Lake Mary Homes with Waterfront

Lake Mary Homes with Waterfront

Lake Mary, located in Seminole County, Florida, is a charming city known for its picturesque landscapes and serene waterfront properties. With its true homes with waterfront, Lake Mary offers residents a unique opportunity to live a life surrounded by natural beauty.

Situated in the heart of Florida, Lake Mary boasts a warm and inviting climate throughout the year, making it an ideal location for those who enjoy outdoor activities and waterfront living. The city is known for its numerous lakes, including Lake Mary itself, which provides residents with stunning views and a tranquil atmosphere.

Homes with waterfront in Lake Mary offer a variety of options to suit different preferences and lifestyles. Whether you prefer a cozy lakeside cottage or a luxurious waterfront estate, Lake Mary has something for everyone. Imagine waking up to the gentle sounds of water lapping against the shore and enjoying breathtaking sunsets from the comfort of your own backyard.

In addition to its natural beauty, Lake Mary also offers a range of amenities and conveniences. The city is home to a vibrant downtown area, where residents can find an array of shops, restaurants, and entertainment options. With its excellent schools, safe neighborhoods, and easy access to major highways, Lake Mary is a popular choice for families and professionals alike.

If you're looking for a place to call home that combines the tranquility of waterfront living with the convenience of modern amenities, Lake Mary is the perfect choice. Explore the true homes with waterfront in this beautiful city and experience the best that Florida has to offer.

Newest Lake Mary Homes with Waterfront

$1,650,000
4 Beds ⋅ 3 Baths ⋅ O6432146 MLS
Welcome to your Lake Mary lakefront oasis. Situated on one of the most spectacular, prime waterfront lots on Lake Mary with over 170 feet of shoreline, this impeccably maintained 4-bedroom, 3-bathroom pool home offers the ultimate Florida lifestyle. Complete with a private dock, covered boat storage, and direct access to swimming, fishing, and water skiing, this property feels like a private wildlife sanctuary where you can watch sandhill cranes and herons against breathtaking sunset backdrops. The outdoor entertainment spaces are unmatched, featuring a resurfaced, propane-heated pool and spa alongside an expansive 30 x 12 covered porch perfect for al fresco dining. Inside, the home is equally impressive, framing panoramic lake views from the primary suite, living areas, kitchen, and breakfast room. Gleaming hardwood floors and an updated exterior elevation elevate the home's curb appeal and interior aesthetic. The thoughtful floor plan includes oversized rooms throughout, highlighted by a unique dual primary suite arrangement that provides luxury accommodations for guests or multi-generational living. The main primary suite features dual walk-in closets, French doors to the screened patio, and an en-suite bath with a jetted tub overlooking the water. A dedicated office provides excellent flex space for a den, nursery, or remote work. Outside, a grand circular driveway offers ample parking and leads to the oversized 2-car garage. The flow of the home is designed for seamless entertaining, starting from the foyer where you are immediately greeted by stunning lake views. The large, open gathering space anchors the home with a cozy brick fireplace, built-in bookshelves, and French doors leading out to your backyard paradise. A separate formal dining room connects effortlessly to the kitchen and a sunlit breakfast room. Location is everything, and this serene paradise sits within close proximity to Lake Mary Elementary and the SunRail station. Residents can easily walk or bike to downtown shops, restaurants, the local farmers market, pickleball courts, and excellent community parks, while enjoying zoning for highly-rated Greenwood Lakes Middle and Lake Mary High School. A rare combination of prime location and lakefront luxury— this is the one you have been waiting for.

284 Evansdale Road, Lake Mary
$4,250,000
7 Beds ⋅ 13 Baths ⋅ O6432857 MLS
A rare opportunity to own one of Central Florida's premier private waterfront estates on the shores of Lake Mary. Privately tucked behind a custom entry gate, this magnificent estate welcomes guests with a grand circular drive, dramatic fountain, and elegant porte cochère, setting the stage for timeless architecture and exceptional craftsmanship. A breathtaking two story foyer with crystal chandelier introduces soaring ceilings, intricate travertine flooring with custom stone medallions, graceful arches, decorative columns, and exquisite millwork. Travertine extends throughout the main living areas, while hardwood flooring adds warmth to every bedroom. Expansive living spaces are designed for entertaining, including a family room with gas fireplace and spectacular lake views. The chef's kitchen features custom solid wood cabinetry, natural stone countertops, two Sub Zero 36 inch built in refrigerators, Viking Professional gas rangetop with integrated griddle and grill, custom range hood, pot filler, GE Monogram Advantium speed oven, convection wall oven, and adjoining butler's pantry. The main residence features two luxurious primary suites with spa inspired baths, Jacuzzi soaking tubs, oversized walk in showers, and dual vanities. One primary suite showcases an extraordinary boutique inspired dressing room with extensive custom wood cabinetry, floor to ceiling storage, glass front displays, abundant drawers and shelving, multiple hanging areas, center island with stone countertop, dedicated vanity, hardwood flooring, soaring ceilings, clerestory windows, and statement chandelier. Every bedroom features its own en suite bathroom. The fully detached Private Guest Residence & Executive Pavilion offers a private two bedroom, two bath residence upstairs and approximately 3,654 SqFt of additional climate controlled space below with executive offices, conference and gathering rooms, fitness room, kitchenette, and flexible living and work areas. An additional garden apartment provides another private dwelling, creating exceptional flexibility for extended family and guests. Resort style outdoor living includes an infinity edge pool and spa, expansive travertine terraces, covered summer kitchen with Viking Professional grill and Alfresco VersaPower side burner, lakeside gazebo, private covered dock with boat lift, and dedicated boat garage. A three bay garage provides additional vehicle storage. Other features include two custom built in aquariums, NuTone central vacuum, fire sprinkler system throughout the main residence, and two 22 kW Generac propane generators with a 1,000 gallon propane tank capable of powering the entire estate, including the air conditioning systems. Conveniently located near top rated Seminole County schools, championship golf, shopping, dining, Downtown Orlando, and Orlando International Airport. An extraordinary combination of luxury, privacy, waterfront living, and versatility. The estate's expansive formal and casual interiors flow effortlessly toward the lake, creating an exceptional setting for intimate gatherings and grand scale entertaining. From the resort inspired pool terrace to the private dock, gazebo, and boat garage, the property is thoughtfully designed to embrace the waterfront lifestyle. Multiple private living accommodations further distinguish this remarkable compound, offering rare versatility for multigenerational living, visiting guests, executive use, and extended stays. Simply exceptional.

1795 W Lake Mary Boulevard, Lake Mary
$609,000
4 Beds ⋅ 3 Baths ⋅ TB8539078 MLS
estate investment property with garage 22' x 22' multi million dollar neighboring properties. zoned AG-1 low taxes great location to growing downtown Lake Mary excellent schools and train station

1715 W Lake Mary Boulevard, Lake Mary
$635,000
4 Beds ⋅ 3 Baths ⋅ O6433472 MLS
Welcome Home to 233 Randon Terrace! Experience the best of Florida living in this stunning, fully renovated waterfront pool home, where modern luxury meets effortless comfort. With approximately $125,000 in recent upgrades and remodeling, this exceptional residence has been thoughtfully transformed with quality finishes and meticulous attention to detail. At the heart of the home is a show-stopping gourmet kitchen designed to impress. Featuring 42-inch cabinetry, double islands, elegant quartz countertops, a stylish tile backsplash, upgraded lighting, sophisticated gold fixtures, a pot filler, range hood, built-in & walk-in pantries, and an LG stainless steel appliance package, this kitchen combines exceptional style with outstanding functionality. With abundant storage and generous workspace, it is perfectly suited for both everyday living and entertaining. The luxuriously remodeled primary suite offers a private retreat, complete with a beautifully updated bathroom featuring a spacious walk-in shower and dual vanities. The secondary bathrooms have also been tastefully renovated, creating a cohesive, modern feel throughout the home. Step outside and discover your own private oasis. The sparkling pool overlooks a peaceful pond, creating a serene backdrop for morning coffee, afternoon swims, or unforgettable evenings with family and friends. Recent exterior improvements include landscape upgrades, new pool screens, and a fresh exterior paint refresh, enhancing the home's curb appeal and outdoor living experience. The extensive recent improvements continue throughout the property, including a 2020 roof, 2026 water heater, 2026 new A/C coil, 2025 pool pump, PEX piping, six-stage water filtration system, and a garage slat wall organization system. Every update has been thoughtfully selected to enhance comfort, functionality, efficiency, and peace of mind. PRICED AT RECENT AUGUST 2026 APPRAISED VALUE, this remarkable home presents an exceptional opportunity to own a beautifully renovated waterfront property at a price supported by a recent appraisal. Every detail has been carefully considered to create a home that is stylish, functional, and truly move-in ready. Luxury, tranquility, thoughtful upgrades, and modern Florida living come together. Come experience this exceptional waterfront pool home and discover why 233 Randon Terrace is the place you've been waiting to call home!

233 Randon Terrace, Lake Mary
$137,000
1 Beds ⋅ 1 Baths ⋅ O6430643 MLS ⋅ #38 BLDG.
• Good-Looking and Affordable, Third-Floor LAKERONT One-Bedroom, One-Bath Condo in a Building Right on the WATER in a RESORT COMMUNITY! HOLY COW! ______ • Owner is in Process of Installing a BRAND NEW HEAT & AIR CONDITIONING System with a 10-Year Warranty Right Now! Brand-New PAINT inside means the home even Smells New! Nice! ______ • Screened Porch Overlooks Awesome Private & Tranquil LAKEFRONT! Right Out Front of your Home is the Well-Kept COMMUNITY POOL and GYM and Mailboxes! Full-Sized LAUNDRY Room Right Off Kitchen! Bright CERAMIC TILE & Laminate Flooring with No Carpets! ____ • Your New Community is Located in the Heart of Gorgeous LAKE MARY with Fabulous Amenities and Awesome Seminole County Public Schools! Well-Manicured Grounds Shaded by OAK TREES! Enjoy a Beautiful Clubhouse, TWO Fitness Centers, TWO POOLS, 2 Tennis Courts, Car Wash, Two Electric Vehicle Charger Stations, an On-Site Laundry just a few steps away! Concierge-Service Garbage Pickup Right at Your Front Door! There is a Dock a FISHING PIER on GREENWOOD LAKE right outside your door, and at nearby Reflection Park, a COMMUNITY BOAT RAMP too! // • Ideally located Near Interstate 4, Alaqua Lakes, Seminole State College, Heathrow & the Heathrow Office Park. Less than 5 minutes to our famous Lake Mary Boulevard District that has so many Stores and Restaurants like Publix, Target, TJ Maxx, HomeGoods, Home Depot, Starbucks & Top Golf…you could live your entire life within these few square miles and never need to leave! Nice! // • Sanford International Airport is just 17 Minutes away and You Will be within a Half-Hour Drive of DOWNTOWN ORLANDO and Thornton Park, DOWNTOWN WINTER PARK, DOWNTOWN SANFORD and the Universal Studios Theme Parks! That makes EVERYWHERE in “Orlando” that you would want to be just 30 minutes away! • Condo Association Fees are only $338.77/ month consisting of $257.62/month to Regency Community, plus $14.60/mo to Master Community… There is an Additional $66.45/mo Special Assessment that will END on December 1, 2027. WATER BILL, Tra ROOF & are Included in the Condo Association Fees too! • Property is THIRD FLOOR Story of 3-Floor Building with no Elevator. Full Sized Utility Room for Washer and Dryer just off Kitchen. Max. of 2 Pets in Unit & each Must be Less than 35 lbs. Room Sizes, Schools, HOA Info and Square Footage Are Deemed Accurate, but are not Warranted. • Sought-After Schools: Longwood Elementary, Greenwood Lakes Middle School, Lake Mary High School!

2516 Grassy Point Drive Unit 306, Lake Mary
$3,000,000
4 Beds ⋅ 2 Baths ⋅ O6427372 MLS
Never before offered for sale, this extraordinary six-acre lakefront estate presents a once-in-a-generation opportunity to acquire one of Lake Mary's most remarkable legacy properties. Set behind the private gates of The Cove, yet uniquely exempt from the community's HOA, the estate is hidden at the end of a long, tree-lined private drive where the landscape unfolds dramatically to reveal more than 800 feet of pristine Crystal Lake shoreline. Spectacular sunset views, abundant wildlife and the timeless beauty of Old Florida create a setting that has become exceedingly rare. High and dry with an expansive homesite overlooking the water, the property offers exceptional flexibility for those envisioning a custom waterfront estate unlike anything else in the area. Whether designing a grand primary residence with a guest house, resort-inspired outdoor living, expansive garages or recreational amenities, the scale, privacy and extraordinary waterfront frontage provide an unparalleled foundation for a truly exceptional estate. The existing century-old home reflects the property's rich history, while a detached two-car garage with an attached bonus room and a separate four-car garage complete with a workshop and expansive storage room provide immediate functionality while future plans take shape. What truly distinguishes this offering is the rare balance of privacy and convenience. Enjoy the exclusivity and security of a gated community without the limitations of HOA restrictions, an increasingly uncommon advantage for luxury buyers seeking the freedom to create a deeply personalized estate. Located just minutes from Lake Mary's thriving Midtown district, residents enjoy an exceptional collection of acclaimed restaurants, boutique shopping, cafés, entertainment, fitness studios and community events, while nearby Interstate 4, SR 417 and the Wekiva Parkway provide effortless access to downtown Orlando, area airports, world-famous attractions, pristine beaches and the very best of Central Florida. Properties of this significance are rarely available, especially those remaining in the same family and offered to the public for the very first time. Combining more than 800 feet of Crystal Lake shoreline, six picturesque acres, remarkable privacy, spectacular sunsets and one of Lake Mary's most desirable locations, 2636 Reagan Trail presents a once-in-a-generation opportunity to create a waterfront estate that will be cherished for generations to come.

2636 Reagan Trail, Lake Mary
$565,000
4 Beds ⋅ 3 Baths ⋅ O6425505 MLS
Welcome to your own lakefront retreat in the highly desirable Chase Groves community! Bring your boat, fishing pole, and suitcase—this beautifully maintained 4-bedroom, 2.5-bath home with a spacious loft is truly move-in ready and offers breathtaking water views from nearly every room. This one-of-a-kind DR Horton home sits on an oversized ¾-acre waterfront lot overlooking beautiful Belair Lake. Inside, you'll love the bright, open floor plan with soaring vaulted ceilings, abundant natural light, hardwood flooring, and elegant crown molding throughout much of the home. The spacious kitchen opens to the family room, creating the perfect space for entertaining while enjoying stunning lake views. A formal living and dining room add flexibility for hosting family and friends. All bedrooms are on second floor. The oversized primary suite is a true retreat, featuring two walk-in closets, dual vanities, a large soaking tub, and separate shower. Two additional bedrooms also include walk-in closets, while the upstairs loft offers endless possibilities as a home office, media room, playroom, or flex space. Step outside to your private backyard oasis, where an open patio overlooks the lake—perfect for morning coffee, evening sunsets, fishing, kayaking, or simply relaxing and enjoying Florida's natural beauty. Conveniently located just minutes from 417, I-4, Downtown Lake Mary, SunRail, shopping, dining, and zoned for top-rated Seminole County schools, this home offers the perfect combination of waterfront living and everyday convenience. Don't miss this rare opportunity to own one of the finest lakefront homes in Chase Groves.

246 Brightview Drive, Lake Mary
$369,000
3 Beds ⋅ 2 Baths ⋅ G5113393 MLS
WELCOME HOME! This charming property on OVER 1/2 ACRE is tucked away on a quiet dead-end street in the heart of Lake Mary. Offering privacy, minimal through traffic, and NO HOA restrictions, this property provides the perfect blend of comfort, convenience, and outdoor space for families and individuals alike. Situated on an oversized fenced backyard overlooking Crystal Lake, the property offers potential for future lake views, access and waterfront enjoyment. While the shoreline area is currently heavily wooded and would require clearing to establish direct access, the setting provides a unique opportunity for those seeking additional outdoor possibilities and a natural backyard backdrop. The property also features a back patio and an additional cement pad in the backyard, offering endless possibilities for outdoor entertaining, recreation, storage, or future improvements. Inside, you'll find several recent updates including a newer A/C system, newer water heater, and a brand-new dishwasher and stove! The home also features a cozy wood-burning fireplace. Conveniently located near shopping, dining, parks, and major commuter routes, the property offers easy access to everything Lake Mary and the surrounding area have to offer. Zoned for Crystal Lake Elementary, Millennium Middle School, and Lake Mary High School. Whether you're looking for privacy, outdoor space, or a centrally located Seminole County address, 214 E Floyd Street offers a rare combination of location, updates, and future potential. Seller states that current insurance policy does NOT require flood insurance.

214 E Floyd Avenue, Lake Mary
$799,900
4 Beds ⋅ 4 Baths ⋅ O6399756 MLS
This beautiful 4 Br/4Ba Home with an Office and a Loft/ Bonus Rm is located on Lake Mary's finest golf course, Timacuan. This home has a three car garage and stunning water views from the front door and is located on a quiet private cul de sac street. Open floor plan with a huge kitchen island, all stainless appliances, separate laundry room, double oven and separate island cooktop. Great room has brand new soaring impact resistant windows with a beautiful view of the pool, spa and oversized pavered pool deck ready for your next large party.. New windows also on front of the house, re pipe in 2024-25, all walk in closets, roof 2020, oversized pool screen 2020, and more. Main closet has built ins. Two baths down, two up. All measurements are approximate. Owner/Realtor

889 Eagle Claw Court, Lake Mary
$209,900
2 Beds ⋅ 2 Baths ⋅ O6396099 MLS ⋅ 35 BLDG.
Price Adjustment and Preferred Lender Credit Available. Welcome home to your updated first floor condo located in the highly desirable gated community of Regency Park at Lake Mary. Updates from 2025 to this 2-bedroom, 2-bath unit include a new 2 ½ ton Goodman HVAC system, new exterior and interior paint and new exterior siding. Other key updates include roof replaced in 2020 and water heater replaced in 2023. The Renovated Kitchen and Bathrooms feature matching Granite counters and Espresso wood cabinets. Split floor plan with interior utility room, easy guest access to second bath from hallway and a large screened-in porch. With a strong rental history and meticulous maintenance, this unit provides an exceptional opportunity for an Owner Occupant or Investment. Enjoy the resort lifestyle complete with two Gated entrances, Fully equipped Fitness Center, Two Crystal Clear Swimming Pools, a Hot tub, and Two Tennis Courts. Additional Community Amenities include Basketball courts, Playgrounds, Clubhouse, Daily Trash Valet, EV Charging Stations, Car Washing Stations and a Peaceful Fishing Pier and Activities on beautiful Greenwood Lake.

2501 Grassy Point Drive Unit 103, Lake Mary
$539,900
3 Beds ⋅ 3 Baths ⋅ O6392884 MLS
Virtually Staged. Flexible living, peaceful lake views, and a beautiful setting in gated Woodbridge Lakes. Set against open green space leading to a tranquil arm of Lake Dawson, this 2,418-square-foot home offers the opportunity to enjoy fishing, kayaking, and paddleboarding just beyond the back lawn. Inside, a versatile floor plan features a first-floor primary suite, soaring ceilings, and multiple living spaces designed for both everyday comfort and entertaining. Just off the foyer, a private bay-windowed room offers the flexibility to serve as a home office or guest room/fourth bedroom, with a convenient half bath nearby. Warm bamboo floors and 10-foot ceilings carry through the main living areas, while the formal living room features dramatic two-story ceilings. A separate family room opens directly to the kitchen, creating an inviting space for gathering. The kitchen features expansive granite countertops, stainless steel appliances, generous prep and storage space, a breakfast bar, pass-through to the family room, and a bright eat-in dining area overlooking the green space and lake beyond. The first-floor primary retreat enjoys peaceful backyard and lake views, with 8-foot sliding glass doors opening directly to the covered patio. The ensuite bath features dual vanities, a garden tub, walk-in shower, and oversized walk-in closet. Upstairs, a spacious loft with a built-in study area overlooks the foyer and provides another flexible living space. Two generously sized bedrooms share a full bath with dual sinks. Step outside to the covered patio and enjoy the peaceful backyard setting, where open green space extends toward Lake Dawson and creates a scenic backdrop for relaxing or entertaining. Thoughtfully maintained with a roof replaced in 2015 (permit on file) and dual AC systems from 2019 and 2021, both recently serviced. Smart-home features include Nest thermostats, a MyQ smart garage door opener, Wyze WiFi irrigation controller, and Ring doorbell, all of which convey. Woodbridge Lakes is a gated community built around its lakes and features a park, playground, basketball court, and fitness area. Conveniently located near I-4, SR 417, the Seminole Wekiva Trail, and Lake Mary's shopping, dining, and everyday conveniences, with access to Seminole County Public Schools.

949 Pickfair Terrace, Lake Mary
$705,000
4 Beds ⋅ 3 Baths ⋅ O6389470 MLS
MOTIVATED SELLER!! **PRICE IMPROVEMENT** Wow! Step into this beautiful meticulously maintained home with stunning views of LAKE DAWSON, Timucuan Golf Course and moss swaying in the breeze from the lake in the large oaks while relaxing on the 36x16 screened porch. Add a floating dock and enjoy canoeing, paddle boarding, kayaking, paddle boating and fishing. The breeze off the lake provides the perfect Zen atmosphere to enjoy reading a book or add a hammock for taking an much earned nap. This 4-bedroom 3 bath, 3 car garage home located in sought after-gated Woodbridge Lakes is in the heart of Lake Mary. The area is the hub of the new Lake Mary Medical Corridor including the newly built Orlando Health Hospital across the street, multiple ER facilities, medical professionals and imaging centers. The 3017sq.ft. home features wood floors throughout the downstairs including the stairs, in the 20x16 living, 11x13 dining and the 20x16 family room. Travertine tile floors in the updated oversized Chef's kitchen and breakfast nook with custom warm wood cabinets, room for 2 Chef's, island, storage galore and granite counter tops make cooking a pleasure. Enjoy your morning coffee and the beautiful lake view sitting in the breakfast nook looking through the bay window. The family room opens to the kitchen and features a custom-built entertainment center. French doors in the family room lead to the 36x16 screened porch with a marvelous view of Lake Dawson. Upstairs and through the double door entry find the huge 16x17 primary suite with more stunning views of the lake, a 12x12 sitting area offers so many possibilities such as using it as a sitting area, personal library, office, nursery or close in the partial wall and add a door for a 5th bedroom. After passing the 2 dual spacious closets with California closet systems you enter the luxurious primary en-suite with a jetted garden tub to relax after a hard day, a separate shower, water closet and a wall of custom cabinets for tons of storage. There are 3 additional generous-sized secondary bedrooms and a bath with upgraded cabinets with drawers and tons of extra storage, granite counters, private water closet and dual sinks. Bedroom 4 offers more of those stunning lake views. A hallway off the family room leads to the 3rd bathroom with shower, upgraded vanity, granite counters and linen closet. More storage is found under the stairs making this home one for those looking for tons of storage. The laundry room offers a laundry sink with cabinet, upper cabinets and the door leading to the 3rd car garage with overhead storage racks, pegboard and more. All of this plus the community offers a community area including a playground, bathrooms, relaxing areas and breezes from the lake. Minutes to I-4, 417, Heathrow Business Park, shopping, fantastic dining, 30 minutes to Daytona Beach or quick trips to the attractions via the new SR429. Everything you want located in a community friendly Orlando suburb. The is the perfect place to call home!!

873 Pickfair Terrace, Lake Mary
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