Middletown, DE Homes for Sale with Community Pool

/64
$625,000

$30K 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
/36
$423,000
- 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
/66
$669,900

$30K PRICE DROP
- 4 Beds
- 3 Baths
- 2,700 Sq Ft
4200 Crosby Ln, Middletown, DE 19709

NEW PRICE!!! 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

Laura Walker

Walker Realty Group LLC

4200 Crosby Ln, Middletown, DE 19709
/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
/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
/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
/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
/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
/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
/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
/2
$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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/2
$559,900

Coming Soon Sep 30
- 3 Beds
- 3 Baths
- 2,475 Sq Ft
1243 Gwynedd Dr, Middletown, DE 19709

Coming soon!

Maria Ruckle Empower Real Estate, LLC

1243 Gwynedd Dr, Middletown, DE 19709
/30
$569,000
- 2 Beds
- 2 Baths
- 1,825 Sq Ft
404 Paper Birch St, Middletown, DE 19709

Ready to trade the "to-do" list for a "must-do" list? Welcome to 404 Paper Birch Street, nestled in the heart of the highly coveted Four Seasons at Baymont Farms. This isn't just a house; it’s your VIP pass to the best chapter of your life. From the moment you pull up, you’ll notice the pristine curb appeal that sets the tone for what’s inside. This home is designed for easy living and effortless

Tony Immediato Compass

404 Paper Birch St, Middletown, DE 19709
/45
$569,900

$10K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,375 Sq Ft
529 Contemplation Way, Middletown, DE 19709

Welcome to 529 Contemplation Way, an exceptional home located in the highly sought-after Whispering Woods 55+ active adult community in Middletown, Delaware, where luxury, convenience, and a carefree lifestyle come together. Designed for buyers seeking the ease of first-floor living without sacrificing space, this beautifully maintained home offers the perfect blend of elegance, flexibility, and

Earl Endrich BHHS Fox & Roach - Hockessin

529 Contemplation Way, Middletown, DE 19709

Showing Results 1 - 40, Page 1 of 4

Delaware New Castle County

Home Prices in Middletown, DE

The median home sale price in Middletown, DE is $525,000, up 2% year-over-year. Homes in Middletown sell in 118 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $525,000	Median Single Family Sale Price $569,950
Median Townhouse Sale Price $442,500	Median 2 Bedroom Sale Price $472,495
Median 1 Bedroom Sale Price $525,000	Average Price Per Sq Ft $211
Number of Homes for Sale 293	Last 12 months Home Sales 748
Months of Supply 4.70	Median List Price $554,000
Median Change From 1st List Price 0%	Median Home Sale Price YoY Change 2%

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

In Middletown, there are currently 125 homes for sale with a community pool, allowing residents to relax and socialize in a shared pool area. These homes provide residents with access to resort-style amenities, offering the convenience of enjoying communal pool facilities without the upkeep required for a private pool. Whether it's a townhouse, condominium, or single-family home, each residence features community pool access, adding value to the property. Take a look at the homes for sale with community pools in Middletown, DE.

Middletown Types of Homes for Sale

Middletown Homes by Price

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Middletown Homes for Sale by Style

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