Winterplace
Homes for Sale in Delray Beach, FL
All 1,647 homes for sale in Delray Beach, FL · median $299,900 · 288 homes for sale in 33445 · Palm Beach County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Beaches MLS
As of November 2026, Winterplace in Delray Beach, FL has 2 homes for sale. Homes listed or recently sold were built 2002–2004; 9 of 9 report an HOA (median $330/mo); none of the 9 geocoded homes sit in a FEMA special flood hazard zone (median elevation 18 ft).
Last 30 days in Winterplace: 1 new listing (median asking $850,000), 2 under contract right now. As of November 7, 2026, All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.
Winterplace's $765K median reflects a community where price is overwhelmingly driven by condition and finish level rather than lot size or age. The PPSF spread is wide—ranging from under $300 to well over $350—telling you immediately that not all homes here are comparable even when square footage is similar. Buyers who understand the difference between dated original interiors and well-executed updates will find real value; those who don't will overpay.
At 47 days on market, Winterplace is moving at a measured pace—slightly slower than the county's more liquid neighborhoods but far from stalled. The flat year-over-year pricing and limited inventory window (five closings) mean this is not a market driven by momentum or urgency; it's a negotiation environment where buyers who can articulate deficiencies have leverage, and sellers who've maintained their homes command full ask.
Figures in this note are as of July 16, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Winterplace right now
🟡 Balanced market. 4.8 months of supply and 50% 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 Beaches MLS records, as of November 6, 2026. Confidence: Low (4 active and pending listings, 0 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 7, 2026 · Live data: Beaches MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winterplace is a mid-sized neighborhood in Delray Beach where price variance is entirely condition-dependent and the market moves deliberately, not fast.
BeachesMLS sales records identify 29 homes in Winterplace that have changed hands since 2017, built between 2001 and 2004 (median 2003), with a median living area of about 2,733 sq ft and a typical 4-bedroom, 2.5-bath layout; 100% are single-family homes. Source: BeachesMLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 11 qualified sales in Winterplace across 2024–2025 (6 in 2024, 5 in 2025), median $775,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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.
The setting & the homes.
Aerial and on-site photos of Winterplace. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WinterplacePhotos from Beaches MLS listings in Winterplace; content deemed reliable but not guaranteed.
Who Winterplace is best for.
Best for
- Buyers with renovation budgets separate from purchase price who can identify value in homes priced below the median for fixable reasons
- Delray Beach buyers seeking a neighborhood where price is set by the home, not hype, and who value negotiation leverage over urgency
- Move-up buyers who understand the PPSF spread and target well-maintained homes that justify a premium
Probably not for
- Buyers expecting a fast-moving market with frequent inventory turnover and immediate comps for every listing
- First-time buyers without contractor relationships or renovation contingency funds who need move-in ready at entry pricing
- Investors relying on short holding periods or predictable appreciation in a community where pricing has been flat year-over-year
The market around Winterplace
Winterplace is too small for its own price trend, so here is the market around it.
In ZIP 33445, 368 homes are on the market and 22% are under contract — a steady corner of Delray Beach.
Across Palm Beach County, 10,960 homes are active and 2,777 pending (20% under contract).
In ZIP 33445 (Delray Beach), 97 homes closed in the last 12 months at a median of $298K ($224/sq ft), with a median 37 days on market. Right now 47 active and 9 pending listings put supply at about 5.8 months — a buyer's market. See the live ZIP 33445 housing market and the Palm Beach County market.
ZIP and county figures describe the wider market, not Winterplace specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Winterplace
Live MLS inventory for Winterplace. 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 · 10 daysTop listingActive · 137 daysUnder Contract · 9 daysUnder Contract · 66 daysActive and pending Winterplace listings as of 2026-11-06, priced high to low. All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc. Tap any home to ask about it.
Winterplace on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Beaches MLS. Map data © OpenStreetMap contributors.
Schools
- Palm Beach County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Banyan Creek (Palm Beach) · Elementary
- Carver Community · Middle
- Atlantic · High
Zoned schools reflect the assignments reported on recent Winterplace listings and can change; always confirm with Palm Beach County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winterplace address.
Shop the zone: Homes zoned for Atlantic High School
The Winterplace buying strategy.
If we were buying in Winterplace 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 Winterplace.
What the PPSF spread tells you
The $324 median per-square-foot figure masks the real story: Winterplace has a wide PPSF range, and that tells you condition is everything. Two homes of identical square footage can differ by tens of thousands of dollars depending on kitchen, baths, flooring, and HVAC age. Buyers who rely on price-per-foot alone will misread value here.
With only five closings in the current window and inventory that turns over in a month and a half, this is not a liquid market where you can wait for the perfect comp. When a well-updated home comes available, it's a narrow window. When a dated one lingers, it's an opportunity to negotiate—but only if you budget for the work and verify scope before you write the offer.
The year-over-year stability suggests Winterplace isn't riding broader market waves; it's priced by the home, not the trend. That makes it predictable for the disciplined buyer and unforgiving for the one who doesn't inspect carefully.
The location and the amenities are priced into every listing in Winterplace. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
Winterplace rewards the buyer who can distinguish cosmetic wear from structural neglect and who knows when to walk from a home priced for condition it no longer has. We pull comps by finish level, not just beds and baths, and we'll tell you when an ask doesn't match the work you'll inherit. In a community where inventory is thin and PPSF variance is high, that clarity is the difference between a solid buy and an expensive lesson.
Winterplace in 15 seconds.
Tools for a Winterplace 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 Winterplace sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winterplace, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winterplace home worth?
Get a no-obligation home value based on real comparable sales in Winterplace, 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 Delray Beach →
Recently off market in Winterplace
Homes in Winterplace that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 2 on record.
- 4795 S Classical Boulevard · off market
- 4889 N Classical Boulevard · off market
| Location | Delray Beach, Palm Beach County, FL · ZIP 33445 |
|---|---|
| Homes in the community | 152 (FL DOR 2025 assessment roll) |
| Years built | 2001–2005 (median 2003.0) |
| Typical living area | 2,907 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Fitness Center, Pool, Clubhouse, Basketball Court, Community Room, Gated |
| For sale right now | 2 active, 2 pending · median asking $837,500 · 4.8 months of supply |
| Owner-occupied (homestead) share | 80% |
Data as of November 6, 2026. All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winterplace key facts,” movewithmomentum.com/neighborhoods/winterplace, data as of November 6, 2026.
Housing distress & ownership in Winterplace, Delray Beach
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc. Deemed reliable but not guaranteed.
Just listed in Winterplace
The newest homes for sale in Winterplace right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 1600 W Classical Boulevard $850,000 · 3 bd · 2.5 ba · 2,997 sq ft · listed Oct 28, 2026 Courtesy of Mutual Trust Realty
- 4858 S Classical Boulevard $825,000 · 3 bd · 3.5 ba · 2,997 sq ft · listed Jun 23, 2026 Courtesy of The Corcoran Group
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Winterplace Right Now (4)
All 4 active and pending Winterplace listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1600 W Classical Boulevard · $850,000 · 3 bd / 2.5 ba · listed Oct 27, 2026 · listed by Mutual Trust Realty
- 4756 S Classical Boulevard · $1,000,000 · 5 bd / 2.5 ba · pending · listed Sep 10, 2026 · listed by Serhant
- 4841 N Classical Boulevard · $619,000 · 4 bd / 2.5 ba · pending · listed Aug 19, 2026 · listed by BEX Realty
- 4858 S Classical Boulevard · $825,000 · 3 bd / 3.5 ba · listed Aug 8, 2026 · listed by The Corcoran Group
Recently sold in Winterplace
- 4889 N Classical Boulevard · sold $565,000
- 4831 S Classical Boulevard · sold $749,900
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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Delray Beach guides & data
- Market data
- Cost of living
- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Palm Beach County)
- Homestead exemption (Palm Beach County)
- Home insurance cost
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- S Classical Boulevard (8 homes on record)
- N Classical Boulevard (7 homes on record)
Recent Developments in Winterplace
Development, infrastructure, retail, and school activity affecting Winterplace, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Retail & Dining
Johnnie-O lists apparel store at 321 E. Atlantic Ave. in Delray Beach
California-born Johnnie-O is listing a Delray Beach store at 321 E. Atlantic Ave. as coming soon, with no opening date announced. The brand already has Florida stores in Naples, Miramar Beach, Watersound and West Palm Beach.
What it may mean for the marketA new apparel retailer adds to the shopping mix along downtown Delray's Atlantic Avenue. The site is less than a mile west of Winterplace.
Source: WhatNow Miami - October 2026Builder Activity
Ocean One breaks ground with 371 rental residences on North Federal Highway in Boynton Beach
Hyperion Group, Winter Properties, WREP and Silverstein Properties held a groundbreaking on October 6 for an eight-story, 371-unit rental project at 114-222 North Federal Highway. The project includes about 25,500 square feet of retail and a $108 million construction loan, with up to $11.5 million in CRA tax increment funding. Completion is estimated for late 2028.
What it may mean for the marketAdds rental inventory and ground-floor retail to downtown Boynton Beach near the Federal Highway corridor. The site is about 5 miles north of Winterplace.
Source: Florida YIMBY - September 2026Parks & Amenities
$280M Palm Beach County parks bond on November ballot would fund fieldhouse, new parks and upgrades
The $280 million bond on the November 3 ballot would be repaid at 5 cents per $1,000 of taxable value over 20 years. Projects include a multisport fieldhouse at Okeeheelee Park, a 125-acre off-highway-vehicle complex near 20-Mile Bend, a 136-acre Sansbury Way Park and a 90-acre Lantana District I Park. The project list may change.
What it may mean for the marketIf approved, the bond would add and upgrade county recreation amenities, including indoor sports space near Okeeheelee Park. The site is about 14 miles northwest of Winterplace.
Source: Stet News - August 2026Parks & Amenities
Delray Beach sets $59.19M guaranteed maximum price for Pompey Park renovation
The city manager's annual report says the city approved a guaranteed maximum price of $59.19 million for the Pompey Park renovation, nearly $4 million below the original estimate. Groundbreaking is scheduled for September 2026. The report also lists a roughly $287 million water treatment plant with completion expected in 2028.
What it may mean for the marketA major park renovation would upgrade recreation amenities in west central Delray Beach once construction is complete. The site is about 2 miles northwest of Winterplace.
Source: Boca Post - July 2026Market
Palm Beach County Total Home Sales Jump for 10th Consecutive Month
Palm Beach County total home sales rose 22.3% year-over-year in June 2026 to 2,456 transactions, with total dollar volume up 53.90% to $2.7 billion. The single-family median sale price increased to $700,000 and the condominium median rose to $325,000.
What it may mean for the marketRising sales volume and median prices signal strengthening demand and higher valuations across the Palm Beach County housing market. The site is about 17 miles north of Winterplace.
Source: MIAMI REALTORS - June 2026Development
Alton Delray in Delray Beach Breaks Ground with $92 Million Construction Loan
Kolter Multifamily broke ground on Alton Delray, a 386-unit multifamily community across six-story buildings on a 12.31-acre former industrial site at 2101 S. Congress Avenue, backed by a $92 million construction loan from Madison Realty Capital. The plan includes 154 workforce housing units under Florida's Live Local Act and 232 market-rate units, with delivery expected in late 2027.
What it may mean for the marketA 386-unit rental community converts a former industrial parcel into new multifamily supply on the Congress Avenue corridor and adds workforce and market-rate housing to the Delray Beach market. The site is about 2 miles southwest of Winterplace.
Source: Florida YIMBY
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.
22% of homes for sale in ZIP 33445 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-11-07).
What it really costs to own in Winterplace
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $9,016/yr across 9 listings here (MLS tax records, 2026-11-07). |
|---|---|
| HOA dues | Median $330/month across 9 MLS listings (most billed monthly; 2026-11-07). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Palm Beach County is $1,753/yr (18,387 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2003 across 9 listings. An original roof here would be about 23 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Winterplace
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Winterplace
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Winterplace will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
Is Winterplace a buyer's or seller's market right now?
How many homes are in Winterplace?
What share of Winterplace is owner-occupied?
When were the homes in Winterplace built?
Who is the best real estate agent for Winterplace?
How do I find a top Delray Beach real estate agent who knows Winterplace?
Can Momentum Realty connect me with an agent for Winterplace?
Where is Winterplace, and what county is it in?
Should you buy in Winterplace?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Beaches MLS, refreshed twice daily (last: November 6, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 33445)) |
| Under-contract shares | Beaches MLS records, as of 2026-11-06 |
| Historical depth | Closed-sale records back to 2026 (2 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 Beaches 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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See how Winterplace fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Winterplace
- Home values · What homes in Winterplace actually sell for
