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

$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! ____ • Brand-New PAINT inside means the home even Smells New! Nice! All Brand-NEW UV-Resistant WINDOWS & SLIDING DOOR in 2023! ____ • 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
$748,500
5 Beds ⋅ 3 Baths ⋅ V4950393 MLS
Virtually Staged. Welcome to 1526 Cherry Lake Way, a waterfront pool home in Cherry Ridge at Heathrow, one of Lake Mary’s most established guard-gated communities. This 5-bedroom, 2.5-bath residence presents a rare opportunity to own in a premier Lake Mary location with water views, a screened pool and lanai, and a refreshed interior ready for its next chapter. The home opens with soaring ceilings, large arched windows, and a bright interior palette that gives the main living areas a clean, elevated feel. The floor plan offers generous living and dining spaces, all bedrooms on the main level, and an upstairs loft/flex room that works well as a media room, office, playroom, or secondary lounge. The primary suite is privately positioned and offers direct access to the main living areas and pool side of the home. The kitchen features solid surface countertops, stainless appliances, light cabinetry, a pantry, and an eat-in area overlooking the lanai. Multiple gathering spaces create flexibility for entertaining, working from home, or creating defined formal and casual living areas. Outdoors, the screened pool and lanai are the centerpiece of the property. The pool deck has been newly painted, the covered lanai offers space for shaded seating, and the waterfront rear setting adds a peaceful backdrop for everyday living and entertaining. The exterior will be fully repainted prior to closing, further enhancing the property’s presentation. Cherry Ridge is part of the Heathrow master-planned community, known for its guard-gated entrance, mature landscaping, sidewalks, parks, playground areas, and proximity to Heathrow Country Club, Seminole County trails, shopping, dining, medical offices, business centers, I-4, SR 417, and the best of Lake Mary and Sanford. This is a strong opportunity to purchase a waterfront pool home in one of Central Florida’s most recognized residential communities.

1526 Cherry Lake Way, Lake Mary
$699,000
3 Beds ⋅ 3 Baths ⋅ O6427393 MLS
Welcome to exquisite resort style living in the private GATED COMMUNITY of Griffin Park in Lake Mary. This immaculate 3 bedroom, 2.5 bath + bonus room, home sits on a premium lot with sweeping conservation and pond views where you can wake up to Florida native wildlife including deer, otters, ducks and turtles. Designed for effortless indoor/outdoor living, the open floor plan flows seamlessly from a gourmet kitchen boasting quartz countertops, gas stovetop, stainless steel appliances, farmhouse sink, endless cabinetry and a countertop island with seating into an expansive family room highlighted by floor to ceiling wainscoting around the fireplace. Glass doors lead to an outdoor entertainer oasis featuring a PAVED and FULLY FENCED patio, podocarpus privacy hedges, a fruiting avocado tree and a 30k summer kitchen complete with a Big Green Egg and outdoor fridge. This property also boasts the exclusive distinction of being the only home permitted for side yard artificial turf. Upstairs, retreat to the massive primary suite offering a sitting area, water views and a spa inspired bath featuring marble ceramic tile, white cabinetry with dark designer hardware, dual sinks, granite countertops, separate soaking tub, shower and an expansive his and hers walk-in closet. A generous bonus room offers the perfect secondary entertaining space or home office, accompanied by spacious guest bedrooms and a convenient upstairs laundry room with a built-in utility sink. Additional interior highlights include all new interior paint 7/2026, designated coat closet, mudroom drop zone, 2 car-high capacity garage hanging storage and designer ceiling fans. Major updates bring complete peace of mind with a brand new 2026 4-ton and 2-zone A/C system backed by a 10 year warranty, alongside a 2019 roof and 2019 tankless hot water heater. Custom family room tv surround and outdoor summer kitchen. Residents enjoy a maintenance free lifestyle with access to a heated resort style pool, community fire pit, rentable clubhouse, walking paths and a dog park located less than a block away. Perfectly situated within walking distance to top rated A- rated Seminole County schools including Lake Mary High School and Greenwood Lakes Middle School, you are also steps from Griffin Farm at Midtown restaurants, boutiques, grocery shopping and fitness centers. With fast access to I-4, the 417 and SunRail, this move-in ready sanctuary offers the ultimate Central Florida lifestyle. HOA takes care of the yard. Family room tv and washer and dryer may convey. Extra neighborhood parking available. Home priced well under market value. Owners did not apply for homestead exemption so new owners will have additional tax savings if they apply. Priced for a quick sale!

570 Wishbone Lane, 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
$739,900
3 Beds ⋅ 4 Baths ⋅ O6421771 MLS
Private Lakefront Home in the Highly Desired Golf Course Community of Timacuan. This pool home features 3 Bedrooms, 3.5 Bathrooms Plus Executive Office. Original owner selected this lot sitting on Lake Natashia with views of Lake Alinole in the front of the home as well. Updated Gourmet Kitchen with Quartz Countertops, Waterfall Edge, and Stainless Steel Appliances. Split bedroom floorplan where each bedroom has its own bathroom plus you have a half bath for guests. Side entry garage and paver driveway. Metal Roof with lifetime limited warranty that is transferable to the buyer. Enclosed Florida Room for additional square footage. Light and Bright from every room with stunning lake views. This home may be under audio and video surveillance.

736 Timacuan Boulevard, 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
$565,000
3 Beds ⋅ 3 Baths ⋅ O6392884 MLS
Welcome to this beautifully maintained 3-bedroom, 2.5-bath lakefront home in the gated community of Woodbridge Lakes in Lake Mary, ideally situated on scenic Lake Dawson—perfect for canoeing, kayaking, and paddleboarding right from your backyard. This light-filled, open-concept floor plan features soaring 10-foot ceilings, rich bamboo flooring across the main living areas, and a desirable first-floor primary suite. The home offers multiple living spaces, including a formal living room, a spacious family room, and a dedicated office/ flex space- perfect for working from home or converted to a 4th bedroom. Upstairs, a versatile loft overlooks the foyer and includes an additional study area, ideal for homework, hobbies, or a second office space. Designed with both comfort and entertaining in mind, the kitchen boasts abundant counter space, granite countertops, stainless steel appliances, a breakfast bar, and a convenient pass-through to the family room. An eat-in dining area completes the space, making it the true heart of the home. Enjoy serene lake views from both the family room and primary suite, each featuring 8-foot sliding glass doors that open to a covered patio—perfect for relaxing mornings or evening gatherings. The spacious primary retreat offers a peaceful escape with dual vanities, a walk-in shower, garden tub, and a large walk-in closet. Upstairs, you’ll find two generously sized bedrooms and a full bath with dual sinks, providing comfort and privacy for family or guests. Ideally located, this home offers easy access to premier shopping, dining, and the scenic Seminole Wekiva Trail for walking and biking. Commuting is a breeze with nearby access to I-4 and 417, and the property is zoned for highly rated Seminole County schools. This is lakefront living at its finest—combining comfort, style, and an unbeatable location. Additional items to note: newer AC units (2019 & 2022), Nest thermostats, MyQ smart garage door opener, Wyze Smart WiFi sprinkler controller, Ring doorbell

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
$395,000
O6378212 MLS
Lakefront lot in Cardinal Oaks subdivision off S. Country Club Road. Five minutes from downtown Lake Mary and Seminole State College. Convenient access to US 17-92 and Fl. 417. 95 feet of Frontage on Lake Lee. Public water and sewer available. Buildable area outside 100-year flood elevation is 5392.9 ft. sq there are no HOA fees.

421 Cardinal Oaks Court, Lake Mary
Start Your Search