Middletown, DE Homes for Sale with Pool

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  /64

  $638,000

  $17K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,875 Sq Ft

  211 E Crail Ct, Middletown, DE 19709

  Welcome to The Estate at St. Anne's! This beautifully updated 4 bedroom, 2.5 bath home offers style, space, and comfort throughout. The stunning updated kitchen features granite countertops, new Cafe'-style appliances, custom subway tile backsplash, new range hood, gorgeous butcher block island and coffee bar, and a spacious eat-in area with built in storage benches, for large family gatherings.

  

  Brynn Beideman

  RE/MAX Associates-Hockessin

  211 E Crail Ct, Middletown, DE 19709
• Explore Middletown

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  /56

  $679,900

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  4200 Crosby Ln, Middletown, DE 19709

  Discover elegance in this move-in ready home. This 4-bedroom, 3-bathroom home with a main-level primary bedroom en-suite is located in one of the most desirable communities, celebrated for its tranquil surroundings and resort-style amenities. Enter through a grand foyer into an expansive, elegant floor plan with soaring ceilings and designer lighting that create an atmosphere of timeless style. A

  

  Laura Walker

  Walker Realty Group LLC

  4200 Crosby Ln, Middletown, DE 19709
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  /57

  $895,000

  Coming Soon Aug 28

  • 5 Beds
  • 4.5 Baths
  • 5,869 Sq Ft

  214 Sammons Pond Dr, Middletown, DE 19709

  Great curb appeal! Spacious 4-bedroom, 4 1/2-bath home with stone and vinyl exterior, a 3-car turned garage, and an impressive 1.73-acre lot within the award-winning Appoquinimink School District and the popular golf community of Back Creek! 9-foot ceilings throughout both the first and second floors! Grand two-story entry with beautiful staircase flanked by formal living and dining rooms. Large

  

  David Landon

  Patterson-Schwartz-Newark

  214 Sammons Pond Dr, Middletown, DE 19709
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  /52

  $443,500

  $2K PRICE DROP

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

  376 Goodwick Dr, Middletown, DE 19709

  2575 SQ FT | POND VIEWS | FINISHED BASEMENT | APPOQUINIMINK SCHOOLSExceptional space and modern living come together at 376 Goodwick Drive in the sought after Preserve at Deep Creek community. Built in 2020, this spacious 3 bedroom, 2 and a half bath townhome offers the size and versatility of a single family home with the convenience of low maintenance community living.The bright

  

  Gina Spiese

  Crown Homes Real Estate

  376 Goodwick Dr, Middletown, DE 19709
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  /19

  $540,000

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

  336 Acasta Dr, Middletown, DE 19709

  PRICED TO SELL - $10k Settlement Assist w/ Full price offer!!! Low-maintenance HOA living Community pool Updated kitchen Bonus room Finished basement Prime location near Routes 1, 13 & 301Don't worry about cutting the grass or shoveling snow!! Our HOA handles that, allowing you to enjoy your weekends relaxing by the community pool. HOA fees also include common area maintenance and snow

  

  Ayana Morton

  Coldwell Banker Realty

  336 Acasta Dr, Middletown, DE 19709
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  /36

  $423,000

  Open Fri 1PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft

  1428 Whispering Woods Rd, Middletown, DE 19709

  Nestled among the trees in the desirable 55+ Whispering Woods community of Middletown, Delaware, this charming coastal-style villa offers the ease of single-level living with a thoughtfully designed layout and quality finishes throughout. Featuring two bedrooms and two full bathrooms, the home combines comfort and style with luxury vinyl plank, plush carpet, and tile flooring.The open floor

  

  Dustin Oldfather

  Compass

  1428 Whispering Woods Rd, Middletown, DE 19709
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  /25

  $725,400

  New Construction

  • 3 - 8 Beds
  • 2.5 - 6.5 Baths
  • 2,705 Sq Ft

  Jameson Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306083, Middletown, DE 19709
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  /37

  $739,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,705 Sq Ft

  1143 Majesty Ln, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  1143 Majesty Ln, Middletown, DE 19709
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  /29

  $642,990

  New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,493 Sq Ft

  Carver Plan at Four Seasons at Pennfield, Middletown, DE 19709

  Foyer with ceiling treatment welcoming you home.Private home office with barn doors, perfect for telecommuting.Spacious great room and dining area with vaulted ceiling.Striking kitchen with lots of counterspace and large pantry.Secluded primary suite with ceiling treatment and walk-in closet.Luxurious primary bath with freestanding vanities and large shower.

  K. Hovnanian Homes Builder

  1415 Pennfield Dr Unit 36482401, Middletown, DE 19709
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  /24

  $755,400

  New Construction

  • 4 - 7 Beds
  • 2.5 - 5.5 Baths
  • 3,018 Sq Ft

  Brady Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306082, Middletown, DE 19709
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  /28

  $779,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 3,383 Sq Ft

  1137 Majesty Ln, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  1137 Majesty Ln, Middletown, DE 19709
• 

  

  /19

  $735,400

  New Construction

  • 4 - 8 Beds
  • 2.5 - 6.5 Baths

  Bethany Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 40571845, Middletown, DE 19709
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  /17

  $547,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,032 Sq Ft

  St. Michael's Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

  Impressive single-story foyer graciously welcoming you home.Spacious kitchen with center island and dining area.Convenient Stuff of Life Room with separate laundry area.Large great room opening to kitchen and dining area.Luxury owner's suite with oversized closet & bath.Gourmet kitchen option perfect for your inner chef.Optional loft for guests.

  K. Hovnanian Homes Builder

  206 Northern Oak St Unit 39839252, Middletown, DE 19709
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  /25

  $775,400

  New Construction

  • 4 - 6 Beds
  • 4.5 - 6.5 Baths
  • 3,500 Sq Ft

  Bridgeport Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306071, Middletown, DE 19709
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  /13

  $585,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,457 Sq Ft

  Lewes Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

  Open and airy kitchen with pantry and oversized island.Cozy dining area adjacent to kitchen for enjoying casual meals.Luxurious owner's suite with dual walk-in closets and large bath.Hall walk-in closet for additional storage.Direct access to laundry room from garage.Covered porch to enjoy evenings outdoors.

  K. Hovnanian Homes Builder

  206 Northern Oak St Unit 36472485, Middletown, DE 19709
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  /40

  $729,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,566 Sq Ft

  1145 Majesty Ln, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  1145 Majesty Ln, Middletown, DE 19709
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  /24

  $705,400

  New Construction

  • 4 - 6 Beds
  • 3.5 - 6.5 Baths
  • 2,478 Sq Ft

  Cassidy Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306072, Middletown, DE 19709
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  /32

  $719,900

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,528 Sq Ft

  2205 Early Ct, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  2205 Early Ct, Middletown, DE 19709
• 

  

  /24

  $765,400

  New Construction

  • 4 - 7 Beds
  • 3 - 6.5 Baths
  • 3,383 Sq Ft

  Chesapeake Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306079, Middletown, DE 19709
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  /26

  $715,400

  New Construction

  • 3 - 7 Beds
  • 2 - 7.5 Baths
  • 2,566 Sq Ft

  Kingfisher Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306081, Middletown, DE 19709
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  /43

  $769,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,018 Sq Ft

  1139 Majesty Ln, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  1139 Majesty Ln, Middletown, DE 19709
• 

  

  /16

  $790,400

  New Construction

  • 4 - 8 Beds
  • 3.5 - 7.5 Baths
  • 3,642 Sq Ft

  Waterford Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306078, Middletown, DE 19709
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  /36

  $689,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,254 Sq Ft

  2206 Early Ct, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  2206 Early Ct, Middletown, DE 19709
• 

  

  /26

  $655,400

  New Construction

  • 3 - 6 Beds
  • 2 - 4 Baths
  • 1,971 Sq Ft

  Whimbrel Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306080, Middletown, DE 19709
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  /33

  $759,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 3,020 Sq Ft

  1141 Majesty Ln, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  1141 Majesty Ln, Middletown, DE 19709
• 

  

  /32

  $669,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,971 Sq Ft

  2204 Early Ct, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  2204 Early Ct, Middletown, DE 19709
• 

  

  /90

  $839,999

  • 6 Beds
  • 4.5 Baths
  • 4,684 Sq Ft

  507 Ibis Ct, Middletown, DE 19709

  **Open House August 22nd 10am-2pm**Welcome to 507 Ibis Court, an exceptional 2023-built K. Hovnanian Stavanger offering 6 bedrooms, 4.5 bathrooms, and more than 4,600 square feet of finished living space in Middletown’s desirable Pleasanton community. Thoughtfully upgraded and already complete, this home offers the appeal of newer construction without the wait.Set on a cul-de-sac and

  Kyle Lounsbury EXP Realty, LLC

  507 Ibis Ct, Middletown, DE 19709
• 

  

  /22

  $499,900

  New Construction

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

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

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

  K. Hovnanian Homes Builder

  206 Northern Oak St Unit 36495347, Middletown, DE 19709
• 

  

  /45

  $789,900

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  1135 Majesty Ln, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  1135 Majesty Ln, Middletown, DE 19709
• 

  

  /19

  $550,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  Killarney I Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

  Cozy porch welcoming guests to your home.Inviting dining room, ideal for hosting dinner parties.Kitchen with large island and corner pantry.Great room with optional HovHub and wet bar.Owner's suite with private bath and oversized walk-in closet.Three-car tandem garage with additional storage.Opt. loft for additional living with bed and full bath.

  K. Hovnanian Homes Builder

  206 Northern Oak St Unit 36451018, Middletown, DE 19709
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  /26

  $543,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft

  Aberdeen II Plan at Four Seasons at Pennfield, Middletown, DE 19709

  Spacious kitchen with island and ample counterspace.Sunlit great room adjacent to kitchen and dining area.Relaxing primary suite with sitting room and luxurious bath.HovHub makes for a great home office or study space.Expansive covered patio, perfect for dining al fresco.HovHall with closet and access to 2-car garage.

  K. Hovnanian Homes Builder

  1415 Pennfield Dr Unit 36480087, Middletown, DE 19709
• 

  

  /23

  $675,400

  New Construction

  • 3 - 6 Beds
  • 2 - 5.5 Baths
  • 2,266 Sq Ft

  Mayberry Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306074, Middletown, DE 19709
• 

  

  /19

  $576,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,462 Sq Ft

  Mont Blanc Plan at Four Seasons at Baymont Farms, Middletown, DE 19709

  Spacious, inviting front entry porch.Kitchen with expansive island and dual pantries.Open great room and dining area ideal for entertaining.Convenient secondary bedrooms for guests.Owner's suite with private bath and walk-in closet.Direct access to laundry room keeping your home tidy.Three-car tandem garage with additional storage.

  K. Hovnanian Homes Builder

  206 Northern Oak St Unit 36472277, Middletown, DE 19709
• 

  

  /12

  $505,990

  New Construction

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

  Asheville Plan at 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
• 

  

  /25

  $745,400

  New Construction

  • 3 - 6 Beds
  • 2 - 6.5 Baths
  • 3,020 Sq Ft

  Shearwater Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306075, Middletown, DE 19709
• 

  

  /13

  $804,900

  New Construction

  • 4 Beds
  • 3 Baths
  • 3,642 Sq Ft

  2200 Early Ct, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  2200 Early Ct, Middletown, DE 19709
• 

  

  /23

  $615,400

  New Construction

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

  Newport Plan at Monarch, Middletown, DE 19709

  New Construction by Schell Brothers. This home will be built with Schellter(tm) Advanced Building Science Technologies providing you an extremely energy efficient home. You'll love the stunning exterior, innovative floor plan, and the multiple structural options that allow you to personalize your home to fit your needs. You will make all of your selections in our state-of-the-art design studio

  Schell Brothers Builder

  540 Ratledge Rd Unit 38306076, Middletown, DE 19709
• 

  

  /29

  $629,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft

  2202 Early Ct, Middletown, DE 19709

  To be built - New Construction! Monarch offers resort-style living featuring high-end finishes and flexible floor plans. At the heart of the community, residents will enjoy an amenity-rich clubhouse complete with a resort-style pool, pickleball and sports courts, and inviting indoor lounge spaces perfect for relaxation or connection. Combining the sophistication of luxury homes with the laid-back

  Andrea Harrington Compass

  2202 Early Ct, Middletown, DE 19709
• 

  

  /49

  $664,900

  • 5 Beds
  • 3.5 Baths
  • 3,175 Sq Ft

  1245 Pimpernell Path, Middletown, DE 19709

  Move-in ready and only 3 years old, this spacious D.R. Horton two-story home offers 5 bedrooms, 3.5 bathrooms, a finished basement, two-car garage, and oversized deck. The basement features a game room with wet bar, media room, workshop or exercise room, full bathroom, and plenty of storage. The welcoming foyer includes a coat closet, while the bright front room offers enough space for both

  Lila F Dudley Realty Mark Associates-Newark

  1245 Pimpernell Path, Middletown, DE 19709
• 

  

  /38

  $494,500

  $3K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,025 Sq Ft

  3 Espalier Ln, Middletown, DE 19709

  Fantastic opportunity in one of the best 55+ communities in the area. Spring Arbor is in the heart of Middletown where you can walk to the movies! This 2025 sf Brooks model is an incredible value and one of only 6 of that model that were built in the community. THREE bedrooms, and two full baths, spacious entry with extra wide hallways, tall ceilings and a tray ceiling in the primary suite.

  Kathleen Pigliacampi Patterson-Schwartz-Hockessin

  3 Espalier Ln, Middletown, DE 19709

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