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Chestnut Creek in Winter Haven

Chestnut Creek

2022 to 2025 single-residential community · Polk County · ZIP 33881

A mid-2020s Highland Homes community on quarter-acre homesites south of Lake Fannie in Winter Haven, the residential read for owner-occupier buyers.

Quarter-acre homesitesMid-2020s constructionWinter Haven address
Live Market Pulse
50/100
Momentum
Buyer-Leaning Market (limited data)
This is a recently built single-residential community, so the honest read is the lot, the home plan, the HOA, and the location, not a portal average over mixed stock. Confirm the HOA dues, any community rules, and the exact lot and plan with the listing.
Free · No obligation
Unlock Off-Market Chestnut Creek

Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.

Built fromLive Stellar MLS data14 years of closingsLocal renovation analysisUpdated twice daily
LiveMarket PulseStellar MLS
n/a
Median Price
0mo
Supply
n/a
Avg DOM
Soft
Seller Leverage
n/a
Median $/Sqft
n/a
1-Yr Price Change
0now
Distress
Jon Brooks, founder of Momentum Realty
Jon's Current Read

"Chestnut Creek is a Highland Homes community in Winter Haven built between 2022 and 2025, so the read is a new-build read: the value drivers are the lot size and position, the specific floor plan and elevation, the HOA budget and rules, and the location south of Lake Fannie, not a townwide average. The community is described as built out on roughly quarter-acre homesites averaging about 80 feet of width, which is generous for new construction and a real differentiator from tighter new-build subdivisions. Because the homes are newly built, structural and system risk is low for now, and the watch items are the HOA dues and reserves over time, the resale picture as the early owners turn over, and the commute math to Winter Haven jobs and US 27. Your leverage is reading the lot, the plan, and the HOA documents honestly, and checking real drive times, before you fall for a new-construction sheen. Confirm every line with the listing and the association documents."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Chestnut Creek is a single-family home community in Winter Haven, Polk County, built by Highland Homes between 2022 and 2025 (Highland Homes community pages and multiple Winter Haven real estate guides, 2026). It sits on the fringe of the city limits south of Lake Fannie, near Country Club Road North, a few miles from downtown Winter Haven and the US 27 corridor.

Listing and builder guides describe the community on roughly quarter-acre homesites that average about 80 feet of width, which gives owners more yard and more space between homes than many newer Winter Haven subdivisions (Highland Homes community pages, 2026). Home plans are generally three to five bedroom single-family designs, with sources citing living areas in a range of roughly 1,800 to 2,800 square feet; confirm the exact plan, bedroom count, and square footage for any specific home.

Because this is a recently built community, the money is made or lost on the lot and the home, not on the address alone. The drivers are the homesite size and position, the floor plan and elevation, the HOA dues and rules, and the location and commute, all of which should be read from the listing and the current association documents.

The pitch is a laid-back, country-style setting close to town: downtown Winter Haven, the Chain of Lakes, and the US 27 corridor are a manageable drive, with Lakeland and the wider Polk County job market within reach. The work is the diligence: read the HOA budget and rules, confirm the lot and plan, and check your real drive times before you buy.

Quick Match

Who Chestnut Creek is best for.

Best for

  • Owner-occupiers who want a newer single-family home with a real yard
  • Buyers who value quarter-acre homesites over tight new-build lots
  • Buyers who want a Winter Haven address near the Chain of Lakes and US 27
  • Buyers who will read the HOA budget, rules, and resale picture closely

Probably not for

  • Buyers who want a downtown or walkable urban setting
  • Anyone unwilling to verify HOA dues, rules, and the exact lot and plan
  • Buyers who want an established, mature-tree neighborhood today
  • Buyers who need a short commute to Tampa or Orlando job centers
Market Pulse

How Chestnut Creek is performing right now

50/100
momentum
Buyer-Leaning Market (limited data)
Seller's marketBalancedBuyer's market
0Months of supplytight
24Median days on marketdays
0 : 0Under contract vs for salestrong demand
0Sold in last 12 monthsliquidity
+0%Asking vs recent sold $/sqftroom to negotiate

Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.

Live from Stellar MLS, as of June 30, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Chestnut Creek listings and the trailing twelve months of closed sales.

8.6A- score
Momentum intelligence
Momentum buy score

Our proprietary read on how a home in Chestnut Creek buys, holds, and resells. See the five factors.

Interactive Map

Chestnut Creek on the map.

Every active, pending, and recently sold home, plotted. Toggle the layers, color the dots by status or lot type, and tap a home for the details.

Listing locations from Stellar MLS; lot type inferred from listing descriptions. Destination pins are approximate. Map data © OpenStreetMap, tiles © CARTO. Flood, school, and commute overlays are on the roadmap.

Nearby & Commute

How far is everything?

The takeaway

Chestnut Creek trades a downtown setting for a generous-lot home near Winter Haven, with Lake Fannie, downtown, and US 27 a manageable drive and the major metros a longer haul.

Drive times from the community. They are approximate and vary with traffic and your exact routine.

Lake Fannie~5 min · to the north
Downtown Winter Haven~10 to 15 min · shops and dining
US 27 corridor~10 to 15 min · regional access
Legoland Florida~20 to 30 min · in Winter Haven
Lakeland~30 to 40 min · to the west
Orlando area~50 to 70 min · to the northeast
Tampa area~70 to 90 min · to the west

Distances and times are approximate and vary with traffic and the specific home. Confirm your real commute at your real departure time.

Nearby Communities

Explore more neighborhoods near Chestnut Creek with Momentum Realty’s local guides.

CACrossroads atLake Region Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.4 miWHWillowbrookNorth Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.5 miLNLake N GolfEstates Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.5 miLSLake SmartPointe Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.6 miLPLucerne ParkReserveWinter Haven, FL · 0.6 miBPBuckeye Pointe Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.7 miCPCanton ParkWinter Haven, FL · 0.8 miPCPeace CreekReserve Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.8 miLLLake Lucerne Homes for Sale in Winter Haven, FLWinter Haven, FL · 0.9 mi

Browse all Florida neighborhood guides →

Carrying cost · the no-CDD edge

No CDD bond means thousands less per year than newer master plans.

Typical CDD community~$2,500/yr
Chestnut Creek (no CDD)$0/yr

Roughly $25,000 saved over 10 years in carrying cost, before resale.

Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.

Schools

15-Second Take
  • Polk County Public Schools
  • Verify the zoned schools by address
  • Magnet and choice options may be available
  • Confirm current ratings before relying on them
  • Private and parochial options nearby

Chestnut Creek is served by Polk County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.

Public

Polk County Public Schools (verify by address)

Verifyrating
By address

Confirm zoned elementary, middle, and high

Verifyrating
Choice

Magnet and choice options may apply

Verifyrating

Buying with schools in mind? We can confirm the exact zoned schools for any Chestnut Creek address.

The takeaway

What is actually shaping value at Chestnut Creek: Winter Haven and Polk County growth along the US 27 corridor, Florida HOA and community rules, and the resale picture as a mostly new community matures. Each item is a factual observation; confirm the specifics with the listing.

Recent Developments in Chestnut Creek

Development Intelligence

Our read on what is being built around Chestnut Creek, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.

Net OutlookBullishContinued Polk County growth and a generous-lot new-build product support demand, with the watch items being HOA dues and reserves over time and the resale picture as the early owners turn over.

Polk County and US 27 corridor growth

Ongoing
BullishNotable impact
SignificanceRadius: Area

Continued population and housing growth across Polk County and the US 27 corridor supports long-term demand for Winter Haven homes.

Mostly new construction reduces near-term risk

Ongoing
BullishNotable impact
SignificanceRadius: Community

As a 2022 to 2025 community, structural and system risk is low for now, which generally helps maintenance and insurance early on.

Quarter-acre homesites differentiate the product

Ongoing
BullishNotable impact
SignificanceRadius: Community

Generous lots averaging about 80 feet of width set this community apart from tighter new-build subdivisions and support owner appeal.

Florida HOA budget and reserve rules

Ongoing
NeutralNotable impact
SignificanceRadius: Community

Florida HOA budgeting and reserve practices can change dues over time, so the association budget and rules are core diligence.

Resale as a young community matures

Ongoing
NeutralNotable impact
SignificanceRadius: Community

As early owners turn over, the resale market sets the real pricing read, so true in-community comps matter more than a portal estimate.

Inland flood and drainage near the lakes

Ongoing
NeutralMinor impact
SignificanceRadius: Community

Proximity to Lake Fannie and the Chain of Lakes makes the FEMA flood zone, drainage, and an insurance quote worth checking per lot.

Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.

Development, infrastructure, retail, and school activity affecting Chestnut Creek, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated June 2026.

Showing the latest, scroll for all updates ↓

  1. January 2024
    Development

    Highland Homes markets Chestnut Creek in Winter Haven

    Highland Homes marketed Chestnut Creek as a single-residential community in Winter Haven on roughly quarter-acre homesites averaging about 80 feet of width, built between 2022 and 2025, with several three to five bedroom plans. Why it matters: A generous-lot new-build product near Winter Haven supports owner-occupier demand, though the lot, plan, and HOA still have to be read per home. Source

Development alerts for Chestnut CreekGet a short monthly email when something new is approved, funded, or opens near Chestnut Creek.

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Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.

The Strategy

The Chestnut Creek buying strategy.

If we were buying in Chestnut Creek, this is the order of operations we would run, and the one we run for our clients.

1

Confirm the HOA dues, budget, and rules first. In a newer community the HOA structure and any planned changes shape the real carrying cost, so read the current association documents.

2

Read the lot size, position, and orientation. On quarter-acre homesites the specific lot, its width, and what backs to it set value within the community.

3

Confirm the exact plan, elevation, and square footage. Highland Homes built several plans here, so verify bedroom count, living area, and finishes for the specific home.

4

Check real drive times to your routine. Confirm the commute to downtown Winter Haven, Lakeland, and US 27 at your real departure time before you buy.

5

Cross-shop other Winter Haven new-build communities on the neighborhoods map if lot size, price, or amenities point you elsewhere.

The Quick Decision
Best Buy
A wider quarter-acre lot with a desirable plan and a private rear exposure
Biggest Risk
HOA changes over time and resale as early owners turn over
Best Lot
A wider homesite with a private back yard and a strong plan
Smart Timing
Confirm the HOA, the lot, and your commute before you offer
Deep-Dive Intelligence

The full read, only if you want it.

The takeaway

On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.

Community Details at a Glance

Chestnut Creek is a recently built single-residential community rather than an amenity-heavy master plan, so the lifestyle is laid-back, country-style living on the edge of Winter Haven. Builder guides describe generous quarter-acre homesites averaging about 80 feet of width, with the Chain of Lakes, downtown Winter Haven, and the US 27 corridor a manageable drive. Community rules, pet and breed restrictions, and any shared common areas vary, so confirm the current rules and what each home includes with the association before you buy.

Chestnut Creek Homes For Sale

What your money buys in Chestnut Creek.

The takeaway

Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.

Here are the broad resale bands in Chestnut Creek today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.

The Entry Home

A smaller three bedroom plan on a standard lot, the affordable way into the community, where condition and lot position drive value.

Lowest entry
The Core Home

A mid-size three or four bedroom plan on a solid quarter-acre lot, the heart of the community resale market.

Most inventory
The Top

A larger four or five bedroom plan on a wider, well-positioned lot with the most updated finishes, the homes that hold value best here.

Strongest resale

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

See Off-Market & Private Listings
What Your Money Buys

What ~$900K buys here.

Three realistic price bands. Where a home lands comes down to condition and lot, not square footage alone.

The Entry Home
A smaller three bedroom plan on a standard lot, the affordable way into the community, where condition and lot position drive value.
The Core Home
A mid-size three or four bedroom plan on a solid quarter-acre lot, the heart of the community resale market.
The Top
A larger four or five bedroom plan on a wider, well-positioned lot with the most updated finishes, the homes that hold value best here.

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

Operator Intelligence

Renovation & Resale Intelligence

The factors that actually move value in Chestnut Creek, condition, lot, and the renovation math, read from current listings and recent sales.

15-Second Take
  • Renovation math decides the deal
  • Better lots and views resell strongest
  • Roof and HVAC age drive the insurance quote
  • Interior lots are where buyers overpay
Proprietary Data

The renovation premium.

Renovated-listing inventory in Chestnut Creek is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.

Lot Value

The lot premium.

On a preferred homesite (water, preserve, corner, or a larger lot), the homesite is the part of your money the market gives back at resale. The house can be renovated; the lot cannot, so premium lots hold their value better than interior ones. How much more they command varies by frontage, view, and condition, which is why we read it home by home against real comparable sales rather than a single headline figure.

Jon Brooks, Momentum Realty
Operator Note

Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.

Resale Strength Scorecard

How well Chestnut Creek holds value.

Our read on the factors that protect resale here, and the one to manage.

Home ageBuilt 2022 to 2025, recent construction
HOA and dues riskConfirm dues, reserves, and rules over time
Flood and drainageInland, verify zone and drainage per lot
Lot size and privacyQuarter-acre homesites, generous for new build
Location and commuteNear Winter Haven, longer to Tampa or Orlando

Momentum analysis based on the community's structure, location, lot scarcity, and housing stock. Not a guarantee of future value.

Jon Brooks, Momentum Realty
Operator Note

The strongest value pocket is usually a renovated home on a good lot priced just under the next tier up. Buyers chasing the single biggest house often pay top prices for what is really a renovation project.

5 Mistakes Buyers Make in Chestnut Creek

15-Second Take
  • Calling the listing agent (who works for the seller)
  • Misjudging the renovation budget
  • Overpaying for an interior lot
  • Underbudgeting the carrying costs
  • Skipping the roof, HVAC, and systems check

The same five mistakes cost buyers the most in any market. Every one is avoidable with the right preparation before you tour.

Chestnut Creek1

Calling the listing agent

The agent on the sign works for the seller. In a market where condition swings price by hundreds of thousands, negotiating against that agent with no one in your corner is the costliest move of all.

Chestnut Creek2

Misjudging the renovation math

A dated home looks like a deal until you price the roof, HVAC, pool, and full modernization honestly. Underbudget the reno and the bargain becomes the expensive house.

Chestnut Creek3

Overpaying for an interior lot

A premium homesite (water, preserve, or a preferred position) carries a real, durable premium. Pay a top price for an interior lot and you are buying the weakest version of the value.

Chestnut Creek4

Underbudgeting the carrying costs

Two similar homes can cost very differently to own once the HOA, any CDD, insurance, and upkeep are priced in. Buyers who do not run the full monthly carrying cost misread the real number.

Chestnut Creek5

Skipping the systems check

An older home means older systems unless updated. Roof age, HVAC age, pool equipment, and prior renovations drive both price and insurability, and a thorough inspection matters more here than in a new build.

“

Chestnut Creek is a mid-2020s single-residential community, not a portal average. The deal is won or lost on the lot, the plan, the HOA, and the commute.

Jon Brooks · Founder, Momentum Realty
Momentum Intelligence

Momentum Buy Score.

Our proprietary 0 to 10 read across the five factors that decide how a home here buys, holds, and resells.

7.2B · Buy Score
Resale Strength7.0/10
Renovation Risk3.0/10
Location Efficiency6.8/10
Long-Term Defensibility7.1/10
Carrying Cost Advantage7.8/10

Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.

Momentum Housing Intelligence

Why our read on Chestnut Creek is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live Stellar MLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No Zestimate, no guesswork.

Live Stellar MLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates
Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking at Deutsche Bank and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.
About the analyst · Our methodology

Which Lots & Views Hold Value Best

Proprietary Data · Lot Value Map

Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.

Value ($/sqft)
$261 value$401 premium
Lake / waterPreserveInterior

Fill = price per square foot; ring = lot type, inferred from listing descriptions. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from Stellar MLS; for orientation, not an appraisal.

15-Second Take
  • In a new community, the lot and plan set value
  • Wider quarter-acre lots with privacy hold value best
  • Confirm the FEMA flood zone and drainage per lot
  • Read the HOA rules before you read the finishes
  • Verify the exact plan, square footage, and lot dimensions

In a newer single-residential community, the part of your money the market protects is the lot size, position, and what backs to it, plus the floor plan and the health of the HOA behind it. Wider quarter-acre lots with privacy and a desirable plan hold value better than narrow lots on busy interior streets. The interior can be updated; the lot, the orientation, and the location cannot. Read the HOA budget and rules, the flood zone, and the drainage first, then price the condition of the home against them.

The 15-Second Verdict

Chestnut Creek in 15 seconds.

Best forOwner-occupiers who want a newer single-family home with a real yard in Winter Haven.
Biggest advantageQuarter-acre homesites and recent construction on the edge of Winter Haven.
Biggest riskHOA changes over time and resale as the early owners turn over.
Sweet spotA wider lot with a strong plan and a private rear exposure.
Avoid ifYou want a walkable urban setting or a short commute to Tampa or Orlando.

HOA Dues, Rules & Reserves

15-Second Take
  • Read the HOA budget and rules, not just the dues figure
  • Confirm the current annual dues with the listing and the association
  • Check the pet, breed, and pool rules for your situation
  • Ask about reserves and any planned dues changes over time
  • Verify deed restrictions and any community standards per home

This is an HOA community, so an association fee applies and typically covers common-area maintenance and community administration. Sources cite an annual HOA fee in a modest range for this community, but figures vary by source and can change, so confirm the current dues, the budget, and any reserves from the latest association documents for the exact home.

Association fees on a community like this generally cover common-area upkeep and community management. Owners maintain their own homes and quarter-acre lots, including any in-ground pool, since builder guides note in-ground pools are allowed while above-ground pools are not. Verify exactly what the fee covers, the pet and breed rules, and any deed restrictions before you buy.

Run Your Numbers

Tools for a Chestnut Creek buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxPolk County millage and the homestead picture.Rent vs buyThe breakeven on owning in Chestnut Creek.Save Our HomesProject your homestead tax cap over time.
The takeaway

Selling here is won on condition and view, not the Zestimate. The right number comes from closed comps matched to your renovation level and lot.

Selling in Chestnut Creek

Price to the lot, the plan, and the community health, not a portal average.

Selling here means pricing to your specific home and lot, not a community-wide estimate. The homesite size and position, the floor plan and elevation, the condition of the home, and the strength of the HOA are what set your number in a newer community.

Momentum listings (YTD)
97.98%
Sold-to-list ratio across our market for our agents, sellers keeping more of their price.
Market average (YTD)
96.73%
The broader metro average sold-to-list ratio over the same period.
Momentum days on market
64 days
Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.
Market days on market
72 days
The broader metro median over the same period.

Sold-to-list and days-on-market figures reflect Momentum Realty listings versus our market average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.

In Chestnut Creek, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping Winter Haven new-build peers, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.

What is your Chestnut Creek home worth?

Get a no-obligation home value based on real comparable sales in Chestnut Creek matched to your condition, lot, and view, 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 homes for sale in Chestnut Creek on the map →
Or get your Chestnut Creek home value & selling guide →

Real comps, not a Zestimate.

Price History: What Homes Here Have Actually Sold For

Median sale prices in Chestnut Creek year by year since 2012, from closed MLS sales. A long track record beats a single estimate, showing what this community has really done through rate cycles rather than what a model predicts.

The real cost & risk here

Before the list price, the Florida math the portals skip. These are Polk County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.

$1,609/mo
Polk County typical true cost to own
$110/mo
Polk County typical home insurance
No CDD
No community development district bond

Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Polk County scorecard.

County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.

Chestnut Creek Market Scorecard

Strong seller's market

Chestnut Creek is currently a strong seller's market. About 1.8 months of supply, a median asking price of $1,019,500, and homes go under contract in about 58 days.

1.8
Months supply
$1,019,500
Median list
$847,500
Median sold
$313
Per sqft
58
Days on mkt
6/8/41
Active/Pend/Sold

Typical home value in the 32224 ZIP is $456,759, about 13.7% above the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

Live data: Stellar MLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

Where is Chestnut Creek?
It is a single-residential community in Winter Haven, Polk County, ZIP 33881, on the edge of the city limits south of Lake Fannie near Country Club Road North, a few miles from downtown Winter Haven and the US 27 corridor.
When was Chestnut Creek built?
Builder and real estate guides describe the community as built between 2022 and 2025 (Highland Homes community pages and Winter Haven real estate guides, 2026). That makes it a recently built, largely new-construction community.
Who built Chestnut Creek?
It was built by Highland Homes, a Florida builder based in Lakeland (Highland Homes community pages, 2026). Confirm the builder, plan, and warranty status on any specific home.
How big are the homesites?
Builder guides describe roughly quarter-acre homesites that average about 80 feet of width, which is generous for new construction. Confirm the exact lot size and dimensions for any specific home.
What home plans are available?
Guides cite generally three to five bedroom single-family plans, with living areas around 1,800 to 2,800 square feet. Confirm the exact plan, bedroom count, and square footage for any specific home.
Is Chestnut Creek sold out?
Several real estate guides describe the Highland Homes phase as sold out, so most activity is resale. Confirm current new and resale availability with the listing, since this can change.
What does the HOA fee cover?
It typically covers common-area maintenance and community administration. Sources cite a modest annual fee, but figures vary and can change, so confirm the current dues and inclusions from the association documents.
Are pets and pools allowed?
Builder guides note pets are allowed with certain breed restrictions, and that in-ground pools are allowed while above-ground pools are not. Confirm the current rules with the association for your situation.
What schools serve Chestnut Creek?
It is served by Polk County Public Schools, with assignment by address that can change. Confirm the exact zoned elementary, middle, and high schools for the specific home, and note that magnet and choice options may apply.
Is this near Lake Fannie and the Chain of Lakes?
Yes, the community sits south of Lake Fannie, part of the Winter Haven Chain of Lakes area. Lake access and rights vary, so confirm any water access and what each home includes.
What is nearby?
Downtown Winter Haven, the Chain of Lakes, and the US 27 corridor are a manageable drive, with Lakeland and the wider Polk County job market within reach. Confirm real drive times for your routine.
Is there storm or flood risk to consider?
Inland Polk County avoids coastal storm surge, but inland flooding and proximity to lakes can still matter. Always check the FEMA flood zone and any drainage notes for the specific lot and get an insurance quote.
Is Chestnut Creek a good investment?
A newer single-family product with generous lots near Winter Haven supports demand, but this is a community with resale dynamics, so the lot, the plan, the HOA, and the commute drive the outcome. This is not a guarantee of future value; read the documents and the math.
How does it compare to other Winter Haven new-build communities?
Many newer Winter Haven communities offer tighter lots or shared amenities at varying price points, while Chestnut Creek leans on larger quarter-acre homesites. Which is the better buy depends on your budget, lot priorities, and amenity needs.
Who is the best real estate agent for Chestnut Creek?
The best agent for Chestnut Creek is one who actively works Winter Haven and knows the community's pricing, HOA and CDD details, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Chestnut Creek.
How do I find a top Winter Haven real estate agent who knows Chestnut Creek?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Chestnut Creek and the wider Winter Haven area.
Can Momentum Realty connect me with an agent for Chestnut Creek?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Chestnut Creek purchase or sale - no call center and no pressure.
The Verdict

Should you buy in Chestnut Creek?

An honest fit check. We will tell you when it is not your community.

Owner-occupiers who want a newer single-family home with a real yardExcellent fit
Buyers who value quarter-acre homesites over tight new-build lotsExcellent fit
Buyers who want a Winter Haven address near the Chain of LakesExcellent fit
Buyers who will read the HOA budget, rules, and resale pictureExcellent fit
Buyers who want low near-term maintenance from recent constructionExcellent fit
Buyers who want a downtown or walkable urban settingProbably not
Anyone unwilling to verify HOA dues, rules, and the exact lot and planProbably not
Buyers who want an established, mature-tree neighborhood todayProbably not
Buyers who need a short commute to Tampa or Orlando job centersProbably not
Buyers unwilling to confirm flood and drainage per lotProbably not

Get the inside read on Chestnut Creek

Whether you are buying a renovation project, comparing the lots and views, weighing the carrying costs, or selling your Chestnut Creek home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.

By pressing Get My Chestnut Creek Game Plan, you agree that EAB RE INVESTMENTS LLC (Momentum Realty) and its agents may call and text you about your inquiry, which may involve automated means and prerecorded or artificial voices, at the number you provided. You do not need to consent as a condition of buying any property, goods, or services. Message and data rates may apply. Message frequency may vary. Reply STOP to opt out, HELP for help. You also agree to our Privacy Policy and SMS Terms.

We respond personally, usually the same day.

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A Momentum Realty Chestnut Creek specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Chestnut Creek - what to look for, questions to ask, and your local expert.
Chestnut Creek median home price history from 2012 to 2026, chart by Momentum Realty
Median sale price in Chestnut Creek, Florida by year (2012 to 2026). Source: Momentum Realty.
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Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Listings courtesy of Stellar MLS as distributed by MLS GRID. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing; deemed reliable but not guaranteed by MLS GRID.

Zoom out before you decide: see the Polk County market guide or every community in the Neighborhood Finder.

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Sell my house fast in Polk County · How Momentum Offers works

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