103 E Chestnut St
Windsor, CO 80550
- 6 Beds
- 4 Baths
- 2,400 sqft
6 Beds
4 Baths
2,400 sqft
Local Information
-- mins to
Description
For Sale By Owner – Fully Renovated Duplex in Prime Downtown Windsor Location
Exceptional opportunity to own a beautifully renovated, fully furnished duplex in one of Windsor's most desirable locations. Situated directly across from the newly improved Chimney Park baseball fields, playground, and community pool, this property offers both lifestyle and income-producing potential.
Each side features 3 bedrooms, 2 bathrooms, updated finishes, fully equipped kitchens, and comfortable living spaces. Both units currently hold valid Windsor short-term rental permits, providing flexibility for short-term, mid-term, or long-term rental strategies.
Whether you're looking for a turnkey investment property, a house-hacking opportunity, or a multi-generational living arrangement, this duplex offers endless possibilities. Live in one unit while generating income from the other, or maximize returns by renting both sides.
Additional highlights include:
Fully furnished and turnkey
Active Windsor short-term rental permits on both units
Walking distance to downtown Windsor, Windsor Lake, parks, restaurants, and shops
Adjacent to walking trails and open green space
Excellent long-term neighboring residents
Strong rental history and income potential
Easy access to schools, recreation, and community events
Rarely does a duplex in such a premier location come available with this level of flexibility and income potential. Enjoy small-town charm, walkability, and a proven investment opportunity all in one property.
Investment property, primary residence, or both—the choice is yours.
Exceptional opportunity to own a beautifully renovated, fully furnished duplex in one of Windsor's most desirable locations. Situated directly across from the newly improved Chimney Park baseball fields, playground, and community pool, this property offers both lifestyle and income-producing potential.
Each side features 3 bedrooms, 2 bathrooms, updated finishes, fully equipped kitchens, and comfortable living spaces. Both units currently hold valid Windsor short-term rental permits, providing flexibility for short-term, mid-term, or long-term rental strategies.
Whether you're looking for a turnkey investment property, a house-hacking opportunity, or a multi-generational living arrangement, this duplex offers endless possibilities. Live in one unit while generating income from the other, or maximize returns by renting both sides.
Additional highlights include:
Fully furnished and turnkey
Active Windsor short-term rental permits on both units
Walking distance to downtown Windsor, Windsor Lake, parks, restaurants, and shops
Adjacent to walking trails and open green space
Excellent long-term neighboring residents
Strong rental history and income potential
Easy access to schools, recreation, and community events
Rarely does a duplex in such a premier location come available with this level of flexibility and income potential. Enjoy small-town charm, walkability, and a proven investment opportunity all in one property.
Investment property, primary residence, or both—the choice is yours.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
$375
Listed
Less than a day ago
Home Details for 103 E Chestnut St
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Interior Details Basement |
Heating & Cooling Heating: Forced AirHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Other |
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Exterior Home Features Roof: CompositionExterior: Wood |
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached |
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Days on Market: <1 day on Trulia |
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Year Built Year Built: 1987 |
Property Type / Style Property Type: Multi FamilyArchitecture: duplex single |
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Price Price Per Sqft: $375 |
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Units in Building: 1 |
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Lot Area: 8600 sqft |
Market trends in Windsor
Last updated May 2026
Avg. sale price
$603K
$25.33KMoM
Sale-to-List Price
99.4%
0.2%MoM
Price per sq ft
$207
$7MoM
Available listings
238
12MoM
Price History for 103 E Chestnut St
| Date | Price | Event | Source |
|---|---|---|---|
| 07/11/2026 | $899,900 | Listed For Sale | N/A |
| 01/17/2023 | $640,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $2,932 |
| Assessment | $640,000 |
Home facts updated by county records
Comparable Sales for 103 E Chestnut St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
1.58 | Multi-Family Home | $3,900,000 | 12/11/25 | - | - | ||
4.93 | Multi-Family Home | $1,385,000 | 08/29/25 | 4 | 4 | 4,400 | |
4.62 | Multi-Family Home | $761,430 | 08/29/25 | - | - | ||
4.79 | Multi-Family Home | $710,145 | 07/31/25 | - | - | ||
4.80 | Multi-Family Home | $725,240 | 08/14/25 | - | - | ||
4.86 | Multi-Family Home | $620,000 | 03/24/26 | - | - | ||
4.86 | Multi-Family Home | $600,000 | 04/30/26 | - | - | ||
4.89 | Multi-Family Home | $520,000 | 02/18/26 | - | - | ||
4.62 | Multi-Family Home | $1,870,000 | 06/17/26 | - | - | ||
4.90 | Multi-Family Home | $535,000 | 04/10/26 | - | - |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 103 E Chestnut St.
What Locals Say about Windsor
At least 121 Trulia users voted on each feature.
97 % Say it's dog friendly
95 % Say there are sidewalks
89 % Say parking is easy
89 % Say yards are well-kept
88 % Say kids play outside
86 % Say car is needed
85 % Say people would walk alone at night
78 % Say it's quiet
77 % Say there's holiday spirit
74 % Say streets are well-lit
61 % Say neighbors are friendly
55 % Say they plan to stay for at least 5 years
47 % Say it's walkable to restaurants
46 % Say there are community events
43 % Say there's wildlife
24 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
This property is for sale by owner and Zillow, Inc. is displaying it at the owner’s request. It is not subject to a listing agreement with Zillow, Inc. or its affiliates.
103 E Chestnut St, Windsor, CO 80550 is a 6 bedroom, 4 bathroom, 2,400 sqft multi-family built in 1987. This property is currently available for sale and was listed on Jul 11, 2026.

