4 Beds ⋅ 3 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

1776 Bobtail Drive, Maitland

$750,000

3 Beds ⋅ 2 Baths ⋅ Highland Park Estates First Add SubDv. ⋅ 32751 Zip Code

HUGE PRICE REDUCTION. Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.

2130 Deloraine Trail, Maitland

$299,000

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

$599,000

2 Beds ⋅ 2 Baths ⋅ West Cove Condo SubDv. ⋅ 32751 Zip Code

TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

1100 S Orlando Avenue Unit 306, Maitland

$799,900

3 Beds ⋅ 2 Baths ⋅ Druid Isle SubDv. ⋅ 32751 Zip Code

LEASE OPTION CONSIDERED for LAKESIDE LIVING in Maitland, Florida! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard-like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!

1501 Druid Isle Road, Maitland

$1,825,000

4 Beds ⋅ 4 Baths ⋅ Maitland Cove SubDv. ⋅ 32751 Zip Code

Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in the living and family rooms, two fireplaces, and custom built-ins showcase quality rarely found today. The spacious layout features four bedrooms and 3.5 baths, including two primary suites ideal for multi-generational living. Generous walk-in closets and a blend of wood, tile, and carpet add comfort and function. A new A/C (Oct 2025) and a 6.5-year-old roof provide peace of mind. Living areas open to a bright rear sunroom with tranquil lake views. Whether you’re entertaining by the fire, enjoying coffee on the porch, or heading out onto the lake, this property delivers the Florida lifestyle at its finest.

1111 Audubon Way, Maitland

$1,800,000

4 Beds ⋅ 5 Baths ⋅ Woodbridge SubDv. ⋅ 32751 Zip Code

Pre-Construction. To be built. Come build your dream home on this exceptional homesite in the heart of Maitland. This stunning new construction single-family residence will feature 4 bedrooms, 4.5 bathrooms, and 3,567 square feet of thoughtfully designed living space across two stories, showcasing sleek modern finishes and open-concept living ideal for today’s lifestyle. Set on a 0.26-acre cleared lot surrounded by majestic oak trees, the home offers a rare sense of privacy and tranquility while still enjoying all the conveniences of city living. Designed for both comfort and entertaining, the home will include spacious living and dining areas, a gourmet kitchen, and generously sized bedrooms, plus a luxurious primary suite retreat. The outdoor space provides ample room to create your ideal backyard oasis, perfectly complementing the home’s modern design. Located less than a mile from Maitland Community Park, you’ll enjoy nearby sports courts, scenic trails, picnic pavilions, and playgrounds. Just a short walk away are Seminary Lake and the SunRail Maitland station, offering effortless access to recreation and commuting alike. This pre-construction opportunity is a rare chance to own a brand-new custom-style home in one of Maitland’s most desirable and well-connected neighborhoods.

1130 Mechanic Street, Maitland

$340,000

3 Beds ⋅ 2 Baths ⋅ Hamlet At Maitland SubDv. ⋅ 32751 Zip Code

This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's world-renowned theme parks. This 1,146 square foot home features an open-concept floor plan. Primary suite includes a walk-in closet and a private suite bathroom, plus two additional bedrooms that provide flexibility for guests, family or a home office. 1 car garage with a large driveway that accommodates 2 more cars. The property's best feature is solar panels owned outright! With an average monthly bill of $35.00!!! Don't miss your chance to make it yours - schedule a private showing today!

1033 Hamlet Drive, Maitland

$850,000

2 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code

Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

219 Quayside Circle, Maitland

$1,345,500

5 Beds ⋅ 5 Baths ⋅ Lake Sybelia Cove SubDv. ⋅ 32751 Zip Code

$50,000 OFF - NEW PRICE !!!! A SUBSTANTIAL OPPORTUNITY WITH EXCEPTIONAL VALUE. This home has timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and a bar with sink and ice icemaker, create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings on the first level. Upstairs, the spacious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a saltwater pool with new equipment and has a new sparkling finish, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience. A great canvas with many possibilities to create a space that truly reflects your modern vision and lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Experience the extraordinary lifestyle this Maitland home provides, CALL TODAY TO SCHEDULE YOUR APPOINTMENT!

755 Cranes Court, Maitland

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Maitland FL Homes for Sale in Orange County

There are 60 homes for sale in Maitland, Florida as of 2026-09-10, at a median list price of $435,000 and a median of 46 days on market. Every active Maitland listing is above, newest first. What follows is what those listings add up to.

Maitland market at a glance

Active listings	60
Median list price	$435,000
Median price per square foot	$296
Median size	1,477 square feet
Median year built	1973
Median days on market	46
On market 60+ days	23 (38.33%)
Priced below original asking	38 (63.33%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-09-10. Updated weekly.

What the numbers say for Maitland buyers

38 of the 60 Maitland homes on the market (63%) are asking less than they did on day one, and 23 (38%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 46 days in who has already cut once is a different negotiation than one of the 37 listings still inside its first 60 days.

Across the 38 Maitland listings that have already come down, the typical reduction is 5.07% off the original asking price. That is the size of a first concession, not a final one.

Maitland homes by price range

Under $250,000	17	28.3%
$250,000 to $400,000	12	20.0%
$400,000 to $600,000	7	11.7%
$600,000 and up	24	40.0%

Property types in Maitland

Single Family Residence	28
Condominium	28
Townhouse	4

Neighborhoods and subdivisions in Maitland

Every Maitland subdivision with an active listing or its own page here, ranked by inventory. A subdivision showing 0 still appears: this is a live MLS feed and inventory changes daily. The 60 homes in named subdivisions are 100% of the Maitland market; the rest are on unplatted land or were listed without a subdivision name.

Subdivision	Active	Median price	Median DOM	Price per sq ft
Lake Maitland Terrace Apts	7	$315,000	40	$386
Park Lake Twnhs	5	$229,000	16	$157
Visconti East	4	$209,950	1	$188
Sun Bay Club Condo	2	$297,000*	174*	$244*
Dommerich Estates 1St	2	$707,000*	12*	$337*
Enclave/Maitland A-F	2	$500,000*	17*	$237*
Highland Park Estates First	2	$984,000*	78*	$399*
Park Lake Grove Condo	2	$253,750*	43*	$191*
Woodbridge	1	$1,800,000*	1*	$505*
Moorings On Lake Maitland Condo	1	$467,000*	60*	$368*
Visconti West Condo	1	$184,900*	28*	$166*
West Cove Condo	1	$599,000*	113*	$532*
Carrington Park A Condo	1	$140,000*	None*	$116*
Lake Sybelia Shores	1	$2,999,000*	52*	$560*
Oakleigh Third	1	$1,075,000*	98*	$259*
Visconti West	1	$190,000*	100*	$171*
Eatonville Lawrence	1	$300,000*	20*	$154*
Winfield	1	$519,999*	119*	$222*
Park Lake Villas Condo	1	$239,000*	1*	$220*
Kings Row	1	$1,995,000*	75*	$664*
Maitland Cove	1	$1,825,000*	176*	$486*
Hamlet At Maitland	1	$340,000*	285*	$297*
Sybelia Place	1	$965,000*	30*	$317*
Moorings On Lake Maitland Condo Bldg 05	1	$850,000*	296*	$583*
Acreage & Unrec	1	$960,000*	2*	$475*
Sheridan Place	1	$1,795,000*	187*	$764*
Replat Blk B Poors	1	$1,499,000*	50*	$311*
Visconti East Bldg 27	1	$199,000*	82*	$155*
Maitland House	1	$375,000*	None*	$370*
Minnehaha Shores	1	$688,000*	136*	$257*
Enclave At Maitland A-F	1	$619,900*	78*	$294*
Dixie Terrace	1	$714,990*	186*	$478*
Dommerich/Maitland Highlands	1	$830,000*	43*	$265*
Lake Sybelia Cove	1	$1,345,500*	498*	$295*
Hollieanna Shores	1	$560,000*	13*	$289*
Maitland Highlands	1	$779,000*	47*	$342*
Maitland Club Rep	1	$1,125,000*	70*	$292*
Dommerich Estates 1St Add Maitland	1	$649,000*	47*	$405*
Druid Isle	1	$799,900*	167*	$363*
Dommerich Hills Second	1	$799,890*	60*	$408*
Building 14 Visconti West	1	$218,400*	1*	$197*
Greenwood Gardens	1	$455,000*	36*	$394*

Subdivision names come from the MLS as agents entered them. Counts as of 2026-09-10. * Medians on rows with fewer than 4 listings are indicative only.

About Maitland

Maitland is a suburban city of 19,543 at the 2020 census and one of the oldest incorporated suburban municipalities in central Florida.

The name traces to Fort Maitland, and through it to Captain William Seton Maitland, who fought in the Second Seminole War and was killed at the Battle of Wahoo Swamp. A military outpost went up in 1838 on the western shore of Lake Fumecheliga, later Lake Maitland.

Christopher Columbus Beasley, probably the first permanent settler, arrived at Lake Maitland in 1871, and a post office opened in his home on January 2 of the following year. The town grew around it.

A SunRail station sits on Highway 17-92, and the city runs a cluster of museums including the Maitland Art Center with its Mayan Revival and Fantasy architecture, the Maitland Historical Museum, the Telephone Museum and the William H. Waterhouse House Museum.

Maitland zip codes

32751 (60 listings)

Maitland homes by property type

Why Maitland shows up under two counties

A Maitland mailing address does not tell you which county the house is in. Homes addressed Maitland sit in both Orange County and Seminole County, and the county line, not the address, is what sets the property tax rate, the school district and which county government issues permits. Two houses can share a Maitland address and answer to different governments.

This page shows the Orange County side: 60 active listings. For the other side, see Maitland homes in Seminole County.

Check the county on the specific parcel before you assume the tax bill or the school zone. The address will not tell you.

Frequently asked questions

How many homes are for sale in Maitland, FL?

There were 60 active residential listings in Maitland as of 2026-09-10, at a median list price of $435,000. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median home price in Maitland, FL?

The median list price in Maitland was $435,000 as of 2026-09-10, or about $296 per square foot. The median home on the market is 1,477 square feet and was built in 1973.

How long do homes take to sell in Maitland?

Median days on market was 46 as of 2026-09-10. 23 of the 60 listings, 38% of the Maitland market, have been listed 60 days or longer, and that is where most of the negotiating room sits.

Are Maitland sellers reducing their prices?

38 Maitland listings, 63.33% of the market, are now asking less than they did originally, at a median reduction of 5.07%. That is the size of a typical first concession here, and it is usually not the last one.

What neighborhoods are in Maitland, FL?

42 named subdivisions had at least one active listing in Maitland as of 2026-09-10, and every one is listed above with its own median price and days on market. Lake Maitland Terrace Apts led with 7 active listings at a median of $315,000.

What zip codes cover Maitland, FL?

Maitland listings sat in 1 zip code as of 2026-09-10: 32751 with 60 active listings.

The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Maitland listing on this page.