Olde Town Real Estate

Olde Town Real Estate

Welcome to Olde Town, a charming subdivision nestled in the heart of Lewes, Delaware, within the picturesque Sussex County. This enchanting community offers a delightful blend of small-town charm and modern convenience, making it an ideal place to call home.

Olde Town is characterized by its tree-lined streets, beautifully landscaped yards, and a warm sense of community that welcomes residents and visitors alike. The architectural styles of the homes reflect a classic coastal vibe, with inviting porches and vibrant gardens that embody the spirit of coastal living. Whether you’re seeking a cozy cottage or a spacious family home, Olde Town offers a variety of options to suit your lifestyle.

One of the highlights of living in Olde Town is the proximity to Lewes' stunning beaches, where you can enjoy sun-soaked days and breathtaking sunsets. The historic downtown area is just a stone's throw away, featuring a delightful array of boutique shops, delicious eateries, and cultural attractions. Stroll along the charming streets, savor fresh seafood, or indulge in local art galleries that showcase the vibrant creativity of the area.

For outdoor enthusiasts, Olde Town is surrounded by nature trails, parks, and scenic waterways, perfect for kayaking, biking, or simply enjoying a leisurely walk. The community also hosts various events throughout the year, fostering a sense of camaraderie among residents.

In Olde Town, you’ll find not just a home, but a lifestyle enriched by community spirit, natural beauty, and the joys of coastal living. Come discover the magic of Olde Town in Lewes, Delaware – where every day feels like a vacation!

Newest Listings in Olde Town

69 Filly Ln, Lewes
$1,225,000
3 Beds ⋅ 3 Baths
69 Filly Lane in Olde Town offers a unique opportunity to build an award-winning Kingfisher model by Schell Brothers, one of Coastal Delaware's most sought-after floor plans. This to-be-built opportunity combines one of the most desirable Lewes locations with the flexibility to personalize your new home through a variety of available options and upgrades. The Kingfisher combines distinctive architecture, spacious living areas, and the convenience of a first-floor primary suite. The impressive two-story great room creates an open, inviting atmosphere, while the generously sized kitchen flows naturally into the main living spaces, ideal for both everyday living and entertaining. A versatile first-floor flex room offers additional space for a home office, formal dining room, or other uses, while the second level provides comfortable accommodations for family and guests. One of the most appealing aspects of this opportunity is the ability to personalize the home. Buyers may select from available structural options, design finishes, and upgrades, allowing them to create a home that reflects their individual preferences and lifestyle. The location is equally compelling. This particular lot location in Olde Town at Lewes is ideally situated adjacent to the Junction & Breakwater Trail and across from the Lewes Public Library, with historic downtown Lewes, Cape Henlopen State Park, local beaches, restaurants, and shopping all just a short distance away. The community also offers a swimming pool, pool house and other amenities for residents to enjoy. With a desirable homesite and the opportunity to customize a popular floor plan, this offering brings together the advantages of new construction and an exceptional Lewes location. The lot can also be purchased separately with no builder tie-in or timeframe to build for $625,000.

69 Filly Ln, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

69 Filly Ln, Lewes
$625,000
Introducing 69 Filly Lane - an exceptional opportunity to build a custom home in Olde Town, one of Lewes’ most desirable new communities. This 0.23-acre unimproved homesite offers a blank slate for a new buyer to create a home tailored to their vision, with no builder tie-in. The location is hard to beat. The homesite is adjacent to the Junction & Breakwater Trail, directly across from the Lewes Public Library, and just a short distance from downtown Lewes, Cape Henlopen State Park, the beaches, shopping and dining. Within the Olde Town community, the lot is conveniently located near the pool and pool house, making it easy to enjoy the neighborhood amenities while staying connected to town and the trail. The community amenities also include a covered grilling and entertaining area, dual sided fireplace and outdoor TV, shuffleboard, bocce and fire pit. With its desirable location and the freedom to build from the ground up, 69 Filly Lane presents a unique chance to create a custom home in the heart of Lewes.

69 Filly Ln, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact:

59 Filly Ln, Lewes
$1,849,999
6 Beds ⋅ 6 Baths
Introducing an exceptional new construction custom home by Sienna Homes, thoughtfully designed to deliver approximately 5,500 square feet of sophisticated living space in the sought-after Olde Town at White’s Pond community of Lewes. Offering 6 bedrooms, 5 full bathrooms and 1 powder room, this impressive residence pairs striking architectural details with elevated finishes and a floor plan designed for both everyday living and effortless entertaining. From the moment you enter, soaring ceilings, engineered wood flooring and abundant natural light create an immediate sense of scale. The dramatic two-story living room serves as a stunning centerpiece, featuring cathedral ceilings and expansive Andersen 100 Series windows. Thoughtful architectural details and an open-concept design create a seamless flow throughout the home’s main gathering spaces. At the heart of the home is a showstopping chef’s kitchen anchored by an impressive 9-foot island with Taj-Mahal Quartzite waterfall countertops. Premium ZLINE stainless steel appliances elevate the space, while generous cabinetry and sophisticated finishes offer the perfect balance of beauty and function. A separate butler’s pantry complete with its own dishwasher and refrigerator provides additional prep and storage space, making entertaining on any scale effortless. Designed with flexibility and luxury in mind, the home features two primary suites. The main-level primary suite creates a private retreat with the added convenience of its own dedicated laundry room. Upstairs, a second primary suite provides another beautifully appointed escape, while a second-floor laundry room adds convenience for the home’s additional bedrooms. With six bedrooms and five-and-a-half baths, the expansive layout offers abundant space for guests, home offices, recreation and multigenerational living while maintaining privacy. Carefully selected finishes and custom details complement the home’s impressive proportions throughout. The exterior continues the home’s commitment to quality with Hardie® board siding, Andersen® 100 Series windows, a two-car garage and outdoor shower—the perfect addition for life at the Delaware coast. Beyond the home, Olde Town at White’s Pond offers a lifestyle equally as impressive as the residence itself. The picturesque 85-homesite community is nestled alongside the 16-acre White’s Pond and offers direct access to the Junction & Breakwater Trail, providing miles of opportunities for walking, running and biking between Lewes and Rehoboth Beach. Residents enjoy an exceptional collection of community amenities including a pool and cabana, bathhouse, outdoor kitchen, outdoor fireplace and fire pit, lounge area, shuffleboard and bocce ball courts. Even better, Olde Town places you within one mile of Lewes Beach, Cape Henlopen State Park, and the restaurants and shops of downtown Lewes—bringing together the privacy of a luxury residential community with remarkable access to everything that makes coastal Lewes so special. 59 Filly Lane isn’t simply new construction—it’s a custom luxury residence designed for elevated coastal living, where exceptional craftsmanship, impressive scale and one of Lewes’ most desirable locations come together. Renderings are for illustrative purposes and may depict furnishings, landscaping, finishes or other features that are not included or are subject to change.

59 Filly Ln, Lewes

Listing courtesy of KW Empower. Contact:

55 Filly Ln, Lewes
$1,299,000
4 Beds ⋅ 4 Baths
BETTER THAN NEW IN OLDE TOWN! Skip the wait of new construction with this pristine, practically brand new east of Route 1 home in Lewes! Offering over 3,400 square feet of thoughtfully designed living space, this home blends coastal elegance with everyday functionality. The main floor serves as the ultimate gathering hub, featuring an open-concept layout centered around a gourmet kitchen equipped with quartz countertops, an oversized island with bar seating, stainless steel appliances, double wall ovens, an electric-cooktop with a range hood, and a walk-in pantry. The adjacent living area centers on a natural gas fireplace and flows seamlessly into the dining space. For effortless main-level living, the private primary suite offers a spa-inspired bath with a dual vanity, soaking tub, separate tile shower, and dual walk-in closets. A dedicated front office/den, powder room, and laundry room complete the first level. Upstairs, a vast loft area provides a flexible second living room, ideal for media, play, or relaxing. Three spacious additional bedrooms and two full baths, ensure family and guests have complete comfort and privacy. Outdoor living is exceptional, featuring a large screened porch that leads out to a beautifully landscaped, fully fenced-in backyard complete with built-in irrigation. Residents of Olde Town enjoy world-class community amenities including a stunning outdoor pool, covered poolside lounge, clubhouse, and shuffleboard court. Enjoy a short walk to one of the many shops or restaurants in Lewes’ historic downtown or enjoy the extensive local bike trails and pristine beaches as this turn-key property offers the ultimate coastal Delaware lifestyle. Don't wait to build - call today!

55 Filly Ln, Lewes

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

72 Filly Ln, Lewes
$1,699,990
5 Beds ⋅ 5 Baths
Welcome to coastal living at its finest — a stunning 5-bedroom, 4.5-bath home ideally located just about a mile from the beach and moments from Downtown Lewes filled with boutique shops, award-winning restaurants, and vibrant local culture. Perfectly positioned within a sought-after community offering direct access to the Lewes–Georgetown Bike Trail, this home blends luxury, comfort, and an active coastal lifestyle. Inside, the home showcases a beautifully designed chef’s kitchen featuring premium finishes, expansive workspace, and an open layout ideal for entertaining and everyday living. The spacious floor plan flows effortlessly into inviting gathering areas and out to a large screened porch complete with a stone fireplace, creating the perfect setting for year-round indoor-outdoor enjoyment. The primary suite is a private retreat highlighted by a spa-inspired bath with a stunning Roman shower, offering both elegance and relaxation. Upstairs, a versatile rear loft opens to a second-story outdoor deck, providing peaceful views and an ideal space for morning coffee or evening sunsets. The fully finished walk-up basement expands the living space with endless possibilities — perfect for guests, recreation, or a home theater. Car enthusiasts, hobbyists, or beach lovers will appreciate the additional recreation garage, offering exceptional storage for bikes, golf carts, or water gear. Combining thoughtful design, upscale features, and an unbeatable location near the beach and trail system, this home delivers the ultimate coastal lifestyle — where every day feels like a vacation.AGENT REGISTRATION REQUIRED.

72 Filly Ln, Lewes

Listing courtesy of DRB Group Realty, LLC. Contact:

65 Filly Ln, Lewes
$1,575,000
6 Beds ⋅ 5 Baths
Discover exceptional new construction by Evergreene Homes in the prestigious Olde Town community. This beautifully designed 5-bedroom, 4.5-bath home offers 3,940 square feet of thoughtfully planned living space, blending luxury, comfort, and flexibility. The main-level owner’s suite provides a private retreat and the convenience of first-floor living, while the second level features additional bedrooms and a large bonus room ideal for a media room, home office, playroom, or additional lounge. An expansive unfinished basement offers incredible potential for future living space, recreation, a home gym, or abundant storage. A large two-car garage provides plenty of room for vehicles, bikes, and beach gear, while the beautiful rear screened porch creates the perfect setting for relaxing, dining, and enjoying the coastal breeze. Located within walking distance of the community pool and Lewes Public Library, the home also offers easy access to the Junction & Breakwater Trail for miles of hiking and biking. With spacious interiors, exceptional indoor-outdoor living, and a sought-after location close to the best of Lewes, this remarkable Olde Town home is an opportunity not to be missed. The staged photos are virtually staged and do not represent furniture or inclusions in the home as they are purely for illustrative purposes only.

65 Filly Ln, Lewes

Listing courtesy of Compass. Contact:

144 Paddock Way Unit LOT 33, Lewes
$725,000
Excellent opportunity in Lewes’ latest custom home community known as Olde Town! This community features 85 homesites with no builder tie-in, all situated within one mile of Lewes Beach, Cape Henlopen State Park, and all the downtown restaurants and shopping attractions. 144 Paddock Way (Lot 33) is located adjacent to community open space and buffer adjacent to Showfield, and only a short walk to the community pool and pool house. The additional amenities include sidewalks, walking trails, and direct access to the 16-mile Junction & Breakwater Trail that spans from Lewes to Rehoboth Beach. Olde Town is sold out and this is a resale opportunity.

144 Paddock Way Unit LOT 33, Lewes

Listing courtesy of Jack Lingo - Rehoboth. Contact:

114 Paddock Way Unit LOT 40, Lewes
$719,000
Excellent opportunity in Lewes’ latest custom home community known as Olde Town! This community features 85 homesites with no builder tie-in, all situated within one mile of Lewes Beach, Cape Henlopen State Park, and all the downtown restaurants and shopping attractions. 114 Paddock Way (Lot 40) is located adjacent to community open space and buffer adjacent to Showfield, and only a short walk to the community pool and pool house. The additional amenities include sidewalks, walking trails, and direct access to the 16-mile Junction & Breakwater Trail that spans from Lewes to Rehoboth Beach. Olde Town is sold out and this is a resale opportunity.

114 Paddock Way Unit LOT 40, Lewes

Listing courtesy of Jack Lingo - Rehoboth. Contact:

77 Filly Ln, Lewes
$639,999
Welcome to Olde Town, a highly sought-after custom home community offering prime location, coastal charm, and true design freedom. 77 Filly Lane presents a rare opportunity to build your custom home in the heart of historic Lewes with no builder tie-in, allowing you to choose the builder and design that fit your vision. Ideally located just one mile from Lewes Beach, Cape Henlopen State Park, and downtown Lewes shopping and dining, this community places you close to everything coastal living has to offer. Enjoy a resort-style pool, green spaces, sidewalks, walking trails, and direct access to the 16-mile Junction & Breakwater Trail. 77 Filly Lane offers the perfect blend of location, amenities, and lifestyle; secure your lot today and start planning your dream home.

77 Filly Ln, Lewes

Listing courtesy of Century 21 Gold Key Realty. Contact:

259 Monroe Ave, Lewes
$1,900,000
4 Beds ⋅ 4 Baths
Welcome to your future dream home in the highly sought-after Olde Town community in Lewes, Delaware. This to-be-built custom residence by Excel Construction Group blends coastal living with modern luxury, offering 4 spacious bedrooms, 3.5 designer bathrooms, and 3,500 square feet of thoughtfully designed living space. The open-concept floor plan creates a seamless flow between the gourmet kitchen, inviting living area, and sun-drenched dining space—perfect for entertaining or relaxing at home. A luxurious primary suite features a spa-inspired en-suite bath and expansive walk-in closet, while the additional bedrooms provide flexible options for guests, a home office, or a growing family. Outdoor living is elevated with a welcoming front porch and a versatile all-season rear porch, ideal for year-round enjoyment and hosting. The oversized garage and designer finishes throughout make this home as functional as it is beautiful. Located just minutes from historic downtown Lewes, pristine beaches, and local dining, this home offers the perfect combination of coastal lifestyle and upscale comfort. Customize your finishes and bring your vision to life! Photos are of a similar home built by the builder.

259 Monroe Ave, Lewes

Listing courtesy of Iron Valley Real Estate Premier. Contact:

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