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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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$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 1,492sq ft $267 / sq ft SFR
Lot Size9,919sq ft Built1958 On Site17days
Cozy, well-loved and well-maintained three bedroom, 2 bath block home in Winter Park. This home has hardwood floors and ceramic tile throughout. Newer windows and newer... more
Cozy, well-loved and well-maintained three bedroom, 2 bath block home in Winter Park. This home has hardwood floors and ceramic tile throughout. Newer windows and newer roof. The lot is 85' x 118'. You will love the location! Location! Location! Location! This could be a good investment, any way you look at it. You can move right in and enjoy the super family friendly neighborhood ... or you can add on extra space and a pool ... or you can use the lot to build your dream home. There are many lots that have sold on this street and the new construction is beautiful. The lots have sold for up to $300,000. You can renovate without the worry of whether you are over building for the neighborhood. This home is less than five minutes from downtown Winter Park, shopping, Whole Foods, Starbucks, restaurants and parks. The children have a short bike ride to three excellent schools in Orange County. less
Listing Provided Courtesy of Watson Realty Corp
Popularity
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$60,000
$387/mo
Monthly Payment:
$387
Principal & Interest:
$222
HOA Dues:
$165
(Based on a 30 year fixed loan at 3.75% with $12,000 down)
Winter Park, FL 32789
Orange County School District
1bed 1bath 645sq ft $93 / sq ft CND
Lot Size2,107sq ft Built1969 On Site17days
Come and see this lovely 1/1 condo in Winter Park on beautiful Lake Killarney. Community has a boat ramp and a pool. Located in Lakeside Manor, a quiet, close knit community.... more
Come and see this lovely 1/1 condo in Winter Park on beautiful Lake Killarney. Community has a boat ramp and a pool. Located in Lakeside Manor, a quiet, close knit community. Call today for more details. Sellers are motivated. less
Listing Provided Courtesy of Dapore Realty Inc
Popularity
$1,100,000
$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 $220,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,214sq ft $342 / sq ft SFR
Lot Size9,563sq ft Built2015 On Site18days
Open Sat Apr 18, 12pm-3pm
Rex-Tibbs brand new modern design home with bright-open floor plan walking distance to downtown Winter Park, Park Ave & the Winter Park Village (Whole Foods Village, shops &... more
Rex-Tibbs brand new modern design home with bright-open floor plan walking distance to downtown Winter Park, Park Ave & the Winter Park Village (Whole Foods Village, shops & restaurants coming soon as well only a couple of blocks away)... located on an almost completely re-developed, beautiful brick street in Olde Winter Park. Transitional interiors with clean lines, expansive glass doors & oversized windows to bring the outside in – very bright, neutral style… Wonderful mature Signature Landscaping along with a picturesque large fenced back yard, covered lanai and pool area that includes expansive travertine deck area for entertaining… This brand new home features a large master suite downstairs with separate nice walk-in closets, spacious bath and open to the pool & lanai... a total of 4 BE / 4 full baths, 10' ceilings up and down, euro-modern sleek island kitchen open to large gathering room w/ fireplace, also a spacious bonus/flex room upstairs... exotic solid wood flooring that is a great durable product, tile, marble & travertine floors, granite/marble tops, custom cabinetry, crown moldings, Thermador stainless appliances along with wine cooler and much more! This home is surrounded by newer homes and a like new neighborhood! less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$395,000
$1,463/mo
Monthly Payment:
$1,463
Principal & Interest:
$1,463
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $79,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,540sq ft $256 / sq ft SFR
Lot Size9,505sq ft Built1945 On Site18days
Enjoy The Winter Park Lifestyle in this Charming Home in the Heart of Winter Park!! This home has a split bedroom plan with large open living space. Beautiful New hardwood... more
Enjoy The Winter Park Lifestyle in this Charming Home in the Heart of Winter Park!! This home has a split bedroom plan with large open living space. Beautiful New hardwood floors spread to the living and dining room, plaster walls, and Gorgeous Kitchen with granite & and hardwood cabinets, Large Florida room or Flex Space in the rear of the home is wrapped with large windows that allow for natural sunlight and views of the large trees. Granite counter tops and hardwood cabinetry are in every bathroom. This home is surrounded by million dollar homes and offered at an entry price. Enjoy the opportunity to live in this wonderful home or bring your plans to build in the most sought after Winter Park street neighboring the "Via’s”. It is waking distance to the Winter Park Racquet Club and is One of Central Florida's most requested school districts. Located minutes to Park Avenue shops, bistros, Rollins College and many majestic Parks. less
Listing Provided Courtesy of Parkland International Realty
Popularity
$349,900
$1,296/mo
Monthly Payment:
$1,296
Principal & Interest:
$1,296
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $69,980 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,525sq ft $229 / sq ft SFR
Lot Size6,651sq ft Built1925 On Site18days
Open Sun Apr 19, 1am-4pm
Welcome to 2600 Winter Park Road. Built in 1925, this Spanish Mediterranean home can claim a designation in the Winter Park Register of Historic places. The original owner since... more
Welcome to 2600 Winter Park Road. Built in 1925, this Spanish Mediterranean home can claim a designation in the Winter Park Register of Historic places. The original owner since 1957 has lovingly cared for and maintained this 3 bedroom, 2 bath home. The entrance to the home is through a segmented arched opening on the front facing gable. The living room features a wood burning fireplace, a cathedral beamed ceiling, original windows and hardwood floors. From the dining room, French doors, open to a screened side porch. The updated kitchen features recessed lighting, granite counters, Kitchen Aid appliances, new hardwood floors and window treatments. One bathroom has a walk-in shower and the second bathroom has a tub/shower. A free standing two-car garage has been attached to the main body of the house by an open breezeway. The house has many unique architectural features and mature landscaping. Seller will transfer a one year home warranty. Walking distance to the new East End marketplace and Blue Jacket Park. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$695,000
$2,574/mo
Monthly Payment:
$2,574
Principal & Interest:
$2,574
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $139,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 6bath 5,184sq ft $134 / sq ft SFR
Lot Size29,185sq ft Built1968 On Site19days
Being already impressed with the exterior of this amazing home, you are going to be more than impressed with the interior as well! Beautiful hardwood, laminate and tile floors... more
Being already impressed with the exterior of this amazing home, you are going to be more than impressed with the interior as well! Beautiful hardwood, laminate and tile floors extend throughout this spacious home. The owner’s retreat and 2 secondary bedrooms are upstairs along with a guest bath with double sinks and a jacuzzi tub and shower. The master suite has an adjacent sitting room great for a nursery, dressing room, workout room, sewing room, library or media nook and an unparalleled view of Garden Lake. Downstairs is an additional bedroom with en-suite bathroom plus large kitchen, family room with fireplace, dining room and office/den/sitting room. Tucked to the rear of the property is a detached in-law suite with a kitchen, bath and bedroom and the upper portion of the oversized detached garage has a partially finished bonus room (currently being used for storage). The grounds are tastefully landscaped and the oversized screened pool has beautiful views of the lake as well. Enjoy your own piece of paradise right here in Winter Park! less
Listing Provided Courtesy of Re/max 200 Realty
Popularity
$1,200,000
$5,195/mo
Monthly Payment:
$5,195
Principal & Interest:
$4,445
HOA Dues:
$750
(Based on a 30 year fixed loan at 3.75% with $240,000 down)
Winter Park, FL 32789
Orange County School District
4bed 4bath 3,579sq ft $335 / sq ft CND
Lot Size3.3acre Built1915 On Site19days
Step back in time as you enter the Alabama Hotel that was converted into The Alabama Condominium in the 1980’s. On the grounds you will find this rare gem, The Victorian... more
Step back in time as you enter the Alabama Hotel that was converted into The Alabama Condominium in the 1980’s. On the grounds you will find this rare gem, The Victorian Temple house. William C. Temple, a patron of Winter Park, is the namesake of the Temple Orange. Temple called his Victorian house “Alabama Lodge” This pristine Victorian home is condo living in a single family home. Private gate entry brings you into the semi-circular driveway at The Vias. The HOA maintains the entire exterior as well as the lush landscaped grounds. This 140 year old home is registered as a “Historic Home”. As you enter you will notice the attention to detail in every corner. Home movie theater, chef’s kitchen with gourmet gas stove, two fireplaces, beautiful hardwood floors, private formal dining room fit for royalty. Stunning master suite with sitting area and additional staircase leading to large bonus room. Beautiful views from the balconies above. Relax on the wraparound porch as you take in the magnificent water view. Lake Maitland rental slip is only $750.00 per year for your boat. This is a one of a kind opportunity to own a piece of history while living the life some can only dream of. less
Listing Provided Courtesy of Real Estate Firm Of Orlando
Popularity
$154,500
$585/mo
Monthly Payment:
$585
Principal & Interest:
$572
HOA Dues:
$13
(Based on a 30 year fixed loan at 3.75% with $30,900 down)
Winter Park, FL 32792
Goldenrod Seminole County School District
2bed 2bath 1,270sq ft $122 / sq ft SFR
Lot Size10,098sq ft Built1985 On Site19days
Charming 2 bedroom, 2 bath home located in the small Garden Grove community in Winter Park. Home features open floor plan with vaulted ceilings. Upon entering there is a... more
Charming 2 bedroom, 2 bath home located in the small Garden Grove community in Winter Park. Home features open floor plan with vaulted ceilings. Upon entering there is a spacious living room with built in fireplace. Kitchen has plenty of counter spaces and cabinets and closet pantry. The kitchen opens to dining area which leads you to the open patio/deck. There is a den/office for additional living area. The master suite features a walk in closet and private bath with shower. There is an inside utility area for added convenience. Great curb appeal with a side entry 2 car garage. Large corner lot with fenced in yard for additional privacy. Conveniently located close to shopping, dining and major highways. Excellent school district! This is a Fannie Mae HomePath property. less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$130,000
$481/mo
Monthly Payment:
$481
Principal & Interest:
$481
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $26,000 down)
Winter Park, FL 32792
Seminole County School District
2bed 1bath 1,024sq ft $127 / sq ft SFR
Lot Size9,263sq ft Built1954 On Site20days
This charming “old winter park” bungalow offering two bedrooms and one bathroom has been nicely updated and is move-in ready!! Perfectly located in a wonderful... more
This charming “old winter park” bungalow offering two bedrooms and one bathroom has been nicely updated and is move-in ready!! Perfectly located in a wonderful neighborhood, this home is located close to major shopping & 1/2 mile from nearby well-rated Winter Park schools, restaurants, lakes & parks. As you enter the home you are greeted by an open combination living room and kitchen. The kitchen offers a stainless appliances with laminate wood flooring throughout. Adjacent to the kitchen there is a mudroom which is accessible from the front driveway which offers a convenient space to store shoes and coats and also connects to the laundry room. Through the kitchen on the backside of the home is a spacious dining room that offers abundant windows with a nice view of the backyard. Off of the dining room there is a cozy Florida room which also has nice views of the huge fenced in backyard and a utility shed. The laminate wood floors continue into the bedrooms. Perfect location and perfect price plus NO HOA FEES, come and see all this lovely home has to offer!!!! less
Listing Provided Courtesy of Keller Williams At The Parks
Popularity
$344,000
$1,274/mo
Monthly Payment:
$1,274
Principal & Interest:
$1,274
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $68,800 down)
Winter Park, FL 32789
Orange County School District
4bed 2bath 2,192sq ft $157 / sq ft SFR
Lot Size15,256sq ft Built1969 On Site20days
Great opportunity in Winter Park to make this property your home. This 4 bedroom, 2 bathroom home situated on a corner lot is ready for a new owner to update it and call it... more
Great opportunity in Winter Park to make this property your home. This 4 bedroom, 2 bathroom home situated on a corner lot is ready for a new owner to update it and call it home. This property is a split bedroom floorplan, has a family/great room with fireplace, large screened patio and nice yard. Please see attachments for PAS requirements and WFHM offer submittal information in MLS document section. less
Listing Provided Courtesy of Re/max Assured
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 32792
Orange County School District
4bed 3bath 2,315sq ft $172 / sq ft SFR
Lot Size12,761sq ft Built1965 On Site20days
first time on market! This traditional beauty has had only one owner and has been lovingly cared for. Bring your pickiest buyers to this spacious, bright and airy home with... more
first time on market! This traditional beauty has had only one owner and has been lovingly cared for. Bring your pickiest buyers to this spacious, bright and airy home with great Winter Park Schools! Your buyers will appreciate the large main living rooms, gorgeous double sided fireplace and over sized master bedroom with ample walk in closet. The fourth bedroom has its own back with a private entrance. This home has French doors that lead to the beautiful pavered pool area. The landscaping is lush and well maintained. Walk out your door and get on the Cady Way Trail. Easy to show! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$350,000
$1,327/mo
Monthly Payment:
$1,327
Principal & Interest:
$1,296
HOA Dues:
$31
(Based on a 30 year fixed loan at 3.75% with $70,000 down)
Winter Park, FL 32792
Seminole County School District
4bed 4bath 2,562sq ft $137 / sq ft SFR
Lot Size16,977sq ft Built1986 On Site20days
Large home in desirable Pelican Bay and Seminole School District. Split plans offers two bedrooms downstairs (master with on-suite and guest bedroom with full bath). Sunken... more
Large home in desirable Pelican Bay and Seminole School District. Split plans offers two bedrooms downstairs (master with on-suite and guest bedroom with full bath). Sunken living room with high vaulted ceilings. Tile throughout entire downstairs including inside laundry area. Upstairs are two more large bedrooms (another master with on-suite and guest bedroom) with hall bath. There is also a small bonus room that could be a study, craft room or play area. This large corner lot gives plenty of room to add a pool or enjoy the yard from the outside deck. Two car garage with plenty of off-street parking. Room to park your boat or RV. Public utilities. The community offers a beautiful park like setting with a basketball court, picnic area and a fishing pier on Lake Florence. There is a launch (riprap) for small boats and canoes. Lake Florence is a ski lake. less
Listing Provided Courtesy of Re/max Town & Country Realty
Popularity
$450,000
$1,667/mo
Monthly Payment:
$1,667
Principal & Interest:
$1,667
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $90,000 down)
Winter Park, FL 32789
Orange County School District
3bed 2bath 1,648sq ft $273 / sq ft SFR
Lot Size7,000sq ft Built1940 On Site20days
Charming Character Home in the Heart of Olde Winter Park!! Quaint brick street, white picket fence & cozy front porch welcome you this Charming Bungalow... Beautiful hardwood... more
Charming Character Home in the Heart of Olde Winter Park!! Quaint brick street, white picket fence & cozy front porch welcome you this Charming Bungalow... Beautiful hardwood floors, plaster walls throughout and living room fireplace. AMAZING Gourmet Kitchen with granite island & professional grade Thermador double ovens, gas cook top, warming drawer & built-in refrigerator, Master suite complete with pedestal sink & clawfoot tub. 14 x 6 Mud Porch includes inside laundry room & plenty of storage! 120 sq ft garden building, open deck & mature landscaping create a beautiful backyard setting! Walk to Park Avenue, Farmers Market & Rollins College!! less
Listing Provided Courtesy of Fannie Hillman & Associates
Popularity
$775,000
$2,871/mo
Monthly Payment:
$2,871
Principal & Interest:
$2,871
HOA Dues:
$0
(Based on a 30 year fixed loan at 3.75% with $155,000 down)
Winter Park, FL 32789
Orange County School District
3bed 3bath 2,334sq ft $332 / sq ft SFR
Lot Size12,046sq ft Built1960 On Site20days
This immaculate & completely updated three bedroom plus office single story home is situated on a quiet street in the sought after “Vias” of Old Winter Park. Floor... more
This immaculate & completely updated three bedroom plus office single story home is situated on a quiet street in the sought after “Vias” of Old Winter Park. Floor plan is open with views of the private back yard & sparking pool with brick paver patio. Spacious kitchen has custom cabinets, granite counter tops, pantry & opens to a light & bright family room. Large dining & living are perfect for family enjoyment or entertaining. Garage is attached & has plenty of additional storage space. Additional amenities include: French doors, custom closets throughout, hard wood & tile floors, custom wood shutters, laundry room with plenty of storage, tile roof & landscape lighting. Updates include: electrical, plumbing, new AC, new pool heater and garage floor coating. This home is move in ready. less
Listing Provided Courtesy of Coldwell Banker Residential Re
Popularity
$150,000
$765/mo
Monthly Payment:
$765
Principal & Interest:
$555
HOA Dues:
$210
(Based on a 30 year fixed loan at 3.75% with $30,000 down)
Winter Park, FL 32792
Orange County School District
3bed 3bath 1,565sq ft $96 / sq ft CND
Lot Size960sq ft Built2008 On Site20days
This lovely Town home (condo) has many features including a spacious floor plan with 3 bedrooms upstairs and 2,5 bathrooms, with the half bath down, corian counter top in... more
This lovely Town home (condo) has many features including a spacious floor plan with 3 bedrooms upstairs and 2,5 bathrooms, with the half bath down, corian counter top in kitchen, bar area seating, ceramic tile in foyer and wet areas, 36" Upper maple cabinets, microwave, refrigerator,cultured marble in baths, 2" horizontal blinds, built in desk, One car garage with Garage Door Opener. Screened Lanai over looking the wooded lot behind it. Perfect for entertaining guests. All on a quiet cul de sac, and close to shopping expressways, restaurants, Hurry! less
Listing Provided Courtesy of Keller Williams Advantage Rlty
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
Content provided and owned by Coldwell Banker Residential Real Estate.
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The information being provided by Mid Florida Regional MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the Mid Florida Regional MLS. Coldwell Banker Residential Real Estate is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of Coldwell Banker Residential Real Estate, a broker participant of Mid Florida Regional MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.

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Data last updated: Saturday, April 18, 2015 at 6:15 AM