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Middletown, DE Homes for Sale with Pool

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  • /22

    $524,990 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

    Lennar Builder
    2405 Greyfriar Loop Unit 36041423, Middletown, DE 19709
  • /13

    $521,500 Open Fri 11AM - 5PM

    • 2 Beds
    • 2 Baths
    • 2,059 Sq Ft

    204 Baldy Ln Unit BELVILLE, Middletown, DE 19709

    Welcome to the Belville Model in the 55+community of Traditions at Whitehall. TO BE BUILT. This inviting 2-Bedroom home has a welcoming foyer which leads you down the hall towards the main living area! An open kitchen and breakfast area which flows into the large great room and is perfect for entertaining! The owner’s suite in the front features a large walk-in closet and owner’s bath with a

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit BELVILLE, Middletown, DE 19709
  • /11

    $614,000 Open Fri 11AM - 5PM

    • 3 Beds
    • 2 Baths
    • 2,477 Sq Ft

    204 Baldy Ln Unit COTTONWOOD, Middletown, DE 19709

    Welcome to the Cottonwood Model, TO BE BUILT, in the highly sought-after 55+ community of Traditions at Whitehall. This 3-bedroom home features a generous Owner’s Suite at the front of the home, complete with double walk-in closets leading to a luxurious en-suite bath, offering a privacy water closet and a 5-foot tile shower. At the rear of the home, you will find the kitchen and dining area that

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit COTTONWOOD, Middletown, DE 19709
  • /41

    $579,000 Open Fri 11AM - 5PM

    • 3 Beds
    • 2 Baths
    • 2,004 Sq Ft

    204 Baldy Ln Unit CAYOT, Middletown, DE 19709

    Welcome to the Cayot Model, in the desirable 55+ community of Traditions at Whitehall. This charming 3-bedroom home has a great open concept floor plan which offers all one floor living and a welcoming dining room and great room upon entry. At the rear of the home, you will find the luxurious owner's suite complete with walk-in closet and an en-suite bath, including a 5-foot tile shower. With a

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit CAYOT, Middletown, DE 19709
  • /24

    $533,990 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

    Lennar Builder
    2405 Greyfriar Loop Unit 36041422, Middletown, DE 19709
  • /33

    $527,000 Open Wed 7AM - 8PM

    • 2 Beds
    • 2 Baths
    • 2,053 Sq Ft

    120 Burlina Blvd Unit BLOOMFIELD MODEL, Middletown, DE 19709

    Welcome to the popular Bloomfield Model in the 55+ community of Traditions at Whitehall. This floor plan has 2-Bedrooms with a standard loft and a generously sized great room open to the kitchen and dining area. You will have plenty of space if you like to entertain. A rear Owner's Suite gives maximum privacy and includes a large walk-in closet and en-suite with a double bowl vanity and 5-foot

    Lindsay Shaffer RE/MAX Elite

    120 Burlina Blvd Unit BLOOMFIELD MODEL, Middletown, DE 19709
  • /23

    $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
  • /21

    $565,825 New Construction

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

    3506 Pipewell Ln, Middletown, DE 19709

    Welcome to the Carson—an elegant and versatile 3-bed, 3.5-bath home spanning 2,389 square feet of above ground living space. The main level features a welcoming foyer that opens into a spacious great room, a bright breakfast nook, and a thoughtfully planned kitchen, creating the perfect hub for gatherings. Homeowners will appreciate the convenience of a first-floor owner’s suite with a walk-in

    Lennar Builder
    3506 Pipewell Ln, Middletown, DE 19709
  • /22

    $400,800 New Construction

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

    3134 Pett Level Dr, Middletown, DE 19709

    Say hello to 3134 Pett Level Drive, our thoughtfully designed Truman floorplan. This 5-bed, 3-bath home offers modern comfort and effortless functionality. The main level centers around an open-concept layout, where the kitchen, dining room, and family room flow seamlessly for everyday living and entertaining. A first-floor owner’s suite with walk-in closet, full bath, and additional bedroom,

    Lennar Builder
    3134 Pett Level Dr, Middletown, DE 19709
  • /26

    $725,000

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

    14 Haggis Rd, Middletown, DE 19709

    Stunning 4BR/3.5BA Duncaneshire Colonial Model by L.C. Homes in the sought-after Estates at St. Anne’s! Located in the Appoquinimink School District, this spacious home offers over 4,475 sq. ft. of living space on a premium .51-acre corner lot with a two-car side-entry garage. Enter the home through the grand two-story foyer featuring hardwood floors and a beautiful turned staircase. The formal

    Lila F Dudley Realty Mark Associates-Newark

    14 Haggis Rd, Middletown, DE 19709
  • /20

    $569,990 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.

    Lennar Builder
    2405 Greyfriar Loop Unit 36041424, Middletown, DE 19709
  • /53

    $465,000

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

    527 Swansea Dr, Middletown, DE 19709

    25K PREMIUM LOT.....Yes this is the one! 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 to host a fun day out

    Ann Marie Germano Patterson-Schwartz-Middletown

    527 Swansea Dr, Middletown, DE 19709
  • /61

    $639,000

    • 3 Beds
    • 2 Baths
    • 1,925 Sq Ft

    5338 Newman Ln, Middletown, DE 19709

    Welcome Home to the Ponds at Bayberry, Middletown’s premier 55plus community! Trade in the lawnmower for your pickleball racket and prepare to retire in style! The tree-lined streets with sidewalks at The Ponds of Bayberry lead you through a stunning community with resort-style living. Natural parks, miles of trails, a glamorous clubhouse with fitness room, library, game room and heated outdoor

    Melissa Scott Real Broker LLC

    5338 Newman Ln, Middletown, DE 19709
  • /59

    $899,999

    • 5 Beds
    • 3.5 Baths
    • 5,092 Sq Ft

    434 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 434 Spring Hollow Drive, a beautiful residence nestled in Middletown's most sought-after community. This home is ideally situated on one of the finest lots, offering tranquil views as it backs onto lush woods. Located on a charming tree-lined street, it's just a short walk to the community clubhouse, which boasts a large pool and fitness center. As you approach the home, the inviting

    Tony Immediato Compass

    434 Spring Hollow Dr, Middletown, DE 19709
  • /2

    $719,163 New Construction

    • 3 Beds
    • 2 Baths

    3032 Barber Ln, Middletown, DE 19709

    Brittany Stephens Blenheim Marketing LLC

    3032 Barber Ln, Middletown, DE 19709
  • /33

    $449,500 Open Wed 7AM - 8PM

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

    1104 Highland St Unit 138, Middletown, DE 19709

    IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Annandale Carriage Town Home. This interior first floor owner suite comes w/a 2nd bedroom, loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full

    Lindsay Shaffer RE/MAX Elite

    1104 Highland St Unit 138, Middletown, DE 19709
  • /42

    $734,500 New Construction

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

    3227 S Central Park Dr, Middletown, DE 19709

    Gorgeous Lot -Backs to open space! 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

    Brittany Stephens Blenheim Marketing LLC

    3227 S Central Park Dr, Middletown, DE 19709
  • /50

    $790,000

    • 4 Beds
    • 4.5 Baths
    • 4,725 Sq Ft

    624 Nesting Ln, Middletown, DE 19709

    The search is over! You will be amazed from the moment you walk inside. A stunning 2 story 4725 sq foot colonial home PLUS finished basement with 4th full bathroom offers the new buyers a turnkey option on an amazing private lot backing to woods that has been professional landscaped with a low maintenance salt water inground pool! Enter into an open foyer with Cathedral ceilings, catwalk above

    Crystal Graham Patterson-Schwartz-Middletown

    624 Nesting Ln, Middletown, DE 19709
  • /64

    $799,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 4,075 Sq Ft

    795 Idlewyld Dr, Middletown, DE 19709

    COMING SOON!!!! Maybe before the date.....Worth the wait....so many upgrades....description coming

    Ann Marie Germano Patterson-Schwartz-Middletown

    795 Idlewyld Dr, Middletown, DE 19709
  • /25

    $504,900 New Construction

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

    1102 Highland St Unit 137 ASHTON, Middletown, DE 19709

    IMMEDIATE AVAILABILITY! Welcome to the 55+ community of Traditions at Whitehall - Ashton Carriage Town Home. This end unit first floor master comes w/a 2nd bedroom & loft, 2.5 baths, 2 car rear load attached garage, front porch, and additional finished upgrades. Community also offers trails, in ground pool w/lounge areas, open clubhouse featuring exercise room, billiards, gathering space, full

    Lindsay Shaffer RE/MAX Elite

    1102 Highland St Unit 137 ASHTON, Middletown, DE 19709
  • /39

    $548,500 Open Fri 11AM - 5PM

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

    204 Baldy Ln Unit BRISTOLE, Middletown, DE 19709

    The Bristol Model is a thoughtfully designed 3-bedroom home that is TO BE BUILT in the highly sought-after 55+ community of Traditions at Whitehall. This home features an open floor plan with a spacious dining area, kitchen, great room, and perfect for modern living and entertaining. The large Owner’s Suite offers two walk-in closets, an en-suite bath with a double vanity, and a luxurious 5-foot

    Lindsay Shaffer RE/MAX Elite

    204 Baldy Ln Unit BRISTOLE, 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
  • /18

    $570,793 New Construction

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

    3029 Ivyhouse Ln, Middletown, DE 19709

    This stunning Sonoma single-family home is now available as a quick move-in! With a spacious single-level floorplan, it truly stands out in the neighborhood. Featuring three bedrooms and two bathrooms, the primary suite offers generous closet space with two walk-in closets and an en suite bath. The added sunroom extension extends the home, creating the perfect space for entertaining guests. The

    Lennar Builder
    3029 Ivyhouse Ln, Middletown, DE 19709
  • /59

    $750,000

    • 4 Beds
    • 4.5 Baths
    • 4,450 Sq Ft

    911 Cadman Dr, Middletown, DE 19709

    Welcome to this stunning, nearly new home located in the highly desirable Preserves of Deep Creek community in Middletown, Delaware. Built just three years ago, this beautifully maintained property offers 4550 sq ft of thoughtfully designed living space with 4 bedrooms, 4.5 bathrooms, and a finished basement complete with a full bath—ideal for entertaining, guests, or a recreation space.Key

    Kim Simpson Thyme Real Estate Co LLC

    911 Cadman Dr, Middletown, DE 19709
  • /37

    $410,000

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

    149 Gazebo Ln, Middletown, DE 19709

    Welcome to 149 Gazebo Lane, a charming, well-appointed, end unit carriage home in the highly sought after Spring Arbor community! You'll love the welcoming 2-story foyer that flows seamlessly into the expansive living & dining areas, complete with gleaming hardwoods & timeless style! The spacious, bright eat-in kitchen features newer appliances & maple cabinetry- perfect for casual meals or

    Rhonda Smith Patterson-Schwartz-Hockessin

    149 Gazebo Ln, Middletown, DE 19709
  • /43

    $574,900 New Construction

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

    21 Golden Raintree Ct, Middletown, DE 19709

    Welcome to the Eastwood home design. An open, ranch style home slated for an October delivery. The popular model features first floor living with bright spaces. Its two bedrooms, home office, and 2 full baths are conveniently on one level. This home also boasts additional living space in the basement with its finished recreation room, and full bathroom. A screen porch overlooking open space is

    Barbara Heilman Delaware Homes Inc

    21 Golden Raintree Ct, Middletown, DE 19709
  • /22

    $519,990 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

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

    $469,509 New Construction

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

    3104 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 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
    3104 Pett Level Dr, Middletown, DE 19709
  • 540 Ratledge Rd Unit 38787057, Middletown, DE 19709

    $575,400 New Construction

    • 3 - 5 Beds
    • 2 - 4 Baths
    • 1,662 Sq Ft

    The Newport Plan at Monarch, Middletown, DE 19709

    Single-Family Home in Monarch. Base price $599,900 - $24,500 incentive = $575,400. The floor plan is easy to navigate, functional, attractive, and gives a sense of space. A tremendous amount of time and effort goes into the exterior design of our homes. The exceptional curb appeal of a Schell Brothers home is not only a reflection of the quality and care that goes into the home but also a huge

    Schell Brothers Builder
    540 Ratledge Rd Unit 38787057, Middletown, DE 19709
  • /38

    $688,893 Open Wed 7AM - 8PM

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft

    548 Longhorn Loop, Middletown, DE 19709

    IMMEDIATE AVAILABILITY!!! Introducing the CHELSEA model in the highly desirable 55+ community of Traditions at Whitehall. This thoughtfully designed 3-bedroom, 2-bath home features an open-concept floor plan with a spacious foyer, 9 ft ceilings, formal dining area, great room w/fireplace & an additional sunroom that flows into the kitchen perfect for entertaining. The Owner’s Suite includes a

    Lindsay Shaffer RE/MAX Elite

    548 Longhorn Loop, Middletown, DE 19709
  • /12

    $603,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,349 Sq Ft

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

    Welcoming foyer leading to private home office. HovHall with convenient valet leading to laundry room. Spacious great room with vaulted ceiling and large windows. Kitchen with corner pantry and large island. Dining area with sliding door to covered patio. Secluded primary suite with large sitting room. Primary bath with large shower and walk-in closet.

    K. Hovnanian Homes Builder
    1415 Pennfield Dr Unit 36479735, 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.

    K. Hovnanian Homes Builder
    206 Northern Oak St Unit 36481335, Middletown, DE 19709
  • /36

    $569,900

    • 3 Beds
    • 2 Baths
    • 1,875 Sq Ft

    4602 Bogart Ln, Middletown, DE 19709

    Welcome to the Ponds at Bayberry, a 55+ community in Middletown Delaware. Offering a 3-year young Kelly Americana with 3 beds and 2 baths, this home has an open floor plan which features LVP throughout the main living areas, 9’ ceilings, a great room with a high-efficiency gas fireplace, dining area and a designer kitchen that boasts 42" cabinets, quartz countertops, combo in-wall microwave and

    Helen Garton EXP Realty, LLC

    4602 Bogart Ln, Middletown, DE 19709
  • /50

    $899,000

    • 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
  • /59

    $565,000

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

    505 Cherry Bark Rd, Middletown, DE 19709

    Welcome to 505 Cherry Bark Road in Four Seasons at Baymont Farms, a premier 55+ active adult community in Middletown, Delaware. This nearly new Eastwood Loft Floorplan, just 2 years young, offers low-maintenance, resort-style living with thoughtful design and modern upgrades throughout. Step inside to an open ranch-style floor plan featuring 3 bedrooms and 2 full baths on the main level—with one

    Amber Durand Patterson-Schwartz Real Estate

    505 Cherry Bark Rd, Middletown, DE 19709
  • /35

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,175 Sq Ft

    5924 Ravel Ln, Middletown, DE 19709

    Welcome to your new home in Bayberry! This 55+ retirement community offers lots of activities and amenities to its residents, including clubhouse, gym, and pool! The home was built in 2021 and has been well kept by its owner so you can essentially buy new construction without the wait! As you enter, you'll be greeted by an open living space with room for a seating area and dining table. The

    Megan Toll KW Empower

    5924 Ravel Ln, Middletown, DE 19709
  • /65

    $750,000

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

    530 Maiden Ct, Middletown, DE 19709

    Your Dream Home Awaits! This stunning six-bedroom showcase beauty—including two with private ensuite baths—offers all the space, comfort, and elegance you’ve been searching for in your new home, with over 3,800sf plus an additional 1,100sf of grand living space in the private finished basement. There’s room for everyone in this beautiful home - especially if you're looking for multi-generational

    Melissa Scott Real Broker LLC

    530 Maiden Ct, Middletown, DE 19709
  • /40

    $589,900

    • 3 Beds
    • 2 Baths
    • 2,050 Sq Ft

    3151 Schuman Dr, Middletown, DE 19709

    Welcome to 3151 Schuman Drive, a stunning Cooper Model home situated on a premier lot in the Village of Bayberry South, Middletown. This elegant residence, one of the few backing to serene woodlands, offers an expansive backyard with unobstructed views, providing unparalleled privacy. Encompassing 2,050 square feet of sophisticated living space, this home boasts three spacious bedrooms and two

    Jeff Stape Compass

    3151 Schuman Dr, Middletown, DE 19709
  • /77

    $457,000

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

    1404 Flintshire Dr, Middletown, DE 19709

    Why not add a new home to your Christmas Shopping List?? Schedule your tour and make an offer today!! TV wall mounts are included and installed if Santa Claus brings you a brand-new TV this year. This beautiful, 4-year-old 3 bedroom 2.5-bathroom townhome is located in the Community of Preserve at Deep Creek in Middletown, DE close to shopping, dining and entertainment in the countryside of

    Jennifer Lindell Century 21 Gold Key Realty

    1404 Flintshire Dr, Middletown, DE 19709
  • /22

    $379,800 New Construction

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

    2674 Fairlight Dr, Middletown, DE 19709

    Introducing the Truman—a thoughtfully designed 5-bed, 3-bath, 2,669-sq-ft home offering modern comfort and effortless functionality. The main level centers around an open-concept layout, where the kitchen, dining room, and family room flow seamlessly for everyday living and entertaining. A first-floor owner’s suite with walk-in closet, full bath, and additional bedroom, provide convenient

    Lennar Builder
    2674 Fairlight Dr, Middletown, DE 19709

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