Cloister Grove
Homes for Sale in Winter Park, FL
All 364 homes for sale in Winter Park, FL · median $684,500 · 158 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 2 closed sales in Cloister Grove Rep in Winter Park, FL since 2017, the most recent in December 2024. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $449,000, 33 median days on market, with 128 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,490 ($6,810 with the full homestead exemption).
There is not enough current MLS activity in Cloister Grove Rep to isolate a pricing pattern with confidence. No amenities are showing up in the active listing data either, which usually means the community's value proposition rests on the home itself and its position within Winter Park rather than on shared facilities.
For now, a buyer or seller here should treat every comparison as house-to-house rather than community-wide. Pull recent closed sales on the specific street or block before anchoring an offer or a list price, since a thin data set can hide a wide spread in condition and lot value.
Nearby homes for sale
No active listings inside Cloister GroveHomes for Sale in Winter Park, FL 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
Cloister Grove Rep sits in Winter Park, Orange County, an area known more for its individual streets and lot character than for master-planned amenity packages, and that pattern holds here with no community amenities currently listed in MLS.
Stellar MLS sales records identify 23 homes in Cloister Grove that have changed hands since 2008, built between 1919 and 2025 (median 1993), with a median living area of about 4,100 sq ft and a typical 4-bedroom, 4.5-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.
County records show 3 qualified sales in Cloister Grove across 2024–2024, median $6M — 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.
Who Cloister Grove is best for.
Best for
- Buyers evaluating a specific Cloister Grove Rep property on its own merits rather than a community amenity package
- Buyers comfortable doing independent diligence on HOA status, condition, and comparable sales before writing an offer
- Sellers whose home's value is carried by the structure and lot rather than shared community features
Probably not for
- Buyers who want a confirmed pool, clubhouse, or recreational amenity as part of the purchase decision
- Buyers who rely primarily on community-wide market statistics to set price expectations
- Anyone expecting a large, current inventory of comparable listings to shop against
The market around Cloister Grove
Cloister Grove is too small for its own price trend, so here is the market around it.
In ZIP 32789, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32789 (Winter Park), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Cloister Grove specifically. Momentum Research analysis of MLS records.
The Cloister Grove buying strategy.
If we were buying in Cloister Grove 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 Cloister Grove.
A Community Without a Listed Amenity Package
When current MLS data shows no identified community amenities, it usually means one of two things: the community is a smaller or older platted subdivision built around individual lots rather than shared recreation, or the active listings simply have not surfaced that detail this cycle. Either way, a buyer should not assume a pool, clubhouse, or HOA-maintained common area exists without confirming it directly.
In practice this shifts the evaluation toward the fundamentals that always matter in Winter Park: lot size and orientation, proximity to the roads and corridors you actually use, and the condition of the specific structure. Absent amenity-driven pricing, value here is set almost entirely by the house.
The location and the amenities are priced into every listing in Cloister Grove. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with limited MLS history and no documented amenities, the work is in verification, not marketing. We confirm HOA status, pull true comparable sales rather than relying on broad area averages, and make sure any offer or listing price is built on the specific property, not on assumptions about the neighborhood.
Cloister Grove 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 Cloister Grove 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 Cloister Grove sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cloister Grove, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cloister Grove home worth?
Get a no-obligation home value based on real comparable sales in Cloister Grove, 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 Winter Park →
Should you buy in Cloister Grove?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2017 (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 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 Cloister Grove
Where is Cloister Grove?
Cloister Grove is a community in Winter Park, Orange County, Florida, ZIP 32789.
Are there homes for sale in Cloister Grove right now?
No active listings inside Cloister Grove at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Cloister Grove have an HOA or CDD?
No HOA is on record for Cloister Grove 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.
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