Winchelsea

Winchelsea, Middletown Delaware

Winchelsea

1032 Jamison Corner Road,

Middletown, DE 19709

55 and Over

Middletown, New Castle County

Off Jamison Corner Road, north of Middletown near Route 1

New Homes

Single-family homes, carriage homes and townhomes

No Golf Course

Clubhouse, pool, fitness center, pickleball, tennis, bocce

Welcome toWinchelsea

Winchelsea, also sold as Venue at Winchelsea, is a 55+ community under its HOA rules off Jamison Corner Road, north of Middletown, planned for 336 homes. It mixes one and two story single-family homes with carriage homes and townhomes, and most plans put the primary suite on the first floor. The clubhouse has a bar area, billiards and a fitness center, with a pool, pickleball, tennis and bocce courts and a dog park outside. The HOA covers lawn care and snow removal.

Winchelsea, Middletown, DE

Experience Gets ResultsWinchelsea Featured Listings

Getting Your BearingsWhere Winchelsea Sits

Winchelsea sits off Jamison Corner Road beside the Town of Whitehall, north of downtown Middletown and south of the C&D Canal, with Route 1 close by.

  • Hospital. The ChristianaCare Middletown emergency department on Middletown Odessa Road is about 5 miles away, and Christiana Hospital near Newark is about 16 miles.
  • Town. Downtown Middletown, with its Main Street shops and restaurants, is about 6.5 miles south. Historic Odessa is about 6 miles.
  • Beaches. Rehoboth Beach is about 75 miles south. The nearest water access is Augustine Beach on the Delaware River, about 8 miles, and the C&D Canal is about 5 miles north.
  • Getting around. Route 1 runs north to Wilmington, about 22 miles, and south to Dover, about 31 miles. Route 301 connects west of Middletown toward Maryland.
  • Inside the community. A clubhouse with a bar area, billiards and a fitness center, an outdoor pool, pickleball, tennis and bocce courts, a dog park, garden plots and walking trails. The HOA covers lawn care and snow removal.

What Is Around YouDay To Day From Winchelsea

  • Medical. Doctors' offices and outpatient services are clustered around the ChristianaCare Middletown campus, about 5 miles away.
  • Groceries. Giant in Middletown, off Route 299, is about 5 miles, and ACME in Middletown is about 5.5 miles.
  • Restaurants. Pithari, on Main Street in downtown Middletown, is about 6.5 miles, with more restaurants along Main Street and Route 299.
  • Nightlife. Volunteer Brewing Company and the Everett Theatre are both on Main Street in downtown Middletown, about 6.5 miles.
  • Parks and outdoors. The Ben Cardin and Michael Castle C&D Canal Trail is about 5 miles north, Silver Lake Park in Middletown about 7 miles, and Lums Pond State Park about 9 miles.
  • Shopping. Middletown's shopping centers along Route 299 and Route 301 are about 5 to 7 miles away, and Christiana Mall is about 14 miles. Delaware charges no sales tax.

If You Like WinchelseaThree Others Worth Your Time

Not the nearest pins on a map, the ones that answer the same question.

  • Traditions at Whitehall. Next door in the Town of Whitehall, about 2 miles away, with the same mix of single-family homes and carriage townhomes and a clubhouse, pool and pickleball.
  • Four Seasons at Pennfield. New single-family 55+ homes off Route 1 in Middletown, about 5 miles east, with a clubhouse and a full amenity package to compare.
  • Four Seasons at Baymont Farm. Single-story plans east of Middletown, about 5 miles away, a useful check against Winchelsea's one-story single-family homes.

All three, like Winchelsea, are 55+ communities. Call us at 302-549-5164 and we will tell you what is for sale in each of them right now.

Learn More AboutWinchelsea 55+

New Luxury 55+ Living in Northern Delaware

Winchelsea 55+ is one of Northern Delaware's premier new 55+ communities. It stands out for its upscale homes and comprehensive HOA.

  • Dedicated 55+ Environment: Winchelsea is an age-restricted community centered around a spectacular clubhouse, with a planned coordinator for events and clubs.

  • Resort-Style Amenities: The planned amenities are robust, featuring a state-of-the-art Clubhouse with a full-service bar area, billiards, and multiple gathering spaces. Outdoors, there is a large, resort-inspired Swimming Pool, Pickleball Courts, a Tennis Court, and a Pet Park.

  • Low-Maintenance Assurance: A key benefit is the highly comprehensive HOA, which includes full lawn care, grounds maintenance, and snow removal. This provides true "lock-and-leave" living.

  • Proximity to Conveniences: The location in Middletown provides excellent access to major shopping, dining, entertainment, and essential healthcare services, including ChristianaCare facilities. The easy access to Routes 1 and 301 makes traveling to Wilmington, Philadelphia, and the Delaware beaches simple.

About the Homes 🗝️

Winchelsea 55+ offers new construction homes with modern, open designs.
Home Types: Single-Family Detached Homes and Attached Homes (Townhomes/Carriage Homes).
Sizes: Homes generally range from approximately 1,728 square feet to about 3,948 square feet.
Price Range (as of late 2025): Prices typically start from the mid-$400,000s up to the mid-$600,000s.
Key Features: All home plans are designed for the 55+ demographic, featuring essential First-Floor Primary Suites in nearly all models, open-concept living, luxury kitchens, two-car garages, and options for dens, lofts, and basements.

About the Amenities 🌳

The community boasts a high-end amenity package centered on wellness and recreation:
State-of-the-Art Clubhouse (with full-service bar area, billiards, gathering rooms)
Lifestyle Coordinator (to manage events and clubs)
Resort-Inspired Swimming Pool and Sun Deck 🏊
State-of-the-Art Fitness Center 💪
Pickleball Courts 🎾
Tennis Court and Bocce Ball Court
Pet Park/Dog Park 🐾
Community Gardens and Scenic Trails

Neighborhood Story 📖

Winchelsea 55+ is built around freedom and convenience. For buyers exploring moving to Middletown, Delaware, and seeking new 55+ communities, this neighborhood provides a worry-free foundation. It's a place where you can put away the lawnmower and snow shovel, with time for fitness and easy travel, while benefiting from Delaware's financial advantages.

Local Area and Proximity 📍

Middletown (19709) offers excellent access in New Castle County:
Healthcare: Quick drive to ChristianaCare Hospital facilities in Middletown.
Shopping & Dining: Minutes from the shops and eateries of downtown Middletown and convenient to major retail centers.
Regional Access: Easy access to Routes 1 and 301, providing quick travel to Wilmington, Philadelphia, and the Delaware beaches.
Recreation: Close to local parks, golf courses (Frog Hollow), and nature preserves (Blackbird Creek Preserve).

HOA and Maintenance 🛠️

The community provides a highly valued, all-inclusive maintenance structure for a worry-free lifestyle.
Approximate Monthly HOA Fee (as of late 2025): Fees are competitive for the level of service, estimated at $170 - $190 per month (varying by home type).
What the Fee Covers: Full maintenance of all resort amenities, common area maintenance, individual lawn care and grounds maintenance, and snow removal.
HOA Appeal: This highly inclusive fee provides the perfect low-maintenance, lock-and-leave freedom for traveling and leisure.

What You Get

Winchelsea is a 55+ community in Middletown under its age restriction, with a clubhouse and HOA-covered lawn care and snow removal.
Clubhouse: a bar area, billiards and gathering rooms, with a planned coordinator for events and clubs.
Pool and fitness: a resort-inspired pool and sun deck and a fitness center.
Courts and grounds: pickleball, tennis and bocce courts, a dog park, community gardens and scenic trails.
HOA fee: estimated at $170 to $190 per month as of late 2025, varying by home type.
Fee covers: amenity maintenance, common areas, individual lawn care and grounds maintenance, and snow removal.
Call us at 302-549-5164 and we will get the current HOA documents and fees for any home you are considering.

Tax Benefits 💰

Middletown is located in New Castle County, benefiting from Delaware's highly tax-friendly status for retirement income:
No Sales Tax: Delaware has zero sales tax. 🚫
Low Property Taxes (as of late 2025): The property tax rate in New Castle County is significantly low (approx. 0.85%), ensuring low annual tax bills.
Retirement Income Exclusions: Residents aged 60 and older can exclude up to $12,500 of eligible retirement income (pensions, 401k/IRA distributions) from state income tax.
No State Social Security Tax: Social Security benefits are not taxed by the State of Delaware.

WINCHELSEA BY LENNAR 
Singles Floor Plans

Browse the floor plans to see which model best suits you:

2 Bed

2 Bath

1728 sq. ft. 

2 Car Garage

2 Bed

2 Bath

1778 sq. ft.

2 Car Garage

3 Bed

2 Bath

1878 sq. ft.

2 Car Garage

2 Bed

2 Bath

1936 sq. ft.

2 Car Garage

2 Bed

2 Bath

2151 sq. ft.

2 Car Garage

2 Bed

2 Bath

2386+ sq. ft.

2 Car Garage

3 Bed

2-1/2 Bath

2389 sq. ft.

2 Car Garage

WINCHELSEA BY LENNAR Carriages Floor Plans

Browse the floor plans to see which model best suits you:

5 Bed

2 Bath

2 Car Garage

2056 sq. ft.

2 Bed

2 Bath

1968 sq. ft. 

2 Car Garage

2 Bed

2 Bath

1965 sq. ft.

2 Car Garage

WINCHELSEA BY LENNARTowns Floor Plans

Browse the floor plans to see which model best suits you:

3 Bed

2 Bath

2443 sq. ft. 

2 Car Garage

5 Bed

2 Bath

2669 sq. ft.

2 Car Garage

WINCHELSEA BY mckee builders

Floor Plans

Browse the floor plans to see which model best suits you:

3 Bed

2 Bath

2051 sq. ft.

2 Car Garage

3 Bed

2.5 Bath

2278 sq. ft.

2 Car Garage

2 Bed

2 Bath

1952 sq. ft.

2 Car Garage

3 Bed

2 Bath

1716 sq. ft.

2 Car Garage

3 Bed

2 Bath

1801 sq. ft.

2 Car Garage

3 Bed

2 Bath

1528 sq. ft.

2 Car Garage

Disclaimer: While we strive to do our best to have the most current information available on our website, please note that availability of models, their prices, and square footage are subject to change without notice by the Builder. For the most current info on models available, pricing and square footage, please contact us.
Call 302-549-5164 or email [email protected] You may want to read this article on Understanding Base Model Pricing.
Active Adults Realty office: 302-424-1890