The broader Longwood, FL market moves fast - homes are spending roughly 27 days on the market and selling at a median price around $385,000. Buyers looking for the best neighborhoods in Longwood along the Markham Woods Road corridor, though, are shopping a different tier entirely: expansive lots, custom architecture, and price points that bear almost no resemblance to that citywide median.
Choosing between Wingfield North and Wingfield Reserve comes down to what you actually want from a community - the amenity package, the housing mix, the HOA structure. Both subdivisions offer acreage and established luxury homes, but they're not identical, and the differences matter. You'll want to look at recent sale prices alongside what the association fees actually cover before you decide which one fits.
Neighborhood Locations and History
Both communities sit off Markham Woods Road, positioned between State Road 434 and Lake Mary Boulevard. That location puts you on a quick shot to Interstate 4 - north toward Daytona Beach and Interstate 95, or south into downtown Orlando and Tampa.
The corridor is a natural draw for commuters and frequent travelers, partly because it connects so easily to the Lake Mary and Heathrow business parks. Wingfield Reserve also gives you convenient routing to the Florida Turnpike, which matters if you're regularly traveling farther afield.
Development Timelines
Construction in Wingfield Reserve got started slightly earlier, with most homes built between 1983 and 1991 by a range of independent builders. That variety shows - you'll see a real mix of custom architectural styles across the subdivision as a result.
Wingfield North followed close behind, with most construction running from 1984 to 1994. A number of homes in this section came from specific regional builders, including Dick Proctor Homes and Jones Clayton Homes, which gives parts of the neighborhood a somewhat more cohesive feel.
Real Estate Prices and Property Details
That $385,000 Longwood median is useful context, but don't lean on it too hard here. In either Wingfield neighborhood, you should expect average selling prices to clear $1 million. These are different communities at a different price point, full stop.
Recent MLS data from July 2026 shows tight inventory in both subdivisions - consistent with the broader Longwood market's 2.7 months of supply. What does vary between the two is the sales volume and the mix of property types.
Wingfield North Market
Wingfield North is a small, exclusive community of single-family homes, with prices historically ranging from $899,000 to nearly $7 million. Over the past year, only two homes changed hands on the local MLS. Those properties averaged an asking price of $1,049,750 and closed at an average of $1,025,000.
Wingfield Reserve Market
Wingfield Reserve sees considerably more turnover - ten homes sold over the past year. The average asking price on those sales was $1,102,670, with an average closing price of $1,062,790.
Unlike Wingfield North, Wingfield Reserve includes both single-family homes and townhomes. Pricing generally runs from roughly $799,900 up to $2,785,000.
Lot Sizes and Landscaping
Both communities are built on a minimum of one acre, and that breathing room is central to the appeal. Wingfield North lots run heavily wooded - mature oaks and pines give the neighborhood a canopied, private feel. Wingfield Reserve offers comparable acreage, with enough space for large setbacks and whatever private landscaping you have in mind.
Homeowners Associations and Community Amenities
Both neighborhoods require you to join a mandatory homeowners association. That's not optional, and the fees are real line items in your monthly housing budget - worth understanding before you fall in love with a particular house.
The two HOAs cover different things at different price points, and the amenity packages reflect that.
Wingfield North Fees and Features
A recently sold property in Wingfield North showed HOA dues of roughly $308 per month, billed semi-annually at $1,845. That covers a security guard at the gated entrance - a meaningful feature if that's a priority for you.
Beyond the gate, residents get access to community tennis courts, parks, playgrounds, sidewalks, and designated water access points.
Wingfield Reserve Fees and Features
Wingfield Reserve runs higher on fees - ranging from $455 to $623 per month for single-family homes, and around $579 for townhomes. In return, those dues cover grounds maintenance, community road upkeep, security, and real estate taxes on the common areas.
The amenity package includes a park, playground, basketball court, tennis courts, and sidewalks. The standout here is something you don't see in many Seminole County communities: on-site horse stables.
Surrounding Longwood Recreation and Retail
Step outside the gates and you're well-positioned for both errands and outdoor time. The Seminole Towne Center Mall and Altamonte Mall are a short drive away for everyday retail. The Markham Woods corridor also connects directly to trail systems and state parks that make this stretch genuinely appealing for people who spend time outdoors.
Parks and Golf Courses
Wingfield North sits right next to the Seminole Wekiva Trail - a paved, 14-mile multi-use path that gets steady use from runners and cyclists. A little farther down the road, Wekiwa Springs State Park offers spring-fed swimming, paddling, horseback riding, and hiking trails.
Golfers have real options nearby. The semi-private Wekiva Golf Club runs an 18-hole, par 72 course designed by Ron Garl and Ward Northrup. If you're looking for private club membership, the Legacy Club at Alaqua Lakes and the Alaqua Country Club are both in the area.
Frequently Asked Questions
What are the main differences in lot sizes and home styles between Wingfield North and Wingfield Reserve in Longwood, FL?
Both neighborhoods require a minimum one-acre lot, so you're getting comparable land in either community. The housing mix is where they diverge. Wingfield North is exclusively single-family homes, built largely by Dick Proctor Homes and Jones Clayton Homes. Wingfield Reserve offers both single-family homes and townhomes, constructed by a wider range of independent builders.
How do the HOA dues and included services compare between these two Wingfield neighborhoods?
Wingfield North dues run around $308 per month and cover a guard-gated entrance, tennis courts, and water access. Wingfield Reserve fees are higher - ranging from $455 to $623 per month - and add road maintenance, security, and access to community horse stables, which is genuinely unusual for this area.
Are homes in Wingfield North and Wingfield Reserve zoned for the same Longwood public schools?
It depends on the specific address and where Seminole County Public Schools district boundaries currently fall. Attendance zones can shift, so you'll want to check the official district zoning maps for any property you're seriously considering rather than assuming based on general location.
Which of these Longwood communities offers better security features, like a 24-hour guarded gate?
Wingfield North has a dedicated security guard at a guard-gated entrance. Wingfield Reserve also includes security services covered through its HOA fees, though the specific entry mechanics vary by subdivision phase.
Is it generally more expensive to buy a custom luxury home in Wingfield Reserve or Wingfield North?
Average sale prices over the past year were close - Wingfield North averaged $1,025,000 and Wingfield Reserve averaged $1,062,790. At the high end, though, the gap is significant: Wingfield North has historical listings reaching nearly $7 million, while Wingfield Reserve tops out closer to $2.78 million.
Do both Wingfield subdivisions have strict HOA restrictions on exterior renovations and tree removal?
Both communities enforce deed restrictions to maintain their luxury standards and minimum one-acre lots. Before you start planning major exterior changes or tree removals on any property in either neighborhood, pull the specific HOA architectural guidelines and read them carefully.
