About this home

Welcome to 502 Chestnut Street, where timeless character and modern luxury come together in this beautifully renovated home. Ideally situated in the heart of historic Milton, this distinctive property offers 3 bedrooms, two of which are primary suites, 3.5 bathrooms and an oversized three-car detached garage. Extensively renovated in 2024, the home thoughtfully incorporates modern comforts and high-end finishes while preserving the architectural details that make it so special. Inside, exposed wood beams, rich hardwood flooring, and original architectural details reflect the home's heritage, while extensive updates provide the convenience of modern living. At the heart of the home is the beautifully redesigned kitchen, featuring sleek cabinetry, striking stone countertops with dramatic veining, stainless steel appliances, a farmhouse-style sink, a walk-in pantry, and a generous center island with an additional prep sink and seating. The kitchen opens to a spacious dining area, creating an inviting setting for everyday living and entertaining. Just beyond, a separate dining room showcases gorgeous exposed wood ceiling beams, adding warmth and character. One of the home's most desirable features is its two primary suites, conveniently located on separate levels, offering flexibility for guests and multigenerational living. The second-floor primary suite is a luxurious retreat, complete with two walk-in closets and a beautifully appointed bathroom featuring heated tile floors, a jetted soaking tub, a glass-enclosed tile shower, and an expansive double vanity. A vaulted ceiling with exposed wood beams overhead complements the contemporary finishes, creating a distinctive space that balances historic craftsmanship with modern elegance. Abundant storage throughout the home adds to its everyday practicality. The spacious screened porch extends the living space beyond the kitchen, offering an inviting retreat surrounded by greenery. Whether enjoying a quiet morning, dining outdoors, or entertaining friends, this beautiful space is designed for relaxation and gathering. A cozy front porch provides another welcoming spot to unwind and enjoy the neighborhood. Equally impressive is the oversized three-bay detached garage, equipped with a car lift that allows for storage of up to four vehicles, a dedicated workshop ideal for hobbies and projects, and a floored loft providing additional storage-a truly exceptional feature in downtown Milton. Beyond the property itself, the location is equally appealing. Just a short stroll from Dogfish Head Brewery, Broadkill River, local restaurants, boutique shops, and the attractions of downtown Milton, this property offers the convenience of a walkable lifestyle in one of Delaware's most beloved small towns. Rich in character, thoughtfully renovated, and ideally located, 502 Chestnut Street offers a rare opportunity to enjoy the craftsmanship of yesterday with the comforts of today. Call to schedule your private tour!

Facts and features

Schools

• Milton Elementary School

  elementary · K-5 · 0.1 mi

  5

• Cape Henlopen High School

  high · 9-12 · 8.9 mi

  8

• Beacon Middle School

  middle · 6-8 · 9.7 mi

  7

• Eagle's Nest Christian Academy

  elementary · K-8 · 0.4 mi

• Mariner Middle School

  middle · 6-8 · 0.5 mi

  6

• H. O. Brittingham Elementary School

  elementary · K-5 · 0.6 mi

  7

Price history

• Nov 6, 2026 · Listed$629,000
• Jan 25, 2021 · Sold$210,000
• Jan 23, 2021 · Listing Removed—
• Nov 2, 2020 · Listed$250,000

Tax history

• 2026$898 tax · $213,600 assessed
• 2024$495 tax · $213,600 assessed
• 2023$494 tax · $10,050 assessed
• 2022$477 tax · $10,050 assessed
• 2020$271 tax · $10,050 assessed
• 2019$271 tax · $10,050 assessed
• 2018$256 tax · $10,050 assessed
• 2017$247 tax · $10,050 assessed

Home value

$417,368

• Quantarium$417,368
• Collateral Analytics$358,000
• Cotality$421,700

Where it is