Crestwood Oaks
Homes for Sale in Safety Harbor, FL

Crestwood Oaks is a compact, owner-occupied enclave in Safety Harbor where larger-than-average homes and a wide build-era range make each listing its own case rather than a clone of the one before it.

Stellar MLS sales records identify 17 homes in Crestwood Oaks that have changed hands since 2009, built between 1973 and 2012 (median 1988), with a median living area of about 2,432 sq ft and a typical 3-bedroom, 2.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Crestwood Oaks is too small for its own price trend, so here is the market around it.

In ZIP 34695, 114 homes are on the market and 25% are under contract — a steady corner of Safety Harbor.

Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).

In ZIP 34695 (Safety Harbor), 222 homes closed in the last 12 months at a median of $520K ($307/sq ft), down 0.8% year over year, with a median 44 days on market. Right now 48 active and 14 pending listings put supply at about 5.1 months — a balanced market. See the live ZIP 34695 housing market and the Pinellas County market.

ZIP and county figures describe the wider market, not Crestwood Oaks specifically. Momentum Research analysis of MLS records.

The defining trait of Crestwood Oaks is stability layered over variety. A homestead share north of 91% across 35 homes tells you this is overwhelmingly a live-in neighborhood, not an investor's block. That tends to translate into homes that have been maintained for long-term ownership, but it also means listings surface infrequently — when one hits the market, it deserves a fast, serious look.

The 1952-to-2012 build range and 1988 median mean you should underwrite each home individually. A house updated over the years and one closer to its original systems can sit in the same neighborhood at very different values, so the median price is best read as a midpoint of a wide, condition-driven spread. The larger median footprint of about 2,656 square feet gives most buyers room to work with, whether that means updating in place or moving in and living with it.

In a 35-home neighborhood with thin turnover, the win comes from reading condition against price correctly and being ready to act. We track what actually trades in Crestwood Oaks, help you separate an updated home from one that needs work before you commit, and pace your offer to a market where the right listing does not come around often.

Listings in this community report association dues of about $252 a year ($21 a month) — the median AssociationFee across 32 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.