Middlebury CT FSBO Homes (72)

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We have 72 homes for sale by owner in Middlebury, CT. The median list price in Middlebury, CT is $659,957 and the average price per square foot is $2,563.

Pending

Condo For Sale

$525,438

3 Bed
3 Bath
1,950 Sqft

N Benson Road #45, Middlebury, CT

An address that elevates your lifestyle - aberdeen estates at benson woods is a premier 55+ adult community... Read More

Homes For Sale

$349,000

2 Bed
1 Bath
1,050 Sqft
0.33 Acre(Lot)

259 White Avenue, Middlebury, CT

Welcome to this charming cape cod-style home nestled in the heart of middlebury, ct. warm hardwood floors flow... Read More

Active Under Contract

Homes For Sale

$699,000

3 Bed
2 Bath
1,877 Sqft
1.18 Acres(Lot)

14 Deer Run Road, Middlebury, CT

Welcome home to middlebury's newest 23 lot subdivision-hunting ridge estates. 14 deer run rd(aka lot 19) is just... Read More

Homes For Sale

$995,000

4 Bed
4 Bath
4,496 Sqft
6.15 Acres(Lot)

593 Park Road Extension, Middlebury, CT

This spacious, custom built home sits on a 6+ acre lot with a large garden area & a barn with 2 garage doors,... Read More

Condo For Sale

$515,000

3 Bed
3 Bath
1,808 Sqft

43 Ridgewood Drive #43, Middlebury, CT

Enjoy living a relaxing and luxurious lifestyle in a most desirable community. as you step into this beautifully... Read More

Homes For Sale

$499,900

3 Bed
3 Bath
1,682 Sqft
0.41 Acre(Lot)

115 Marney Drive, Middlebury, CT

Welcome to 115 marney drive! this spacious split level home has so much to offer to a family of any size! not... Read More

Condo For Sale

$560,000

3 Bed
3 Bath
2,122 Sqft

39 Ridgewood Drive #39, Middlebury, CT

Luxury living in this stunning 2122+ sqft portman elite end unit in sought ridgewood community. this 3-bed,... Read More

Homes For Sale

$600,000

3 Bed
3 Bath
2,262 Sqft
1.04 Acres(Lot)

116 Bronson Drive, Middlebury, CT

Welcome to this beautifully updated home, perfectly located in the heart of middlebury! this charming... Read More

Homes For Sale

$629,000

4 Bed
3 Bath
2,088 Sqft
0.82 Acre(Lot)

76 Three Mile Hill Road, Middlebury, CT

Exceptional craftsmanship & refined luxury. welcome to 76 three mile hill rd, where modern updates meet timeless... Read More

Condo For Sale

$680,000

3 Bed
4 Bath
2,277 Sqft

1 Dogwood Court #1, Middlebury, CT

Wow-this is it! the original model home is back on the market for the first time, offering exceptional quality... Read More

Condo For Sale

$569,900

2 Bed
3 Bath
2,593 Sqft

112 Periwinkle Drive #112, Middlebury, CT

Welcome to benson woods - an exclusive community of 78 single-family homes designed for active adults. this... Read More

Condo For Sale

$575,000

3 Bed
3 Bath
1,882 Sqft

180 Ridgewood Drive #219, Middlebury, CT

Welcome to this luxury end-unit condo built in 2022 w/ 3-bed, 2.5-bath in sought-after ridgewood.1882 sqft w/ 4... Read More

Condo For Sale

$565,000

3 Bed
3 Bath
2,130 Sqft

29 Winding Trail #29, Middlebury, CT

Beautiful portman condo in sought-after ridgewood community. stunning 3-bed, 2.5-bath condo built by toll... Read More

Condo For Sale

$659,000

4 Bed
4 Bath
2,376 Sqft

1 Winding Trail #1, Middlebury, CT

Don't wait to see this turn key home in the desirable ridgewood of middlbury, one of the areas newest and most... Read More

Homes For Sale

$689,999

3 Bed
3 Bath
2,328 Sqft
1 Acre(Lot)

15 Brookside Drive #15, Middlebury, CT

This stunning colonial home features a beautifully landscaped level lot with an expansive side yard. as you... Read More

Homes For Sale

$435,000

3 Bed
2 Bath
1,403 Sqft
0.25 Acre(Lot)

58 Middlebury Terrace, Middlebury, CT

Three bedroom cape cod style home in the heart of middlebury, ct! sitting on a corner lot, this cozy cape offers... Read More

Homes For Sale

$594,900

3 Bed
3 Bath
1,392 Sqft
0.97 Acre(Lot)

58 Shadduck Road, Middlebury, CT

This beautifully renovated colonial seamlessly blends classic elegance with modern updates. featuring gleaming... Read More

Pending

Homes For Sale

$499,000

3 Bed
2 Bath
1,476 Sqft
1.2 Acres(Lot)

713 Whittemore Road, Middlebury, CT

Welcome to this wonderful classic cape cod home. situated on over an acre of land, this house exudes character... Read More

Active Under Contract

Homes For Sale

$1,150,000

4 Bed
6 Bath
4,254 Sqft
1.84 Acres(Lot)

45 E Farm Road, Middlebury, CT

Over 5000 total finished sqft in this gorgeous custom colonial with 3 car garage situated on 1.84 acres in a... Read More

Condo For Sale

$721,000

2 Bed
3 Bath
2,290 Sqft

3 Pine Ridge #23, Middlebury, CT

Welcome to granite woods - 2024 hobi award winner for best detached 55+ community. only six homes remain in this... Read More

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Middlebury - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in Middlebury 44

	Average Price
1 Bed Homes For Sale in Middlebury (1)	$ 350,000
2 Bed Homes For Sale in Middlebury (1)	$ 399,000
3 Bed Homes For Sale in Middlebury (20)	$ 615,480
4 Bed Homes For Sale in Middlebury (21)	$ 821,559
5+ Bed Homes For Sale in Middlebury (1)	$ 799,900

AVERAGE PRICE

$ 597,188

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 285

Condos For Sale By Owner in Middlebury 11

	Average Price
2 Bed Condos For Sale in Middlebury (10)	$ 630,550
3 Bed Condos For Sale in Middlebury (1)	$ 589,500

AVERAGE PRICE

$ 600,856

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 299

Townhomes For Sale By Owner in Middlebury 14

	Average Price
3 Bed Townhomes For Sale in Middlebury (14)	$ 542,563

AVERAGE PRICE

$ 593,569

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 253

Land For Sale By Owner in Middlebury 8

	Average Price
Land For Sale in Middlebury (8)	$ 551,141

AVERAGE PRICE

$ 551,141

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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Learn More About Middlebury, Connecticut

Currently there are 44 homes for sale, 11 condos and apartments for sale, 8 vacant land for sale and 14 townhomes for sale in Middlebury

Currently Middlebury has 77 properties on the market for sale. The inventory was last updated 04/21/2025. Of these properties, 44 single family homes are for sale by their owners in Middlebury, and 11 condos are for sale by their owners in Middlebury. The average price of the single family homes for sale in Middlebury, is $597,188, the average condo price in Middlebury, is $600,856. The average price per square foot of the active inventory is $209. This is based the living area square footage.

Over the last year, there have been 0 of properties sold in Middlebury. Of these properties, 0 single family homes have sold by their owners in Middlebury, and 0 condos have sold by their owners in Middlebury. The average sales price of the single family homes sold in Middlebury, is $. Single family homes have been selling for per square foot of living area. The average sales price of the condos for sale in Middlebury, is $. Condos have been selling for per square foot of living area.

The most active subdivisions with listings for sale in Middlebury, are:

If you are thinking of selling your Middlebury home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 04/21/2025

Middlebury CT FSBO Homes (72)

N Benson Road #45, Middlebury, CT

259 White Avenue, Middlebury, CT

14 Deer Run Road, Middlebury, CT

593 Park Road Extension, Middlebury, CT

43 Ridgewood Drive #43, Middlebury, CT

115 Marney Drive, Middlebury, CT

39 Ridgewood Drive #39, Middlebury, CT

116 Bronson Drive, Middlebury, CT

76 Three Mile Hill Road, Middlebury, CT

1 Dogwood Court #1, Middlebury, CT

112 Periwinkle Drive #112, Middlebury, CT

180 Ridgewood Drive #219, Middlebury, CT

29 Winding Trail #29, Middlebury, CT

1 Winding Trail #1, Middlebury, CT

15 Brookside Drive #15, Middlebury, CT

58 Middlebury Terrace, Middlebury, CT

58 Shadduck Road, Middlebury, CT

713 Whittemore Road, Middlebury, CT

45 E Farm Road, Middlebury, CT

3 Pine Ridge #23, Middlebury, CT

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Middlebury - Statistics and Home Trends

Actives Activity Chart

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

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Learn More About Middlebury, Connecticut

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