Chesterfield Heights 2Nd
Homes for Sale in Clearwater, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Chesterfield Heights 2Nd Add in Clearwater, FL has 1 home for sale. Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $385,000, $277 per square foot, a median 31 days on market, sellers accepting 96% of original asking (-2% versus the prior year). Homes listed or recently sold were built 1959–1969. At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $7,460 ($6,650 with the full homestead exemption).
Chesterfield Heights 2nd Add is a small, established Clearwater pocket of 87 homes built between 1958 and 2004, with the median dwelling dating to 1959. That age profile is the story here: price is driven far less by any consistent floor plan and far more by condition. A home that has been reworked mechanically and cosmetically will command a very different number than an original one on the same street, so expect a wide, condition-driven spread rather than a tidy price band.
With homes this age and a median living area around 1,444 square feet, buyers are largely paying for the lot, the location, and whatever updating a seller has already done. For sellers, that means renovation work tends to show up in the price; for buyers, it means underwriting the house on its bones, not its finishes. We only have a two-closing window here, so treat any single sale as a data point, not a trend.
Chesterfield Heights 2Nd right now
🟡 Balanced market. 4.0 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 12, 2026. Confidence: Low (1 active and pending listings, 3 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($385K) is down 2.5% from the prior 12 months ($395K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Low (3 and 3 sales in the two windows).
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Updated September 12, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Chesterfield Heights 2Nd market snapshot (as of September 12, 2026): the median sale price is about $385K ($277 per sq ft over the trailing 12 months of closed sales), a median 31 days on market for closed sales, and 4.0 months of supply, a balanced market. The trailing-12-month median is down 2% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
Chesterfield Heights 2Nd is a community of 44 homes in Clearwater, Pinellas County, built between 1958 and 1972 (median 1959.0), with a median living area of about 1,538 square feet. 73% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a compact, mostly mid-century enclave in Pinellas County where the housing stock is more uniform in age than in condition. What you pay depends heavily on how much of the original home has been updated.
Who Chesterfield Heights 2Nd is best for.
Best for
- Buyers seeking a modestly sized home in an established Clearwater location and willing to inspect older systems closely
- Renovation-minded buyers who want to build value through updating rather than pay for it upfront
- Long-hold owner-occupants who value a stable, low-turnover street over frequent inventory
Probably not for
- Buyers who require newer construction and modern finishes out of the gate
- Anyone needing large living space, since homes here center around 1,444 square feet
- Investors expecting steady, high-volume turnover to trade in and out of quickly
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($385K) IS the median in the snapshot above, and the move from 2025 ($395K) IS the -2.5% one-year change.
Windows contain 0 to 10 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Deemed reliable but not guaranteed.
Chesterfield Heights 2Nd Add Market Scorecard
Chesterfield Heights 2Nd Add is currently a balanced market. About 4.0 months of supply, a median asking price of $475,000, and homes go under contract in about 41 days.
Typical home value in the 33756 ZIP is $362,892, about 13.6% 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.
Homes For Sale Right Now in Chesterfield Heights 2Nd
Live MLS inventory for Chesterfield Heights 2Nd. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Chesterfield Heights 2Nd listings as of 2026-09-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Tap any home to ask about it.
Chesterfield Heights 2Nd on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
The Chesterfield Heights 2Nd buying strategy.
If we were buying in Chesterfield Heights 2Nd 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 Chesterfield Heights 2Nd.
A condition-driven mid-century pocket
The building span runs from 1958 to 2004, but with a median year built of 1959, the neighborhood reads as predominantly original mid-century construction with a handful of newer infill. Living areas center around 1,444 square feet, so these are modest, single-story-scale homes by today's standards. The variable that separates one sale from the next is roof, systems, and interior updating — not square footage.
About 78% of homes here carry a homestead exemption, which points to a largely owner-occupied street rather than an investor-churned one. That tends to mean homes are held longer and turnover is limited, which is consistent with the thin closing activity in our current window. Buyers should be patient about inventory; sellers should recognize that a well-prepared listing stands out in a market this quiet.
The location and the amenities are priced into every listing in Chesterfield Heights 2Nd. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Chesterfield Heights 2Nd buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (6.6). Basis: Recent Direction -2.5% year-over-year; Liquidity & Demand 4.0 months of supply; Owner Commitment 73% owner-occupied; Pricing Power 96.5% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a low-turnover, condition-driven neighborhood like this, pricing comes down to reading each home individually rather than leaning on a comp average. We walk the systems, weigh what has actually been updated against what still looks original, and tell you plainly where a given house sits on that spectrum. With few recent closings to anchor on, that hands-on read is worth more than any formula.
Chesterfield Heights 2Nd 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 Chesterfield Heights 2Nd 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 Chesterfield Heights 2Nd sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chesterfield Heights 2Nd, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chesterfield Heights 2Nd home worth?
Get a no-obligation home value based on real comparable sales in Chesterfield Heights 2Nd, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Chesterfield Heights 2Nd?
How long do homes in Chesterfield Heights 2Nd take to sell?
Is Chesterfield Heights 2Nd a buyer's or seller's market right now?
How many homes are in Chesterfield Heights 2Nd?
What share of Chesterfield Heights 2Nd is owner-occupied?
When were the homes in Chesterfield Heights 2Nd built?
Who is the best real estate agent for Chesterfield Heights 2Nd?
How do I find a top Clearwater real estate agent who knows Chesterfield Heights 2Nd?
Can Momentum Realty connect me with an agent for Chesterfield Heights 2Nd?
Should you buy in Chesterfield Heights 2Nd?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Chesterfield Heights 2Nd with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 33756)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2015 (34 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.
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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 Chesterfield Heights 2Nd Add fits the bigger picture — live prices, inventory, and Momentum Scores: