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Windermere Homes for Sale

The Butler Chain of Lakes in Windermere is one of Florida’s most popular areas for lakefront property. Located just 12 miles southwest of Orlando, Windermere is a suburban community in close proximity to theme parks. The town is home to Isleworth Golf Club and Keene’s Pointe Golf Club. Yellow Dog Eats, 33 & Melt and Dexter’s of Windermere are some of the popular restaurants in the area. Local parks include Lake Down Park, Palmer Park, Central Park, Fernwood Park, and Park Among the Lakes. Windermere Preparatory School, Premier Academy, and Family Christian School are highly rated private schools.

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Explore all properties for sale in Windermere, FL in the greater Orlando area listed below. As you search through listings please be sure to contact us with any questions or to schedule a viewing.

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11035 Schooner Way Windermere FL 34786

Windermere, FL11035 Schooner Way

Price$7,500,000

Est. Mortgage: $/month

MLS Number O5992601

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 15,000
  • Year Built 2022

Pre-Construction. To be built. Where Art Meets Architecture! Build your Custom Dream Home with state of the art energy efficiency engineering in the tranquility of the sought after Town of Windermere. Surrounded by the Butler Chain of Lakes. Award winning architects, JWB, and award winning builder, William Edward Construction. Per builder, lot can support a 10,000 - 15,000 square foot custom home. Price will vary as applicable.

Listing Courtesy of LAKESIDE REALTY WINDERMERE INC

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Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11940 Lake Butler Boulevard Windermere FL 34786

MLS Number O5992327

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 6,549
  • Year Built 1985

UNIQUE ESTATE HOME SET ON 300 FEET OF LAKE BUTLER SHORELINE WITH 300' SEAWALL. This private, gated lakefront home is set on 2.4 acres in old Windermere, with over 6,500 SF heated and over 10,600 SF covered and under roof; 5 bedrooms, 6.5 bathrooms, a resort style pool overlooking serene Lake Butler. CALLING ALL CAR COLLECTOR AND BOATING ENTHUSIASTS! This home has all of your needs covered with a 5-car garage and 2-car porte-cochere, plus 500-gallon fuel tank and 1000-gallon diesel tank with ability to fuel on the water or in your motor court - a feature you won't find at any other home on the Butler Chain. The “grandfathered” extra wide dock & boathouse features a sun deck, one boat slip and 2 jet ski with electric hoists. There is also a boathouse with bathroom and storage. The previous owner received Orange County approval for a future on-site guesthouse. Windermere is “The Town Among the Lakes,” and is known for its gorgeous estate homes, historic downtown featuring shops, dining, weekly farmer's market, and excellent schools. Don't miss this opportunity to own a large slice of Florida Paradise on the famed Lake Butler, which is a rare opportunity. Book your private tour today!

Listing Courtesy of JULIAN PROPERTIES,INC.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11049 Bridge House Road Windermere FL 34786

Windermere, FL11049 Bridge House Road

Price$6,450,000

Est. Mortgage: $/month

MLS Number O5986780

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 10,112
  • Year Built 2005

Presenting a custom-crafted Mediterranean mansion secluded behind its own private gates, perched along the shores of Lake Butler, inside guard-gated Reserve at Lake Butler Sound. Unmistakable elegance abounds with soaring two-story ceilings, polished travertine and wood floors, arched windows, signature precast stone gas fireplace, multiple oversized French doors, coffered ceilings, and grand details throughout. Built to impress by master craftsman Jim Akers, this estate residence features 5 bedroom suites, 9 bathrooms, executive office, a first-floor gentlemen's card game room with built-ins plus separate home theater within its more than 10,000 square feet of living space. Family gathering areas include the expansive chef's kitchen with island provide a generous space for entertaining and every day living. Top of the line appliances include double dishwashers, six-burner gas cooktop, side by side Sub Zero refrigerators, and two sinks. Covered lanai provides a private resort-style retreat with sparkling pool and spa with waterslide and lazy river-style feature, under a fully-screened colonnade enclosure, plus outdoor family room with gas fireplace and summer kitchen. Set along the shores of Lake Butler on the famed Butler Chain of Lakes, this magnificent property includes 432 feet of lake frontage, including a boat dock with lift. The owner's retreat offers a private sanctuary complete with separate sitting area, large closet with secondary upstairs dressing room with rows of custom cabinets for shoes and dresses - plus double vanities, jetted tub, and walk-in shower within its luxurious setting. The pavered motor court with private gates and 4-car garage sets the stage for secluded lakefront living unlike anything else.

Listing Courtesy of STOCKWORTH REALTY GROUP

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5507 Worsham Court Windermere FL 34786

Windermere, FL5507 Worsham Court

Price$5,949,000

Est. Mortgage: $/month

Pending

MLS Number S5036746

  • Residential
  • Area Windermere
  • Mls Status Pending
  • Square Feet 10,200
  • Year Built 2008

Custom estate perfectly situated on the 14th green of the Isleworth Country Club. This Isleworth mansion features an exquisite transitional, contemporary and timeless interior, beautiful golf views and plenty of space for perfect family gatherings. The unparalleled grand open floor plan greets you with a massive soaring two-story foyer and living room featuring floor-to-ceiling windows with spectacular golf front views. Entertain friends and family in the fully equipped theatre or the generous summer kitchen area complemented by an expansive private pool and spa. Retreat and relax in the elaborate main floor master suite complete with a spectacular marble bathroom featuring deluxe spa, extensive his and hers vanity, multiple showers, a very generous closet and a private terrace to the spa. Create the ultimate atmosphere for entertaining in the formal dining room or al fresco dining in the covered lanai and extensive terraces. This magnificent home and its unique hand-selected finishes include: artisan-crafted cabinetry, grand marble stairs, wood and marble floors, exquisite door frames, unique chandeliers, a formal study with custom fireplace, a spectacular home office, an additional second floor master bedroom, a five-car garage: two of which have been converted to flex study/office/play room areas (can be converted back), elevator, plenty of private outdoor space and basketball hoop. This picturesque home site is move-in ready!

Listing Courtesy of CENTURY 21 CARIOTI

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12422 Park Avenue Windermere FL 34786

Windermere, FL12422 Park Avenue

Price$4,950,000

Est. Mortgage: $/month

MLS Number O5967251

  • Land
  • Area Windermere
  • Mls Status Active
  • Acreage 2.19
  • Subdivision Chaine Du Lac

WELCOME TO PARK AVENUE. This tremendous opportunity offers 2.19 acres of sprawling possibilities with Southeastern exposure and sweeping lake views. Nestled on the gorgeous shoreline of Lake Butler among the famed Butler Chain of Lakes, within one of Windermere's most desirable communities - Chaine Du Lac - this exclusive homesite truly has it all. The gates within the gates that this property offers ensure that the estate that is built here will boast both privacy and security. With over 200 feet of lake frontage and amazing water views you will get to enjoy all of the beauty, nature and wildlife that Florida lake living has to offer. There is a Brazilian hardwood boat dock that leads out over the lake and includes a 2000SF observation deck, boat and jet ski hoist. The property also features private launch access for your personal watercraft and a 3' concrete seawall. The opportunities to build your dreams into reality are limitless. Schedule your showing today! ***Seller will consider a lot split offering 1 acre site offered at $2.6M. Only portion in last image outlined in red represents split option. More information available upon request.***

Listing Courtesy of JULIAN PROPERTIES,INC.

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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9905 Lake Louise Drive Windermere FL 34786

Windermere, FL9905 Lake Louise Drive

Price$4,360,000

Est. Mortgage: $/month

Pending

MLS Number O5945140

  • Residential
  • Area Windermere
  • Mls Status Pending
  • Square Feet 7,122
  • Year Built 2005

Nestled on more than an acre within the private guard-gated community of Isleworth, this extraordinary custom golf-front estate offers exquisite living in the heart of one of the finest golf club communities in the world. Built by leading custom home builder Pellegrini Homes, this stunning Italian masterpiece spans more than 7,100 square feet with lavish detail, impeccable resort-style grounds and plenty of privacy creating a golf-front haven. Beautifully handcrafted cypress grand entrance doors reveal a gracious, open interior featuring custom stone columns, broken-edge Castle tile and a curved, floating staircase. The roof is fully custom with natural terra-cotta tile imported from Colombia, and all of the interior walls are faux, Venetian plaster or trompe l'oeil. From the formal living room with soaring windows framing the tropical pool and grounds to the dining room enrobed in deep red Venetian plaster, the curated interiors were thoughtfully planned to feature custom complementary finishes while offering views of an arch from every angle. An unparalleled venue for indoor-outdoor entertaining, the main gathering area within the home comprises the luxurious custom kitchen featuring a copper ceiling, professional Viking appliances and a large walk-in pantry together with the family room and built-in bar designed after a five-star hotel bar. Oversized hurricane-grade sliding glass doors can be fully pocketed to unite the interior with the expansive screened lanai featuring a large television, fireplace and custom full-size grill outfitted with dual burners, a Viking commercial hood and heat lamps. The estate boasts four en-suite bedrooms including the spacious owner's retreat which offers a peaceful sitting area and a stunning custom bath featuring Kohler's massive RiverBath circular tub, dual vanities, a large walk-in shower, two water closets and a spacious wardrobe with island, cherry built-ins and a second washer and dryer. Unique living spaces within the home include the study, accented by custom cherry cabinets with burl wood inserts and a leathered ceiling, as well as the lodge-style Gentlemen's Private Retreat outfitted with custom pool table, a full bar, exposed wood beams and wormy chestnut walls reclaimed from a 200-year-old Virginian homestead. Twin three-car garages are separated by a private motor court and custom Ramada and offer newly finished epoxy floors and plenty of space for oversized vehicles - a car enthusiast's dream. The fabulous resort-style grounds offer a true island retreat complete with a custom private beach featuring Marco Island sand, a heated saltwater pool with fountains, a formal garden with bronze statues representing the four seasons, a gazebo and a custom putting green-all surrounded by an abundance of lush, tropical landscaping with views of Isleworth's 16th tee.

Listing Courtesy of ISLEWORTH REALTY LLC

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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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11307 Bridge House Road Windermere FL 34786

Windermere, FL11307 Bridge House Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number O5923495

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 6,661
  • Year Built 2006

Elegantly appointed Mediterranean home built by Ray Coudriet located on the Butler Chain of Lakes. Beautiful property for the discriminating buyer nestle directly on Lake Butler. 5 Bedrooms, 5.2 Baths, with Direct access to the BUTLER BAY CHAIN of LAKES consisting of over 11 lakes and in the exclusive community of The Reserve at Lake Butler Sound. This wonderful home boasts designer touches throughout, including your own Elevator, 2 Sets of Stairs, Theatre downstairs as well as Master Bedroom, Study, and a Second Bedroom. Grand Foyer leads to a welcoming Living Room with unsurpassed views of Lake Butler and opening up to a Private Terrace leading to a timelessly designed Pool and Spa, and Extensive Patio and Gardens. Grand Foyer boasts an elaborate hand painted ceiling canvas with ceilings opening up to the second floor. Other features, are huge closets, pantries, custom built-ins throughout, 2 Terraces and 2 Balconies. Outdoor Large Terrace with Stone fireplace perfect for entertaining, master with sitting area, outdoor bathroom and shower plus complete summer kitchen with Fridge, Cook Top, Grill, Sink and lots of Cabinetry. Outdoor spaces and Gardens and pool are designed with timeless Elegancy and Craftmanship.

Listing Courtesy of REAL ESTATE FIRM OF ORLANDO

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$
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$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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13125 Casabella Drive Windermere FL 34786

Windermere, FL13125 Casabella Drive

Price$3,699,000

Est. Mortgage: $/month

MLS Number O5978607

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 7,561
  • Year Built 2018

Smart Mansion at Casabella. Welcome to the Toll Brothers "The Marcello", a 7,561SF home is fully automated and integrated with Alexa you can control the entire home through a IPAD or on your phone anywhere in the world. This 5 Bedroom home sits on a prime half acre lot with a pond in the front and rear for your privacy. You will enjoy peace and quiet with the sound of the fountains on your back and front yard pond. The moment you enter the home tranquility reigns, with a gorgeous double staircase and balcony that will stand out from any other home in the neighborhood. On the first floor you will find a large Master Bedroom Suite with a view to the pond and features a oversized Master Bathroom with two generously sized walk-in closets. On the second floor, there are 4 extra size bedrooms featuring its own ensuite bathroom. A huge flex space upstairs offers plenty of room for a game room, homework nook, or even a second living room. The kitchen is equiped with top of the line Jenn-Air appliances, beautiful counter tops, and loads of cabinet space. In the kitchen/Eating Kitchen/Living Room space is suited for entertaining as it is large and open area where you will find 2 X-Large Size Wine Coolers with capacity of 320 bottles and a wet bar. With ceramic porcelain tile on the main areas will bring a touch of modernity combined with the Italian Furniture and artworks making this home magnificent, on the staircase and second floor the charm of the hardwood flooring takes to a warm and cozy feeling. Once you arrive at the enclosed patio you will find the amazing summer kitchen, fully equiped with top choices Pizza Oven, BBQ Grill, Refrigerators/coolers so you can entertain all your guests on this totally climatized space built with hurricane graded windows and doors, leading to the pool area now you are on the most amazing backyard with your 850SF pool and Jacuzzi surrounded by podocarpus and hand picked plants and trees. Now is time to make the dreams come true, this awarded community "Casabella at Windermere" is strategically located in Windermere near to SuperMarket, Shopping, Hospitals, Gym, highways and Disney Parks, great place for jogging, bike ride, morning walks. searching for tranquility and quality of life, the possibilities are endless.

Listing Courtesy of LA ROSA REALTY,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6845 Valhalla Way Windermere FL 34786

Windermere, FL6845 Valhalla Way

Price$3,499,000

Est. Mortgage: $/month

MLS Number O5988419

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 7,438
  • Year Built 2012

Keene's Pointe stunning estate home located on the 17th fairway of The Golden Bear Club featuring golf, tennis, fitness, swimming and dining. This home has it all. From the moment you enter through the beautiful leaded glass doors, you are greeted with quality from the stone and hardwood floors to the custom features throughout. Formal living and dining rooms set the stage and take you to through the wet bar with refrigeration and a wine cellar to the well-appointed kitchen with large walk-in pantry, 2 dishwashers, and Wolf and SubZero appliances. The family room boasts custom built-ins, a gas fireplace, wood beamed ceiling and two sets of glass doors leading to the lanai. Off the family room is the game room with 1/2 bath and a bar, perfect for entertaining. There is also an office with built-ins and French doors accessing the front porch. Across from the office is the first ensuite with walk-in closet. The master suite overlooks the pool and has a spectacular bath with two closets, jetted tub and a hide-away door leading you to the first set of garages. There are also two more ensuites downstairs with walk-in closets, a spacious laundry and mud area with built-ins. The beautiful hardwood staircase leads you to the second floor to the great room with wood-paneled ceiling, wet bar with ice and refrigeration, built-in bookcases and balcony overlooking the golf course. Also upstairs is a half bath and the 5th ensuite with walk-in closet. The screened lanai is the perfect setting for entertaining or relaxing with heated salt water pool/spa, paved deck with living and dining areas, gas fireplace and summer kitchen. There is so much more to offer, call for your private viewing today.

Listing Courtesy of SOUTHERN REALTY GROUP LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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13643 Lake Cawood Drive Windermere FL 34786

Windermere, FL13643 Lake Cawood Drive

Price$3,200,000

Est. Mortgage: $/month

Pending

MLS Number O5973104

  • Residential
  • Area Windermere
  • Mls Status Pending
  • Square Feet 8,203
  • Year Built 2017

Luxury HOME 8 Bedroom (all Suite) - with One acre lot in exclusive Lake Cawood Estates in Windermere. Built from ICF insulated concrete blocks for superior energy efficiency and hurricane protection with foam roof insulation, barrel tile roof and $25k whole house generator included. Built only three years ago this home features the latest in technology and designer trends-whole house zoned audio system, multi point camera security system, 4 tankless energy efficient hot water heaters, three top of the line American Standard a/c units, designer light fixtures, wood plank effect ceramic tile flooring to all common areas, luxury bathrooms to ALL bedrooms. Triple attached garage and attached carport for plenty of parking spaces and storage. The huge block paved driveway at the front of home leaves plenty of space for guests too. The home features multiple living spaces-the formal sitting room to the front of house with faux fireplace, the large family room that acts as the hub of the home and den off the kitchen as an ideal informal hang out or playroom. The formal dining room features a custom ceiling with LED lights, silver tile feature wall and plenty of space to seat 12 in comfort. Butler's pantry just off the dining room has sink, beverage fridge and cabinets. The kitchen is a chef's dream with GE Monogram appliances throughout including a built-in pizza oven, two dishwashers, gas range and electric double wall oven. Huge kitchen island with waterfall edge granite worktop. The informal breakfast area has a custom table with matching granite top included in the sale. Large walk-in pantry with separate 'mud room' with dual beverage fridges, washer and dryer and ample storage as well as access to car port. All 6 bedrooms have private baths, walk-in closets-Two bedrooms have custom closets by California Closets. Large guest suite downstairs with direct pool access, all other bedrooms upstairs. Multipurpose room also features its own bathroom upstairs and currently used as a playroom and movie theater with screen and projector included. Could be used as a 7th bedroom. Huge loft area with bar including two refrigerators, dishwasher, ice machine, and sink is a great entertaining space. Access to the south balcony where you can view Disney fireworks from the comfort of your home. Second laundry room upstairs with washer, dryer, ample cabinets and Belfast sink. Outside the home really wows-A huge lanai houses a custom built summer kitchen with waterproof cabinets-48” DSC grill, separate teppanyaki cooking surface, multiple fridges including a beer tap, ice maker and so much more. Undercover dining space and seating area. Leading from the lanai is the fantastic pool, custom designed and built by well-respected Artisan Pools. Water feature powered by separate pump, LED lighting, separate raised spa and waterproof TV included in sale. Top of the line electric and gas water heaters installed. Synthetic grass surrounds the pool area leading to fire pit patio. Separate gym / multipurpose room accessed via courtyard with rubber flooring and mirrored wall. The level acre lot affords a huge yard for anything you can dream of. Located less tha a mile from Publix and multiple restaurants the location cannot be beat and zoned for new Windermere High School. Too many features to mention in this beautiful home.

Listing Courtesy of WEBB FLORIDA REALTY LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4705 Joanna Garden Court Windermere FL 34786

Windermere, FL4705 Joanna Garden Court

Price$3,185,000

Est. Mortgage: $/month

MLS Number O5956126

  • Residential
  • Area Windermere
  • Mls Status Active
  • Square Feet 6,060
  • Year Built 2007

Exquisite Mediterranean trophy home located in world renowned Isleworth Golf and Country Club. This magnificent estate features 4 bedrooms, 4 full baths, 2 half baths. Finished with the highest quality materials and craftsmanship and stunning architectural details. Oversized gourmet kitchen with walk in pantry. There are two master suites and detached guesthouse. Fantastic outdoor living and dining area with fireplace, summer kitchen with amazing pool and spa. Isleworth is conveniently located minutes from the attractions, restaurant row, The Millenia Mall, and Downtown Orlando. Members of Isleworth Country Club can enjoy world class amenities with unrivaled service.

Listing Courtesy of MASTERS REALTY INTERNATIONAL LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3959 Mckinnon Road Windermere FL 34786

Windermere, FL3959 Mckinnon Road

Price$3,000,000

Est. Mortgage: $/month

MLS Number O5967487

  • Land
  • Area Windermere
  • Mls Status Active
  • Acreage 6.35

Fantastic development opportunity! Desirable Windermere location - 6.35 acres on McKinnon road perfect for new custom home development. Across McKinnon Road there is an additional .44 acre lot on the lake. There is a total of 6.79 acres for sale and two legal descriptions on this listing. This parcel offers a unique development opportunity for homes with very large lots and is surrounded by homes in the 1-2M+ range. Conveniently located near shopping, Braddock Park and easy highway access.

Listing Courtesy of CARLISLE REALTY,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.45% last updated on Jan 13, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to MFRMLS as of January 20, 2022 . All data is obtained from various sources and has not been, and will not be, verified by broker or MFRMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.