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Winter Park Homes for Sale

Winter Park, FL is a family friendly, upscale suburban community. The city is located just seven miles northeast of Orlando. Park Avenue has a variety of upscale shops, restaurants, and art galleries. Winter Park Village offers outdoor shopping and restaurants. Popular nightlife attractions include Luma, Prato, Cocina 214, and Boca. Central Park has beautiful fountains, a rose garden, and seasonal events. Homes in Winter Park include condos, townhomes, and single family homes. The city is home to Rollins College, a private coed liberal arts school founded in 1885.

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Explore all properties for sale in Winter Park, 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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1245 W Fairbanks Avenue Winter Park FL 32789

MLS Number O5898942

  • CommercialSale
  • Property SubType Office
  • Subdivision Killarney Estates
  • Square Feet 20,384
  • Acreage 1.05

Winter Park, FL Iconic, Landmark, Trophy Property. Fully leased with long term credit tenant history. High Visibility Prime Corner location at Fairbanks Avenue and 17-92 (Orlando Avenue) in Affluent Winter Park, an affluent sub-market of the Orlando Florida area. Extremely stable investment with minimal landlord responsibilities. Recently Modernized Elevators, Each Elevator opens directly to each full floor office suite. Recent Fire System Devices replaced throughout the building. Recent lobby and bathroom renovations. Truly a unique investment and 1031 Exchange opportunity for investment. Ample Surface Parking. Free Standing 3 lane Bank Drive Through. Full Financials are available upon request to a qualified buyer investor. 1031 Exchange Opportunity. Thank you for looking.

Listing Courtesy of FLORIDA PREMIER REALTY GROUP

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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1001 Anchorage Court Winter Park FL 32789

Winter Park, FL1001 Anchorage Court

Price$5,750,000

Est. Mortgage: $/month

MLS Number O5910921

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 9,277
  • Year Built 2020

Magnificent new construction Downtown Winter Park estate, built by one of the country's top builders, this architectural masterpiece is situated just steps from Park Avenue's upscale shopping & restaurants. This fabulous estate features 5 bedrooms, 6 ½ baths and over 9,000 square feet of living space . The great room features 18 ft ceilings, oversized doors and arched windows allowing an abundance of natural light, stunning floor to ceiling Nero Marquina marble fireplace and laser cut stainless art panels. The main floor is covered in white Thassos marble accented with black granite inlays. The SEMTA custom cabinetry kitchen is a modern chef's dream, boasting high gloss imported cabinetry, cabinet doors polished to a mirror finish, a La Cornue stove, Subzero and Wolf appliances as well as Calcutta marble countertops. The adjacent spacious family room overlooks the pool and spa as well as the fruit garden. The first floor master retreat has over 1200 sq ft with a one of a kind custom closet, a gas fireplace, a 12 ft zero entry shower and hardware by Lefroy Brooks . The main floor also features his and hers large offices, complete with marble covered wet bar, and state of the art automation. The 90 ft grand hallway is highlighted by a sweeping stair and spectacular iron railing. The upper level features 4 oversized En Suite bedrooms that lead out to an enormous 60ft wide deck that overlooks the pool and spa, stately rear yard with fruit trees and a putting green. A juice bar kitchen is a wonderful addition to your own 1500 sq ft gym, featuring cardio room , free weight room tv, speakers, floor to ceiling mirrors and more . The home continues to impress with custom millwork throughout, two laundry rooms and bespoke lighting fixtures with Control 4 automation. Perfect for outdoor entertaining, the home showcases a summer kitchen equipped with beverage fridge, prep area and Viking cooktop as well as a separate 50 ft lanai. For the car collector, there are dual two car garages with custom glass doors. Outside you will find a large travertine courtyard drive, leading to an expansive corner lot all this on a quiet cul-de-sac just a short walk from Park Ave. One or More photos has been virtually staged.

Listing Courtesy of COLDWELL BANKER REALTY

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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55 Trismen Terrace Winter Park FL 32789

Winter Park, FL55 Trismen Terrace

Price$4,895,000

Est. Mortgage: $/month

MLS Number O5932285

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 6,690
  • Year Built 1955

Presenting to the market for the first time in 54 years and on a double lot with approximately 200 feet of water frontage within footsteps of Park Avenue, situated on Lake Osceola. Exquisite estate resting on two waterfront lots that introduce you to luxury living with endless possibilities. This park-like, incredible property can be kept as one expansive lakefront estate. The main residence is a four-bedroom home with five baths, along with a separate one-bedroom, one-bath guest house. Encapsulated by gorgeous greenery and lush landscape, the property resembles a perfect blend of elegance and seclusion. Natural light floods the interior through floor-to-ceiling windows and glass doors. The master suite invites you to unwind and relax and features a spa-like bath with dual vanities, a separate shower and a generous walk-in closet. Tropical tranquility awaits outside with a palatial pool and sitting area surrounded by natural beauty. Make your way to the guesthouse, comprised of soaring wood ceilings and an abundance of casement windows. A boater's haven, this residence offers a boathouse and dock on Lake Osceola, allowing you to set sail from your backyard. Further features include natural gas service, three tankless hot water heaters, five air conditioning units in the main house and one in the guest house, whole house generator, as well as an oversized two-car garage with a motor court. This magnificent property has been lovingly maintained over the decades with well-designed additions and renovations, and magnificent grounds and landscaping. Encompassing nearly 8,000 total square feet on approximately an acre of property, this lakefront gem is a picturesque paradise just waiting for your arrival.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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171 Genius Drive Winter Park FL 32789

Winter Park, FL171 Genius Drive

Price$4,095,000

Est. Mortgage: $/month

MLS Number O5933713

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,273
  • Year Built 2000

An exquisite Chain of Lakes offering awaits the most discerning of lakefront homebuyers in the heart of Winter Park. Being presented for the first time on the market, this meticulous masterpiece was built by Carlos Posada and boasts authentic Charleston architecture with the utmost attention to detail throughout. The main home has +/- 4,300 square feet and the media room or private guest quarters w/ full bath over the garage has an additional +/- 950 square feet. Upon arrival, you are greeted by a beautiful brick paver driveway that winds through lush landscaping with a mature tree canopy and gorgeous greenery. The solid mahogany double entry doors invite you inside to a gracious interior flooded with natural light. Complemented with reclaimed gorgeous hardwood flooring throughout, the first floor is comprised of spacious living areas that are perfect for entertaining. The gourmet kitchen welcomes the chef in the family with inset cabinetry, a 60-inch Viking range, a large island with seating and a spacious dining area with a fireplace. A separate dining area is just down the hall for more formal occasions with doors opening to a fabulous private courtyard with fountain. Family and friends can gather in the great room, adorned with built-ins and a wall of windows and doors that offer awe-inspiring views of the pool and lake. Retreat to the first-floor master suite, a secluded escape with French doors that lead to the outside, along with a spa-like master bath complete with dual vanities, a soaking tub and a separate double-head shower. With three more bedrooms and an open loft upstairs, there is plenty of room to accommodate family and friends. Meanwhile, recreation abounds with a bonus room over the three-car garage. Complete with a full bath and private entry, this space offers plenty of entertainment flexibility or would work well as an additional, private fifth-bedroom suite. Further features include a side entry with a mudroom and a large laundry room. An opulent oasis, the sprawling backyard (arguably the best lot with a deeper peninsula on the eastern shore of Lake Mizell) encompasses a paver patio with a seating area and overlooks the stunning pool area. The stunning scenery is enhanced with lovely lake views and a boat dock on the water. Ideally situated on Lake Mizell and set back from the street, this home is adjacent to the Windsong community but is one of only four lakefront properties without the HOA obligation. For your picturesque piece of paradise, this remarkable residence embodies luxury living at its finest.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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690 N New York Avenue Winter Park FL 32789

Winter Park, FL690 N New York Avenue

Price$3,850,000

Est. Mortgage: $/month

MLS Number O5935400

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,901
  • Year Built 2021

Pre-Construction. To be built. Greens at Park. This address says it all…690 N. New York Avenue, where unparalleled luxury meets quintessential Winter Park lifestyle. Iconic English cottage architecture. This is a once in a lifetime opportunity to own a single family (fee simple) luxury real estate home in the heart of Winter Park. Located just steps from Park Avenue's upscale shops and restaurants while providing stunning views of the famous Winter Park golf course. The 6 estate lots will be built by the distinguished, FG Schaub Custom Homes known for his Grand open space which has become synonymous with him and his architect David Larson, Ltd. These homes will be fully customizable yet offering several luxury features: -Energy-efficient homes with the latest in smart home technology -Interior features include 11'4'' ceilings on the first floor and 9'4” on the second floor -Transitional room with a retractable screen and custom pool -Sub-Zero/Wolf appliance package including the washer and dryer -Fitness room with rubberized flooring, and many more high-end finishes -Each home will be equipped with a customized elevator As part of this exclusive community the exterior maintenance will be handled by the association, making the Greens at Park truly a sanctuary to call home. *Photos are not actual and are intended for inspirational purposes.

Listing Courtesy of THE HOPE GROUP

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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5500 Howell Branch Road Winter Park FL 32792

Winter Park, FL5500 Howell Branch Road

Price$3,500,000

Est. Mortgage: $/month

MLS Number O5919481

  • Residential
  • Area Winter Park/Aloma
  • Mls Status Active
  • Square Feet 2,363
  • Year Built 1986

Rare 10+ acres with 3 adjoining parcels 5500,5490,5510 in Winter Park. Potential Commercial Perfect opportunity to build multi-family, subdivision, strip mall, church, or private estate. This property offers endless possibilities for development. located off the main highway and minutes from downtown winter park. Seller motivated will entertain all reasonable offers. Seller financing available.

Listing Courtesy of LEGACY REALTY HOLDINGS LLC

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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511 W Canton Avenue Winter Park FL 32789

Winter Park, FL511 W Canton Avenue

Price$3,500,000

Est. Mortgage: $/month

MLS Number O5941194

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 8,910
  • Year Built 2013

Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge a connection with nature. Expansive entertaining spaces flow outside to the Grande Courtyard. Commercial grade Chef's Kitchen with three stately islands and solid granite waterfall counters above the polished porcelain glass tile accentuate natural light. Dimmable lighting allows for opulent control of mood and ambiance. Private bedroom suites, all boast sleek en-suite baths, generous closets with elaborate built-ins, wonderful views, and private courtyard access. Every detail was carefully selected and quality crafted for efficient and luxurious living. An automatic shade system gifts seclusion at the touch of a button. The Spacious Master Bedroom is the ultimate retreat with spa-style amenities. A custom-designed 19+ car garage, with 20' ceilings, and ample space for lift installation awaits the exotic and classic car collector or RV enthusiast. This secured automotive palace also features temperature control and abundant lighting. Enjoy refined boutique shopping and fine dining as you stroll Park Avenue from home. Convenient access to Orlando's entertainment venues, theme parks, cultural centers and coastline. Ask your CPA about the advantages of transitioning to Florida Homestead & schedule your exclusive private tour of this remarkable residence today.

Listing Courtesy of CHARLES RUTENBERG REALTY ORLANDO

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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1210 Alberta Drive Winter Park FL 32789

Winter Park, FL1210 Alberta Drive

Price$3,495,000

Est. Mortgage: $/month

MLS Number O5936507

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,449
  • Year Built 1991

An exquisite European retreat on nearly an 3/4 of an acre with lake frontage featuring a private dock across the street, on Lake Osceola on the Winter Park Chain of Lakes. This location is unmatched in privacy, in one of the most pristine areas of Winter Park, a short distance to Park Avenue, and situated on a double lot tucked away on a dead-end street. A meandering brick walking path leads you to the recently renovated lakefront boat dock with plenty of room for entertaining or just soaking in the gorgeous sunsets. This custom home enjoys nearly 5,500 square feet and many possibilities to make the function suit your family, boasting 4-5 bedrooms, a downstairs master and an additional first-floor guest or in-law suite. In addition, formal dining, living spaces with hardwood floors, an open kitchen family plan with doors to the covered porch, pool and a generous backyard, with over 31,000 square feet in total. An expansive island is the focal point of the kitchen with exotic granite countertops, Wolf stainless steel appliances, an eat-in kitchen area and travertine floors. Outdoor living features beautiful slate decking, a breezy lanai, pool/spa a summer kitchen with an additional side patio, all add to the elegant lifestyle. The property is surrounded by a detailed brick wall adding to the beauty of the grounds. The details are endless, with meticulous craftsmanship in the intricate moldings, volume-detailed ceilings, hardwood floors, main and back staircases, slate roof and three masonry gas fireplaces with a hand-carved marble mantle in master. A three-way split plan offers incredible privacy for all. A three-car garage with two circle driveways, perfect set up for entertaining, are just more reasons to make this your home. This is a rare offering call today for a private showing.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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2403 Euston Road Winter Park FL 32789

Winter Park, FL2403 Euston Road

Price$3,490,000

Est. Mortgage: $/month

MLS Number O5887686

  • Land
  • Area Winter Park
  • Mls Status Active
  • Acreage 8.34
  • Subdivision Glencoe Sub

Bring your seaplane and build your lakefront masterpiece. Situated among million-dollar properties, this is prime waterfront with approximately 432 feet on a private peninsula of spring-fed & pristine Lake Killarney. This is actually two lots (total of 1.514 buildable acreage). Seaplanes land at local favorite Hillstone for lunch and by the evening, the fire pits are lit to watch daylight fade and the stars awaken. This hidden gem is located within proximity to Winter Park's exclusive shopping and dining. Residents can work, play and take advantage of all the nearby cultural offerings. Lake Killarney spans 234 acres & is known for nature watching, scenic strolls, paddleboarding, watersports, waterplanes, elegant waterfront dining at nearby venues and much more. Lake levels are properly maintained with 2 drainage wells. Centrally located - near Winter Park Village, Rollins College, Park Ave Shopping District, Farmers Market, Whole Foods and more. Lake Killarney offers true privacy, with no public access. This property offers land, lifestyle and location. *Sale includes 2 lots: 2401 & 2403 Euston.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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315 Virginia Drive Winter Park FL 32789

Winter Park, FL315 Virginia Drive

Price$3,150,000

Est. Mortgage: $/month

Pending

MLS Number O5919018

  • Land
  • Area Winter Park
  • Mls Status Pending
  • Acreage 1.22
  • Subdivision Shadow Hill

WINTER PARK CHAIN OF LAKES Construction ready 1.22 acre Lot...bring your own builder! Rarely Available Old Winter Park home site on pristine Lake Virginia with unspoiled views looking out towards the Nature Conservancy and Rollins College. Nestled among stately classic Florida homes and mature cypress, this desirable “.68 acres high and dry” ready-to-build site with a new boat house is located on a quiet cul-de-sac perfect for family and friends. An Easy Breezy bike ride or walk takes you to all the charms of downtown Winter Park and Rollins College. We think you will agree; this neighborhood is one of the region's most sought after for its walkability, resort lifestyle and character. A full set of city-approved blueprints for a 12,000+ Environmentally Responsible luxury residence are included in the sales price...save a significant amount of time and money without demolition costs or site prep! Executed by Master Builder Jones Clayton Construction and highly noted Mark-Michaels Interior Design; adapt the plan with this Award Winning Team or bring in your own creatives and make a personal statement on this significant lakefront property.

Listing Courtesy of STOCKWORTH REALTY GROUP

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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125 S Interlachen Avenue Winter Park FL 32789

MLS Number O5930531

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,160
  • Year Built 2020

Life doesn't get more luxurious or convenient than at South Interlachen Place! This prestigious community consists of six exquisitely built townhomes, boasting turn-key living at its finest. Expanding over 4,000 SF, Unit 6 is the marquis CORNER UNIT, and showcases the perfect blend of privacy and accessibility, with high-end finishes in all directions. The ideal and functional floorplan is complimented by a private elevator, oversized 2-car garage with a storage room, premium LED lighting controlled by the Lutron system, and expansive floor-to-ceiling Low-E, UV-tinted windows that welcome an abundance of natural light. The front patio greets guests as they enter the living space on the main level. This FIRST LEVEL includes a state-of-of-the-art kitchen offering Sub-Zero and Wolfe appliances, a natural gas cooktop, full wine refrigerator, island with seating, living room/dining room combo, and sunny nook for a dinette table or a cozy TV area in the kitchen. The SECOND LEVEL houses the private Main Suite, luxe main bath with a spectacular walk-in closet, a laundry closet with a washer and dryer, and an office/flex space complete with built-in cabinets, stone countertops, and a beverage refrigerator. On the THIRD LEVEL you will find an open bonus room, plus 2 more sunny bedrooms, with wood floors and fabulous closets, and 2 bathrooms. Enter the townhome from your individual elevator, and ride past the 3 levels of living space up to the ROOFTOP TERRACE, where you'll find a full summer kitchen, a gas fireplace, and a covered area for dining. This entertaining area also offers a powder bath, just steps away. The expansive individual garage bays and storage rooms are located beyond the main gated entrance to the underground garage, with guest parking. Only 3 of the newly constructed townhomes remain available. Designed by award-winning Slocum Platts Architects, the premium construction utilizes smart technology for lighting, security, and energy efficiency. Located only steps from Park Avenue's shops and restaurants, South Interlachen Place offers the ultimate affluent lifestyle. * Please ask for a Floorplan, Spec Sheet, and preview the 2 attached Virtual Tours: Matterport and a Video Tour!

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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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1806 Gipson Green Lane Winter Park FL 32789

Winter Park, FL1806 Gipson Green Lane

Price$2,800,000

Est. Mortgage: $/month

MLS Number O5916871

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,481
  • Year Built 2001

Over-Sized Lot. The fabulous Winter Park Custom Builder Rex-Tibbs has designed this Winter Park home, that is located in one of Winter Park's most beautiful and private neighborhoods, no HOA, situated in a Cul-de-sac street. It is serenely nestled between the shores of Lake Maitland and the historic Park Avenue of Winter Park with custom designed landscaping and paver driveway. This Mediterranean home sits on nearly HALF an Acre and is designed with rounded archways, barrel tiles roof, volume high ceilings and French doors. Very desirable split floor plan with Master Suite, home office and Cabana bath on the 1st floor. Master Bathroom with double vanities, his & hers walk-in closets, jetted spa tub, walk-in shower with tile inlays. Bright-open and airy feel to this home with plenty of natural sunlight with deep crown & base molding and maple floors. The gourmet kitchen boasts a Center Island and sunny breakfast nook, 5-burner natural gas range, GE Monogram Stainless Appliances, granite surfaces and abundant cherry wood cabinets. Kitchen/Family room combo is the heart of this home with wet bar area and a marble fireplace. The backyard has a covered sitting area, off the pool with retractable power awning, retractable power screens around the pool area and an outdoor natural wood fire pit with lovely wood seats around it. The pool that is heated with solar and electric system. Private gym and infrared sauna upstairs. 3 cars oversize garage with custom build cabinets and shelves. This home is a must see, with quick walk to Park Maitland School located a few steps down the street! has upgrades worth more than 150K.

Listing Courtesy of RINKER REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 2021
* 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 May 14, 2021 . 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.