Milton Homes with Pool

Milton Homes with Pool

Welcome to Milton, Delaware – a charming town nestled in the heart of Sussex County, where small-town charm meets coastal convenience. Known for its rich history, vibrant arts scene, and picturesque landscapes, Milton is the perfect place to call home. With its close-knit community and welcoming atmosphere, this delightful town offers an array of amenities, making it an ideal spot for families, retirees, and everyone in between.

One of the standout features of Milton is its beautiful homes, many of which come with inviting pools that provide a refreshing escape during the warm summer months. Imagine soaking up the sun in your own backyard oasis, hosting lively barbecues, or enjoying peaceful evenings under the stars, all while having the luxury of a private pool at your fingertips. These homes not only offer a stylish living space but also an outdoor retreat that enhances your lifestyle.

Milton is conveniently located just a short drive from Delaware’s stunning beaches, including the popular Rehoboth Beach and Lewes Beach. Residents can enjoy a plethora of recreational activities, from boating and fishing to hiking and biking along scenic trails. The town is also home to a variety of shops, restaurants, and local events that foster a sense of community and connection.

Whether you’re searching for a cozy cottage or a spacious family home, Milton’s real estate market has something for everyone. With homes featuring pools, you can indulge in a resort-style living experience right in your own backyard. Discover the charm of Milton today and find your perfect home in this delightful Delaware town!

Newest Milton Homes with Pool

$349,000
2 Beds ⋅ 2 Baths
Turnkey Coastal Haven in Paynters Mill! This Home is all its Fully Furnished with an Updated Kitchen in a Prime Lewes/Milton Coastal Location. Welcome to easy, resort-style living in the highly sought-after community of Paynters Mill! This beautifully updated, fully furnished turnkey condo offers the ideal balance of modern comfort, convenience, and endless coastal charm—just pack your bags and start enjoying the beach lifestyle from day one. The Interior Highlights are : Gourmet Updated Kitchen: Cook and entertain in style with newly updated cabinetry, stylish modern hardware, and gorgeous quartz countertops. Spacious Open Floor Plan: The seamless flow between the kitchen, dining, and main living areas creates an inviting atmosphere filled with natural light—perfect for relaxing or hosting guests. Primary Retreat: Enjoy a generous main bedroom suite complete with a private ensuite bathroom and a roomy walk-in closet. Peace of Mind: Features an HVAC system replaced just one year ago and an oversized 1-car garage providing plenty of room for parking, extra storage, or your beach gear. Paynters Mill offers a unique, vibrant neighborhood feel where everything you need is just steps away. Take advantage of the Resort stle Amenities of community clubhouse, fitness center, outdoor pool, hot tub, library, playground, basketball court, and tennis courts. Community offers walkable lifestyle where you can stroll right from your front door to local neighborhood favorites including a hair salon, cozy breakfast nook, delicious pizza shop, and local dining. The location is a Cyclist’s Paradise with direct access to the local bike trail system (Georgetown-Lewes Trail) making it effortless to hop on your bike and ride straight into Downtown Lewes with seamless connections onward to Rehoboth Beach. Location, Location, Location! Situated just minutes from Historic Downtown Lewes & Savannah Beach, the Tanger Outlets, premier shopping, and dining along Route 1, as well as the Cape Henlopen State Park and coastal Delaware's finest beaches. Whether you're looking for a low-maintenance primary residence, a coastal getaway, or a turnkey investment, this Paynters Mill gem is ready for you!

16359 Abraham Potter Run Unit #205, Milton

Listing courtesy of RE/MAX Associates. Contact: 3026450800
$534,900
3 Beds ⋅ 2 Baths
Experience effortless coastal living in this meticulously maintained award-winning 6 year young energy efficient Vandelay model home featuring a 4' rear extension across the back of the home and a bright and sunny morning room. Large windows bathe the interior with light and the inviting entryway welcomes you home. A spacious owners suite includes a large walk-in custom designed "California closet", private bath and plenty of room for a king sized bed and reading chair. Designed for entertaining, the open-concept layout seamlessly connects the great room, dining area, sunroom and kitchen all backing to a peaceful wooded setting. The heart of the home features a chef inspired kitchen with stainless steel appliances, pantry, granite counter tops and breakfast bar with abundant storage and prep space. Two additional bedrooms share a hall bath on the opposite side of the home offering privacy for guests and family. Relax on the front porch and enjoy the serene beauty and privacy of the mature woods off the back deck and beautifully designed paver patio and hardscape. Woodbridge's fully equipped clubhouse with bar, kitchen and entertainment room is the gathering spot for meetings and social events. It features a workout room, pool and ping pong tables, library, comfy seating around the fireplace and three large-screen TV's. The clubhouse opens onto a beautiful large gated pool, and a playground is available for children's enjoyment. Residents enjoy the walking trails, and nearby bike trails, award winning beaches, tax-free shopping, fine dining and entertainment.

22492 Ridgecrest Dr, Milton

Listing courtesy of NextHome Tomorrow Realty. Contact: 3026014171
$545,000
3 Beds ⋅ 2 Baths
Escape to peaceful wooded living without sacrificing convenience in this beautifully upgraded Insight Home located just minutes from Historic Downtown Milton, Lewes, Millsboro, and Delaware's award-winning beaches. Backing to mature woods and a community buffer, this property offers exceptional privacy while placing shopping, dining, breweries, healthcare, and coastal attractions within easy reach. Designed for easy one-level living, the bright open floor plan features luxury vinyl plank flooring throughout with no carpet, abundant natural light, custom built-in bookcases, and quality finishes that make this home truly move-in ready. The gourmet kitchen is the centerpiece of the home, featuring White Ice granite countertops, stainless steel appliances, a glass tile backsplash, under-cabinet lighting, and generous cabinet and prep space perfect for everyday living or entertaining family and friends. The private owner's suite continues the home's luxury feel with an upgraded bath showcasing quartz countertops, a custom tiled shower, rainfall shower head, and built-in bench. Additional bedrooms and living spaces provide flexibility for guests, a home office, or hobbies. Step outside to your own private backyard retreat where a low-maintenance Trex deck overlooks mature trees and protected community green space, creating a peaceful setting rarely found in today's market. Raised garden beds, professional landscaping, and a five-zone irrigation system complete the outdoor experience. Built by Insight Homes with Green Home energy-efficient construction, this home offers long-term value with a conditioned crawl space, dual-zone heat pump with propane backup, tankless on-demand water heater, central vacuum system, floored attic storage, extra laundry room cabinetry, garage pulley storage system, and Delaware Electric Cooperative electric service. If you've been searching for a move-in-ready home that combines modern upgrades, energy efficiency, one-level living, wooded privacy, and a central location close to Milton, Lewes, Millsboro, beaches, restaurants, shopping, and everyday conveniences, this home is one you won't want to miss. Schedule your private showing today.

22498 Ridgecrest Dr, Milton

Listing courtesy of Coldwell Banker Premier - Lewes. Contact: 3026452881
$415,000
3 Beds ⋅ 2 Baths
This well priced, 3 bedroom rancher offers a full basement, a spacious garage, a fenced in backyard and has been recently painted. This home is like new and shows exceptionally well in the desirable community, Anthem, in the quaint town of Milton. Just minutes from the town of Lewes and all the restaurants and shopping is mere miles away. The community offers an excellent location, a nice clubhouse and a spacious pool. Whether this is the first home, the last home, or a second home, Anthem and this home on Hawthorne Trail is likely a nice cozy fit. This home is truly move in ready with a functional layout and excellent outdoor spaces for your enjoyment. The full, oversized, unfinished basement provides a ton of room for storage or room to expand... Don't wait for this one to pass you by, call today to explore life at the beach!

28493 Hawthorne Trl, Milton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (302) 539-9040
$575,000
3 Beds ⋅ 3 Baths
Nestled within the serene enclave of Woodfield Preserve, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Why wait months for new construction when you can have this two year young home NOW! Better yet, all remaining transferable builder warranties convey to the new owner. New home feel, without the new build wait! Spanning 1,730 square feet, this meticulously crafted home features three spacious bedrooms and three elegantly appointed bathrooms, designed to cater to both relaxation and functionality. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, enhanced by abundant natural light and tasteful recessed lighting. The gourmet kitchen is a culinary enthusiast's dream, boasting upgraded countertops, a generous island, and energy-efficient stainless steel appliances, including a gas range and dishwasher. A well-designed pantry ensures ample storage, while the combination of plush carpeting and stylish laminate plank flooring adds warmth and sophistication throughout. The primary suite is a true retreat, featuring a luxurious walk-in closet and a spa-like bathroom complete with a stall shower and a soothing tub shower, perfect for unwinding after a long day. Outside, the property is equally impressive. The meticulously maintained grounds feature lush landscaping, complemented by a lawn sprinkler system and charming sidewalks that invite leisurely strolls. Enjoy tranquil views of the nearby pond, creating a picturesque backdrop for outdoor gatherings or quiet moments of reflection. The community amenities elevate the living experience, offering access to a sparkling in-ground pool, a state-of-the-art fitness center, and a welcoming clubhouse, perfect for socializing with neighbors. Parking is a breeze with an attached two-car garage and additional driveway space, ensuring convenience for you and your guests. The home is designed with modern living in mind, featuring a tankless water heater and energy-efficient appliances that contribute to a sustainable lifestyle. This property is not just a home; it's a lifestyle choice that embodies comfort, elegance, and community. Experience the perfect blend of luxury and tranquility in this stunning Woodfield Preserve residence, where every detail has been thoughtfully curated for your enjoyment. Home is being sold furnished (see Inclusions and Exclusions) unless buyer requests removal of specific items.

15288 Crape Myrtle Rd, Milton

Listing courtesy of Keller Williams Realty. Contact: 3026887653
$600,000
5 Beds ⋅ 4 Baths
Welcome to this beautifully maintained Coastal Model in the highly sought-after Woodfield Preserve community. Offering five spacious bedrooms, three-and-a-half bathrooms, and a desirable first-floor primary suite, this home blends modern comfort, thoughtful design, and coastal elegance. Designed for both everyday living and effortless entertaining, the open-concept floor plan is filled with natural light and offers generous living spaces throughout. The inviting three-season room overlooks a peaceful pond, creating the perfect place to enjoy your morning coffee, unwind with a good book, or gather with friends and family year-round. Step outside to the rear patio and take in the tranquil water views while enjoying the privacy and beauty of your backyard setting. Irrigation well to save money. The spacious primary suite provides the convenience of first-floor living, while four additional bedrooms offer exceptional flexibility for guests, multigenerational living, or a dedicated home office. A new HVAC system adds comfort and peace of mind, making this home truly move-in ready. Why wait months for new construction when you can move in right away? This home is available for a quick closing, allowing you to begin enjoying the coastal lifestyle sooner. As an added advantage, buyers may also benefit from the traditional Delaware transfer tax split, offering the potential for significant savings compared to many new construction purchases. Woodfield Preserve offers an outstanding lifestyle with resort-style amenities just moments from your door, including a clubhouse, fitness center, outdoor pool, pickleball and tennis courts, playground, dog park, yoga space, billiards room, and a full calendar of community activities. Golf enthusiasts will appreciate being adjacent to The Rookery Golf Course, while beach lovers will enjoy convenient access to Broadkill Beach, Lewes Beach, Rehoboth Beach, Cape Henlopen State Park, and the charming shops, restaurants, and breweries of historic downtown Milton. Combining generous living space, peaceful pond views, exceptional community amenities, immediate availability, and an unbeatable coastal location, this home offers the perfect blend of comfort, convenience, and value in one of Sussex County's most desirable communities. Schedule your private showing today and discover why so many buyers are choosing to call Woodfield Preserve home."

22430 E Cypress Way, Milton

Listing courtesy of Coldwell Banker Premier - Lewes. Contact: 3026452881
$599,900
5 Beds ⋅ 3 Baths
You will find so much more than meets the eye in this impeccably maintained home located just outside the Town of Milton. Offering an exceptional combination of space, flexibility, and thoughtful design, this impressive residence features five spacious bedrooms and three full baths, making it ideal for multi-generational living, extended family, or hosting guests visiting Delaware's beaches. Step inside to discover an inviting open-concept floor plan highlighted by hand-scraped engineered hardwood flooring, extensive custom trim, abundant recessed lighting, and a spacious gathering room that flows seamlessly into the chef's kitchen. Designed to impress, the kitchen boasts granite countertops, stainless steel appliances, ample cabinetry, and generous workspace perfect for everyday living and entertaining alike. The first-floor primary suite serves as a private retreat with an oversized layout, expansive walk-in closet, and luxurious en-suite bath featuring a custom tiled shower. This level also includes a private guest or family suite complete with its own living room, kitchenette, full bath, two additional bedrooms, and a separate exterior entrance—creating an ideal space for extended family, overnight guests, or independent living. Upstairs, you'll find even more flexible living space with a large family room or home office, an additional kitchenette, two generously sized bedrooms, and a shared full bath, providing endless possibilities to fit your lifestyle. Outdoor living is equally impressive with a spacious screened porch overlooking the private backyard, where a refreshing pool and tranquil wooded backdrop create the perfect setting for relaxing, entertaining, or simply enjoying the peaceful surroundings. With its versatile floor plan, quality finishes, and outstanding location just minutes from downtown Milton, area beaches, shopping, and dining, this exceptional property offers a rare opportunity to enjoy comfort, privacy, and room for everyone—all under one roof.

29123 Finch Ln, Milton

Listing courtesy of Bryan Realty Group. Contact: (302) 227-4414
$515,000
4 Beds ⋅ 3 Baths
Welcome to Easy Coastal Living at 16272 Ashlar Loop Designed for the way today's buyers want to live, this beautifully maintained, recently painted and new flooring installed is located in Windstone and combines the convenience of one-level living with the flexibility of additional space for family, guests, hobbies, or a home office on the 2nd floor. The thoughtfully designed floor plan features a spacious first-floor primary suite and everyday living areas all on the main level plus 2 additional bedrooms and bath, while the second floor offers additional bedroom, bathroom and a versatile loft—perfect for visiting family, grandchildren, or creating the extra space you need without sacrificing comfort or privacy. Beyond the exceptional floor plan, this home is filled with features that enhance everyday living. Unwind in the screened porch overlooking a beautifully landscaped community green space with mature trees that create a serene, park-like setting. The expansive common area behind the home provides added privacy and a sense of openness rarely found in neighborhood living, while the professionally landscaped yard, complete with an irrigation system and blooming hydrangeas, adds to the home's outstanding curb appeal and low-maintenance lifestyle. Inside, buyers will love the move-in-ready finishes, including new luxury vinyl plank flooring and new carpet in the bedrooms, a warm gas fireplace, and a well-appointed kitchen featuring granite countertops, stainless steel appliances, a gas range, stylish backsplash, center island, pantry, and even an additional refrigerator in the garage for extra convenience. Storage is another standout feature with garage storage racks, a dedicated storage closet, and a walk-in attic providing abundant space for seasonal items and organization. Located in the highly desirable Windstone community, residents enjoy an active, welcoming neighborhood with active clubhouse and community pool, while remaining just minutes from the Delaware beaches, shopping, dining, golf, and everything the Lewes, Milton, and Rehoboth Beach areas have to offer. Whether you're looking for a primary residence or a low-maintenance coastal retreat, 16272 Ashlar Loop offers the perfect balance of comfort, flexibility, upgrades, and lifestyle—making it the kind of home buyers are excited to tour and easy to imagine themselves living in.

16272 Ashlar Loop, Milton

Listing courtesy of Coldwell Banker Premier - Lewes. Contact: 3026452881
$575,000
4 Beds ⋅ 3 Baths
Click on virtual tour! Welcome to this beautifully crafted Schell Brothers home in the highly sought-after Paynters Mill community in Milton, Delaware. This spacious 4-bedroom, 3 full bath residence offers the perfect blend of quality construction, thoughtful design, and coastal charm—all beginning with the inviting curb appeal of a classic front porch. Step inside to an open-concept floor plan with soaring vaulted ceilings and a bright, airy living space ideal for both everyday living and entertaining. The gourmet kitchen features GE appliances, abundant tall Maple cabinetry, and granite countertops with a breakfast bar. A sunny breakfast nook with a bay window provides the perfect casual dining space. The adjacent family room is anchored with a gas fireplace and a dramatic two-story vaulted ceiling. From here, you can access the outdoor deck, patio, and fire pit—creating a seamless indoor-outdoor living experience. The main level features a guest bedroom or a perfect home office. This adjoins a newly renovated full bathroom. A formal dining room adds an elegant touch for hosting gatherings. The main-level primary suite provides comfort and convenience with a private bath. The second level features a generously sized additional two bedrooms and a full bath. A huge loft offers plenty of flexible space for family and guests. Another great feature is the interior access to the conditioned concrete crawl space, providing tons of storage. Enjoy outdoor living in the private backyard with a wood burning firepit, ideal for relaxing after a day at the nearby Delaware beaches. Residents of Paynters Mill enjoy resort-style amenities including a clubhouse, pool, fitness center, walking trails, tennis, pickleball, basketball, and a tot lot. Enjoy expansive open space on the great lawn. The HOA provides full lawn care, landscape irrigation from a community well, garbage pickup, and street snow removal. Ideally located just steps from the Paynter's Mill shops- Abbott’s Grill, The Nook, and Titanic Pizza. Just minutes from downtown Milton, Lewes, and Rehoboth Beach- this home offers easy access to shopping, dining, and coastal attractions. Don’t miss the opportunity to own this exceptional home in one of Sussex County’s most desirable communities!

16475 Howard Millman Ln, Milton

Listing courtesy of Monument Sotheby's International Realty. Contact: (302) 227-6767
$320,000
2 Beds ⋅ 2 Baths
Back on the Market but with a new price! Location says it all here: this 2-bedroom, 2-bathroom home sits inside Paynters Mill, one of the area's most amenity-rich communities, with Lewes Beach, Cape Henlopen State Park, and downtown Lewes and Milton all just a short drive away. This two-story property welcomes you upstairs with cathedral ceilings and a wall of natural light that carries through the great room, anchored by a gas fireplace for cooler evenings. Granite counters and generous cabinet space make the kitchen easy to work in, and the pass-through to the dining area keeps things open for entertaining. Slide open the door to your private balcony for a quiet view over the community. The primary suite includes a walk-in closet and its own full bath, and the second bedroom sits on the opposite side of the unit for privacy when guests stay over. What sets this home apart, though, is what's outside the front door. Paynters Mill is built around its Georgian-style manor clubhouse, home to a fitness room, library, and gathering spaces for residents. The outdoor pool stretches 75 feet with a full sundeck, and sports courts cover tennis, pickleball, and basketball. Nearly two miles of paved paths loop past ponds and flowering trees, with a quarter-mile track and outdoor exercise stations built in along the way. The village green at the heart of the neighborhood adds even more space to relax outdoors, right alongside the manor house and pool. Grab a bite at Abbott's Grill or one of two other on-site restaurants, book a haircut, or drop into the yoga studio — all without getting in the car. This is coastal Delaware living with the work already done for you. Schedule your showing today.

16433 Abraham Potter Run Unit #505, Milton

Listing courtesy of Empower Real Estate, LLC. Contact: 3027382300
$1,145,000
4 Beds ⋅ 5 Baths
Completed in 2025 and positioned on one of Miralon's premier pond-front homesites, this exceptional Cassidy offers the luxury of new construction without the wait, complete with extensive designer upgrades already in place. This thoughtfully designed home features four bedrooms, four full baths, a powder room, private office, loft, and exceptional indoor and outdoor living spaces. A welcoming covered front porch leads to an impressive foyer where engineered hardwood flooring, plantation shutters, and custom finishes set the tone throughout. Just off the entry are a private office with double French doors, a guest bedroom with a charming window seat, a full bath, and an oversized mudroom with abundant storage. The dramatic great room features soaring beamed ceilings, a floor-to-ceiling fireplace, and walls of windows overlooking the pond. The gourmet kitchen is designed for entertaining with an oversized island, farmhouse sink, premium Wolf appliance package with Sub-Zero refrigerator, abundant cabinetry, a walk-in pantry with coffee bar, and a custom wet bar with beverage refrigerator adjoining the dining area. The first-floor primary suite offers tranquil pond views, a spa-inspired bath with oversized walk-in shower and dual vanities, and two walk-in closets. Custom California Closet systems are featured throughout the home, including all bedroom closets and the pantry. A private guest suite with its own bath, a well-appointed laundry room with custom cabinetry and utility sink, and a powder room complete the first floor. Upstairs, a spacious loft opens to a covered balcony and is complemented by a fourth bedroom, full bath, and more than 300 square feet of unfinished walk-in attic storage, providing exceptional flexibility for future expansion or storage. Outside, the expansive paver patio creates the perfect setting for entertaining or relaxing while overlooking one of the community's most desirable pond settings. The oversized garage includes an electric vehicle charging connection. Miralon offers resort-style amenities including scenic walking trails, an outdoor pool with sun ledge, sauna, pickleball courts, fitness center, and built-in grilling area, all just minutes from Lewes, Rehoboth Beach, shopping, dining, and everything Coastal Delaware has to offer.

29307 Otto Dr, Milton

Listing courtesy of RE/MAX Realty Group Rehoboth. Contact: 3022274800
$1,200,000
4 Beds ⋅ 5 Baths
Former Schell Brothers model home with designer furnishings included! This exceptional residence offers the rare opportunity to own a beautifully finished former model by Schell Brothers, one of the area’s most respected builders, with all model home furniture and decorator items conveying. Perfectly positioned on an amazing homesite in a desirable neighborhood, this home delivers the elevated style, thoughtful design, and move-in-ready you have been dreaming about. From the moment you arrive, the home makes a statement with its inviting covered outdoor living area, custom paver patio, outdoor fireplace, built-in grilling area, and beautifully landscaped setting. Inside, the home showcases bright, open living spaces, designer lighting, curated furnishings, custom wall treatments, and a coastal-modern aesthetic throughout. The kitchen is a showpiece, featuring sleek cabinetry, a large island, upgraded finishes, stylish pendant lighting, and seamless flow into the dining and living areas. Every room feels professionally designed because it was — from the relaxing Coastal bedroom spaces and spa-inspired baths to the charming loft, office nook, laundry room, and multiple gathering areas. The full finished basement expands the living space dramatically, offering a custom bar, lounge area, game room, and plenty of room for entertaining guests or enjoying movie nights at home. With the model home furnishings, artwork, décor, and designer touches included, this is far more than a home — it is the one you have been waiting for. Beautifully appointed, thoughtfully upgraded, and ready to enjoy from day one, this former Schell Brothers model is a standout opportunity in a wonderful neighborhood and setting. Schedule your private showing today and don't let this one get away!

19898 Lightship Cove Dr, Milton

Listing courtesy of Coldwell Banker Realty. Contact: 3025391777
Start Your Search