown, DE 19709
    /27

    $475,900

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft

    525 Contemplation Way, Middletown, DE 19709

    Welcome to 525 Contemplation Way, nestled in the highly sought-after 55+ community of Whispering Woods in Middletown, Delaware! This beautiful 3 bedroom, 2 full bathroom maintained home offers low-maintenance living with all the benefits of an active, resort-style lifestyle. Whether you're looking to downsize or embrace a vibrant new chapter, this home and community check every box. Located just

    Eric Buck Long & Foster Real Estate, Inc.

    525 Contemplation Way, Middletown, DE 19709
  • 1381 Pole Bridge Rd, Middletown, DE 19709
    1381 Pole Bridge Rd, Middletown, DE 19709
    1381 Pole Bridge Rd, Middletown, DE 19709
    /44

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 3,169 Sq Ft

    1381 Pole Bridge Rd, Middletown, DE 19709

    Motivated Seller! Here it is, your own piece of ground with a whole lot of extras. 1381 Pole Bridge Road offers nearly 8 acres with a pole building, in-ground heated pool, and 3,619 square foot home in Appo School District. This property offers privacy and serenity rarely found New Castle County. The home features and open concept layout with kitchen, dining, and family room flowing together on

    Travis L. Dorman RE/MAX Elite

    1381 Pole Bridge Rd, Middletown, DE 19709
  • 900 S Vernon St, Middletown, DE 19709
    900 S Vernon St, Middletown, DE 19709
    900 S Vernon St, Middletown, DE 19709
    /42

    $364,900

    • 3 Beds
    • 1 Bath
    • 2,000 Sq Ft

    900 S Vernon St, Middletown, DE 19709

    New photos coming! The seller just refinished the hardwood floors throughout and they are beautiful! The basement has new epoxy flooring, shutters have been painted, and the outside is freshly landscaped. Welcome to 900 S Vernon St, located in the heart of Middletown, DE, within the desirable Sharondale community. This charming brick rancher features three bedrooms, one full bathroom, a fully

    Kelly Clark Crown Homes Real Estate

    900 S Vernon St, Middletown, DE 19709
  • 253 Wickerberry Dr, Middletown, DE 19709
    253 Wickerberry Dr, Middletown, DE 19709
    253 Wickerberry Dr, Middletown, DE 19709
    /98

    $769,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 5 Baths
    • 5,100 Sq Ft

    253 Wickerberry Dr, Middletown, DE 19709

    Welcome to 253 Wickerberry Drive in the sought after community of PARKSIDE. This home from the moment you pull up has such wonderful curb appeal...The Stone Front, the front porch and the lovely landscaping. Come inside to this beautiful traditional home that has so much to offer, 5 bedrooms, 5 bathrooms large office, great kitchen with a large morning room, a finished basement and one of the

    Ann Marie Germano Patterson-Schwartz-Middletown

    253 Wickerberry Dr, Middletown, DE 19709
  • 417 Morning Glory Ln, Middletown, DE 19709
    417 Morning Glory Ln, Middletown, DE 19709
    417 Morning Glory Ln, Middletown, DE 19709
    /22

    $430,000

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

    417 Morning Glory Ln, Middletown, DE 19709

    Welcome to your ideal low-maintenance lifestyle in this beautifully maintained 2-bedroom, 2-bath home featuring a spacious loft and inviting outdoor space. Nestled in a vibrant 55+ community of Springmill, this residence offers the perfect blend of comfort, convenience, and style. The beautiful landscaping welcomes you inside where you'll find an open-concept layout with a large kitchen with

    Ann Marie Deysher Patterson-Schwartz-Hockessin

    417 Morning Glory Ln, Middletown, DE 19709
  • 404 Paper Birch St, Middletown, DE 19709
    404 Paper Birch St, Middletown, DE 19709
    404 Paper Birch St, Middletown, DE 19709
    /38

    $570,000

    • 2 Beds
    • 2 Baths
    • 1,825 Sq Ft

    404 Paper Birch St, Middletown, DE 19709

    Why wait for new construction when you can have it all—right now? This impeccably maintained and neutral designed 2-bedroom, 2-bath home WITH POTENTIAL FOR THIRD BEDROOM in the Baymont Farms 55+ community could be yours without the hassle of new construction. Skip the dust and delays and move right in! From the moment you arrive, the welcoming front porch sets the tone. The open-concept

    stephanie kelly Patterson-Schwartz - Greenville

    404 Paper Birch St, Middletown, DE 19709
  • 629 Spring Hollow Dr, Middletown, DE 19709
    629 Spring Hollow Dr, Middletown, DE 19709
    629 Spring Hollow Dr, Middletown, DE 19709
    /78

    $665,000

    • 4 Beds
    • 3.5 Baths
    • 3,950 Sq Ft

    629 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 629 Spring Hollow Dr, where every inch is dripping with beauty and elegance. In one of Middletown's most sought after communities of Parkside, 629 Spring Hollow Dr is situated on a corner lot with beautiful views, endearing front porch, board and batten siding, stone skirting, and gorgeous landscaping - the curb appeal leaves nothing to be desired. Professionally designed from top to

    Megan Aitken Keller Williams Realty

    629 Spring Hollow Dr, Middletown, DE 19709
  • 577 Whispering Trail, Middletown, DE 19709
    577 Whispering Trail, Middletown, DE 19709
    577 Whispering Trail, Middletown, DE 19709
    /54

    $479,900 Open Sun 12PM - 2PM

    • 2 Beds
    • 3 Baths
    • 2,200 Sq Ft

    577 Whispering Trail, Middletown, DE 19709

    Welcome home to this impeccably maintained Coleridge model, ideally situated within the sought-after Active Adult Community of Springmill in Middletown, Delaware. This residence has been meticulously cared for and offers recent upgrades, including a new roof, HVAC system, and electric water heater, ensuring peace of mind for years to come. Upon entering, you’ll be greeted by gleaming hardwood

    Vicky Miller Patterson-Schwartz-Middletown

    577 Whispering Trail, Middletown, DE 19709
  • 574 Whispering Trail, Middletown, DE 19709
    574 Whispering Trail, Middletown, DE 19709
    574 Whispering Trail, Middletown, DE 19709
    /61

    $465,000

    • 3 Beds
    • 2 Baths
    • 2,150 Sq Ft

    574 Whispering Trail, Middletown, DE 19709

    55 Community living at it's finest. 2-Bed + Loft in Active 55+ Community . Excellent Condition & Full of Charm!Welcome to this beautifully cared-for 2-bedroom, 2-bath home in a vibrant and friendly 55+ neighborhood! This home is in excellent condition and it shows, from the sparkling clean interiors to the thoughtful updates throughout. You’ll immediately notice the pride of ownership, with

    Kim Simpson Thyme Real Estate Co LLC

    574 Whispering Trail, Middletown, DE 19709
  • 1032 Applecross Dr, Middletown, DE 19709
    1032 Applecross Dr, Middletown, DE 19709
    1032 Applecross Dr, Middletown, DE 19709
    /68

    $750,000

    • 6 Beds
    • 5 Baths
    • 4,500 Sq Ft

    1032 Applecross Dr, Middletown, DE 19709

    Welcome to 1032 Applecross Drive in the Preserve at Deep Creek. This expansive & well-appointed home is the largest in its community and offers all the high-end features and amenities you could possibly want, and a blank canvas to make your very own! Spanning over 4,500 square feet amongst three levels of living spaces, the highlights include a bright & open floorplan with 9-foot ceilings, a

    Michael McKee Long & Foster Real Estate, Inc.

    1032 Applecross Dr, Middletown, DE 19709
  • 119 Tuscany Dr, Middletown, DE 19709
    119 Tuscany Dr, Middletown, DE 19709
    119 Tuscany Dr, Middletown, DE 19709
    /79

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 3,125 Sq Ft

    119 Tuscany Dr, Middletown, DE 19709

    PARKSIDE - Welcome to 119 Tuscany Drive, an elegant and inviting residence located in the heart of Middletown and within the APPOQUINIMINK SCHOOL DISTRICT. This exquisite 5-bedroom, 3.5-bathroom home offers a harmonious blend of sophistication and comfort. Newly built in 2015 by Lifestyle Builders, this home has been lovingly maintained by its original owners. Enter the foyer to find gleaming

    Andrea Harrington Compass

    119 Tuscany Dr, Middletown, DE 19709
  • 114 Austrian Pine Ct, Middletown, DE 19709
    114 Austrian Pine Ct, Middletown, DE 19709
    114 Austrian Pine Ct, Middletown, DE 19709
    /74

    $755,000

    • 4 Beds
    • 4 Baths
    • 4,155 Sq Ft

    114 Austrian Pine Ct, Middletown, DE 19709

    Now featured at $755,000This stunning new home in the highly sought-after Four Seasons at Baymont Farms is now even more appealing! This home offers the perfect blend of luxury, convenience, and value in a premier 55+ community. Don't miss out on this rare opportunity to own a spacious 4-bedroom, 4-bathroom home in a fantastic location!Property Features:*4 Spacious

    Maha Johnson EXP Realty, LLC

    114 Austrian Pine Ct, Middletown, DE 19709
  • 1343 Bohemia Mill Rd, Middletown, DE 19709
    1343 Bohemia Mill Rd, Middletown, DE 19709
    1343 Bohemia Mill Rd, Middletown, DE 19709
    /20

    $5,100,000

    • 4 Beds
    • 4.5 Baths
    • 4,650 Sq Ft

    1343 Bohemia Mill Rd, Middletown, DE 19709

    Welcome to Candyland: Where Dreams Gallop Free! There hasn’t been anything like this to hit the Middletown market in over 30 years.Nestled amidst paradise for both equestrian enthusiasts and opulence living. Picture this: a sprawling 120-, plus ,acre horse farm that captivates the senses and ignites the imagination, consists of 3 parcels, with five houses and two in ground pools on the

    Kim Simpson Thyme Real Estate Co LLC

    1343 Bohemia Mill Rd, Middletown, DE 19709
  • 1343 Bohemia Mill Rd, Middletown, DE 19709
    1343 Bohemia Mill Rd, Middletown, DE 19709
    1343 Bohemia Mill Rd, Middletown, DE 19709
    /29

    $5,100,000

    • 4 Beds
    • 4.5 Baths
    • 4,650 Sq Ft

    1343 Bohemia Mill Rd, Middletown, DE 19709

    Welcome to Candyland: Where Dreams Gallop Free! There hasn’t been anything like this to hit the Middletown market in over 30 years.Nestled amidst paradise for both equestrian enthusiasts and opulence living. Picture this: a sprawling 120-, plus ,acre horse farm that captivates the senses and ignites the imagination. Welcome to Candyland, where every corner is a sweet surprise waiting to be

    Kim Simpson Thyme Real Estate Co LLC

    1343 Bohemia Mill Rd, Middletown, DE 19709
  • 3130 Pett Level Dr, Middletown, DE 19709
    3130 Pett Level Dr, Middletown, DE 19709
    3130 Pett Level Dr, Middletown, DE 19709
    /22

    $489,990 New Construction

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

    3130 Pett Level Dr, Middletown, DE 19709

    Welcome to Middletown’s newest active adult community, The Venue at Winchelsea. This 3 Bed 2.5 baths 2443 square feet end-unit Taylor is a brand new two-story, townhome that is designed to promote low-maintenance living with a sophisticated twist. As you enter, you’re greeted by a dedicated study, perfect for a home office, as well as a first floor laundry room. The well-equipped kitchen features

    Builder Photo

    Lennar

    Builder

    3130 Pett Level Dr, Middletown, DE 19709
  • 3126 Pett Level Dr, Middletown, DE 19709
    3126 Pett Level Dr, Middletown, DE 19709
    3126 Pett Level Dr, Middletown, DE 19709
    /22

    $499,700 New Construction

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

    3126 Pett Level Dr, 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’re greeted by a dedicated study, perfect for a home office, as well as a first floor laundry room. The well-equipped kitchen features modern stainless steel appliances, sleek quartz countertops, and plenty of white, airy 42 cabinetry, making it perfect for

    Builder Photo

    Lennar

    Builder

    3126 Pett Level Dr, Middletown, DE 19709
  • 3112 Pett Level Dr, Middletown, DE 19709
    3112 Pett Level Dr, Middletown, DE 19709
    3112 Pett Level Dr, Middletown, DE 19709
    /22

    $503,000 New Construction

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

    3112 Pett Level Dr, 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’re greeted by a dedicated study, perfect for a home office, as well as a first floor laundry room. The well-equipped kitchen features modern stainless steel appliances, sleek quartz countertops, and plenty of cabinetry, making it perfect for storing all of

    Builder Photo

    Lennar

    Builder

    3112 Pett Level Dr, Middletown, DE 19709
  • 2812 Armoury Ln, Middletown, DE 19709
    2812 Armoury Ln, Middletown, DE 19709
    2812 Armoury Ln, Middletown, DE 19709
    /43

    $539,000 Open Sat 10AM - 6PM

    • 3 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    2812 Armoury Ln, Middletown, DE 19709

    **Welcome to Middletown's hottest selling active adult community** Welcome to 2812 Armoury Lane- MOVE IN READY and just waiting for you! This perfect homesite overlooks the beautiful clubhouse with all the amenities to enjoy just steps away!! The Carson is a thoughtfully designed home ideal for those who prefer a more traditional layout with the modern functionality of a first-floor primary

    David Vasso Atlantic Five Realty

    2812 Armoury Ln, Middletown, DE 19709
  • 1521 Lesterfield Way, Middletown, DE 19709
    1521 Lesterfield Way, Middletown, DE 19709
    1521 Lesterfield Way, Middletown, DE 19709
    /24

    $649,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,121 Sq Ft

    1521 Lesterfield Way, Middletown, DE 19709

    Kitchen, dining area & great room flow under a vaulted ceiling. Fireplace creates a cozy focal point in the great room. Kitchen with stacked Stone Grey cabinets & glass-front uppers. Dining area opens to a screened deck for outdoor living. Primary suite features ceiling detail & window-lined sitting room. Private primary bath with dual sinks & spacious walk-in closet. Finished basement offers

    Builder Photo

    K. Hovnanian Homes

    Builder

    1521 Lesterfield Way, Middletown, DE 19709
  • 3227 S Central Park Dr, Middletown, DE 19709
    3227 S Central Park Dr, Middletown, DE 19709
    3227 S Central Park Dr, Middletown, DE 19709
    /42

    $757,065 New Construction

    • 3 Beds
    • 2 Baths
    • 2,757 Sq Ft

    3227 S Central Park Dr, Middletown, DE 19709

    Great opportunity to buy at the new 55+ Parks Edge at Bayberry- The Tracy II Quick Delivery! Come experience the active adult lifestyle that home owners are raving about: a vibrant social scene, luxury amenities, stunning outdoor spaces and a place that will make you feel welcome and at home form the day you move in. Enjoy maintenance-free living with grass cutting and snow plowing taken

    Brittany Stephens Blenheim Marketing LLC

    3227 S Central Park Dr, Middletown, DE 19709
  • 3128 Pett Level Dr, Middletown, DE 19709
    3128 Pett Level Dr, Middletown, DE 19709
    3128 Pett Level Dr, Middletown, DE 19709
    /26

    $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
  • 206 Northern Oak St Unit 36473802, Middletown, DE 19709
    206 Northern Oak St Unit 36473802, Middletown, DE 19709
    206 Northern Oak St Unit 36473802, Middletown, DE 19709
    /22

    $547,900 New Construction

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

    Eastwood Loft Plan at K. Hovnanian’s® 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

    Builder Photo

    K. Hovnanian Homes

    Builder

    206 Northern Oak St Unit 36473802, Middletown, DE 19709
  • 1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
    /12

    $634,900 New Construction

    • 3 Beds
    • 3 Baths
    • 2,810 Sq Ft

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

    Included Extra Suite, ideal for multi-generational living and long-term guests. Private home office off of foyer, to work from home with plenty of space. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage, for extra

    Builder Photo

    K. Hovnanian Homes

    Builder

    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
  • 206 Northern Oak St Unit 36481335, Middletown, DE 19709
    206 Northern Oak St Unit 36481335, Middletown, DE 19709
    206 Northern Oak St Unit 36481335, Middletown, DE 19709
    /23

    $536,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,859 Sq Ft

    Dorchester Plan at K. Hovnanian’s® Four Seasons at Baymont Farms, Middletown, DE 19709

    Elegant foyer welcoming guests to your home. Convenient single-story living. Laundry room with plenty of space to fold and iron. Kitchen with spacious corner pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private owner's suite with large walk-in closet and spa bath.

    Builder Photo

    K. Hovnanian Homes

    Builder

    206 Northern Oak St Unit 36481335, 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

    $549,900 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    1415 Pennfield Dr Unit 36502364, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041417, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041417, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041417, Middletown, DE 19709
    /24

    $325,000 New Construction

    • 5 Beds
    • 2 Baths
    • 2,056 Sq Ft

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

    This new two-story home is ready for modern lifestyles. The luxurious owner’s suite is tucked into a private rear corner on the first floor off the open-concept floorplan shared between the kitchen, living and dining areas for simple transitions and multitasking. Another bedrooms is located at the front of the home. Three additional bedrooms can be found on the second floor. This plan is part of

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041417, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
    /22

    $519,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,936 Sq Ft

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

    This single-story home is designed to offer comfort and luxury at the same time. Off the foyer is a flex space for versatile uses and a formal dining room, followed by an open concept main living area with backyard access. In addition to the expansive owner’s suite with a private full-sized bathroom, there is a secondary bedroom that can be used for overnight guests or personal needs. A two-car

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041427, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041427, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041427, Middletown, DE 19709
    /21

    $502,990 New Construction

    • 2 Beds
    • 2 Baths
    • 1,778 Sq Ft

    Tuscany 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.

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041427, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041425, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041425, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041425, Middletown, DE 19709
    /22

    $514,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,878 Sq Ft

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

    This cozy single-story home features a low maintenance layout with an open concept kitchen, dining area and family room that leads out to the backyard. Near the foyer are two comfortable bedrooms that can be used for a home office or hobby room, while the spacious owner’s suite is tucked away in the back for added privacy. A two-bay garage and versatile basement with endless possibilities

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041425, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041426, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041426, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041426, Middletown, DE 19709
    /21

    $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.

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041426, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041424, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041424, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041424, Middletown, DE 19709
    /20

    $564,990 New Construction

    • 2 Beds
    • 2 Baths
    • 2,386 Sq Ft

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

    This luxurious two-story home is designed like a single-story where everything you need is located on the first floor, including a flex space, formal dining room, an open-concept main living area and the expansive owner’s suite. For versatile needs, there is a secondary bedroom as well as an upstairs bonus room that is sure to amaze guests. Complete the basement for even more space.

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041424, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041428, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041428, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041428, Middletown, DE 19709
    /23

    $547,990 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.

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041428, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041420, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041420, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041420, Middletown, DE 19709
    /23

    $400,800 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

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041420, Middletown, DE 19709
  • 2405 Greyfriar Loop Unit 36041422, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041422, Middletown, DE 19709
    2405 Greyfriar Loop Unit 36041422, Middletown, DE 19709
    /24

    $559,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

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

    On the first level of this new two-story home is a spacious owner’s suite complete with an adjoining bathroom and walk-in closet. At the heart of the layout is an open-plan design shared among the kitchen, Great Room and breakfast nook, with glass sliders to extend to the backyard. Upstairs is a sprawling loft to suit a multitude of needs and two secondary bedrooms, one of which has direct access

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041422, 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

    $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.

    Builder Photo

    Lennar

    Builder

    2405 Greyfriar Loop Unit 36041419, Middletown, DE 19709
  • 2814 Armoury Ln, Middletown, DE 19709
    2814 Armoury Ln, Middletown, DE 19709
    2814 Armoury Ln, Middletown, DE 19709
    /21

    $549,905 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,389 Sq Ft

    2814 Armoury Ln, Middletown, DE 19709

    Discover the perfect blend of comfort and sophistication at 2814 Armoury Lane, a 3 bedroom, 2.5 bath. A gourmet kitchen overlooking the great room with a fireplace creates a warm and inviting centerpiece for both daily living, and entertaining. Boasting sleek quartz countertops, airy white cabinetry, stainless steel appliances, and a gas cooktop and wall oven, this kitchen is a chef’s dream! The

    Builder Photo

    Lennar

    Builder

    2814 Armoury Ln, Middletown, DE 19709

Showing Results 41 - 80, Page 2 of 3

Delaware New Castle County Middletown

Homes for Sale with Pool in Middletown, DE

How to Buy a Home How to Finance a Home How to Sell a Home

In Middletown, there are currently 90 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Middletown, DE and discover your ideal residence.

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 © 2025 CoStar Group