Maitland Shores Homes for Sale

3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

$5,500,000

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordinary new-construction residence by Developer & Builder Group represents far more than exceptional modern design. Its distinction lies equally in what you see and in what you don't see, the extraordinary level of construction, engineering, materials, and craftsmanship behind every detail. Built with reinforced concrete, steel, and iron framing and incorporating exceptionally high construction specifications, the residence was created with an uncompromising commitment to structural integrity, durability, and long-term quality. From its substantial structural components to its impact-resistant glass and carefully sourced materials, the home reflects a philosophy rarely found in residential construction: build beautifully, but build exceptionally well. Offering approximately 4,636 square feet of heated living space and 5,260 total square feet, the residence features 4 bedrooms, 4.5 bathrooms, a private pool, and an attached two-car garage. Expansive floor-to-ceiling impact-resistant Techno Glass walls define the architecture, bringing abundant natural light into the interiors while creating a striking connection between indoor and outdoor living. At the center of the home is a dramatic 16-foot custom Costa One-Tree solid steel installation a true architectural work of art and one of the many elements created specifically for this residence. The same uncompromising approach continues throughout the interiors. Imported Italian porcelain flooring, sophisticated lighting fixtures imported from Greece, and carefully selected European finishes elevate every space. The gourmet kitchen features one-inch-thick Italian quartz countertops, imported Italian cabinetry, an extended entertaining island, premium Wolf appliances, and a Sub-Zero refrigerator. Two luxurious primary suites, one on each level provide exceptional flexibility and privacy, each complemented by a beautifully appointed bath and custom walk-in closet. Private balconies crafted with exquisite boat wood create intimate outdoor retreats, while the private pool completes the home's sophisticated indoor-outdoor lifestyle. The setting is equally exceptional. Via Tuscany offers a coveted Winter Park address near Interlachen Country Club and only minutes from Park Avenue's renowned dining, boutiques, museums, and cultural attractions, with convenient access to Downtown Orlando. This is a residence for the buyer who understands that true luxury is not defined by finishes alone. It is defined by the quality of the materials, the integrity of the construction, the precision of the craftsmanship, and the attention given to what lies behind the walls as much as what is visible within them. RESILIENT BY DESIGN. EXCEPTIONAL BY CONSTRUCTION. REFINED IN EVERY DETAIL.

2661 Via Tuscany, Winter Park

$5,600,000

5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park

$3,500,000

4 Beds ⋅ 4 Baths ⋅ Maitland Shores 1st Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with gas fireplace, all flowing seamlessly into the stunning chef’s kitchen. Designed for entertaining, the kitchen features two large islands, exotic granite countertops, under-cabinet lighting, and premium Thermador appliances including a 6-burner gas range with griddle. The walk-in butler’s pantry has a beverage cooler and ice maker adds both style and functionality. The adjoining breakfast area is framed by grand windows overlooking the pool, cabana, and canal. The luxurious downstairs primary suite enjoys tranquil water views and a spa-inspired bath with travertine stone floors, marble counters, custom cabinetry, soaking tub, walk-in shower with steam and generous closet space. Upstairs you’ll find three additional bedrooms and a spacious bonus room, while a separate bonus suite above the garage provides future space for a media room, gym or guest retreat. The interior of the home is highlighted by hardwood floors, plantation shutters, decorative moldings and designer lighting throughout. The outdoor living area is equally impressive. French doors open to a covered porch with classic Old Winter Park brick, leading to a travertine-surrounded pool and private cabana with a wood-burning fireplace. Exterior highlights include a metal roof, durable cement board siding and wooden shutters. Don’t miss this limited opportunity to have immediate and easy access to the coveted Winter Park Chain of Lakes. *Some photos have been virtually staged*

2240 Venetian Way, Winter Park

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Orange County › Winter Park › Maitland Shores

Maitland Shores, Winter Park

Maitland Shores is a neighborhood in north Winter Park, in the 32789 and 32751 zip codes, built mostly in the 2000s. Homes are block and stucco. Most homes fall between about 2,000 and 5,200 square feet under air, the median lot is roughly a third of an acre, and a two car garage is standard.

Maitland Shores has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $75 annually for those who join. Confirm the position on a specific parcel before relying on it.

What the homes are

Built Mostly built in the 2000s, with homes from 1925 to 2025.
Construction Block and stucco. Shingle roofs on 47% of homes.
Style Traditional, Mediterranean. Predominantly two story.
Size Most homes fall between about 2,000 and 5,200 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five, then three.
Garage A two car garage is standard.
Lot The median lot is roughly a third of an acre.
HOA Optional rather than mandatory, so there is no deed restricted membership. Dues run about $75 annually for those who join. Confirm on a specific parcel before relying on it.

Where Maitland Shores is

Maitland Shores, centered at 28.622901, -81.341831. 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 Maitland Shores, 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	22 min	11.7
Walt Disney World	37 min	30.8
Orlando International Airport	32 min	24.8
Universal Orlando	29 min	18.9

Public schools nearby

Dommerich Elementary School 5 min, 1.4 mi
Lakemont Elementary School 7 min, 2.1 mi
English Estates Elementary School 8 min, 2.4 mi
Lake Sybelia Elementary School 8 min, 2.7 mi

Private schools nearby

Maitland Montessori School 4 min, 1.7 mi
Center Academy Maitland 5 min, 2.0 mi
Christian Education at Woodruff Academy 8 min, 2.2 mi

Parks and recreation

John Langdon Park 1 min, 0.1 mi
Howell Branch Preserve 4 min, 1.0 mi
John Hudson Park 3 min, 0.8 mi
Kings Row Park 2 min, 0.6 mi

Groceries and errands

DG Market 3 min, 1.2 mi
Publix Super Market at Maitland Place 4 min, 1.7 mi
Publix Super Market at Casselberry Commons 5 min, 1.6 mi
The Ancient Olive Gourmet of Winter Park 12 min, 2.8 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Maitland Shores 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 Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Maitland Shores actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 5 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 November 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 Maitland Shores

$2,024,000Median sale price

$508Median per square foot

63 daysMedian days to contract

5Homes sold in 12 months

Sale prices ran from $952,000 to $2,600,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
3,000 sq ft and up	4	$2,112,000	$516	35 days

A price per foot taken from the whole neighborhood should never be applied straight to one house.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 2 sales, closed at 95.8% of asking6 days

Reduced at least once 3 sales, closed at 94.2% of the reduced price160 days

Sellers who held their number went under contract in a median 6 days. Sellers who had to reduce took 160 days and still closed at 94.2% of their already reduced price, after a typical cut of $195,000.

Seller concessions

40%Of sales included a seller credit

$3,000Typical credit when there was one

2 of 5Sales 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 3 sales60%

Cash 2 sales40%

Cash was 40% 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 Maitland Shores, 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 Maitland Shores in Winter Park, Orange County, covering closed sales from 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 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.