Druid Hills Estates Homes for Sale

3 Beds ⋅ 2 Baths ⋅ Druid Hills Estates 1st Add SubDv. ⋅ 32751 Zip Code

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.

1060 Gregory Drive, Maitland

$394,900

3 Beds ⋅ 2 Baths ⋅ Druid Hills Estates SubDv. ⋅ 32751 Zip Code

Virtually Staged. Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath block home offers approximately 1,750 square feet of living space on a .33-acre double corner lot in Maitland. Located across two parcels, the property provides additional outdoor space, added privacy, a partial new wood fence, and a beautiful live oak canopy. Inside, luxury vinyl flooring flows throughout the home, complemented by fresh interior and exterior paint, new ceiling fans, and updated door hardware. The refreshed kitchen features newer cabinets, granite countertops, and coordinating appliances. A Florida room provides flexible space for a home office, sunroom, playroom, or additional sitting area. Both bathrooms have been updated. The guest bathroom includes a tub-and-shower combination, new tile surround, new hardware, pedestal sink, mirror, and light fixture. The primary bathroom features a new vanity, mirror, and lighting. Major improvements include a roof replaced in 2021, water heater replaced in 2024 and a new septic system installed in 2024. Conveniently located near downtown Maitland, Winter Park, Altamonte Springs, Longwood, Casselberry, and downtown Orlando, this home offers comfortable living with easy access to shopping, dining, employment centers, and major roadways.

1202 Oranole Road, Maitland

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Seminole County › Maitland › Druid Hills Estates

Druid Hills Estates, Maitland

Druid Hills Estates is a neighborhood in northwest Maitland, in the 32751 zip code, built mostly in the 1960s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,700 and 2,400 square feet under air, the median lot is roughly a quarter acre, and a two car garage is standard.

Most of Druid Hills Estates carries no mandatory HOA.

What the homes are

Built Mostly built in the 1960s, with homes from 1957 to 1975.
Construction Block and stucco. Shingle roofs are near universal.
Style Ranch, Traditional. Predominantly single story.
Size Most homes fall between about 1,700 and 2,400 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Garage A two car garage is standard.
Lot The median lot is roughly a quarter acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Druid Hills Estates is

Druid Hills Estates, centered at 28.641779, -81.377142. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Druid Hills Estates, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	17 min	9.5
Orlando International Airport	32 min	28.0
Winter Park	16 min	5.1
Heathrow and Lake Mary offices	21 min	12.7

Public schools nearby

Lake Orienta Elementary School 4 min, 0.9 mi
Lake Sybelia Elementary School 7 min, 2.1 mi
Hungerford Elementary School 8 min, 2.7 mi
Dommerich Elementary School 14 min, 4.2 mi

Private schools nearby

Orangewood Christian School, Elementary Campus K4-6th 4 min, 0.9 mi
St. Clement Orthodox Christian Academy 3 min, 0.8 mi
King of Kings Lutheran Church and Christian School 3 min, 0.8 mi
Brooke House Academy, Maitland 5 min, 1.5 mi

Parks and recreation

Sunshine Park 3 min, 0.8 mi
Sandspur Rd. Bike Trail 6 min, 2.1 mi
Greenwood Park 6 min, 1.8 mi
Turnbull Park 4 min, 1.5 mi

Groceries and errands

Publix Super Market at Maitland Place 8 min, 2.1 mi
Publix Super Market at Palm Springs Crossing 8 min, 2.5 mi
Sage Willow 6 min, 2.1 mi
Wymore Superette 6 min, 2.1 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Druid Hills Estates by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Seminole County Public Schools before it matters to a decision.

Places and drive times from Google, checked 9 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Druid Hills Estates actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 3 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated October 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Druid Hills Estates

$515,000Median sale price

$262Median per square foot

43 daysMedian days to contract

3Homes sold in 12 months

Sale prices ran from $505,000 to $533,500.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 2 sales, closed at 98.7% of asking24 days

Reduced at least once 1 sale, closed at 98.4% of the reduced price58 days

Sellers who held their number went under contract in a median 24 days. Sellers who had to reduce took 58 days and still closed at 98.4% of their already reduced price, after a typical cut of $80,000.

Seller concessions

67%Of sales included a seller credit

$10,750Typical credit when there was one

2 of 3Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Conventional 2 sales67%

Cash 1 sale33%

Cash was 33% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Druid Hills Estates, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Druid Hills Estates in Maitland, Seminole County, covering closed sales from 13 October 2025 through 8 October 2026, refreshed monthly and current as of October 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.