Olde Town Real Estate

Olde Town Real Estate

Welcome to Olde Town, a charming subdivision nestled in the picturesque city of Lewes, Delaware, within the scenic Sussex County. Known for its rich history and stunning coastal landscapes, Olde Town offers a unique blend of small-town charm and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a tranquil lifestyle by the sea.

As you stroll through the tree-lined streets of Olde Town, you'll be captivated by the inviting atmosphere and friendly neighbors. The subdivision features a variety of beautifully designed homes, from quaint cottages to spacious family residences, all thoughtfully situated to maximize privacy and community engagement. Each property reflects the coastal aesthetic of the area, with lovely landscaping that enhances the natural beauty of the surroundings.

Residents of Olde Town enjoy easy access to Lewes's vibrant downtown, where a delightful array of shops, restaurants, and cultural attractions await. Spend your days exploring the local farmers’ market, indulging in fresh seafood at waterfront eateries, or soaking up the sun on the nearby beaches. For outdoor enthusiasts, the Cape Henlopen State Park offers miles of scenic trails, pristine beaches, and opportunities for fishing, biking, and birdwatching.

With its perfect blend of community spirit, natural beauty, and proximity to the Atlantic Ocean, Olde Town is not just a place to live; it’s a lifestyle. Discover the charm of Olde Town and make it your new home in Lewes, where the coastal breeze and warm community welcome you with open arms. Your dream home awaits!

Newest Listings in Olde Town

$1,595,000
6 Beds ⋅ 5 Baths
Discover exceptional coastal living in this beautifully designed 5-bedroom, 4.5-bath home located in the highly sought-after Olde Town community of Lewes. Thoughtfully crafted by Evergreene Homes for both everyday comfort and memorable gatherings, this home offers an ideal blend of elegance, functionality, and timeless style. A welcoming front foyer sets the tone, leading to an expansive open-concept layout anchored by a sprawling great room designed for effortless entertaining. The elegant formal dining room provides the perfect setting for holiday celebrations, dinner parties, and special occasions, while the thoughtfully upgraded interior finishes add sophistication throughout the home. The main-level primary suite offers a private retreat with the convenience of first-floor living, while upstairs, a spacious loft and oversized bonus room provide endless flexibility for a media room, home office, fitness space, unfinished basement, and additional guest accommodations. With five bedrooms and generous living areas throughout, there is room for everyone to relax and unwind. Nestled within Olde Town, one of Lewes' most desirable communities, this exceptional home combines coastal charm, modern comfort, and an outstanding location just moments from the beaches, dining, shopping, and recreation that make Lewes one of Delaware's most treasured destinations. Pictures are for illustrative purposes only.

65 Filly Ln, Lewes

Listing courtesy of Compass. Contact: 3022734998
$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: (302) 227-3883
$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: (302) 227-3883
$1,799,990
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. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing. AGENT REGISTRATION REQUIRED.

HOMESITE 82 Filly Ln, Lewes

Listing courtesy of DRB Group Realty, LLC. Contact: 2404579391
$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: 3023695397
$1,699,000
4 Beds ⋅ 4 Baths
BETTER THAN NEW! Completed in 2025 and barely lived in, this SCHELL Brothers–built Kingfisher is move-in ready and waiting for its next owner. Located in the premier community of Olde Town, you’ll be just over a mile from Lewes Beach and moments from the restaurants, shops, and charm of downtown Lewes. With direct access to the bike trail, you’re a short ride to the Delaware Bay or the Atlantic Ocean at Cape Henlopen State Park. Inside, the sought-after Kingfisher floor plan delivers the open-concept living today’s buyers crave. The kitchen, family room, and dining room blend seamlessly to create a warm, inviting space perfect for everyday living and effortless entertaining. A screened-in porch and rear deck extend the living area outdoors for relaxing or hosting guests. The first-floor primary suite feels like a private retreat, featuring a soaking tub, upgraded shower, and two walk-in closets. An additional first-floor office provides flexibility and could easily serve as a fifth bedroom. Upstairs, a central loft connects three spacious, private bedrooms, accompanied by two full bathrooms—ideal for family or visitors. Known for quality craftsmanship and premium finishes, Schell Brothers delivers again with this exceptional design and build. If you’re seeking a high-end home in an upper-tier community near the best of the Delaware shore, this property deserves your attention. Easy to tour and impossible to forget—schedule your visit today. Don't wait, the beach is calling!

15 Filly Ln, Lewes

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (302) 539-9040
$569,900
Final developer-owned lot available in Lewes’ sought after custom home community—Olde Town! This exceptional opportunity offers one of the last chances to build your dream home in a thoughtfully designed neighborhood featuring 85 homesites with no builder tie-in. Ideally located less than one mile from Lewes Beach, Cape Henlopen State Park, and the charming shops, restaurants, and attractions of downtown Lewes, Olde Town perfectly blends coastal convenience with natural beauty. Community amenities include a resort-style pool and pool house, sidewalks, scenic walking trails, and direct access to the 16-mile Junction & Breakwater Trail connecting Lewes and Rehoboth Beach. Don’t miss this rare opportunity to secure one of the final available homesites in one of the Delaware beaches’ most sought-after new communities.

91 Filly Ln Unit #LOT 1, Lewes

Listing courtesy of Jack Lingo - Lewes. Contact: (302) 645-2207
$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 3,000 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: 3027414545
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