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Winter Park, FL Real Estate — Homes For Sale in Winter Park, FL

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Winter Park Real Estate Overview

Originally founded as a resort destination by affluent New Englanders in the late 1880s, Winter Park is today known for its majestic trees, beautiful parks, brick-lined streets, stunning homes, a private liberal arts college, educational museums, sparkling lakes, and amazing shops. Winter Park is located just 15 minutes from the...
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$120,000
$496/mo
Monthly Payment:
$496
Principal & Interest:
$424
HOA Dues:
$72
(Based on a 30 year fixed loan at 3.38% with $24,000 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 1,020sq ft $118 / sq ft CND
Lot Size3,553sq ft Built1977 On Site18days
This is a great investment opportunity! This 2 bedroom 2 bathroom unit has tile flooring throughout, an enclosed family room, vaulted ceilings, and a fenced in yard. Windward... more
This is a great investment opportunity! This 2 bedroom 2 bathroom unit has tile flooring throughout, an enclosed family room, vaulted ceilings, and a fenced in yard. Windward Square is located within minutes to shopping, dining, and major roadways. less
Listing Provided Courtesy of CENTRAL FLORIDA REALTY EXPERTS
Popularity
We show you every available listing. Here's how
$875,000
$3,096/mo
Monthly Payment:
$3,096
Principal & Interest:
$3,096
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $175,000 down)
Winter Park, FL 32789
Orange County School District
4bed 5bath 4,218sq ft $207 / sq ft SFR
Lot Size15,075sq ft Built2016 On Site18days
Pre-construction. To be built. Exquisite Winter park custom pool home. Builder has a number of floor plans and style homes for this site and can even help with a fully custom to... more
Pre-construction. To be built. Exquisite Winter park custom pool home. Builder has a number of floor plans and style homes for this site and can even help with a fully custom to meet your needs. Drive the lot and if interested please set up a time for a design meeting. Short distance to upscale dining and shopping, yet enjoy the quiet established community on the shores of lake Killarney. The best of both worlds! less
Listing Provided Courtesy of RE/MAX SHOWCASE
Popularity
$995,000
$3,521/mo
Monthly Payment:
$3,521
Principal & Interest:
$3,521
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $199,000 down)
Winter Park, FL 32789
Orange County School District
5bed 4bath 3,637sq ft $274 / sq ft SFR
Lot Size11,342sq ft Built2006 On Site19days
Click on the amazing 3D interactive tour link to preview this spectacular home! This exquisite custom Mediterranean home located on one of Olde Winter Park's "Tree Streets"... more
Click on the amazing 3D interactive tour link to preview this spectacular home! This exquisite custom Mediterranean home located on one of Olde Winter Park's "Tree Streets" features a gourmet kitchen with an extra vegetable sink in the island, 5 burner natural gas range, stainless steel appliances including range hood and wine refrigerator in the butlers pantry, and a double sided gas fireplace as seen from both the family room and formal living room. Other features include surround sound speakers, plantation shutters, travertine flooring throughout downstairs living areas, a spacious downstairs master bedroom with a huge spa-like bathroom with Jacuzzi tub and his and hers walk-in closets. 4 large bedrooms upstairs including a "Jack and Jill" bedroom layout. Tray ceilings, crown molding and custom built in features in the family room and 5th bedroom reflect the superior quality of this custom built home. Pavers on the driveway and the lanai/pool deck area as well as the tongue and groove ceilings above the spacious lanai extends the quality of the home to the outer areas and completes the feel of luxury that this home exudes. Take a dip in the open pool, or relax in the heated spa while enjoying the beautiful Florida weather. The exterior of this home was repainted in 2015, Nest thermostats were added to increase the energy efficiency of the home, and carpets were replaced within the past two years. The large back yard is completely fenced with easy to maintain vinyl fencing. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$284,500
$1,006/mo
Monthly Payment:
$1,006
Principal & Interest:
$1,006
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $56,900 down)
Winter Park, FL 32789
Fairview Shores Orange County School District
3bed 2bath 1,649sq ft $173 / sq ft SFR
Lot Size4,748sq ft Built2002 On Site19days
Timeless charm with this "florida cottage style" 3 bedroom / 2 bathroom home located in desirable winter park! This 2 story home features a wrap-around porch plus a private... more
Timeless charm with this "florida cottage style" 3 bedroom / 2 bathroom home located in desirable winter park! This 2 story home features a wrap-around porch plus a private balcony off the master suite! Open kitchen includes solid wood cabinets, stone counters, stainless steel appliances, breakfast bar, and a dining area! Wood and tile flooring throughout! Cathedral ceilings, crown molding, and ceiling fans in every bedroom! Back room features a bar area and french door to the open deck and fenced yard - perfect for entertaining! Conveniently located near winter park shopping & restaurants and i4! Move in ready! Don't miss out on this unique opportunity! less
Listing Provided Courtesy of SLOANE REALTY, LLC
Popularity
$1,090,000
$3,897/mo
Monthly Payment:
$3,897
Principal & Interest:
$3,857
HOA Dues:
$40
(Based on a 30 year fixed loan at 3.38% with $218,000 down)
Winter Park, FL 32789
Orange County School District
5bed 3bath 3,940sq ft $277 / sq ft SFR
Lot Size18,789sq ft Built1982 On Site20days
Escape to this luxury nature retreat in convenient location! 100+ feet on Howell Creek overlooking Mead Gardens conservation park in established Sevilla. Modern meets comfort in... more
Escape to this luxury nature retreat in convenient location! 100+ feet on Howell Creek overlooking Mead Gardens conservation park in established Sevilla. Modern meets comfort in this stunning renovation; 5 bed " 3 way split plan " 3 bath, pool home. Brazilian hardwood floors, custom designed details/cabinetry, window treatments, built in speakers and tons of natural light throughout. Gourmet kitchen, S&W cabinetry, Quartz counters, Electrolux stainless appliances; convention oven/warming oven; super quiet Bosch dishwasher PLUS huge walk in pantry. Open family room, soaring ceilings with custom designed FP, rough cut marble & indirect lighting; French doors to pool area. Huge master suite with bonus room " office, nursery, exercise " with lovely views. Soothing spa-like master bath; jetted tub, shower, dual sinks. Guest room with full bath/pool access. North wing; Jack & Jill bath adjoins 2 large bedrooms with closets w/organizers, built in desks. 5th bedroom/bonus room is incredible sunny & bright flex space. Large Pebble Tec pool & paver deck, custom design railing for optimal privacy and views, outdoor shower, covered area for entertaining. Bring your camera and binoculars for bird watching and exotic flora & fauna! Circular drive for guests, 3 car oversized garage, storage galore. Impeccably maintained, move in condition. less
Listing Provided Courtesy of KELLER WILLIAMS WINTER PARK
Popularity
$499,000
$1,765/mo
Monthly Payment:
$1,765
Principal & Interest:
$1,765
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $99,800 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 1,737sq ft $287 / sq ft TWN
Lot Size5,227sq ft Built2015 On Site20days
Pre-Construction. To be built. Designed by Phil Kean, an internationally recognized, and award-winning Architect. This modern townhome is located in desirable Winter Park.... more
Pre-Construction. To be built. Designed by Phil Kean, an internationally recognized, and award-winning Architect. This modern townhome is located in desirable Winter Park. Immediately upon walking through the front door you are greeted by a stunning courtyard with plenty of space to relax. You will continue to enjoy the view of the courtyard while inside as the first floor living area has an abundance of floor to ceiling windows. High level finishes throughout the two story townhome which includes three upper level bedrooms, two full baths, one half bath, and a two car garage. This townhouse is located minutes to Park Avenue and Downtown Orlando that offer premier dining, shopping and entertainment. Convenient access to I4. Floor Plan available. Pre-construction pricing. less
Listing Provided Courtesy of BHHS FLORIDA REALTY
Popularity
$1,800,000
$6,548/mo
Monthly Payment:
$6,548
Principal & Interest:
$6,370
HOA Dues:
$178
(Based on a 30 year fixed loan at 3.38% with $360,000 down)
Winter Park, FL 32789
Orange County School District
3bed 4bath 3,778sq ft $476 / sq ft CND
Lot Size21,602sq ft Built2008 On Site22days
Central Florida's most distinctive, historic and established in-town living experiences. Welcome your guest directly from your own front door located on Virginia Avenue. Sit on... more
Central Florida's most distinctive, historic and established in-town living experiences. Welcome your guest directly from your own front door located on Virginia Avenue. Sit on your corner covered porch to read the morning paper or enjoy dinner alfresco. This is the largest and only town home that has a covered porch and direct street access to your very own private garage, with all of the finishes and fixtures of a brand new, modern-day building. Luxurious finishes are coupled with high-end appliances and fixtures in this two store, 3 bed, 3 1/2 bath unit. Open floor plan with a large kitchen and dining room. The master bedroom with enormous walk-in closet. The finishes include Pella windows and doors, Kohler fixtures, Sub-Zero, Wolf and Bosch appliances, Trane air conditioning and other quality components that luxury Buyers demand. Crown molding, granite counter tops in the kitchen and all baths, walk-in closets in every bedroom, over sized walk-in shower and garden bath in the second master suite, attached garage with direct access to the street and a private entry to the unit are also included. The Douglas Grand location is irreplaceable, one block from Park Avenue shopping district, across the street from Central Park, one block from Hannibal Square and walking distance to hundreds of retailers, restaurants and wine bars - a true city-living experience in Central Florida's most unique town - Winter Park. Home is elevator ready, hurricane proof windows, exterior cameras. less
Listing Provided Courtesy of FLORIDA ONE REAL ESTATE LLC
Popularity
$359,900
$1,277/mo
Monthly Payment:
$1,277
Principal & Interest:
$1,273
HOA Dues:
$4
(Based on a 30 year fixed loan at 3.38% with $71,980 down)
Winter Park, FL 32792
Orange County School District
4bed 3bath 2,394sq ft $150 / sq ft SFR
Lot Size11,581sq ft Built1969 On Site23days
Winter park pines remodeled 4 bedroom 3 bath split bedroom home. The home features a tile roof and double pane windows. Wood floors throughout the house except the florida room... more
Winter park pines remodeled 4 bedroom 3 bath split bedroom home. The home features a tile roof and double pane windows. Wood floors throughout the house except the florida room is tile floors. Crown molding and new baseboards. The kitchen has been remodeled with lots of cabinet space, granite counter tops, an island, stainless steel appliances. New owner can install a gas stove. The house has been rewired. All new faucets and shower heads. All led lighting. Electric fireplace in family room. New ac unit. Tankless water heater. New water softener. Large 13x7 air conditioned laundry room. Enjoy the "park like" setting in the back yard, complete with gazebo with a fountain and fish pond plus a variety of plants. Cady way trail is just down the street for walking and biking and the winter pines golf course is at the end of ranger. A few minutes drive to park ave in winter park. less
Listing Provided Courtesy of RE/MAX 200 REALTY
Popularity
$346,500
$1,956/mo
Monthly Payment:
$1,956
Principal & Interest:
$1,226
HOA Dues:
$730
(Based on a 30 year fixed loan at 3.38% with $69,300 down)
Winter Park, FL 32789
2bed 2bath 1,148sq ft $302 / sq ft CND
Lot Size1.6acre Built1969 On Site23days
Completely renovated two bedroom, two bath unit at Lake Virginia Condos. Top floor, end unit has gorgeous views of both Lake Virginia AND the canal and a screened-enclosed... more
Completely renovated two bedroom, two bath unit at Lake Virginia Condos. Top floor, end unit has gorgeous views of both Lake Virginia AND the canal and a screened-enclosed balcony that provides the perfect space to relax and take in the scenic beauty. Elegantly decorated, the home has been updated to showcase hardwood floors in both the master and guest bedroom, stone flooring throughout the living areas, remodeled bathrooms, and a gorgeous kitchen complete with granite counters, custom solid cabinetry, and newer appliances. Dry bar with built-in wine refrigerator just off the dining room is great for entertainment and additional storage. Located right around the corner from Park Avenue, Lake Virginia Condominiums offers residents a short walking distance to nearby shops and restaurants, a community pool, assigned parking, and chain-of-lake access. With panoramic views and a modern interior, this home is by far one of the best units in the building. less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$2,848,000
$10,079/mo
Monthly Payment:
$10,079
Principal & Interest:
$10,079
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $569,600 down)
Winter Park, FL 32789
Orange County School District
3bed 5bath 4,160sq ft $685 / sq ft TWN
Lot Size15,232sq ft Built2016 On Site23days
Pre-construction, to be built. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen... more
Pre-construction, to be built. Only two residences remain! Your opportunity to own unprecedented luxury in the most exclusive area of Winter Park has arrived. South Interlachen Place is around the corner from world famous Park Avenue, across the street from the Alfond Inn, and just a stones throw from the Winter Park Chain of Lakes. Comprised of six exquisitely appointed townhouses, South Interlachen Place is being built with premium level specifications; a standard of luxury usually only found in cosmopolitan world-class destinations. Award winning architect, Randall Slocum of Slocum Platts Architects, placed privacy as his top priority in creating the design for South Interlachen Place. Every fee-simple residence has a private two-car garage, private elevator to all levels, and lush, mature landscaping defining the entrances. A truly unique aspect of the design is the extraordinarily large and private roof top terrace for each individual residence providing both covered and open areas for outdoor dining and entertaining; each with a fireplace and powder bath. The residences are designed with "universal" features throughout; allowing for invisible accessibility that can respond to changing life styles. Each townhouse embraces smart technology for entertainment, lighting, energy management and security. There is just too much more to list here. Live in one of the most beautiful Winter Park residences in a truly exceptional downtown location - live at South Interlachen Place. less
Listing Provided Courtesy of REGAL R.E. PROFESSIONALS LLC
Popularity
$725,000
$2,565/mo
Monthly Payment:
$2,565
Principal & Interest:
$2,565
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $145,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,289sq ft $220 / sq ft SFR
Lot Size11,226sq ft Built2004 On Site23days
Stunning custom designed four bedroom, three and one half bath home located on one of the most quiet streets in Winter Park! Amazing floor plan with more than 2,900 square feet... more
Stunning custom designed four bedroom, three and one half bath home located on one of the most quiet streets in Winter Park! Amazing floor plan with more than 2,900 square feet of living space showcases a formal dining room, a spacious kitchen overlooking the light and bright family room, a private master suite, a first floor office/den and a second story bonus room! This house has it all! Finishes include hardwood flooring, crown molding, high ceilings and plantation shutters. The kitchen offers stainless appliances, granite countertops, a breakfast area and bar stool seating. Adjacent butler's pantry leads into the separate formal dining room. Downstairs master bedroom is generous in size with a walk in closet, soaking tub with separate shower and a dual sink vanity. A home office/den completes the home's first floor. Three additional bedrooms and a bonus room are located on the second story. Enjoy looking out over the beautiful neighborhood from the upstairs front balcony. A two-car garage is set back in the rear of the property with ample storage space. Minutes from Park Avenue, walk thru some of Winter Parks charming neighborhoods to your favorite shops and restaurants. Call to schedule your showing today! less
Listing Provided Courtesy of KELLY PRICE & COMPANY LLC
Popularity
$495,000
$1,751/mo
Monthly Payment:
$1,751
Principal & Interest:
$1,751
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $99,000 down)
Winter Park, FL 32789
Orange County School District
4bed 3bath 2,406sq ft $206 / sq ft SFR
Lot Size13,533sq ft Built1969 On Site24days
So inviting and not to be missed, this 4 bedroom, 3 bath Winter Park pool home is exceptional! Many renovations have been done, including the kitchen with granite, stainless... more
So inviting and not to be missed, this 4 bedroom, 3 bath Winter Park pool home is exceptional! Many renovations have been done, including the kitchen with granite, stainless appliances & new cabinets, French doors opening to a relaxing covered patio & pool area with new fencing, new roof, wood floors installed and much more. Located in "A" rated school district, plus minutes to shopping, restaurants and playing fields, this sparkling residence is one to include on your showing list to view! less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$1,295,000
$4,582/mo
Monthly Payment:
$4,582
Principal & Interest:
$4,582
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $259,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 4,328sq ft $299 / sq ft SFR
Lot Size10,899sq ft Built1976 On Site24days
Open Sun May 1, 2pm-4pm
Elegant "VIA BELLA home nestled on one of WINTER PARKs most sought-after streets. Traditional brick architecture and pedestrian access to Lake Osceola comes with this classic... more
Elegant "VIA BELLA home nestled on one of WINTER PARKs most sought-after streets. Traditional brick architecture and pedestrian access to Lake Osceola comes with this classic home. Lush and mature landscaping creates complete privacy. Florida outdoor living with entertainment areas, pool bath, summer kitchen and tropical pool with terraced flagstone pool deck. This home is for entertaining! Gorgeous kitchen with gourmet appliances, custom cabinets, Carrara marble counter tops and a farmhouse sink. Olde world charm brick archway that takes you from the kitchen into a breakfast nook w/ beautiful natural lighting that overlooks the pool. The spacious formal dining room flows into a living room with a fireplace, tongue/groove ceilings, and glass doors that open out to the outdoor patio. Lower level has well-appointed stately office/ study with a wood-burning fireplace, tongue & groove wood ceiling and French doors leading out to the summer kitchen. Spacious Master bedroom, new master bath, enormous 204 SF walk-in closet, French doors open to a private screened patio off the Master Suite, and 12x12 flex room that is perfect for an art studio or workout room. Second bedroom has vaulted ceilings that flow into a 15X15 sitting area with tons of storage/closet space. This home is equipped with a whole house generator and is on well irrigation. This elegant Winter Park home has been extensively renovated. Walking distance to PARK AVE boutiques and restaurants. Home was appraised in March 2015 for $1,470,000. less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$299,900
$1,061/mo
Monthly Payment:
$1,061
Principal & Interest:
$1,061
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.38% with $59,980 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,216sq ft $247 / sq ft CND
Lot Size2,504sq ft Built1983 On Site25days
Open Sat Apr 30, 2pm-4pm
Located in Winter Park, close to Rollins College and Park Avenue, this ground floor 2 bedroom 2 bath split plan condo is a true find. Light bright and airy, the living area is... more
Located in Winter Park, close to Rollins College and Park Avenue, this ground floor 2 bedroom 2 bath split plan condo is a true find. Light bright and airy, the living area is open and framed with 4 sets of sliding glass doors. A wood burning fireplace warms the few cold days we have in Florida. Through the sliding glass doors, you can see the back yard with a wooden deck, benches, and planters. The kitchen has lots of cabinets, glass tile back splash, closet pantry, and all appliances. There is an eat-in area in the kitchen as well. An attached one car garage bay includes the washer/dryer hookup, water heater, and storage area. There are only four units in Azalea Lane Condos and the Association is run by the Owners. The buildings are scheduled to be pressure washed, caulked, and painted. less
Listing Provided Courtesy of PARKLAND INTERNATIONAL REALTY
Popularity
$275,000
$1,249/mo
Monthly Payment:
$1,249
Principal & Interest:
$973
HOA Dues:
$276
(Based on a 30 year fixed loan at 3.38% with $55,000 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 1,214sq ft $227 / sq ft CND
Lot Size5,861sq ft Built1986 On Site25days
Amazing 2 BR/2BA condo steps from Lake Killarney. This condo is on the first floor next to the dock and the pool and is the most desirable in the complex. Roll over and look out... more
Amazing 2 BR/2BA condo steps from Lake Killarney. This condo is on the first floor next to the dock and the pool and is the most desirable in the complex. Roll over and look out over the lake from the master bedroom.You can't ask for a better location across from the Winter Park Village. Enclosed Florida room with new windows in 2008. Owner installed water softner and purification system. Wood laminate floors throughout. Don't be afraid to make an offer. less
Listing Provided Courtesy of CMTG REAL ESTATE GROUP
Popularity
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Local real estate services provided by:
Coldwell Banker Residential Real Estate
Coldwell Banker Residential Real Estate
5951 Cattleridge Ave
Sarasota, FL 34232

844.662.5638
Website provided and owned by Coldwell Banker Residential Real Estate.
 
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Data last updated: Saturday, April 30, 2016 at 8:01 PM. Properties in listings may have been sold or may no longer be available.