West Windsor Homes

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  $299,925

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft

  41 Chestnut Dr, Windsor, CT 06095

  Welcome to 41 Chestnut Drive, a charming and well-maintained Cape Cod style home nestled in a quiet Windsor neighborhood, perfect for those seeking comfort, convenience, and classic New England character. This bright and inviting residence has 2 spacious bedrooms with an extra room for either a den or an office, 2 full baths with one being totally renovated, with a flexible floor plan that blends

  

  Jason Kemp

  Five Stars Realty

  (860) 737-9994

  41 Chestnut Dr, Windsor, CT 06095
• Explore West Windsor

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  /27

  $2,000 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 972 Sq Ft
  • House for Rent

  925 High Path Rd, Windsor, CT 06095

  Two-bedroom unit in desirable Chateau Woods Complex. Open living concept - large living/dining room with slider leading out to your private patio with views of nature. This condo features new easy to maintain flooring throughout; Jack and Jill bathroom with two separate half baths on both sides of shower/bath area; lots of closet space including a large walk-in closet. Bedrooms that fit any size

  

  Mavourneen Costello

  NextHome Elite Realty

  (860) 851-4219

  925 High Path Rd, Windsor, CT 06095
• 

  $500,000 Sold Oct 09, 2025

  464 Prospect Hill Rd, Windsor, CT 06095

  • 4 Beds
  • 3 Baths
  • 2,949 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Above List Price
  • $170/SF
  • 72 Days On Market

  Last Listing Agent Michael Barile Barile Realty Group

  464 Prospect Hill Rd, Windsor, CT 06095
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  Est $420,544 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  406 Old Village Cir Unit 406, Windsor, CT 06095

  406 Old Village Cir Unit 406, Windsor, CT 06095
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  /2

  $259,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,194 Sq Ft

  99 Pepperbush Way, Windsor, CT 06095

  3-bedroom, 2.5-bath raised ranch offering comfort and convenience in a desirable setting. This home features a 2-car attached garage, natural gas heat, and public utilities for ease of living. The lower level offers even more living space with a family room, half bath, laundry, and direct access to the garage. With its functional floor plan and sought-after utilities, this home is ready for its

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 300-2726

  99 Pepperbush Way, Windsor, CT 06095
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  /66

  $1,920 - $3,350 total monthly price

  The Preserve at Great Pond

  Studio - 3 Beds

  100 Lexington St, Windsor, CT 06095

  Welcome to The Preserve at Great Pond – where comfort and luxury meet. Embraced by nature, yet close to urban conveniences, our luxury apartments in Windsor, CT, cater to city dwellers and outdoor adventurers alike. Add in the thoughtful collection of services and amenities, and you’ll have everything you expect from a true home.Live the luxury life in any of our studio, one, two, or

  100 Lexington St, Windsor, CT 06095
• 

  $360,000 Sold May 30, 2025

  11 Merli Rd, Windsor, CT 06095

  • 3 Beds
  • 1.5 Baths
  • 1,710 Sq Ft
  • Built 1995

  Last Sold Summary

  • 6% Above List Price
  • $211/SF
  • 2 Days On Market

  Current Estimated Value $372,801

  Last Listing Agent Maureen Bohrer Howard Hanna Rand Realty

  11 Merli Rd, Windsor, CT 06095
• 

  Est $482,560 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,479 Sq Ft

  74 Commons Crossing, Windsor, CT 06095

  74 Commons Crossing, Windsor, CT 06095
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  $389,900

  • 3 Beds
  • 2.5 Baths
  • 1,942 Sq Ft

  14 Loren Cir, Windsor, CT 06095

  Tucked at the end of a quiet cul-de-sac, this beautifully maintained raised ranch offers a perfect blend of comfort and modern updates. The bright open layout features gleaming recently refinished hardwood floors, an inviting living and dining area, and a remodeled kitchen with granite countertops, stainless steel appliances, and tile flooring. Upstairs you'll find three spacious bedrooms,

  

  Mike Albert

  RE/MAX RISE

  (959) 215-6076

  14 Loren Cir, Windsor, CT 06095
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  /14

  $1,600 total monthly price

  • 1 Bed
  • 1.5 Baths
  • 723 Sq Ft
  • Apartment for Rent

  962 High Path Rd, Windsor, CT 06095

  Spacious 1 bedroom, 2 bathroom condo unit for rent in The Chateau Wood Complex in Windsor. Come enjoy the open concept living area, updated kitchen, and community pool. Lower monthly bills with heat and hot water included! Conveniently located near shopping, restaurants, and major highways. Available Feb 1st.

  Marc Krawiec The Bridge Realty Inc

  962 High Path Rd, Windsor, CT 06095
• 

  $125,000 Sold Oct 02, 2025

  297 High Path Rd Unit 297, Windsor, CT 06095

  • 1 Bed
  • 1.5 Baths
  • 736 Sq Ft
  • Built 1972

  Last Sold Summary

  • 17% Below List Price
  • $170/SF
  • 16 Days On Market

  Last Listing Agent Jessamyn Davila Coldwell Banker Realty

  297 High Path Rd Unit 297, Windsor, CT 06095
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  Est $475,875 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,482 Sq Ft

  21 Marble Faun Ln Unit 21, Windsor, CT 06095

  21 Marble Faun Ln Unit 21, Windsor, CT 06095
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  $299,994 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  552 Stone Rd, Windsor, CT 06095

  Welcome to this charming 3-bedroom ranch located in Windsor, CT! Set in a peaceful semi-rural neighborhood yet just minutes from Route 20 and I-91, this home offers the perfect balance of comfort and convenience. Located right around the corner from Rainbow Reservoir, offering opportunities for boating, fishing, kayaking, paddleboarding, or jet skiing. Inside, you'll find original hardwood floors

  Eric Tellier Trend 2000 Real Estate

  552 Stone Rd, Windsor, CT 06095
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  /20

  $2,200 per month plus fees

  • 2 Beds
  • 2.5 Baths
  • 1,020 Sq Ft
  • Townhouse for Rent

  266 High Path Rd, Windsor, CT 06095

  Property Id: 2247514Welcome home to this charming 2 bedroom, 2.5 bathroom townhouse in Windsor, CT. Built in 1972, this property features modern amenities such as a dishwasher, washer, and dryer. Enjoy off-street parking, a swimming pool, and on-site laundry. Water, sewage, and garbage included. Don't miss out on this gem! Available starting 11/23/2025 for $2200/month and $3,000 security

  266 High Path Rd, Windsor, CT 06095
• 

  $430,000 Sold Aug 07, 2025

  30 Holly Cir, Windsor, CT 06095

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft
  • Built 1966

  Last Sold Summary

  • 1% Above List Price
  • $170/SF
  • 29 Days On Market

  Current Estimated Value $434,302

  Last Listing Agent Michael Price KW Legacy Partners

  30 Holly Cir, Windsor, CT 06095
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  Est $126,000 Not Listed For Sale

  801 Stone Rd, Windsor, CT 06095

  801 Stone Rd, Windsor, CT 06095
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  /11

  $325,000

  • Land
  • 12.18 Acres
  • $26,683 per Acre

  490 Old Day Hill Rd, Windsor, CT 06095

  Attention Farmers!! This 12+ acre location is strictly for the farmers. With a tobacco barn and newly updated potato barn this piece of property is ready for you to start your farming business. Agents please reach out for the specific guidelines with this property or read the agent notes

  Heather Heeb Keller Williams Realty-Longmdw

  490 Old Day Hill Rd, Windsor, CT 06095
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  /15

  $1,500 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Apartment for Rent

  338 Dunfey Ln Unit D, Windsor, CT 06095

  Welcome home to this beautiful condo, a hidden gem nestled right in the heart of Windsor. Just off Exit 37 on I-91, this spacious unit boasts two large bedrooms, a generous dining room, and stunning hardwood floors throughout. Indulge in cooking in the updated kitchen and enjoy the convenience of a shared basement with laundry facilities. Take a relaxing stroll around this peaceful,

  Naihommy Colon Rainbow Realty

  338 Dunfey Ln Unit D, Windsor, CT 06095
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  $452,000 Sold Oct 14, 2025

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 1,957 Sq Ft
  • Built 1991

  Last Sold Summary

  • 8% Above List Price
  • $231/SF
  • 4 Days On Market

  Last Listing Agent Melissa Rothman eXp Realty

  Unlisted Address
• 

  Est $422,044 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1846 Poquonock Ave, Windsor, CT 06095

  1846 Poquonock Ave, Windsor, CT 06095
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  /30

  $545,000

  • 4 Beds
  • 5 Baths
  • 3,102 Sq Ft

  2080 Poquonock Ave, Windsor, CT 06095

  Looking for an open-concept colonial with 3000+ square feet? Search no further than 2080 Poquonock Ave. Property is located in the sought-after town of Windsor, CT. Interested in curb appeal well this is it. The exterior and interior is a combination of contemporary with a touch of georgian. One step inside and you'll be captivated by the style, elegance, and workmanship. Greet your guests in the

  Alexander Pryor Coldwell Banker Realty

  2080 Poquonock Ave, Windsor, CT 06095
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  /20

  $2,100 per month plus fees

  • 2 Beds
  • 1.5 Baths
  • 1,050 Sq Ft
  • Condo for Rent

  21 Waterview Dr, Windsor, CT 06095

  Property Id: 2256639Welcome to your new home here at 21 Waterview Drive in Windsor, CT available immediately! This charming 2 bed, 1.5 bath unit boasts fully equipped kitchen, in-unit washer/dryer, central AC/heat, and a cozy fireplace. 2 large bedrooms, one with his/her closets and the other with a very large walk in closet. Close proximity to groceries, restaurants, shopping,

  21 Waterview Dr, Windsor, CT 06095
• 

  $347,450 Sold Jan 31, 2025

  23 Last Leaf Cir Unit 23, Windsor, CT 06095

  • 2 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2009

  Last Sold Summary

  • 9% Below List Price
  • $179/SF
  • 121 Days On Market

  Current Estimated Value $363,014

  Last Listing Agent Elaine Birthwright-Rowe New Haus Group LLC

  23 Last Leaf Cir Unit 23, Windsor, CT 06095
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  Est $572,000 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,084 Sq Ft

  211 Sunnyfield Dr, Windsor, CT 06095

  211 Sunnyfield Dr, Windsor, CT 06095
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  /35

  $459,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft

  225 Rollingbrook, Windsor, CT 06095

  Striking curb appeal meets enduring sophistication in this stately, four bedroom Colonial home nestled in a peaceful neighborhood. A spectacular, remodeled kitchen boasts beautiful, new white cabinetry and quartz countertops, stainless steel appliances, new flooring, an island/breakfast bar, new recessed and pendant lighting, a vaulted ceiling, a skylight, a spacious dine-in area and a slider to

  Sharon Rispoli Berkshire Hathaway NE Prop.

  225 Rollingbrook, Windsor, CT 06095
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  /22

  $1,900 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 1,020 Sq Ft
  • Apartment for Rent

  244 High Path Rd Unit 244, Windsor, CT 06095

  This 2 bedroom, 2.5 bathroom condominium is available for immediate move-in. The property is located in an end unit within a cul-de-sac in a residential community. On the main level, the unit offers a living area, a dining room, and a half bathroom. The kitchen is equipped with an electric stovetop, refrigerator, and dishwasher. The upper level includes two bedrooms, with the primary bedroom

  Nicole Allen Ardent Trust Property Mngmnt

  244 High Path Rd Unit 244, Windsor, CT 06095
• 

  $480,000 Sold Jan 03, 2025

  1580 Poquonock Ave, Windsor, CT 06095

  • 5 Beds
  • 2 Baths
  • 2,908 Sq Ft
  • Built 1806

  Last Sold Summary

  • $165/SF
  • 9 Days On Market

  Current Estimated Value $495,928

  Last Listing Agent Clifford Knight Agnelli Real Estate

  1580 Poquonock Ave, Windsor, CT 06095
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  Est $438,508 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft

  508 Stillwater, Windsor, CT 06095

  508 Stillwater, Windsor, CT 06095
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  /7

  $1,900,000

  • Land
  • 79 Acres
  • $24,051 per Acre

  999 Stone Rd, Windsor, CT 06095

  There are two abutting parcels that offer a total of 79 acres. 999 Stone Road is a 56.7 acre parcel that is zoned Agricultural. 965 Stone Road is a 22.3 acre parcel that is zoned Industrial. The parcels are level and wooded with some open areas. The two parcels combined offer an opportunity for Industrial, Agricultural or potential Residential development. This very convenient location is just

  John Waters Berkshire Hathaway NE Prop.

  999 Stone Rd, Windsor, CT 06095
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  /23

  $3,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • House for Rent

  7 Dally Farm Rd, Windsor, CT 06095

  Welcome to this beautifully updated Raised Ranch in Windsor, perfectly move-in ready just in time for the holidays. Built in 1992, offering 2,300 sq. ft. of bright, modern living space, this stylish 4 Beds, 2 Full Baths home has been thoughtfully refreshed from top to bottom in November 2025. The entire interior has been professionally painted, creating a clean and contemporary feel throughout,

  Laura Hardacre Coldwell Banker Realty

  7 Dally Farm Rd, Windsor, CT 06095
• 

  $435,000 Sold Aug 19, 2025

  2 Marble Faun Ln, Windsor, CT 06095

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Above List Price
  • $250/SF
  • 2 Days On Market

  Current Estimated Value $432,220

  Last Listing Agent Bonnie Farmer Berkshire Hathaway NE Prop.

  2 Marble Faun Ln, Windsor, CT 06095
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  Est $329,117 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,463 Sq Ft

  16 Whitward Place, Windsor, CT 06095

  16 Whitward Place, Windsor, CT 06095
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  /35

  $329,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,125 Sq Ft

  23 Griswold Dr, Windsor, CT 06095

  What a gem! With wonderful curb appeal, tucked away on a peaceful cul-de-sac and the graceful ease of single-level living, this three bedroom Ranch is truly a rare property. Spacious and inviting, the living room boasts a gorgeous fireplace with a spectacular Heatilator, dazzling hardwood floors, recessed lighting and a bay window that fills the space with natural light. Ideal for evening dinners

  Sharon Rispoli Berkshire Hathaway NE Prop.

  23 Griswold Dr, Windsor, CT 06095
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  /18

  $2,900 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Townhouse for Rent

  501 Old Village Cir, Windsor, CT 06095

  Experience the charm of the highly sought-after Villages at Poquonock in this exceptional End Unit Townhouse Condominium. Designed for modern living, this home features an open-concept layout that effortlessly blends the living room, dining area, and kitchen-ideal for both everyday comfort and entertaining. The first floor includes a spacious primary bedroom with an en-suite bath, providing

  Jeyackumar Manickam William Raveis Real Estate

  501 Old Village Cir, Windsor, CT 06095
• 

  $355,000 Sold Jun 12, 2025

  808 Matianuck Ave, Windsor, CT 06095

  • 2 Beds
  • 2 Baths
  • 1,709 Sq Ft
  • Built 1930

  Last Sold Summary

  • 15% Above List Price
  • $208/SF
  • 4 Days On Market

  Current Estimated Value $349,797

  Last Listing Agent Patty Kilpatrick ERA Blanchard & Rossetto

  808 Matianuck Ave, Windsor, CT 06095
• 

  Est $351,124 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,472 Sq Ft

  3 Whitward Place, Windsor, CT 06095

  3 Whitward Place, Windsor, CT 06095
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  /40

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,360 Sq Ft

  10 Cleary Ln, Windsor, CT 06095

  Nestled on a quiet cul-de-sac, this beautiful 4-bedroom, 2.1-bath ranch offers over 2,300 sq. ft. of stylish living space. The sunken living room is a true showstopper, featuring dramatic floor-to-ceiling windows that flood the space with natural light. A spacious dining room overlooks the living area, creating an open and inviting layout perfect for gatherings. The master suite and family room

  Tammy Ferrauola Eagle Eye Realty PLLC

  10 Cleary Ln, Windsor, CT 06095
• 

  $682,000 Sold Sep 15, 2025

  35 Jubrey Dr, Windsor, CT 06095

  • 4 Beds
  • 3.5 Baths
  • 3,191 Sq Ft
  • Built 2010

  Last Sold Summary

  • 5% Above List Price
  • $214/SF
  • 37 Days On Market

  Current Estimated Value $669,636

  Last Listing Agent Sherri Schwartz Coldwell Banker Realty

  35 Jubrey Dr, Windsor, CT 06095
• 

  Est $328,693 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,193 Sq Ft

  33 Early Dawn Cir, Windsor, CT 06095

  33 Early Dawn Cir, Windsor, CT 06095
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  /38

  $535,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,164 Sq Ft

  33 Old Village Cir, Windsor, CT 06095

  Stunning freestanding unit at The Villages at Poquonock with many premium upgrades and beautiful natural light. The pretty & functional foyer opens to an open floor plan featuring an island kitchen with high end appliances, a dining area with sliders to the back patio, and a living area with a spectacular modern feature wall with a centrally mounted flat-screen TV and cozy electric fireplace

  Bonnie Collins William Raveis Real Estate

  33 Old Village Cir, Windsor, CT 06095

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