Old Preston Hollow is the original estate section of Preston Hollow in North Dallas, known for winding country lanes, creeks, mature trees and some of the largest and most expensive home sites inside the city of Dallas. It grew out of the estate developments of the 1920s and 1930s along Northwest Highway between roughly Preston Road and Midway Road, and it kept its rural character after Preston Hollow became a township in 1938 and later joined the city. Many lots run from under an acre to two or three acres.
At The Agency Dallas, our agents work with buyers and sellers throughout Preston Hollow. This guide covers where Old Preston Hollow is, what sets it apart from the rest of the area and what buyers should know.
Where is Old Preston Hollow?
Old Preston Hollow originally spanned Northwest Highway from roughly Preston Road to Midway Road. The broader Preston Hollow area now stretches much farther north, but the oldest estate sections sit closest to that original corridor. Within it are smaller named additions and neighborhoods that buyers and agents use to describe specific pockets, including:
- Preston Hollow Addition, often cited for some of the most expensive homes in Dallas
- Dentwood Addition, known for one-to-three-acre estate sites
- Maywood Estates and Preston Elms, with many homes from the 1930s through the 1960s
- Meadowbrook and the creekside pockets near Bachman Creek and its tributaries
For the area as a whole, see whether Preston Hollow is a good place to buy a house.
What makes Old Preston Hollow different from the rest of Preston Hollow?
Much of greater Preston Hollow was built out later on more regular lots. Old Preston Hollow kept the scale and setting of its estate beginnings. Buyers notice these differences:
- Lot size. Many homes sit on half an acre to an acre, and estate sites of two to three acres exist, especially on streets like Strait Lane, Park Lane and parts of Deloache Avenue. Our guide to which Dallas neighborhoods have the largest residential lots puts this in context.
- Country lanes. Narrow, curving streets without sidewalks and with heavy tree canopy give the area a rural feel unusual for a major city.
- Creeks and topography. Spring-fed creeks, ponds and rolling ground run through several pockets, which adds privacy and value.
- Architecture. Old Preston Hollow mixes historic estates by noted Dallas architects with Mid-Century Modern homes and newer custom builds.
- City of Dallas. Unlike Highland Park and University Park, Old Preston Hollow is inside the City of Dallas and is served by Dallas ISD, with many of the city's best-known private schools nearby. See what private schools are closest to Preston Hollow.
What should buyers know before buying in Old Preston Hollow?
- Price the land first. On large lots, land is often most of the value. An older home on a prime site may be priced mostly for the dirt.
- Check creeks and drainage. Creekside lots can carry floodplain or erosion issues. Order a survey and review flood maps early.
- Understand city rules. Dallas zoning, setbacks and any neighborhood-specific standards affect what you can build. Some streets also have deed restrictions.
- Expect thin comparables. Estate sales are infrequent, so valuation takes judgment rather than a simple price-per-square-foot comparison.
- Budget for big-house maintenance. Large homes and grounds carry higher insurance, landscaping and upkeep costs.
Should I build new or buy an existing home in Old Preston Hollow?
Both are common. Many buyers purchase an older home to rebuild on a large lot, while others look for a restored estate or a recent custom home. The decision usually comes down to the condition of the existing house, how much the buyer values its architecture and the time and cost of building. Our article on building new or buying existing in Preston Hollow walks through the tradeoffs.
How The Agency Dallas works in Old Preston Hollow
The Agency Dallas is an independently owned luxury real estate brokerage at 8111 Preston Road, close to Old Preston Hollow. Estate sales in Preston Hollow are a regular part of our work. Our agents prepare written valuations that separate land and improvements, and our in-house marketing team builds the campaign for each listing. For sellers weighing their options, our guide on how to sell a luxury estate in Preston Hollow is a good starting point.
How do prices vary within Old Preston Hollow?
Old Preston Hollow is not priced as one market. Two homes a few streets apart can differ by millions, and the reasons are usually visible on a site plan before they show up in a listing:
- Street. Estate streets such as Strait Lane, Park Lane and parts of Deloache Avenue carry the highest land values. Interior streets with smaller lots trade lower.
- Acreage and frontage. A lot that is wide at the street and deep enough for a motor court, pool and guest house is worth far more per acre than an irregular or narrow parcel of the same size.
- Creek and floodplain. Water adds beauty and privacy, but floodplain can shrink the buildable area. Two creekside lots of equal size can have very different value once the survey is in hand.
- Improvements. A restored architect-designed estate, a recent custom home and a dated house priced for the land sit in different price bands even on the same street.
How should buyers read Old Preston Hollow sales data?
Price per square foot, the number most buyers reach for first, is often misleading here. A small older house on two acres can show a very high price per square foot because the buyer paid for the land. A large new home on a modest lot can show a lower figure even though it sold for more. A better approach is to compare land value per acre for similar streets, then add or subtract for the house. Sales are also infrequent, so it is common to look back further than the usual six to twelve months and to weigh private sales the MLS does not show. Our article on how luxury homes get valued when there are few comparable sales explains the method.
Frequently asked questions
What is Old Preston Hollow?
Old Preston Hollow is the original estate section of Preston Hollow in North Dallas, centered on the Northwest Highway corridor between roughly Preston Road and Midway Road. It is known for large lots, country lanes, creeks and mature trees, and it includes some of the most expensive residential properties in the City of Dallas.
How big are the lots in Old Preston Hollow?
Lot sizes vary. Many homes sit on roughly half an acre to an acre, while estate sites of two to three acres exist in pockets such as Dentwood Addition and along streets like Strait Lane and Park Lane. Buyers should confirm acreage with a survey and county appraisal records.
Is Old Preston Hollow in Highland Park ISD?
No. Old Preston Hollow is in the City of Dallas and is served by Dallas ISD. Many families in the area choose private schools, and several of the city's best-known private schools are within a short drive.
When did Preston Hollow become part of Dallas?
Preston Hollow incorporated as a township in 1938 and was later annexed into the City of Dallas. Its estate character dates to the development of the 1920s and 1930s along the Northwest Highway corridor.
Do Old Preston Hollow homes sell off market?
Some do, especially larger estates. Because inventory is limited and many owners value privacy, private sales are part of the market. Buyers benefit from working with agents who follow the area closely.
Sources: DougNewby.com, Old Preston Hollow neighborhood guide; Wikipedia, "Preston Hollow, Dallas." Accessed October 30, 2026.
