My personal ranking of homes in Skyrim:
Lakeview Manor: Easily #1. Fairly secluded with a wonderful view of Lake Ilinalta. In the woods, so you can go hunting right out your front door. However, troubles include a neighboring conjurer (possible necromancer?), occasional bandits, and occasional giant.
Breezehome: #2. Would place at #1 if not for LM's seclusion. The OG starter home. Whiterun as a whole is beautiful. Farms and wild game all around so you don't have to worry too much about food. Very competent and wise government with Balgruuf as Jarl. Just don't get involved in the Grey-Mane/Battle-Born dispute. Trust me. Also, house is made of wood and in a dry environment. Be wary of stray flames.
Heljarchen Hall: #3. Basically on Whiterun/Pale border. Again, be wary of flames. Wide, open land so you can hunt fairly well. Or start a farm (Heljarchen Farm mod is right beside Heljarchen Hall).
Proudspire Manor: #4. Beautiful architecture. In Solitude, so you are arguably in the safest city. Real-estate price is egregiously high, though. Politics are fairly mild aside from the war, and Falk is a pretty competent steward. Just avoid Erikur at all costs. 100% recommend attending the Burning of King Olaf festival.
Windstad Manor: #5. Hjaalmarch is mostly swamp to the North and snowy mountains to the South. Windstad Manor is on the Northern end of the swamps on the coast, so be ready for exceptionally cold winters. Beautiful view of Solitude and the Sea of Ghosts, though. (Additionally, neighboring the Windstad Mine mod area.) Be wary because it has the High Gate Ruins on one side and Ustengrav on the other. The swamp is also filled with frostbite spiders and the occasional chaurus.
Severin Manor: #6. Large, spacious interior with wonderful Dunmer architecture. All utilities you could need. House Redoran is a fairly competent local government. However, almost no work since the mine closed. Ash is everywhere from Red Mountain, so be sure to have something to cover your mouth and nose. Also, try not to wake up working on some strange shrines against your will.
Hjerim: #7. Beautiful architecture. Windhelm as a whole has wonderful architecture and rich history. However, it is very cold and the other residents are very unpleasant. If you're looking for an empathetic population, do not come to Windhelm. Additionally, beware of a killer on the loose.
Honeyside: #8. Only below Hjerim due to the presence of the Thieves Guild and the Black-Briars in Riften. Otherwise, very nice home. Back door leads right out the the shore of Lake Honrich, so prime fishing spot. Most likely humid with occasional rotting wood, though.
Vlindrel Hall: #9. Dwemer architecture is fascinating. However, doesn't really have anything else going for it. Forsworn are all throughout the Reach, including inside Markarth (don't let the guards lie to you). The Silver-Bloods are arguably worse than the Black-Briars. More likely to get killed than in Windhelm, and more likely to end up in prison than Riften. Plus, Thalmor actively reside in Understone Keep. Avoid Markarth unless absolutely necessary.
Winterhold: No home in Winterhold. Residence at the College doesn't count. 0/10.