Crestwood Oaks
Homes for Sale in Safety Harbor, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 16 closed sales in Crestwood Oaks in Safety Harbor, FL since 2006, the most recent in June 2026. Across Safety Harbor as a whole, 184 homes closed in the last 12 months at a median of $533,750, 43 median days on market, with 45 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $10,350 ($9,540 with the full homestead exemption).
Crestwood Oaks is a small pocket of 35 homes in Safety Harbor, and price here is driven far more by condition than by any single benchmark. With a build range spanning 1952 to 2012 and a median build year of 1988, you are looking at a genuinely mixed vintage — some homes carry decades of updates, others are closer to original. That spread is the story: the median sale price is a starting point for conversation, not a substitute for walking the specific house.
The median living area sits around 2,656 square feet, which is generous for a neighborhood of this size, so buyers are largely comparing larger footprints against each other. With only 35 homes and a homestead share above 91%, turnover is thin and most owners are living in the home rather than renting it. For sellers that scarcity is leverage; for buyers it means patience and readiness to move when the right condition-and-price match appears.
Nearby homes for sale
No active listings inside Crestwood Oaks right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
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.
Who Crestwood Oaks is best for.
Best for
- Long-horizon buyers who want a larger home and plan to stay put rather than flip
- Buyers comfortable underwriting an older home on its condition and updates rather than a headline price
- Those willing to wait for the right listing in a low-inventory pocket
Probably not for
- Buyers who need to close quickly and want several homes to choose from at once
- Investors seeking rental turnover in a heavily owner-occupied street
- Anyone wanting new-construction systems and finishes without renovation work
The market around Crestwood Oaks
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 23% are under contract — a steady corner of Safety Harbor.
Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).
In ZIP 34695 (Safety Harbor), 224 homes closed in the last 12 months at a median of $520K ($307/sq ft), up 0.5% year over year, with a median 44 days on market. Right now 47 active and 11 pending listings put supply at about 5.2 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 Crestwood Oaks buying strategy.
If we were buying in Crestwood Oaks today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Crestwood Oaks.
A small, settled street with a mixed vintage
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.
The location and the amenities are priced into every listing in Crestwood Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
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.
Crestwood Oaks in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Crestwood Oaks buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Crestwood Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Crestwood Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Crestwood Oaks home worth?
Get a no-obligation home value based on real comparable sales in Crestwood Oaks, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Safety Harbor →
Should you buy in Crestwood Oaks?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 13, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2006 (16 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Crestwood Oaks fits the bigger picture — live prices, inventory, and Momentum Scores:
Schools serving nearby communities
We do not have a confirmed school assignment for Crestwood Oaks. These are the public schools most often assigned to other communities in ZIP 34695; zones change and vary by address, so confirm with the district before you buy.
- Safety Harbor Elementary · Public · FLDOE grade A (assigned to 2 nearby communities)
- Safety Harbor Middle · Public · FLDOE grade A (assigned to 2 nearby communities)
- Countryside High School · High · FLDOE grade A (assigned to 2 nearby communities)
Assignments from district data for neighboring communities; grades are official Florida Department of Education school grades (2025-26).
Common questions about Crestwood Oaks
Where is Crestwood Oaks?
Crestwood Oaks is a community in Safety Harbor, Pinellas County, Florida, ZIP 34695.
Are there homes for sale in Crestwood Oaks right now?
No active listings inside Crestwood Oaks at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Crestwood Oaks have an HOA or CDD?
No HOA is on record for Crestwood Oaks in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Crestwood Oaks with Momentum Realty’s local guides.
Crestwood Oaks Market Scorecard
Crestwood Oaks is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34695 ZIP is $506,185, about 5.6% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.