This guide is arranged by price, from cheapest to most expensive. This does not just detail the cost of the house, but the cost of furniture, the usefulness and appearance of the house, and has other handy information regarding whichever unit you plan on purchasing.
Benirus Manor
Location: Anvil
Price: 5000 Gold
Furnishing Cost: 0 per unit
Description of Unit:
A lovely fixer upper. Complete with two floors, a garden, terrace and basement.
How To Acquire:
The Manor was originally the property of Velwyn Benirus, but he has pressing issues in the Imperial City and wants to sell it ridiculously cheap. It's completely furnished and he's prepared to sell it for 5000 gold? Something must be wrong. Well, it is. The manor is haunted. To exorcise the spirits, you must complete the mission Where The Spirits Have Lease. Afterwards the manor is restored and becomes quite liveable.
Usefulness:
Benirus Manor is located in Anvil, and it seems that terribly few of the games main events take place in this region. It is mainly useful during certain sections of the Dark Brotherhood and Thieve's Guild missions and at one or two points during the Main Quest. Otherwise, it's only handy if you plan on doing all of the Anvil missions. But still it's the cheapest house in the game and well worth it.
Personal Opinion:
Benirus Manor (post exorcism) is very nice, but unlike the other houses that you work for and furnish yourself (for the most part) this estate is missing one critical thing. It never really feels like home. Its usefulness is limited to boot, but still it is a mansion that you acquire through a relatively easy quest, so I can't really complain.
Waterfront Shack
Location: Imperial City, Waterfront District
Price: 2000 Gold
Furnishing Cost: ~750 per unit
Description of Unit:
A one-room shack; not much to look at.
How To Acquire:
Speak with the Vinicia Melissaeia at the Office of Imperial Commerce in the Market District.
Usefulness:
Since the Imperial City is both the center of Cyrodiil and the majority of the game's events, this house's usefulness is limitless. It's particularily useful during the Main Quest and early Thieve's Guild quests. It's also useful for the entirety of the Arena Quest Line.
Personal Opinion:
While this house is not much to look at, it's low price and usefulness more than make up for it. It's an ideal beginner home and will probably be your “favorite home” throughout the game.
Riverside Shack
Location: Bravil
Price: 4000 Gold
Furnishing Cost: ~1200 per unit
Description of Unit:
A squalid little shack; technically one-room, but with dividers.
How to Acquire:
Speak with Count Bravil during audience hours to purchase.
Usefulness:
This shack is really useful during the middle of the Thieve's Guild quests and at the end of the Dark Brotherhood quests. It's particularly useful for Thieve's Guild members because you are in the same town as both a fence and a Doyen (your fence actually lives above you).
Personal Opinion:
This was the first house I got and the one that I have used the most. It's not much to look at, but it is my personal favorite. Mainly because I'm an evil bastard who has done all the evil quests.
Townhouse
Location: Leyawin
Price: 7000 Gold
Furnishing Cost: ~1800 per unit
Description of Unit:
A modest little house in the center of town.
How to Acquire:
Speak with Count Leyawin.
Usefulness:
A house in Leyawin is about as useful as a house in Anvil, but there is one particular point in the game where this house can make your life easier. When you take on the mission for Count Leyawin to hunt the Black Bow Bandits, it's nice to be able to return home.
Personal Opinion:
For the additional 3000 Gold, this house is not very different from the one you bought in Bravil, but it is slightly roomier (a trait which will disappear when you furnish it). Still, though, it's a nice house when you've started making a name for yourself.
Cabin
Location: Bruma
Price: 10,000 Gold
Furnishing Cost: ~1800 Gold
Description:
A very cozy cabin conveniently located inside the Main Gate.
How To Acquire:
Speak with Countess Carvain.
Usefulness:
This house is between the cheap and the opulent. It is very useful during the Main Quest, because of its proximity to Cloud Ruler Temple and the final encounter with Oblivion Gates. It is also useful for new members of the Thieve's Guild, since Ongar The World-Weary lives a few doors away.
Personal Opinion:
I like the idea of cabins, and this house has a kind of ski lodge feel to it. This is also the first house to have multiple levels (not counting Benirus Manor) which means more room to store stuff.
http://www.uesp.net/wiki/Oblivion:White_Stallion_Lodge
as well as some others it appears, take a look at this page, which has every house in the game.
http://www.uesp.net/wiki/Oblivion:Houses#Leyawiin]
Great article though, I enjoyed reading it, hope those links help