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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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$159,000
$589/mo
Monthly Payment:
$589
Principal & Interest:
$589
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $31,800 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
3bed 2bath 1,765sq ft $90 / sq ft SFR
Lot Size8,363sq ft Built1962 On Site34days
SHORT SALE. Excellent opportunity to own in the Eastbrook subdivision of Winter Park.
SHORT SALE. Excellent opportunity to own in the Eastbrook subdivision of Winter Park. less
Listing Provided Courtesy of BREC PROPERTIES INC
Popularity
We show you every available listing. Here's how
$1,895,000
$7,020/mo
Monthly Payment:
$7,020
Principal & Interest:
$7,020
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $379,000 down)
Winter Park, FL 32789
Orange County School District
10bed 7bath 8,674sq ft $218 / sq ft SFR
Lot Size1.5acre Built1956 On Site35days
Winter Park Lakefront 1.5 Acre Estate! This is a one of a kind lakefront property that has it all. The large open kitchen is well appointed with a 6 burner gas cook top, a... more
Winter Park Lakefront 1.5 Acre Estate! This is a one of a kind lakefront property that has it all. The large open kitchen is well appointed with a 6 burner gas cook top, a double oven, 2 dishwashers, 2 microwaves, 2 sinks, an icemaker and 3 pantries. The downstairs also features the master bed and bath, a library, exercise room and an office. Beautiful views of the resort sized pool and lake are seen from most every room upstairs and down. The guest house overlooks the pool as well and sports a full kitchen and bath. Recreation choices are plenty with the pool, putting green, half court basketball court and boat dock with a screened in room and covered boat slip. Don’t delay in setting your appointment to view this Winter Park gem. less
Listing Provided Courtesy of HEWITT RESIDENTIAL, LLC
Popularity
$299,000
$1,107/mo
Monthly Payment:
$1,107
Principal & Interest:
$1,107
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,800 down)
Winter Park, FL 32789
Orange County School District
6bed 2bath 2,384sq ft $125 / sq ft SFR
Lot Size12,100sq ft Built1940 On Site35days
Large corner lot available - zoned R2 - over 1/4 acre parcel located on easily accessible street - walking and biking distance to Rollins College, Hannibal Square, Park Avenue... more
Large corner lot available - zoned R2 - over 1/4 acre parcel located on easily accessible street - walking and biking distance to Rollins College, Hannibal Square, Park Avenue and more. Picturesque brick street, steps to Lake Midget with new construction homes in the neighborhood. List price includes adjacent parcel: 1049 N. Kentucky Ave. with tax I.D. 12-22-29-2556-02-100 and legal description of "Fairbanks Park O/46 Lot 10 Blk B". List price also includes: designs, plans, construction ready documents, city approval and replat of land for three 1700 SF town house units - common wall, fee simple homes with no HOA. Property can be replatted to three parcels using current city approved plans. Zoned for Winter Park High School. Option 1: Build three townhomes, already approved. Option 2: Build a duplex if preferred. Option 3: Renovate current two buildings on property...your choice!!!! less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$399,000
$1,478/mo
Monthly Payment:
$1,478
Principal & Interest:
$1,478
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,800 down)
Winter Park, FL 32789
Orange County School District
N/Asq ft N/A / sq ft LND
Lot Size6,909sq ft BuiltN/A On Site35days
Design/Build opportunity with award-winning Phil Kean Design Group on one of the top streets in Winter Park. Charming brick street, great location, convenient to all that Winter... more
Design/Build opportunity with award-winning Phil Kean Design Group on one of the top streets in Winter Park. Charming brick street, great location, convenient to all that Winter Park has to offer - great grade A schools. List price reflects lost cost only. Rendering shown offers 4250 heated/cooled square feet. less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$399,000
$1,478/mo
Monthly Payment:
$1,478
Principal & Interest:
$1,478
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,800 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,403sq ft $284 / sq ft SFR
Lot Size6,909sq ft Built1947 On Site35days
Design/Build opportunity with award-winning Phil Kean Design Group on one of the top streets in Winter Park. Charming brick street, great location, convenient to all that Winter... more
Design/Build opportunity with award-winning Phil Kean Design Group on one of the top streets in Winter Park. Charming brick street, great location, convenient to all that Winter Park has to offer - great grade A schools. List price reflects lot cost only. Rendering shown offers 4250 heated/cooled square feet. less
Listing Provided Courtesy of PHIL KEAN REAL ESTATE LLC
Popularity
$75,000
$277/mo
Monthly Payment:
$277
Principal & Interest:
$277
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $15,000 down)
Winter Park, FL 32792
Seminole County School District
2bed 2bath 953sq ft $79 / sq ft CND
Lot Size941sq ft Built1973 On Site38days
Back on market due to buyer financing. Remarkably updated 2Bed/2Bath condo. Luxurious, yet affordable! Modern kitchen with granite countertops, wood cabinets, upgraded kitchen... more
Back on market due to buyer financing. Remarkably updated 2Bed/2Bath condo. Luxurious, yet affordable! Modern kitchen with granite countertops, wood cabinets, upgraded kitchen faucet, and glasstop range. Bathrooms feature travertine tiled showers and new cabinets. The Stratford is very convenient location with a community pool. Move in ready and in great condition. Make an offer today! Unit must be owner occupied as association has rental restrictions less
Listing Provided Courtesy of SMART SOLUTIONS REALTY LLC
Popularity
$299,900
$1,111/mo
Monthly Payment:
$1,111
Principal & Interest:
$1,111
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $59,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,669sq ft $180 / sq ft SFR
Lot Size10,719sq ft Built1973 On Site38days
Open Sun Feb 14, 11am-1pm Agent Insights
Winter Park! Beautifully Renovated 1 level Open Floor-plan Home with Split Bedrooms! Proudly built up on a Large and Nicely Landscaped quarter acre lot located on a Cul-de-sac.... more
Winter Park! Beautifully Renovated 1 level Open Floor-plan Home with Split Bedrooms! Proudly built up on a Large and Nicely Landscaped quarter acre lot located on a Cul-de-sac. Great Curb Appeal! Courtyard entrance with Brick Pavers, Fountain, and a Garden wall. Gorgeous Remodeled Kitchen Overlooks the Large Family room that includes Custom Built in Cabinetry and French doors leading to your Outdoor Oasis – a 45foot long Screened Lanai with a Built in Grill, Summer Kitchen, and porcelain tile! The Amazing Backyard is your Private Park with Mango and Papaya Trees, Brick paver walkway, and a Sculpted Landscape wall. Kitchen has Stainless appliances and a Large Granite Island with Bar and seating. Formal Dining Room with French Doors open up to the Outdoor Living space. Upgraded Fixtures throughout, Natural Light Tubes, and Beautiful Wood laminate flooring. Master has a Private screened and covered Patio and the Remodeled Master Bath a Tub with Jets. House is nestled on a quiet Cul-de-sac and lined street! Roof new in 2010. All Highly Desired Schools!! - Dommerich Elementary, Maitland Middle, and Winter Park High. Short drive to Winter Park – Park Ave boutiques, shopping, dining. Take Advantage of this Great Opportunity! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity N/A
$1,099,900
$4,075/mo
Monthly Payment:
$4,075
Principal & Interest:
$4,075
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $219,980 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 3,277sq ft $336 / sq ft SFR
Lot Size9,048sq ft Built2016 On Site39days
Pre-Construction. To be built. Stone, glass and warm woods combine to make this gorgeous Transitional home blend into the beautiful setting. A sparkling pool and covered lanai... more
Pre-Construction. To be built. Stone, glass and warm woods combine to make this gorgeous Transitional home blend into the beautiful setting. A sparkling pool and covered lanai will provide a place to spend your summer days. The open kitchen features custom cabinetry and solid surface counters. The stainless appliance package includes a built in fridge, 36" gas cook top and built in ovens. Rectified porcelain floors are in all bathrooms with wire brushed,wide plank wood in the master bedroom and main living areas. The spacious downstairs master bedroom has a luxurious bath that features a large shower with a full body "spa". The master closet includes a custom shelving system and has plenty of room to share. There is a separate guest suite down that would make a perfect home office 3 large en suite bedrooms upstairs make this a perfect home for a growing family. Great location with Baldwin Park and Park Avenue just a few moments away. Smart home technology can control security system, HVAC, lighting, and more. This energy package in this home includes 2 tank less hot water heaters, radiant barrier insulation and double paned windows. Call today for a an appointment to see the plan a specifications for this outstanding home! less
Listing Provided Courtesy of COLEDEV REAL ESTATE LLC
Popularity
$240,000
$911/mo
Monthly Payment:
$911
Principal & Interest:
$889
HOA Dues:
$22
(Based on a 30 year fixed loan at 3.75% with $48,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 3bath 2,006sq ft $120 / sq ft SFR
Lot Size6,639sq ft Built1987 On Site39days
Beautiful 4/3 home in Winter Park, FL. Sellers are the original owners, and they have kept this home in perfect condition. Home offers high vaulted ceilings, stainless steel... more
Beautiful 4/3 home in Winter Park, FL. Sellers are the original owners, and they have kept this home in perfect condition. Home offers high vaulted ceilings, stainless steel appliances and a cozy fire place. Three bedrooms are located upstairs and the master suite is located on the first floor. The backyard is perfect for entertaining and family gatherings, with plenty of room for a pool. Well maintained yard, with partial sprinkler system. Home is district to sought after Seminole County schools. There is a HOA, but it is only $65 quarterly, which takes care of the tennis courts and the basketball court. House is minutes from downtown Winter Park, restaurants, and entertainment. Great home and location, and will not last long! Contact me today. less
Listing Provided Courtesy of WATSON REALTY CORP
Popularity
$228,900
$849/mo
Monthly Payment:
$849
Principal & Interest:
$848
HOA Dues:
$1
(Based on a 30 year fixed loan at 3.75% with $45,780 down)
Winter Park, FL 32792
Seminole County School District
3bed 2bath 1,715sq ft $133 / sq ft SFR
Lot Size8,000sq ft Built1969 On Site40days
Well kept Winter Park home, this has LOCATION, LOCATION with many upgrades. 3/2 with thermal pane windows, new blinds, newly painted in nice neutral colors. A slate floor foyer... more
Well kept Winter Park home, this has LOCATION, LOCATION with many upgrades. 3/2 with thermal pane windows, new blinds, newly painted in nice neutral colors. A slate floor foyer greets you and welcomes you into this home. The living room and dinning room are bright and in neutral colors. The kitchen has an eat in area and is open to the family room. The bedrooms are all large and there is ample storage throughout. The mature landscaping offers shade and a garden like feel in the backyard. Look no further for a home with great schools, very convenient to shopping and major roads, but located in small quite neighborhood. This is a real move in ready home waiting for you! Home warranty currently on property and can transfer to new owners too! less
Listing Provided Courtesy of KAREN CARLONE REAL ESTATE
Popularity
$1,100,000
$4,128/mo
Monthly Payment:
$4,128
Principal & Interest:
$4,075
HOA Dues:
$53
(Based on a 30 year fixed loan at 3.75% with $220,000 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 4,233sq ft $260 / sq ft SFR
Lot Size19,993sq ft Built1979 On Site40days
This beautifully-renovated home is a must-see. The main house boasts 4 bedrooms, 3 full and 2 half baths. As you enter the kitchen from the foyer, the sliding glass doors recess... more
This beautifully-renovated home is a must-see. The main house boasts 4 bedrooms, 3 full and 2 half baths. As you enter the kitchen from the foyer, the sliding glass doors recess into the walls completely for a full kitchen open to the oversized pool patio, perfect for Florida living and entertaining. Underlit granite and stainless appliances including convection oven, range with good and warming drawer complete this chef's dream room. The huge master bedroom and sitting room is complete with a dressing room/ walk-in closet. Similarly, the master bathroom is oversized with separate shower and tub along with private outdoor shower and garden. Bamboo floors throughout the home finish out the contemporary redesign. There is also a 1/1 freestanding attached building for office, studio, guest house or mother-in-law suite with private entrance. Salt water pool and spa are screened with lots of space to entertain. Updates include new ACs, roof, electrical, plumbing and landscaping in the last 5 years. Two side yards, a circular driveway, parking pad and two car garage complete this half acre corner lot in sought-after Sevilla. less
Listing Provided Courtesy of FANNIE HILLMAN & ASSOCIATES
Popularity
$106,000
$392/mo
Monthly Payment:
$392
Principal & Interest:
$392
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $21,200 down)
Winter Park, FL 32789
Orange County School District
2bed 2bath 956sq ft $111 / sq ft CND
Lot SizeN/Asq ft Built1969 On Site41days
Enjoy carefree living in this lovely community located on beautiful Lake Killarney with a community pool and clubhouse overlooking the water. Spacious central courtyard grounds... more
Enjoy carefree living in this lovely community located on beautiful Lake Killarney with a community pool and clubhouse overlooking the water. Spacious central courtyard grounds create a park-like feeling of tranquility. Great for vacation home or downsizing. This 2 bedroom, 2 bath condo has new paint, carpet and 2" faux wood blinds in all windows. Crown molding in the living/dining area. Newer Energy-Efficient windows. Laundry room is just steps from the back door. Minutes from Winter Park Village, Park Avenue and Rollins College. Jump on I-4 and be downtown or FL Hospital in no time at all. This is a NO PETS community & has rental restrictions. less
Listing Provided Courtesy of PATHWAY PROPERTIES LLC
Popularity
$2,450,000
$9,077/mo
Monthly Payment:
$9,077
Principal & Interest:
$9,077
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $490,000 down)
Winter Park, FL 32789
Orange County School District
5bed 7bath 6,285sq ft $390 / sq ft SFR
Lot Size32,129sq ft Built2011 On Site41days
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011... more
Magnificent estate home & unique oversized property in the heart of the Via's... premier location on triple lot (3/4 acre) on quiet street... This home was custom built in 2011 with Hal George at Parkland Homes, top quality craftsmanship & exquisite trim / moldings thru-out, bright-open floor plan, high detailed ceilings, generous room sizes, designer lighting, lots of great windows & french doors... Fabulous 1st floor master retreat with lavish bath along with his & her baths/dressing areas... Wonderful huge gourmet island kitchen with commercial appliances & extensive cabinetry, elegant "club room" with full bar & paneled walls, large beautiful formal dining & living rooms with windows/french doors both sides, and a library downstairs... Upstairs includes 4 bedroom suites, game room & bonus room... The outdoor living is nothing short of spectacular with tremendous grounds, expansive covered lanai (invisible remote retractable screens), classic pool area & walled in private yard... Enjoy the Winter Park Racquet Club, tennis courts, & access to Lake Maitland "chain of lakes" next door... A perfect entertaining home & property!! less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
Popularity
$1,189,000
$4,405/mo
Monthly Payment:
$4,405
Principal & Interest:
$4,405
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $237,800 down)
Winter Park, FL 32789
Orange County School District
5bed 6bath 5,511sq ft $216 / sq ft SFR
Lot Size22,599sq ft Built1970 On Site41days
Come tour this beautiful Hampton-esque estate substantially renovated in 2015 to provide an open floorplan and upgrades throughout for maximum comfort and elegance! City... more
Come tour this beautiful Hampton-esque estate substantially renovated in 2015 to provide an open floorplan and upgrades throughout for maximum comfort and elegance! City approved to accommodate a large pool! Situated on a huge, half-acre+ lot.195ft of frontage on prestine Howell Creek, flowing into Lake Virginia. Launch a kayak or paddle board right from your back yard! Manicured landscaping provides gorgeous curb appeal. Walk to Park Ave! Property neighbors Bonnie Burn Park. Luxury finishes include: hardwood, natural stone, & marble flooring; Anderson low-e windows, full masonry fireplace, crown moldings and mill work throughout! The upstairs is highlighted by the 1,000sf master suite, featuring an integrated sitting area, vaulted ceilings, huge CA closet, French doors opening to a private covered balcony, huge walk-in shower with body spray system, jetted tub, separate vanities and on-suite laundry room. Open first floor formals & family room with views to the chef`s kitchen showcased by granite counter tops, large working island w/farm sink, SS appliances, double ovens & huge walk-in pantry! Dinette with wet bar, wine cooler and open views looking out onto your back yard and creek. Two large patios and upstairs deck, great for your evenings of wine & cheese. The 2 car garage has a separate work shop & storage area. The 2nd floor also includes another large bedroom with adjoining bath and a bonus room for home office, gym, media room, or easily convert to an extra bedroom. Click v-tour for 3D pans. less
Listing Provided Courtesy of MILLENNIUM HOMES REALTY
Popularity
$410,000
$1,519/mo
Monthly Payment:
$1,519
Principal & Interest:
$1,519
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $82,000 down)
Winter Park, FL 32789
Garden Acres Orange County School District
4bed 2bath 2,057sq ft $199 / sq ft SFR
Lot Size12,719sq ft Built1938 On Site41days
Open Sun Feb 14, 1pm-4pm
This charming winter park home has been updated through the years w/ stainless steel appliances, kitchen cabinets, granite countertops, roof, ac, crown molding, gutters &... more
This charming winter park home has been updated through the years w/ stainless steel appliances, kitchen cabinets, granite countertops, roof, ac, crown molding, gutters & exterior paint. Location is minutes to park avenue's boutiques & restaurants, rollins college, florida hospital, college park & downtown orlando's business district. Formal living is light & bright w/ a cozy wood burning fireplace. Formal dining has custom built-in cabinetry. This home is perfect for family or entertaining w/ an open floor plan & over-sized fenced lot. There is plenty of room for a pool. less
Listing Provided Courtesy of COLDWELL BANKER RESIDENTIAL RE
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: Sunday, February 14, 2016 at 6:07 AM. Properties in listings may have been sold or may no longer be available.