1060 GREGORY DRIVE, MAITLAND, FL, 32751
Active11 days on marketListed Oct 1, 2026MLS #O6445281
About this home
1060 GREGORY DRIVE
Some homes have a character that simply cannot be recreated—and 1060 Gregory Drive is one of them. Built in 1962 and tucked beneath mature oaks draped in Spanish moss, this three-bedroom, two-bath Maitland home celebrates its original charm while offering the updates today’s buyers appreciate. Warm hardwood floors flow through the home, while a dramatic brick feature wall separates the living and family rooms, with a fireplace facing each space. It is a memorable architectural detail that makes both rooms feel welcoming and distinct. The updated kitchen pairs shaker-style cabinetry with granite countertops and stainless steel appliances, while plantation shutters and ceiling fans add comfort and classic style throughout. The primary bedroom features dual closets. The guest bathroom also benefits from a new vanity. Step outside to an expansive backyard deck with plenty of room for dining, entertaining and lingering beneath the trees on beautiful Florida evenings. Major improvements include an ELECTRICAL UPDATE 2026, ALL NEW DUCTWORK 2026, HVAC and REROOF 2020, WATER HEATER 2022, a NEW FENCE installed in 2023 and REPIPED 2009. Set in an established Maitland neighborhood with quick access to Winter Park, Maitland and Interstate 4, this is a home with a story, a setting and a style all its own. Come experience the character, comfort and tree-lined charm that make 1060 Gregory Drive feel like home from the moment you arrive.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,734
Sqft
0.28 ac
Lot size
2
Garage
1962
Year built
One
Levels
$305
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,704 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,704/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+16.9%
$/sqft vs Maitland actives
$305 vs $266
Days on market
11 vs 61 typical
Where $305/sqft sits among the 96 Maitland actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Maitland
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Maitland. See the full Maitland guide →
MAITLAND 32751 — neighborhood snapshot
Population
22,853
Median age
38.7
Median income
$94,277
Median home value
$433,100
Avg household
2.27
Households w/ children
2,397
For the school run
Seminole County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Maitland market
$508K → $550K
Maitland median sold, yr/yr
96.9%
Sale-to-list ratio (12 mo)
54 of 96
Maitland actives have cut their price
Median sold price, Maitland, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 56% above the MAITLAND 32751 median. See the full Maitland market guide →
Paper trail
This home's history
Reality check
What actually sold near 1060 GREGORY DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’26$530,000
1055 DRUID DRIVE · same community
3 bd · 2 ba · 1,684 sqft · $315/sqft · 32 DOM
Sold · Oct ’25$550,000
1004 GREGORY DRIVE · same community
3 bd · 2 ba · 1,835 sqft · $300/sqft · 57 DOM
Sold · Aug ’26$510,000
1065 GREGORY DR · same community
3 bd · 2 ba · 1,929 sqft · $264/sqft · 32 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
John Carpenter
CFO/Broker · CENTURY 21 Edge
Tours, negotiation, and every question about 1060 GREGORY DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1060 GREGORY DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from John's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1060 GREGORY DRIVE FAQs
What would the monthly payment be for 1060 GREGORY DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,704/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 1060 GREGORY DRIVE?+
The most recent tax bill on record (2025) was $2,349. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Maitland?+
At $529,000, this home is listed about 18% above the Maitland median of $450,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1060 GREGORY DRIVE?+
Lake Orienta Elementary School (elementary), Milwee Middle School (middle), Lyman High School (high) — Seminole County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS WINTER PARK · Jill Healey. MLS #O6445281.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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