Lakeside At Shadowbay
Homes for Sale in Longwood, FL

All 208 homes for sale in Longwood, FL · median $469,900 · 72 homes for sale in 32779 · Seminole County homes for sale

Community in Longwood · Seminole County · ZIP 32779
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Built fromLive Stellar MLS data20 years of closingsUpdated twice daily

As of September 2026, the MLS records 10 closed sales in Lakeside At Shadowbay in Longwood, FL since 2006, the most recent in January 2026. Across Longwood as a whole, 289 homes closed in the last 12 months at a median of $489,000, 26 median days on market, with 45 homes for sale today. At that median and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $7,420 ($6,820 with the full homestead exemption).

Part of the Lakeside master-planned community in Oviedo, FL — see all Lakeside homes for sale (4 listings across 4 villages and sections in the MLS).

Live · Lakeside At Shadowbay Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Lakeside At Shadowbay is a defined community inside Longwood, in Seminole County. Because I don't have current inventory or price data in front of me for this snapshot, I'll be straight with you: what sets price here is going to come down to the specifics of the individual home — condition, updates, lot, and how it stacks against whatever else is listed at the same moment. There's no substitute for pulling live comps before you anchor on a number.

For a buyer, that means the posture is do-your-homework: know what a comparable, recently sold home in this pocket looked like before you decide any asking price is fair. For a seller, it means condition and presentation carry the negotiation — a well-prepared home in a small, named community like this competes on its own merits, not on a headline average.

Nearby homes for sale

No active listings inside Lakeside At Shadowbay 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.

236 S SHADOWBAY BOULEVARD
$1.74M · 0.2 mi away
5 bd · 3.5 ba · 3,216 sqft
236 S SHADOWBAY BOULEVARD
Listed by LISTED SIMPLY
486 N PIN OAK PLACE #206
$159K · 0.2 mi away
2 bd · 1 ba · 969 sqft
486 N PIN OAK PLACE #206
Listed by SCOTT LOCHRIDGE
486 N PIN OAK PLACE #308
$170K · 0.2 mi away
2 bd · 2 ba · 1,110 sqft
486 N PIN OAK PLACE #308
Listed by REAL BROKER, LLC
474 S PIN OAK PLACE #308
$150K · 0.2 mi away
2 bd · 2 ba · 1,110 sqft
474 S PIN OAK PLACE #308
Listed by WEMERT GROUP REALTY LLC
498 N PIN OAK PLACE #304
$140K · 0.2 mi away
1 bd · 1 ba · 823 sqft
498 N PIN OAK PLACE #304
Listed by SCOTT LOCHRIDGE
470 S PIN OAK PLACE #112
$175K · 0.2 mi away
2 bd · 1 ba · 959 sqft
470 S PIN OAK PLACE #112
Listed by KELLER WILLIAMS CLASSIC

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

The 60-Second Overview

Lakeside At Shadowbay is a named community within Longwood, in Seminole County — a specific pocket rather than a sprawling subdivision, which tends to make each individual home's condition and setting matter more than any market-wide figure.

Stellar MLS sales records identify 7 homes in Lakeside At Shadowbay that have changed hands since 2012, built between 1985 and 1986 (median 1985), with a median living area of about 1,592 sq ft and a typical 3-bedroom, 3-bath layout; 100% are condominiums. 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.

Best for

  • Buyers targeting a particular Longwood location and willing to wait for the right home
  • Owners planning to invest in condition and presentation to compete on merit
  • Long-hold buyers who value a defined community over a high-turnover market

Probably not for

  • Buyers who need many comparable listings to choose from at once
  • Shoppers who want to anchor a decision on a single headline figure
  • Anyone needing to close fast in a community where inventory can be limited

The market around Lakeside At Shadowbay

Lakeside At Shadowbay is too small for its own price trend, so here is the market around it.

In ZIP 32779, 162 homes are on the market and 31% are under contract — a fast-moving corner of Longwood.

Across Seminole County, 1,646 homes are active and 585 pending (26% under contract).

In ZIP 32779 (Longwood), 400 homes closed in the last 12 months at a median of $518K ($250/sq ft), up 3.1% year over year, with a median 25 days on market. Right now 25 active and 12 pending listings put supply at about 2.3 months — a healthy market. See the live ZIP 32779 housing market and the Seminole County market.

ZIP and county figures describe the wider market, not Lakeside At Shadowbay specifically. Momentum Research analysis of MLS records.

If we were buying in Lakeside At Shadowbay today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Lakeside At Shadowbay.

Best Buy
Buyers who want a specific home in a defined Longwood community rather than endless options.
Biggest Risk
Thin, community-specific inventory means fewer comps to lean on when pricing.
Sweet Spot
A move-in-ready home priced to its condition and setting, not a market average.
Avoid If
You need constant selection and a large pool of interchangeable listings.

A Longwood pocket, read on its own terms

The value proposition here is location within Longwood and the character of the specific homes that come available, not a churn of constant listings. In a smaller, defined community, the comp set is narrow, which cuts both ways — fewer directly comparable sales to lean on, but also less noise diluting what a genuinely well-kept home is worth.

Practically, that puts the work on the front end. Before you make an offer or set a list price, we walk the actual home, look at what has traded nearby, and price to the property rather than to a generality. That is the honest way to handle a community this specific.

The location and the amenities are priced into every listing in Lakeside At Shadowbay. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

We cover Seminole County closely and we'd rather tell you the truth about a single home than hand you an average. For Lakeside At Shadowbay, that means live comps, an in-person read on condition, and a clear-eyed take on where a given property really sits — including when the fit is wrong for you.

Lakeside At Shadowbay in 15 seconds.

Best forBuyers who want a specific home in a defined Longwood community rather than endless options.
Biggest advantageA narrow comp set rewards a well-kept, well-presented home.
Biggest riskThin, community-specific inventory means fewer comps to lean on when pricing.
Sweet spotA move-in-ready home priced to its condition and setting, not a market average.
Avoid ifYou need constant selection and a large pool of interchangeable listings.

HOA, CDD & Fees

In short
  • HOA dues reported around $600/month (about $7,200/yr) · median of 3 MLS listings, most billed monthly
  • Any club/amenity membership is billed separately

Listings in this community report association dues of about $600 per month ($7,200 a year) — the median AssociationFee across 3 MLS records, normalised to a monthly figure; most are billed monthly. 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, 2026-09.

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

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Lakeside At Shadowbay sales matched to your home.

What is your Lakeside At Shadowbay home worth?

Get a no-obligation home value based on real comparable sales in Lakeside At Shadowbay, 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 Longwood →

Real comps, not an automated estimate.
Buyers targeting a particular Longwood location and willing to wait for the right homeExcellent fit
Owners planning to invest in condition and presentation to compete on meritExcellent fit
Long-hold buyers who value a defined community over a high-turnover marketExcellent fit
Buyers who need many comparable listings to choose from at onceProbably not
Shoppers who want to anchor a decision on a single headline figureProbably not
Anyone needing to close fast in a community where inventory can be limitedProbably not

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: September 14, 2026)
Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-sale records back to 2006 (10 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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Common questions about Lakeside At Shadowbay

Where is Lakeside At Shadowbay?

Lakeside At Shadowbay is a community in Longwood, Seminole County, Florida, ZIP 32779.

Are there homes for sale in Lakeside At Shadowbay right now?

No active listings inside Lakeside At Shadowbay at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.

Does Lakeside At Shadowbay have an HOA or CDD?

No HOA is on record for Lakeside At Shadowbay 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 Lakeside At Shadowbay with Momentum Realty’s local guides.

SLShadowbay Lake Vista At0.0 mi away · 1 for saleSShadowbay0.2 mi away · 129 homes, built 1981–00WAWindsor At Sabal Walk A Condominium0.2 mi awayCutler Cove0.2 mi away · 1 for saleCAClubside At Sabal Point A Condominium0.3 mi away

Browse all neighborhood guides →

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Lakeside At Shadowbay Market Scorecard

No active listings

Lakeside At Shadowbay is currently a no active listings market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
$275,000
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/2
Active/Pend/Sold

Typical home value in the 32779 ZIP is $544,583, about 5.8% below 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.