Here are Winchester listings for rentals and roommates -- find yourself a whole new living arrangement by choosing from apartments, homes for rent, and other rooms for rent.
Also, if you're only passing through Winchester for a brief period of time, find short term rentals or vacation rentals.
107 Strawberry Ln |
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107 Strawberry LnWinchester, KY$2,400
Vacation Rentals, Unknown
This house is new,never been lived in, four bedroom, 2.5 bathrooms, large kitchen with a family room, covered porch, 2 car garage.... |
5440 Van Meter Rd |
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5440 Van Meter RdWinchester, KY$1,750
Vacation Rentals, Unknown
Coming available soon! 3 bed 2 bath modular home in the country. New carpet and freshly painted. Surrounded by a cattle farm on a quiet road just east of Lexington. Minutes from Hamburg Shopping...... |
3 Wainscott Ave |
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3 Wainscott AveWinchester, KY$1,125
Vacation Rentals, Unknown
Section 8 Friendly! Undergoing new renovation! Rental Requirements: - Security deposit equal to 1-months rent - 1-year lease minimum - Income must be 2.5x the monthly rent - 2 Pet maxima. $250...... |
202 Washington Sq |
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202 Washington SqWinchester, KY$1,600
Vacation Rentals, Unknown
Fully updated with LVP flooring, freshly painted, granite counter tops and large storage shed. Property is sec8 approved. - no smoking - no pets - no previous evictions.... |
408 Tremont Ln |
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408 Tremont LnWinchester, KY$1,900
Vacation Rentals, Unknown
Wonderful 4 bedroom, 21/2 baths, updated kitchen with new cabinets, granite counter tops, plus all stainless steel appliances! The house has a great layout with a large bedroom on the first floor,...... |
21 Maryland Ave |
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21 Maryland AveWinchester, KY$1,025
Vacation Rentals, Unknown
This cute little 1950s bungalow has all the vintage charm you want with the new upgrades you desire including updated central heating and air. Not only does this single family home have a detached...... |
522 Hidden Hills Way |
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522 Hidden Hills WayWinchester, KY$1,200
Vacation Rentals, Unknown
Beautiful , Super clean ,3 bedroom, 2 bath house with garage . Features open great room . New flooring through out , recently painted . ABSOLUTELY NO PETS , NO HUD, NO Smoking Apply online at...... |
34 Spring St |
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34 Spring StWinchester, KY$1,200
Vacation Rentals, Unknown
Spacious Single Family Home available on corner lot. Large rooms, tons of kitchen cabinet space, hard surface flooring, large yard, front porch and more! Approved applications are required prior to...... |
157 Strode Station Cir |
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157 Strode Station CirWinchester, KY$850
Vacation Rentals, Unknown
If you saw the last unit just like this one, you know it went super fast. Don't miss out on this one! 2 bedroom, 1 bath duplex on Strode Station Circle. Ground floor living with hardwood floors,...... |
159 Strode Station Cir |
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159 Strode Station CirWinchester, KY$850
Vacation Rentals, Unknown
If you saw the last unit just like this one, you know it went super fast. Don't miss out on this one! 2 bedroom, 1 bath duplex on Strode Station Circle. Ground floor living with hardwood floors,...... |
260 Prescott Ln |
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260 Prescott LnWinchester, KY$1,795
Vacation Rentals, Unknown
Welcome Home! Charming Features throughout our 3 Bedroom 2.5 Bath home. Vinyl-Plank flooring gleaming throughout, a combination of stylish and natural lighting. Our New Construction is waiting for...... |
114 Andover Dr |
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114 Andover DrWinchester, KY$1,250
Vacation Rentals, Unknown
4 bedroom 2 bath home rent ready! This property features a carport for your convenience. This home will not last long. Please inquire for a showing. Thank you!... |
402 Mount Vernon Dr |
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402 Mount Vernon DrWinchester, KY$850
Vacation Rentals, Unknown
Y'all, we have another one! 2 bedroom, 2 bath mobile home in Yorktowne Estates. New carpet, tons of cabinet space, kitchen island, laundry room. Two spacious bedrooms and two full baths with new...... |
230 Prescott Ln |
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230 Prescott LnWinchester, KY$1,695
Vacation Rentals, Unknown
This beautiful home awaits you with new flooring, and paint. Located in a desirable neighborhood, this spacious house offers 3 bedrooms and 2.5 bathrooms, providing ample space for you and your...... |
153 Strode Station Cir |
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153 Strode Station CirWinchester, KY$850
Vacation Rentals, Unknown
Coming soon... 2 Bedroom, 1 Bath duplex. This ground floor unit features hardwood floors, fresh paint, in unit laundry room, gas cooking, central heat & air, off street parking and more! Up to two...... |
413 Country Club Dr |
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413 Country Club DrWinchester, KY$1,350
Vacation Rentals, Unknown
COMING SOON! Welcome home to this inviting 2-bedroom, 2-bathroom residence that seamlessly blends modern comfort with classic charm. Nestled in a tranquil neighborhood, this property offers the...... |
121 Buckner St |
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121 Buckner StWinchester, KY$1,175
Vacation Rentals, Unknown
This beautiful 3 bedroom 1 bathroom house is Now Available! Featuring tons of cabinet space, hardwood flooring throughout, spacious rooms and so much more!! Take some time today to see your new...... |
125 Buckner St |
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125 Buckner StWinchester, KY$1,175
Vacation Rentals, Unknown
This beautiful 2 bedroom 1 bathroom house is Now Available! Featuring tons of cabinet space, hardwood flooring throughout, spacious rooms and so much more!! Take some time today to see your new...... |
106 Fulton Ave |
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106 Fulton AveWinchester, KY$1,000
Vacation Rentals, Unknown
Ranch house on quiet street with very large, fenced-in backyard. Off street parking. Central HVAC. Additional basement storage area.... |