Winter Park Chain of Lakes Homes For Sale

Viewing Lake Home Real Estate Priced from $0 - $200,000,000.
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MLS# O5777806

Maitland, Florida - Homes For Sale 1850 E Adams Dr, Maitland, Fl 32751 | MLS Number: O5777806

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1850 E Adams Dr, Maitland, Florida 32751
Price: $6,650,000

Bedrooms: 6 Bathrooms: 7.0
Living Square Footage: 7,984

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Boasting modern Hacienda-style architecture and 280 feet of lakefront on Lake Maitland, this gorgeous 3.24 acre gated residence offers nearly 14,000 total square feet. An architectural gem crafted with the finest finishes, Siberian oak hardwood floors are found in all living areas. Built by Liberty Development and designed by Wolfe-Rizor Interiors, quality abounds throughout this six-bedroom, six-and-two-half-bath modern masterpiece. The winner of the Grand Aurora Award for Best Kitchen, every detail has been carefully selected. From the custom-designed copper vent head to the black leathered granite countertops and Thermador appliances, the stunning kitchen is truly a chef’s delight. A butler’s pantry includes a full-size commercial refrigerator and freezer and spacious area for a breakfast bar or catering station. The stunning master retreat is a welcome escape with a private outdoor spa and sitting area. An expansive patio, sparkling pool, spa and summer kitchen with Wolf grill, Sub-Zero appliances and separate fire pit allow for effortless entertaining. Whether playing or spectating, a private on-site tennis court and putting green are perfect for enjoying the outdoor Florida lifestyle. The four-car garage provides extra storage space and an 800-square-foot dock holds two boats. A 620-square-foot apartment is ideal for hosting guests. Breathtaking views and a luxury lifestyle are ensured at this one-of-a-kind Chain of Lakes estate.

MLS# O5749462

Winter Park, Florida - Homes For Sale 1360 Alabama Dr, Winter Park, Fl 32789 | MLS Number: O5749462

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1360 Alabama Dr, Winter Park, Florida 32789
Price: $6,500,000

Bedrooms: 7 Bathrooms: 10.0
Living Square Footage: 10,600

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Stunning Mediterranean Lakefront Estate. Across from the secret gardens of Kraft Azalea Park sits this palatial 1-acre estate with over 10,000 SF of luxurious living space, private tennis court, resort-style pool, and more! Offering formal living areas, gourmet chef’s kitchen, open great room, his and her home offices, elevator, 12-person home theater, billiard room, and six guest suites, each with a private en suite, and a separate guest apartment with kitchen, this home leaves nothing to be desired. Detailed with high-end finishes throughout, the home is exquisite in every way. Polished travertine and hardwood flooring, trim moldings, wrought-iron railings, 27’ ceilings, and a whole-house entertainment system are just a few of the custom details that have been installed throughout the home. Walkout balconies off the front and rear of the home take full advantage of the home’s picturesque surroundings. The nearly 1,000 SF second floor lanai overlooks the pool and tennis courts and the attached 4-car garage, a rare and highly desirable find, along with the front circular drive provide a sophisticated entry for visiting guests. Private boathouse on Lake Maitland faces westward and offers gorgeous sunset views and convenient access to Winter Park’s main attraction the Chain of Lakes. Located on one of the most prestigious drives in town, this extraordinary home is like no other and is just a short walking distance from the award-winning restaurants and boutique shops along Park Avenue.

MLS# O5763783

Winter Park, Florida - Homes For Sale 1941 Legion Dr, Winter Park, Fl 32789 | MLS Number: O5763783

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1941 Legion Dr, Winter Park, Florida 32789
Price: $4,795,000

Bedrooms: 5 Bathrooms: 6.0
Living Square Footage: 9,692

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
One of kind Zachary Kauffman masterpiece on 1+acre on Lake Maitland now available. With his renowned attention to quality & detail, this 5+bed/5+bath has timeless traditional features + every modern amenity you can dream of. Thoughtfully designed w/stunning lake views from every room; Grand foyer welcomes to formal LR w/2 sided FP adjoining cozy Library, both w/custom millwork. East Wing is for FUN; Sports Room & Bar, w/5 TVs, impressive granite bar. Mirrored Exercise Studio, 6 seat Theatre. West Wing: Formal DR, Butler’s Pantry w/wine frig to huge open Kitchen & FR. Gourmet stainless Dacor package; convection gas oven/range, microwave & warming drawers; Bosch DW, Thermador frig & freezer. Custom cabinetry, huge granite island, walk in pantry. Great entertaining space w/gorgeous view, walk out to lanai. Lux Master w/massive balcony, FP, coffee bar, Spa bath w/soaking tub, w/c + bidet, his/hers custom closets. 2nd level East Wing: 3 BRs ensuite w/walk ins + balconies; double desk, 2nd utility rm, loft w/charming shiplap, private office. South Wing: entry from motor court, 2 car gar, Home Office, Mudroom/drop zone, Utility w/craft bar, BR en suite, PLUS Bonus Studio w/kitchenette. Addl detached 3 car gar, 800 sq/ft 1/1 Guest Apt. Outdoor is private Florida oasis: huge paver lanai overlooks lake, Cypress trees, saltwater pool w/spa & beach. Gazebo w/Dacor grill, frig & FP. Covered Boathouse w/lift for sport boat + 2 jet skis; lg dock area for fishing & daydreaming. Full Feature list provided on request.

MLS# O5761045

Winter Park, Florida - Homes For Sale 935 Greentree Dr, Winter Park, Fl 32789 | MLS Number: O5761045

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935 Greentree Dr, Winter Park, Florida 32789
Price: $4,300,000

Bedrooms: 4 Bathrooms: 4.0
Living Square Footage: 4,975

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Exquisite inside and out! This magnificent Georgian-style estate home was meticulously constructed by Posada Custom Homes and is located in one of Winter Park's most desirable neighborhoods offering all the allure of fine lakefront living and just minutes from Park Avenue’s popular shopping, dining and cultural gems. Situated on a secluded lot this residence enjoys a picture-perfect setting and views with 105 feet of shoreline overlooking the north shore of Lake Osceola part of the Winter Park chain of lakes. Superior craftsmanship and attention to architectural detail emanate throughout the 4,975 SqFt of living space. This impressive property features an inspired layout starting with the exquisitely designed public spaces and continues throughout the rest of the home. The spacious owner’s retreat features a balcony overlooking the lake, customized walk-in closets, morning bar, gas fireplace and bath with luxurious fixtures and finishes. Two additional oversized ensuite bedrooms open onto a balcony and a third floor game room offers the perfect hideaway. Additional amenities include an elegantly appointed formal living room, dining room with butler's pantry, family room with fireplace and adjacent wet bar, gourmet kitchen with custom cabinetry and top of the line appliances, coffered ceilings, extensive custom woodwork and built-in cabinetry, stone and hardwood flooring, slate roof, copper gutters, elevator, salt water pool/spa, boat dock, summer kitchen, whole house generator, and a three-car garage.

MLS# O5783619

Maitland, Florida - Homes For Sale 890 W Trotters Dr, Maitland, Fl 32751 | MLS Number: O5783619

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890 W Trotters Dr, Maitland, Florida 32751
Price: $4,200,000

Bedrooms: 5 Bathrooms: 6.0
Living Square Footage: 5,849

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
2019 NEW CONSTRUCTION MODERN FARMHOUSE LOCATED ON LAKE MAITLAND THE LARGEST OF ALL THE WINTER PARK CHAIN OF LAKES. THOUGHTFULLY DESIGNED WITH LUXURY ENTERTAINING AND WATERFRONT LIVING IN MIND. SITUATED ON JUST OVER AN ACRE LOT AND HAS BOTH LAKE AND CANAL FRONTAGE. OFFERING, 5 BEDROOMS, 5 FULL BATHS, TWO HALF BATHS, TOP OF THE LINE APPLIANCES, SUCH AS SUBZERO, WOLF, BOSCH, TO NAME A FEW. THIS LUXURIOUS HOME HAS A VERY OPEN FLOOR PLAN MAKING IT FEEL VERY WARM AND COZY DESPITE ITS LARGE SIZE. THERE ARE TWO BEDROOMS ON MAIN LEVEL INCLUDING THE MASTER SUITE JUST BEHIND THE HIDDEN DOOR WITH 3 MORE BEDROOMS ON THE TOP FLOOR. THE MANCAVE HAS A FULL WORKING BAR INCLUDING SINK, FRIDGE AND ICE MACHINE, COVERED WOOD CEILING, BRICK WALL, CONCRETE FLOORING ALL LEADING OUT TO THE LANAI WHICH INCLUDES AN OUTDOOR KITCHEN, CABANA AND SALT WATER POOL MAKING IT PERFECT FOR ENTERTAINING. THERE IS ALSO A SEPARATE EIGHT SEAT THEATER ON THE SECOND FLOOR OF THE HOME WITH BAR SEATING THAT GIVES ADDITIONAL SEATING AND A SNACK BAR/STATION WHICH GIVES PLENTY OF ROOM TO STORE THE POPCORN WITH CUSTOM CABINETRY AND A FRIDGE. THIS HOME IS EXTREMELY HIGH TECH WITH VIRTUALLY EVERY SYSTEM RUNNING OFF OF YOUR SMARTPHONE OR IPAD. THIS "SMART HOME" FUNCTIONALITY INCLUDES FEATURES SUCH AS LIGHTING CONTROLS, 3 ZONE HVAC COOLING SYSTEM, SONOS MUSIC SYSTEM THROUGHOUT, 3 GARAGE DOORS, 7 CAMERA'S, SECURITY SYSTEM AND SO MUCH MORE. THIS HOME HAS IT ALL! CALL FOR YOUR PRIVATE SHOWING TODAY!

MLS# O5766961

Winter Park, Florida - Homes For Sale 1013 Temple Grv, Winter Park, Fl 32789 | MLS Number: O5766961

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1013 Temple Grv, Winter Park, Florida 32789
Price: $3,995,000

Bedrooms: 5 Bathrooms: 5.5
Living Square Footage: 5,797

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Beautiful home on Winter Park Chain of Lakes. Stunning estate on Lake Osceola with long private driveway to home that has gorgeous views of pool, gardens and lake. This one of a kind property has it all; privacy and charm in a fantastic Winter Park location. Large living room with lake views, fireplace and bay window. Large gourmet kitchen with top of the line appliances and eat in area overlooking pool and terrace down to the lake. Master bedroom has dramatic vaulted ceilings and cozy fireplace. Call for more information or to arrange a private showing of this beautiful Winter Park Lakefront Home.

MLS# O5784820

Winter Park, Florida - Homes For Sale 375 Virginia Dr, Winter Park, Fl 32789 | MLS Number: O5784820

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375 Virginia Dr, Winter Park, Florida 32789
Price: $3,895,000

Bedrooms: 5 Bathrooms: 4.5
Living Square Footage: 7,538

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Lakefront, Location, Luxury. Move right into this beautiful lakefront custom home on cul-de-sac with views of Rollins College. Located on desirable Lake Virginia. 5 bedroom, 4.5 bath with wine room, bonus room, office, media room, exercise room, and bright second floor Florida room with lake views as well. Large Master with expansive balcony for perfect sunset views on the lake. Gourmet kitchen with large eat in granite counter sitting area that opens onto family room and out to covered rear patio and outdoor grill station. Absolutely perfect for entertaining inside and out! Home has 2 master suites for first and second story living. Built-ins and architectural detail throughout add to the quality and value of this one of a kind Winter Park home. Spacious second story bunk room ideal for guests adjacent to bonus/game room. Thoughtfully designed split floor plan with so many extras you will love. Call for private viewing. Buyer to verify measurements.

MLS# O5750309

Winter Park, Florida - Homes For Sale 1400 Green Cove Rd, Winter Park, Fl 32789 | MLS Number: O5750309

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1400 Green Cove Rd, Winter Park, Florida 32789
Price: $3,495,000

Bedrooms: 5 Bathrooms: 6.0
Living Square Footage: 6,384

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Timeless, classic, sophisticated, and exceedingly peaceful… A once in a lifetime opportunity to live in a premier Winter Park Chain of Lakes estate home on almost an acre, walking distance to downtown Park Avenue. This one-owner custom home was designed by esteemed architect Steve Feller and expertly built by Don Jernigan with high quality workmanship and thoughtful detail throughout. Enter into a grand foyer with sweeping staircase, overlooking the formal living room’s two story wall of windows showcasing beautiful Lake Maitland. The first floor has large and accommodating spaces, all with lake views, perfect for entertaining with a separate living room, formal dining room, & family room adjacent to the kitchen. The kitchen was renovated 3 years ago with all white cabinets, a beadboard island, stainless appliances, granite countertops, double ovens, a breakfast bar and large eating nook with abundant windows conveying brightness and light. There is also a 1st floor bedroom suite and an elegant, traditional home office with paneled walls. The 2nd floor has a master bedroom suite with large bathroom and huge walk-in closet, as well as 3 additional bedroom suites, a bonus loft, & media room with bar area. Features include fireplaces, crown molding, hardwood floors, French doors, coffered ceilings, built-ins, and lots of storage. Appx 119’ of lake frontage, perfectly manicured lawn, boat house & dock (as is), 2 car garage with capability to add 3rd, and zoned for Dommerich, Maitland Middle, and WPHS.

MLS# O5778520

Winter Park, Florida - Homes For Sale 455 Lakewood Dr, Winter Park, Fl 32789 | MLS Number: O5778520

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455 Lakewood Dr, Winter Park, Florida 32789
Price: $3,300,000

Bedrooms: 4 Bathrooms: 5.0
Living Square Footage: 5,018

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Private and sophisticated Winter Park lakefront with stunning views of Lake Osceola. Light and bright with a very open floor plan this residence offers great space for entertainment. The home features two living rooms with a wall of windows, a family room, a bonus room and formal dining room. Tastefully updated with new hardwood floors, new doors and plantation shutters. Updated kitchen with a Thermidor 6 burner gas stove, 2 ovens and an over sized pantry. There is a wet bar in the family room with and icemakeer. The master bedroom on the main floor features a generous sitting area and his and hers master bath that opens to a screened porch with a hot tub - with all new equipment - overlooking the lake. One more bedroom completes this level. The lower level has 2 additional bedrooms and a bath. The outdoors is an entertainer’s dream. The upper level with an extensive porch also has a recently added pergola, a re-surfaced pool, and a refinished deck. The lower lower deck features an inviting white sandy beach and a boathouse with plenty of storage for all your water toys. 2 outside extra closets and and an outdoor pool shower complete the outdoors. Great opportunity to live in a beautiful lakefront home on a quiet street close to Park Avenue with all that Winter Park has to offer!

MLS# O5792559

Winter Park, Florida - Homes For Sale Winter Park, Fl 32789 | MLS Number: O5792559

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Winter Park, Florida 32789

DUE TO RESTRICTIONS THE ADDRESS FOR THIS PROPERTY CANNOT BE SHOWN. PLEASE CONTACT ME FOR MORE INFORMATION ON THIS PROPERTY
Price: $3,300,000

Bedrooms: 4 Bathrooms: 4.0
Living Square Footage: 5,095

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Winter Park Chain of Lakes! Amazing opportunity to own this custom-built home with 110 feet of frontage on beautiful Lake Osceola! You will love coming home to this open-concept single-story home, totally renovated in 2016, with bleached oak floors throughout. Panoramic water views are yours from almost every room in the house, which features a 500-bottle temperature-controlled wine room with glass walls off the living room; a spacious dining room; and chef’s kitchen with two large Calcutta marble islands, all new stainless steel Thermador appliances, custom soft-close inset cabinets with glass fronts, and custom pullouts. This 5100-square-foot home boasts 4 bedrooms, 3 full & 2 half baths, an office, family room, and two wood-burning fireplaces. This home has too many amazing features to list – custom everything! Outdoors, enjoy the tiered back yard with Signature landscaping; heated pool with cabana; 22 x 28 sport court; boat house, dock, and electric boat lift, all overlooking the sparkling blue water of Lake Osceola. This property offers total privacy, but is just minutes from Park Avenue’s shops, restaurants, festivals & parks. Move In and Love Where You Live!

MLS# O5509686

Winter Park, Florida - Homes For Sale 740 Palmer Ave, Winter Park, Fl 32789 | MLS Number: O5509686

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740 Palmer Ave, Winter Park, Florida 32789
Price: $3,175,000

Bedrooms: 5 Bathrooms: 4.5
Living Square Footage: 4,810

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
If you’re looking for the quintessential Winter Park Lakefront Estate Home this is it! Designed by acclaimed architect Gamble Rogers this magnificent home has double waterfrontage on both Lake Osceola and the Venetian Canal. Located on an oversized 1-acre lot, this home has a formal presence including a grand, circular driveway entrance and a classic front elevation that showcases a 2nd story balcony overlooking majestic palms. As you walk through the front door your eyes are immediately drawn to the unobstructed views of the water; just about every room in the house offers views of the lake. Along the back of the house (lakeside) you’ll find the formal living room, sitting room/den, dining room and kitchen; there’s also a downstairs guest suite with full bath. Upstairs is the master bedroom, along with three additional bedrooms and two full baths. There is an abundance of storage of throughout the home and the entire estate is impeccable and representative of timeless elegance and class. Surrounded by both historic and brand new multi-million dollar estates this one-of-a-kind property is walking distance to Park Avenue and just minutes to the Interlachen Golf & Country Club, Winter Park Racquet Club, and more.

MLS# O5758266

Winter Park, Florida - Homes For Sale 581 Sylvan Dr, Winter Park, Fl 32789 | MLS Number: O5758266

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581 Sylvan Dr, Winter Park, Florida 32789
Price: $2,595,000

Bedrooms: 3 Bathrooms: 4
Living Square Footage: 4,503

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
This premier Winter Park lakefront property on Lake Osceola provides an opportunity to build anew, renovate or use existing home on an absolutely beautiful elevated lot of approximately 0.75 acres. It overlooks arguably the most beautiful serene cove on the Chain of Lakes. Enjoy magnificent, long, picturesque sunset views while also being on an extremely private lot. The property is set up well to gate off the entrance with over 300 feet of depth, so the new home would be set back noticeably from the street. There are approximately 90-100 feet on the lake and majestic oaks and cypress trees on the property. The buyer can build about 10,000 square feet or more on this property. Boat to the downtown Winter Park area on one of only two lakes on the Chain of Lakes in City of Winter Park with no boat ramp. This is one of the quietest lakes in terms of boating activity as boaters must go through canals to get to this lake.

MLS# O5753089

Maitland, Florida - Homes For Sale 500 Minnehaha Rd, Maitland, Fl 32751 | MLS Number: O5753089

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500 Minnehaha Rd, Maitland, Florida 32751
Price: $2,499,000

Bedrooms: 4 Bathrooms: 4
Living Square Footage: 3,986

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Just Reduced! Absolutely stunning, private lakefront estate on the shores of Lake Minnehaha. Tucked away, off a quiet street, this gated estate home features gorgeous panoramic views of the water, a grand interior with an open and luxurious layout, four bedrooms, four full baths, a home office, gourmet kitchen, and more. Covered lanai with phantom screens creates the ideal setting for enjoying those picture-perfect views and beautiful sunrises over the water. Inside you’ll find that there has been no detail over looked. Elegant natural stone flooring flows throughout the main living areas, while dark, espresso hardwood floors have been installed in the bedrooms and office. The home’s high ceilings are complimented with wood beams in the living room and fantastic natural light that shines through the glass sliders. The gourmet kitchen is open and features an island with seating, built-in oven, gas cooktop, paneled refrigerator, and butler’s pantry. The master suite is generous in size and is accompanied by a master bath with his and her walk-in closets, dual vanity areas, spa bath and shower. Despite the amazing interior living space, you’ll want to spend your time outside. Located on over an acre of land, this home boats 130’ of water frontage and comes with a private dock and saltwater pool. Zoned for A-rated public schools, you’re also just minutes award-winning restaurants and boutique shops along Winter Park’s famed Park Avenue and the Racquet Club and Interlachen Golf & Country Club.

MLS# O5731623

Winter Park, Florida - Homes For Sale 2550 Venetian Way, Winter Park, Fl 32789 | MLS Number: O5731623

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2550 Venetian Way, Winter Park, Florida 32789
Price: $2,250,000

Bedrooms: 4 Bathrooms: 4.0
Living Square Footage: 4,875

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
DON'T MISS THIS SPECTACULAR CUSTOM WATER-FRONT HOME OF YOUR DREAMS! Jump on your boat and cruise out to Lake Maitland and the entire Winter Park Chain of Lakes! Located in the "VIAs" of Winter Park. Easy access to everything you love about Winter Park, Maitland and Orlando. Downstairs: Chef's Kitchen with walk-in pantry, Double Oven Gas Stainless Thermador Range, Integrated Refrigerator, Island with prep. sink, Wine Refrigerator, Breakfast Bar - All Open to the Spacious Family Room! Water Views Everywhere! Downstairs Master Suite with huge walk-in closets, separate shower and soaking tub, Private Water Closet w/ bidet. Half Bath with both interior and exterior access. Another Half Bath next to the Over-Sized Laundry Room. Over-Sized Garage: 2 cars Plus! The Boathouse may be calling you but the outdoor living spaces will beckon you to stay! Upstairs: Three more bedrooms, Two Bathrooms, Media Room, Gym/Bonus Room and a Versatile, Open Loft Space for use as a game room and Upstairs Family Room. Enjoy Breezes and Water View from the Upstairs Balcony. Schools: The Trifecta of: Dommerich Elementary, Maitland Middle and Winter Park High! Be sure to check out the Virtual Tour and Photos to fully appreciate this home. It's even better in person!

MLS# O5766352

Winter Park, Florida - Homes For Sale 531 Virginia Dr, Winter Park, Fl 32789 | MLS Number: O5766352

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531 Virginia Dr, Winter Park, Florida 32789
Price: $2,250,000

Bedrooms: 4 Bathrooms: 3.5
Living Square Footage: 4,955

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Wonderful Lake Virginia one story pool home at the end of quiet Virginia Drive in Timberlane Shores. This home has great entertaining spaces with living room, oversized family room with a wall of windows overlooking the lake & beautiful Knowles Chapel, adjacent to open kitchen and large dining room. Three-way split plan with a master wing, another hall with 2 bedrooms, and an additional guest bedroom/bathroom. Huge bonus room allows for perfect flex space. Kitchen has gas range, dual ovens, Miele dishwasher, and breakfast bar. Master bedroom is spacious and tranquil with lake views, walk-in closet, and bathroom with dual sinks and Jacuzzi tub. Features include hardwood floors throughout, fireplace, tongue & groove vaulted ceiling, French doors, and 3 car garage including an office. Stunning backyard has covered porch, outdoor kitchen, large swimming pool, big yard, and amazing boathouse with storage. Convenient location to downtown Winter Park, Park Avenue, and Baldwin Park. Zoned for the new Audubon K-8 and Winter Park High School.

MLS# O5790373

Maitland, Florida - Homes For Sale 620 Bentley Ln, Maitland, Fl 32751 | MLS Number: O5790373

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620 Bentley Ln, Maitland, Florida 32751
Price: $1,995,000

Bedrooms: 5 Bathrooms: 4.5
Living Square Footage: 5,521

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
A rare gem in a private setting on the famed WINTER PARK CHAIN OF LAKES awaits your move! Situated on a no-outlet lane, this beautiful LAKEFRONT ESTATE boasts unexpected far reaching views over Lake Minnehaha. Immediately you are drawn through the elevated main floor to the open-air infinity pool/spa, seeing water w/no boundaries. This secluded, single-owner residence was purposefully designed w/every detail in mind, capturing stunning lake views, conveying natural light in nearly every room. The open floor plan offers great space for entertaining! Completing the first level is a sizable master suite, an exercise room, a guest BR w/en-suite bathroom & a cozy, handsomely-appointed home office w/built-in cabinetry. The grand staircase leads to a media/game room w/a 44+ft exterior deck & 3 BRs on the upper level. Quality features include a gourmet kitchen w/high-end appliances & granite countertops, gas fireplace, a full home sound system, 2 staircases & duel 2-car garages… too MANY to name so make this retreat a must see to appreciate! Zoned for WPHS, located in Maitland w/close access to the SunRail & Hwys 17-92 to I-4, this home is blocks from a forested community park w/tennis/sports courts, miles of trails, picnic pavilions & playgrounds. Relax in this lakefront lifestyle, enjoy water toys or take a backyard boat ride to downtown Winter Park’s shops, restaurants & cultural activities. Start living your dreams in this exceedingly peaceful oasis, it's the perfect location on the Winter Park Chain!

MLS# O5791816

Maitland, Florida - Homes For Sale 42 Minnehaha Cir, Maitland, Fl 32751 | MLS Number: O5791816

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42 Minnehaha Cir, Maitland, Florida 32751
Price: $1,899,000

Bedrooms: 4 Bathrooms: 4.5
Living Square Footage: 4,445

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Beautiful Winter Park Chain of Lakes Home on Lake Minnehaha - one of the best kept secrets on the Chain benefiting from less transient boaters & a slalom run! Almost 1-acre (.80) HIGH & DRY, 90’ seawall/frontage with custom fencing for panoramic view. Large covered boat house, boat dock & lift for easy enjoyment of outdoors. Expansive paver deck, covered lanai, elaborate pool/spa, & pool bath. Experience breath-taking views from the moment you open the front door! The sunsets will have you back outside to take some pics! Open floor plan has stunning lake views from the downstairs main living areas, master suite, office/exercise room & the huge 2nd floor main room/balcony. Lots of natural light throughout. Sliding glass doors open up the main living areas to the outdoors! Master wing is exceptional with its views, oversized shower/sauna, spa bath, & dual-room wood-burning fireplace. There is a wood-burning fireplace in the family room which is surrounded with lake views! Extensive upgraded woodworking, 12’ ceilings, 9” crown molding and 11” baseboards throughout. Downstairs main area has stunning 12’ architectural ceilings, beams, and entry copper inlay. This home is perfect for entertaining large groups with its sliders and open flow! The upstairs provides a theatre used as a music room, and large area used as a game room, or could be a second master suite. Custom cabinetry throughout. Sound system throughout. Custom closet systems utilize the 12’ ceilings. Owner is Licensed FL

MLS# O5765419

Winter Park, Florida - Homes For Sale 410 Lakewood Dr, Winter Park, Fl 32789 | MLS Number: O5765419

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410 Lakewood Dr, Winter Park, Florida 32789
Price: $1,890,000

Bedrooms: 5 Bathrooms: 6.5
Living Square Footage: 5,036

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Winter Park Chain of Lakes, Lake Osceola waterfront property, with over 100 feet of shoreline, ready for a new custom home or renovate the existing structure. A beautiful elevated lot, a rare find, with breathtaking sunsets, the way lot is situated which will also allow for interesting architecture, bringing the outdoor landscape in, capturing every view the lake offers in a very private setting. Winter Park Chain of Lakes includes 5 connected lakes through a Venetian canal system and allows for boating, kayaking, jet skiing and more. Existing home is over 5,000 sf, 5 bedrooms with downstairs walk out. Lovely open and inviting living spaces, large rooms, separate living and dining rooms. This opportunity doesn’t present itself often and with little lakefront left to be built on it is a great overall investment. Lot has gorgeous mature trees making the lot feel very secluded and private. A perfect location to enjoy the Florida outdoor lifestyle that only the Chain of Lakes and Winter Park affords with a short stroll to Park Avenue, Rollins, Sunrail, restaurants, shops and great schools. Doesn’t get any better than this.

MLS# O5772511

Maitland, Florida - Homes For Sale 281 Shell Point E, Maitland, Fl 32751 | MLS Number: O5772511

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281 Shell Point E, Maitland, Florida 32751
Price: $1,885,000

Bedrooms: 4 Bathrooms: 3.5
Living Square Footage: 4,024

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
ALMOST HALF ACRE (20823 sq ft) HIGH AND DRY featuring 180 ft of picturesque shoreline on Lake Maitland, largest of the Winter Park Chain of Lakes! This move in ready home boasts a Cypress studded lake frontage and covered boathouse ready for water fun and relaxation. Expansive landscaped back lawn has a paver path leading to the fire pit, large pool, open deck and spacious covered lanai area, perfect for the outdoor Florida lifestyle. Inside, you’ll enjoy spectacular views of the lake from almost every room! An abundance of natural light fills the spacious chef’s kitchen which features stainless appliances, granite island and bar overlooking the cozy family room with a fireplace and glass doors that lead to the deck. The living room and dining room are adjacent to the kitchen and open to the covered lanai. The large downstairs bedroom has a private bath, kitchenette and patio with views of the lake. Perfect for in-law suite or an additional game room. A dedicated office is finished w/ built-in desks and book shelves. The master wing is exceptionally spacious w/ large bath, dual vanities, granite counters, spa tub and oversized shower. Enjoy your morning coffee on the private balcony. Plus 2 large bedrooms: one which leads to an upstairs balcony. Situated on quiet cul-de-sac and convenient to Maitland, Winter Park, and A+ schools. Home Warranty and house plans available.

MLS# O5762356

Winter Park, Florida - Homes For Sale 2031 Venetian Way, Winter Park, Fl 32789 | MLS Number: O5762356

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2031 Venetian Way, Winter Park, Florida 32789
Price: $1,625,000

Bedrooms: 5 Bathrooms: 3.5
Living Square Footage: 3,556

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Tremendous character and charm throughout this stunning Santa Barbara-style Mediterranean resting on almost a 1-acre lot in the Vias. Waterfront estate size property on the Winter Park Chain of Lakes with boat dock and lift. This five-bedroom, three-and-a-half-bath residence enjoys a park-like backyard with pool, three-car garage, and has been extensively remodeled over the years. An open flexible floor plan, updated electrical and plumbing and enhancements provide flexibility for any interior styling. Fabulous entry to a vaulted wood beam grand room with gas fireplace and built-in serving cabinet. The home has 18-inch Travertine tile, plaster walls, built-ins, and extensive woodwork/moldings. The gourmet kitchen has a central island, breakfast bar, Miele espresso maker, steam oven, induction stove, Wolf double convection ovens, two dishwashers and Sub-Zero refrigerator. The downstairs Master retreat is spacious with spa bath & sitting area. The upstairs bedroom suites have French doors leading out to balconies overlooking the tropical pool area and waterfront. The gathering room has pocket sliding glass doors leading to a gorgeous brick patio/pool area and expansive lawn to enjoy family sports and entertainment. Perfectly located at the end of a quiet street in one of the most desirable neighborhoods in Winter Park convenient to parks, WPRC & ICC. Boat, kayak, paddleboard or ride your jet skis through the 6 lakes connected by beautiful canals and enjoy all that the lake lifestyle has to offer.

MLS# O5769819

Winter Park, Florida - Homes For Sale 906 Poinciana Ln, Winter Park, Fl 32789 | MLS Number: O5769819

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906 Poinciana Ln, Winter Park, Florida 32789
Price: $1,595,000

Bedrooms: 4 Bathrooms: 4
Living Square Footage: 3,309

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Thoughtfully conceived and designed, this award winning, custom built Lake Maitland waterfront estate is sure to impress! Crafted all on one level, this charming lakefront splendor boasts soaring ceilings and exquisite one-of-a-kind architectural features throughout. Dine in the luxurious, well-equipped kitchen while enjoying unparalleled views of your private storage dock and Winter Park's prized Lake Maitland! Entertain guests on your covered lanai and luscious backyard, or showcase the ample interior with plenty of space for work and play. Host the entire family in the home's generously sized four bedrooms, each featuring a private on-suite bathroom. This home is the pinnacle of Winter Park living. With its supreme sense of privacy, elegant finishes and proximity to commuter roads, it is no wonder that this brilliant masterpiece estate is the Parade of Homes Winner!

MLS# O5726674

Winter Park, Florida - Homes For Sale 275 Stirling Ave, Winter Park, Fl 32789 | MLS Number: O5726674

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275 Stirling Ave, Winter Park, Florida 32789
Price: $1,385,000

Bedrooms: 3 Bathrooms: 2.5
Living Square Footage: 3,046

Type: Single Family Residence

Winter Park Chain of Lakes Home Description:
Fantastic Lakefront opportunity on Winter Park Chain of Lakes. Endless potential for this one of a kind location with views of Rollins College and a boathouse on Lake Virginia. Large lot bordered by canal/stream on one side and a few blocks to walk to Park Avenue and Rollins. This house has the potential for complete remodeling with over 3000 square feet of living area currently and capabilities to expand. Existing house has vaulted ceilings, 2 fireplaces, and a master bedroom with a large deck overlooking Rollins and Lake Virginia. Very mature landscaping and lot size could make for a great new home location as well. One of the best priced WP Chain of Lakes opportunities. Sellers motivated.

MLS# O5797604

Winter Park, Florida - Homes For Sale 1602 Alabama Dr #203, Winter Park, Fl 32789 | MLS Number: O5797604

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1602 Alabama Dr #203, Winter Park, Florida 32789
Price: $874,444

Bedrooms: 2 Bathrooms: 2
Living Square Footage: 2,053

Type: Condominium

Winter Park Chain of Lakes Home Description:
LAKEFRONT! PHENOMONAL RENOVATION! IMPRESSIVE! This completely renovated flat boasts 2053 square feet of LOVELY! Highlights include an enchanting sun room with skylights & a wall of windows to enjoy breathtaking views of Lake Maitland & the manicured grounds of the Historic Alabama Hotel located in the VIAS of Winter Park. Delightfully light & bright great room plan with hardwood floors & crown molding throughout offers a custom kitchen with white cabinetry, quartz counters, quaint breakfast bar & stainless steel appliances. The gracious Master Suite complete with walk-in closet & beautiful bath with marble tile is stunning. Serene Lakefront deck for relaxation & boat slips available for residents only. Extras include: inside laundry room with storage, 1 deeded covered parking space & plenty of guest parking, keyed entry lobby, elevator, climate controlled storage unit & on site manager. Rentals are not permitted but small pets are welcome! Stroll to shoppes & dining on Winter Park's Park Avenue. Graceful space & Exquisite location! WELCOME HOME!

MLS# O5774020

Winter Park, Florida - Homes For Sale 1600 Alabama Dr #101, Winter Park, Fl 32789 | MLS Number: O5774020

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1600 Alabama Dr #101, Winter Park, Florida 32789
Price: $775,000

Bedrooms: 2 Bathrooms: 2
Living Square Footage: 1,322

Type: Condominium

Winter Park Chain of Lakes Home Description:
Beautiful 2 bedroom/2 bath condo on the first floor in the historical Alabama! Located in the heart of Winter Park and in walking distance to Park Avenue this unit was part of the original dining room of the 1921 Alabama hotel. Boasting 14' ceilings, crown and base molding as well as original and pristine oak flooring throughout this ground floor condo. Featuring the largest courtyard within this building, as well as a custom built fountain, 1 assigned carport and 1 additional parking spot. None of the chandeliers convey! Enjoy drinks on the large lakefront dock overlooking the association deeded boat slips with fresh water and electrical outlets on Lake Maitland. The association sits on over 3 acres, provides a pool, fitness center, sauna, clubhouse, kayak/canoe racks with access to the Winter Park chain of lakes. Included in the monthly HOA: water, sewer, trash removal, roof, pool, fitness room, sauna, elevators, ground maintenance and landscaping, building exterior maintenance and repairs, manager, building insurance, individual private storage room and bike storage.

MLS# O5761130

Winter Park, Florida - Homes For Sale 311 E Morse Blvd #6-20, Winter Park, Fl 32789 | MLS Number: O5761130

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311 E Morse Blvd #6-20, Winter Park, Florida 32789
Price: $425,000

Bedrooms: 1 Bathrooms: 1
Living Square Footage: 1,137

Type: Condominium

Winter Park Chain of Lakes Home Description:
Enjoy million dollar views for less than half the price ! This unit is lakeside on the top floor of the tallest building in Whispering Waters, a marvelous example of Mid-Century architecture. Floor to ceiling glass affords unobstructed and spectacular views of Lake Osceola and rocket shots at the Cape on clear days. This upscale and redone aerie is above the tree tops and affords stunning moon rise and sun rise scenes. Condo fees include all utilities, exterior, pool , and ground maintenance. This is a one of a kind unit and is perfect for year round or as a winter retreat. It is in the heart of downtown Winter Park and all the famed Park Avenue amenities.

MLS# O5787446

Maitland, Florida - Homes For Sale 206 Quayside Cir #ph, Maitland, Fl 32751 | MLS Number: O5787446

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206 Quayside Cir #ph, Maitland, Florida 32751
Price: $399,000

Bedrooms: 2 Bathrooms: 2
Living Square Footage: 1,270

Type: Condominium

Winter Park Chain of Lakes Home Description:
The Moorings on Lake Maitland! Unique opportunity to own the wonderful PENTHOUSE condo. Elevator in the building makes this condo an easy top floor access! Spacious great room with high ceilings, split floor plan, and an lots of natural light. The enclosed patio overlooks beautiful Lake Maitland, and has glass windows. Wonderful master suite with walk-in closet. Unit has laundry room as well as a storage room right outside your unit. Enjoy magnificent SUNRISE and SUNSET while relaxing on your enclosed patio, immersed in the beauty of the tranquil waters and Florida breezes. Dedicated covered parking. The Moorings. Very well run with no assessments coming up. Walk to Lake Lily and nearby restaurants. Call to schedule a viewing today.

MLS# O5796832

Maitland, Florida - Homes For Sale 202 Quayside Cir #304, Maitland, Fl 32751 | MLS Number: O5796832

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202 Quayside Cir #304, Maitland, Florida 32751
Price: $375,000

Bedrooms: 2 Bathrooms: 2
Living Square Footage: 1,270

Type: Condominium

Winter Park Chain of Lakes Home Description:
STUNNING and SOPHISTICATED condo located in the heart of Maitland with LAKE MAITLAND VIEWS! Dramatic entry gives you the feeling of a penthouse elevator. This newly renovated one level condo is very open, light and bright with wonderful oversized living area that transitions to a screened lanai, perfect for outdoor entertaining and enjoying the gentle lake breezes. Gourmet kitchen is equipped with rich Italian-made walnut finished cabinetry, soft close drawers, Schott Ceran cooktop, stainless steel accent toe kick plate, counter depth refrigerator in “sunset bronze”, built in wall oven/microwave combination, custom quartz “calacatta”countertops, eat in area PLUS bar top counter for additional seating. Gracious master retreat with separate door to lanai. Beautiful bath with double sinks, shower and oversized closet with custom built-ins. Split bedroom plan with second bedroom being an en-suite. Indoor laundry. This turn key unit is appointed with designer lighting on dimmer’s, new 6” baseboards, Sherwin Williams Cashmere paints, carpet by Shaw, porcelain 24” rectified flooring throughout. Enjoy all the amenities this lakefront complex has to offer: fishing on lakefront dock, pool, clubhouse PLUS 1 covered carport space and owner's storage closet. Steps from Lake Lily, Antonio’s and Luke’s! Short drive to Park Avenue. Shows very well!!

MLS# O5765521

Winter Park, Florida - Homes For Sale 690 Osceola Ave #209, Winter Park, Fl 32789 | MLS Number: O5765521

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690 Osceola Ave #209, Winter Park, Florida 32789
Price: $350,000

Bedrooms: 2 Bathrooms: 2
Living Square Footage: 1,148

Type: Condominium

Winter Park Chain of Lakes Home Description:
Love where you live! This two bed, two bath condo has it all. It is located on beautiful Lake Virginia, right on the Fern Canal that links this lake to Lake Osceola and the entire Winter Park Chain of Lakes. The condo has been lovingly updated with custom cabinets, granite counters and stainless appliances. Crown moulding, newer noise-reduction sliding windows to the balcony, newer A/C and water heater make this condo a must see. This is lake side living at its best, without the high cost. Just steps away from all that makes Winter Park such a special place. Fine dining, great museums, Rollins College and superior shopping are all close by. Lake Virginia Condos has an updated pool and spa, beautiful landscaping, a guest suite for your overnight visitors, workout room, wonderful re-decorated club room with kitchen, outdoor gas grill and fire pit, and a fabulous new boat dock is in the works.

MLS# O5741823

Maitland, Florida - Homes For Sale 1100 S Orlando Ave #101, Maitland, Fl 32751 | MLS Number: O5741823

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1100 S Orlando Ave #101, Maitland, Florida 32751
Price: $269,000

Bedrooms: 2 Bathrooms: 2
Living Square Footage: 1,248

Type: Condominium

Winter Park Chain of Lakes Home Description:
LAKESIDE LIVING! Simply GORGEOUS 2 Bedroom 2 Bathroom END-UNIT Condo in WEST COVE, Maitland ! This exquisite unit offers a breathtaking view of LAKE MAITLAND and lots of windows to allow in the FLORIDA sunshine! The Community offers RESORT STYLE living with amenities that include a clubhouse, a LAKESIDE community pool and spa, a fitness center, bike storage, kayak and canoe storage, docks, a fishing pier, barbecue and picnic area, car wash, security, TWO elevators, on-site manager and maintenance staff, and an assigned covered parking space with additional guest parking. The unit boasts a foyer entry, lots of storage & linen closets, tile in the main area, and carpeting in the main living space and bedrooms. The galley kitchen is sure to delight featuring a window for natural light, updated cabinetry, granite countertops, and ample storage. WEST COVE is centrally located for easy access to highways, a walk to Lake Lily, Maitland Farmers Market, The Enzian Theatre, various restaurants, and shopping! Call TODAY to find out how you can make this YOUR NEW home! **Assigned BOAT SLIPS available on first come first serve basis**


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