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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: 2.97% last updated on Feb 25, 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$6,595,000

Est. Mortgage: $/month

MLS Number O5916191

  • 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 the first time ever as three properties combined over the years all within footsteps of Park Avenue and situated on Lake Osceola. Exquisite estate resting on three waterfront lots totaling 1.5-2 acres of land that introduces you to luxury living with endless possibilities. This “park-like” incredible property can be kept as one large estate or divided into as many as three lakefront and/or canal properties. Among the offerings are a four-bedroom main house with five baths, along with a separate one-bedroom, one-bath guesthouse. 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, featuring a spa-like bath with dual vanities, a separate shower and a generous walk-in closets. 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 own backyard. Further features include natural gas service, three tankless hot water heaters, five air-conditioning units in the main house and one in the guesthouse, whole house generator, as well as an oversized two-car garage with motor court. This wonderful home has been lovingly maintained over the decades with well designed additions/renovations and magnificent grounds/landscaping... Encompassing nearly 8,000 total square feet upon two spacious acres, 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: 2.97% last updated on Feb 25, 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 mew 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: 2.97% last updated on Feb 25, 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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1460 Via Tuscany Winter Park FL 32789

Winter Park, FL1460 Via Tuscany

Price$4,250,000

Est. Mortgage: $/month

Pending

MLS Number O5924805

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 7,535
  • Year Built 2009

Truly unrivaled opulence! An architectural and design masterpiece, this breathtaking estate boasts elegance at its finest. Nestled on Winter Park's most desirable drive, Via Tuscany, this property defines quintessential Winter Park luxury, providing ample privacy and ultimate exclusivity. Boasting 7,535 square feet of unparalleled luxury and exquisite finishes, this home has every 1st class amenity imaginable - ranging from a charming carriage (guest) house to rare natural slate and copper roof and gutters. Custom built with immaculate design and intentional charm around every corner, this light and airy home features 6 bedrooms, and 6.2 bathrooms. The first floor reveals stunning Pecky Cypress beams, a romantic master suite with timeless character, a sitting room, spacious walk-in closet and rich design that draws you out the French doors into the stunning gardens and pool. Also situated on the main floor is a dining room, office/lounge, multiple living rooms, 2 fireplaces, butler's pantry, laundry, and work station. The luminous kitchen is a chef's dream with top-of-the-line Wolf, Sub-Zero and Meile appliances, Busby cabinets throughout adorned with Calacatta Gold marble counters. Moving into the great room you'll find floor to ceiling folding glass doors that vanish, allowing flawless indoor/outdoor living that opens to the exceptional outdoor space hosting a tranquil heated pool and spa, gardens and fully equipped summer kitchen. Crafted with wide-plank natural oak floors and elegant lighting and drapery throughout the home, no detail is spared. On the 2nd floor, a grand layout reveals character and design throughout each of the 4 upstairs bedrooms and 3 bathrooms, all equipped with walk-in custom closets, beautiful marble finishes and unique design features throughout. An upstairs laundry, gym/flex room, work station and sitting area provides maximum use of the grand layout. Additional conveniences include smart home capabilities, tankless water heaters, and security. No detail was spared for this unmatched Winter Park escape.

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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1830 Gipson Green Ln Winter Park FL 32789

Winter Park, FL1830 Gipson Green Ln

Price$4,195,000

Est. Mortgage: $/month

Pending

MLS Number O5902307

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 6,444
  • Year Built 1999

Luxury and elegance abound in this private, gated Winter Park Chain of Lakes estate, nestled on almost an acre at the end of a secluded cul-de-sac, with elevated views of beautiful Lake Maitland. Remodeled by award-winning interior designer, Betsy Godfrey, and designed with entertaining in mind, the rooms are large, timeless and sophisticated. Entry foyer has 14' custom doors, Onyx and Italian marble floors, and opens onto living room and dining room with floor to ceiling windows with lake views. Gourmet kitchen with Caesarstone counters, Sub Zero refrigerator & freezer, refrigerator drawers, Wolf gas stovetop, double ovens & dishwashers, and Miele built-in microwave, steamer, and coffee maker. Floorplan is fantastic with kitchen open to family room with gas fireplace and a wall of folding glass doors, spacious “Museum Room” & wet bar, climate-controlled wine room with brick floors, 2 offices, huge upstairs bonus, and 3-way split bedroom plan with downstairs master and downstairs guest suite. Master suite has 2 oversized walk-in closets and one of the most luxurious marble clad bathrooms of all time centered on a glass shower with 2 rain showers & high velocity water massager, plus jacuzzi tub, towel warmer, and endless storage. Upstairs houses 3 bedroom suites and bonus room. Features include Venetian plaster walls, Oak hardwood floors, plantation shutters, remote controlled blinds, designer wallpaper, intricate millwork, 3 car garage. The back has multiple patios - the summer kitchen, the central patio, and the fireplace area off of master bedroom, all overlooking the gorgeous black bottom pool and travertine deck. Boat house with 2 lifts for jet ski & boat. Perfect Winter Park location, close to Park Avenue and all that downtown has to offer.

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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433 E New England Avenue Winter Park FL 32789

MLS Number O5922446

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 8,325
  • Year Built 1905

Known as the Webster-Wagner House this extraordinary residence exudes vintage character and timeless charm, located on one half acre in downtown Winter Park. This historic home's original construction dates back to 1920. This property has been beautifully restored, renovated, and expanded in 2009; thoroughly updated for today's modern world. With its exceptional craftsmanship of the original construction and meticulous renovation; the home maintains the charm of a historic home with the ease and comfort of newer construction. This inviting floor plan offers a variety of spaces for family to connect, study, and work; perfect for todays lifestyle. The inspired entry and foyer allow a visitor to enjoy a sense of arrival. The formal areas are elegantly appointed and accented throughout with natural light. A completely unique office/library is private with extensive custom built ins and highlighting the finer woodwork of the Craftsman Society. Completely redone the fabulous gourmet kitchen with oversized islands and a bar with wine area are perfect for entertaining family and friends. Complete with stone flooring, marble countertops, top of the line stainless appliances, and an abundance of custom cabinetry the kitchen is a chefs delight. Entertain family and friends in the gracious family room, nicely finished with stone flooring and a fireplace leading to covered porch and sparkling heated pool and spa. The double master retreats offer privacy with large closets and spa like master baths. Large secondary bedrooms are in keeping with growing and extended families. A separate guest house is great for extended visitors. This timeless property is located within walking distance to fabulous Park Avenue known for fine dining, bistros, and great shopping.

Listing Courtesy of CORCORAN PREMIER REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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$3,500,000

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: 2.97% last updated on Feb 25, 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: 2.97% last updated on Feb 25, 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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668 W Morse Boulevard Winter Park FL 32789

Winter Park, FL668 W Morse Boulevard

Price$3,485,000

Est. Mortgage: $/month

MLS Number O5815144

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,819
  • Year Built 2020

Under Construction. Introducing Phil Kean's latest project - The Morse + Pennsylvania Townhomes. A private enclave of high-end urban lock + leave residences comprised of 3 single family homes and 4 shared-wall townhomes. This Phil Kean Designs 3-story home has 5819 heated SF of gorgeous, breath-taking living, along with a private yard, refreshing cocktail pool, summer kitchen, multiple outdoor lanais and terraces, and a three-car attached garage! A private elevator gives you access to all three floors, from the chef's kitchen and living areas on the first floor, the master suite with loft and office on the second floor, and three additional ensuite bedrooms plus a 22x15 loft and a covered lanai and open terrace on the third floor. Interiors done by Phil Kean Interiors using high-end finishes, a designer lighting and plumbing package, a Wolf/Subzero appliance package, an all marble master bath, hardwood floors, and much more. Sliding glass walls and tons of windows give this home plenty of natural light. Ten foot ceilings and a 2-story family room elevate this home's wow factor! Centrally located in Winter Park's downtown corridor, you can walk to Park Avenue, Hannibal Square, the Farmer's Market, Hillstone's and more! Easy access to I-4, Advent Hospital and downtown Orlando. Call today for more information. Five of the seven total residences are already under contract with building 5 selected to be 2021's New American Home.

Listing Courtesy of PHIL KEAN REAL ESTATE LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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650 Clay Street Winter Park FL 32789

MLS Number O5852283

  • CommercialSale
  • Property SubType Office
  • Subdivision Lawndale Annex
  • Square Feet 12,287
  • Acreage 0.17

List Price includes 3 parcels: This listing includes two other Parcels that are all being sold together. Parcel 12-22-29-5000-04-040, which is a parking lot that serves as this parcel's parking lot. Parcel 12-22-29-5000-04-011, is a one-story building also owned by the seller. See MLS Listing #o5852270 for further details of the additional property. Both buildings and parking lot comprise the SE corner of Fairbanks and Clay.

Listing Courtesy of WEICHERT REALTORS HALLMARK PROPERTIES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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1788 W Fairbanks Avenue Winter Park FL 32789

MLS Number O5852270

  • CommercialSale
  • Property SubType Office
  • Subdivision Lawndale Annex
  • Square Feet 12,287
  • Acreage 0.44

List Price is for 3 Parcels: This listing includes two other Parcels that are all being sold together. Parcel 12-22-29-5000-04-040, which is a parking lot that serves as this parcel's parking lot. Parcel 12-22-29-5000-04-050, is a two-story building also owned by the seller. See MLS Listing#O5852283 for further details. Both buildings are ADA compliant.

Listing Courtesy of WEICHERT REALTORS HALLMARK PROPERTIES

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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1300 N Park Avenue Winter Park FL 32789

Winter Park, FL1300 N Park Avenue

Price$3,295,000

Est. Mortgage: $/month

Pending

MLS Number O5903134

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 6,214
  • Year Built 2007

A timeless Gary Hancock Mediterranean designed estate situated on a wrapping corner on Park Avenue, truly one of the finest streets in Winter Park. This one-of-a-kind gated estate with guest house offers the perfect combination of elegant living and casual elegance and is exquisitely appointed. An old Winter Park bricked gated, circle drive welcomes you into foyer & formal living space which showcases a stone fireplace and walnut glass doors that flank each wall providing natural light and seamless views to outdoor living and pool. A spacious floor plan with a generously sized family room includes a vaulted ceiling with architectural wood beams, additional fireplace and custom backlit built-ins all open to kitchen. The kitchen features custom cabinetry, double islands, one with bar seating, eat-in kitchen space and butler area with wet and dry bar, for ease of entertaining that connects to formal dining and sitting room. Living spaces surround outdoor lifestyle areas which include 2 covered porches with travertine decking and an arbor with an outdoor fireplace. Double master suites, main floor master is generously sized and connects to the home office. A beautiful, curved stair with hand-forged iron detailed railing leads you to an additional upstairs owner's retreat and 2 additional bedrooms each with their own private baths, and a bonus space with front and back of the house balcony porches. The guest house boasts both living and bedroom retreats plus a full bath and room for an efficiency kitchen, perfect for out of town guests or flexible space. Additional rooms include upstairs and downstairs laundry, walk-in pantry, side entry 3-car garage on New York side with gate. Every angle of this home was thought of and impeccably landscaped and lighted. This is a fabulous house for entertaining and enjoying the coveted Winter Park lifestyle with Park Avenue steps away, great dining & shopping, Rollins, Chain of Lakes, Central Park and more. Please call for a private showing.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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 February 26, 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.