The picturesque town of Middlebury is where you can find a friendly blend of small-town warmth and cultural depth., and is home to the prestigious Middlebury College. Dine, shop, or attend the theater in Middlebury's downtown. Burlington is just a short drive away, but you will never feel forced to make the trip with all of the services, shopping, and entertainment you need just minutes away.

The mountains, forests, and lakes invite you to pack a picnic, jump into a swimming hole, hike trails, or go camping. In the summer golf, tennis, and biking are popular pastimes, as well as enjoying nearby Lake Champlain. In the winter cross-country skiing or downhill skiing at the Middlebury College Snow Bowl are just a few ways to enjoy the snow.

Search our complete listing of homes & real estate for sale in Middlebury, Vermont.

 

42 Currently Available
2 Chipman Heights, Middlebury
Residential
2
2
1,156
0.2900
1953
$5,563

Listed Apr 23rd, 2019

MLS# 4747096

By Beth Stanway of IPJ Real Estate

This is your chance to be on Chipman Hill! One level living with mountain views. The attached garage opens into the family room which has a wood stove to keep you warm in the winter. It also has new bamboo floors. The family room opens to the kitchen, which has seating at the peninsula. The open living/dining room has shiny hardwood floors and a picture window that has mountain views. Just off the dining area is the most amazing screened in porch. The perfect place for a nap! There...

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2020 Case Street, Middlebury
Residential
3
2
1,572
1.4000
1900
$4,927

Listed Apr 12th, 2019

MLS# 4745344

By Amey Ryan of IPJ Real Estate

What a place to be! This farmhouse takes advantage of south facing windows and a huge yard with tons of room to run, play, plant and party! You'll find a new patio, a playset and a gorgeous sunset view over fields and to the Adirondack Mountains in the distance. Conveniently located to points both north and south of the town of Middlebury and E. Middlebury village (think Waybury Inn/Pub, swimming holes, tennis courts, playgrounds). On the first floor you'll find the living room, with...

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14 Kings Row, Middlebury
Residential
2
1
1,026
0.3900
1952
$4,504

Listed Apr 8th, 2019

MLS# 4744375

By Amey Ryan of IPJ Real Estate

Very nicely maintained, easy to manage home in the quaint village of East Middlebury. Walk to the tennis courts/playground, the Waybury Inn (great pub, room for guests!) and the favorite local swimming hole at the bottom of sand hill! Enjoy the ease of living in a renovated home with an updated kitchen, updated bathroom, lovely hardwood floors and a full and dry basement. Outside you'll find a very manageable yard (flat, easy mowing) and a covered carport with lots of extra space to store...

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16 Evergreen Lane, Middlebury
Condo
1
1
720
1982
$3,104

Listed Mar 29th, 2019

MLS# 4742627

By Courtney Houston DeBisschop of IPJ Real Estate

Easy living at its best, nice and fresh one bedroom unit. All on one level. Slate floors throughout, bedroom with ensuite bath. Open concept with living area facing the west, sliding door leading to a private deck space. Bonus room on the second level that is partially finished and also unfinished attic space. Tons of storage.

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1 Piper Road, Middlebury
Residential
4
3
2,184
0.2500
1870
$3,640

Listed Mar 26th, 2019

MLS# 4742071

By AMY YOUNG of Four Seasons Sotheby\'s Int\'l Realty

There are many new improvements to this charming two family home. New flooring, updated bathrooms, and fresh paint throughout the main house. The second apartment can be used as a in-law apartment or can be rented as additional income.

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1 Piper Road, Middlebury
Multi-Family
2
4
3
2,184
0.2500
1870
$3,640

Listed Mar 26th, 2019

MLS# 4742009

By AMY YOUNG of Four Seasons Sotheby\'s Int\'l Realty

There are many new improvements to this charming two family home. New flooring, updated bathrooms and fresh paint throughout the main house. The second apartment can be used as a in-law apartment or can be rented for additional income.

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111 Oak Drive, Middlebury
Residential
4
3
2,567
1.2500
1986
$8,604

Listed Mar 26th, 2019

MLS# 4741962

By Jill Fraga of The Real Estate Company of Vermont, LLC

Get ready to call this spacious cape your new home! Featuring four bedrooms, two full baths and a half bath, there is plenty of room for family and guests. From the mudroom off the two car garage, enter into the sun-filled kitchen offering tons of counter and cabinet space. The large island with butcher block countertop is perfect for food prep and entertaining alike as it opens directly to the family room. Hardwood flooring from the kitchen flows into the dining room and living room which...

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56 Monarch Court, Middlebury
Mfg/Mobile
2
2
1,008
1992
$781

Listed Mar 20th, 2019

MLS# 4741378

By Nikhil Plouffe of Addison County Real Estate

Everything a mobile home has to offer and more! Located on a quiet cul de sac, this cozy home is perfect for anyone looking to live in a quiet neighborhood at a good price. This home consists of open living area, master suite, 10'x20' enclosed porch and a storage shed. Lot rent includes municipal water, septic maintenance, trash, recycling and road maintenance. Outdoors comes with a flower bed for the gardener in you. Enjoy the ease of one-level living! Buyers must be approved by Addison...

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1788 Halladay Road, Middlebury
Residential
3
3
2,528
10.0700
1977
$9,599

Listed Mar 3rd, 2019

MLS# 4738596

By Amey Ryan of IPJ Real Estate

Killer location on Halladay Road with spectacular Adirondack Mountain views and a pretty great view of the Green Mountains too! The original house (the western portion) was built in 1977 by Weissman & Demong. It was built as a modest three bedroom home with lovely spaces and cozy corners. In 2003, the owners hired Salamander Construction to completely renovate the main living area on the first floor and add a large mudroom, 1/2 bath, office, laundry room and a beautiful master bedroom...

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122 South Ridge Dr., Middlebury
Residential
3
3
1,944
0.7200
2010
$7,887

Listed Feb 9th, 2019

MLS# 4735939

By Sarah Peluso of IPJ Real Estate

Live in one of Middlebury's newest neighborhoods! Located in South Ridge, this cape style home has everything you need. Enter into the mudroom with tile floor and laundry- a great place to leave your muddy boots! The open concept kitchen/dining/living area is full of natural light, and is the perfect place to entertain. The kitchen has stainless steel appliances, with windows out to the backyard. Handsome new red maple floors in the living/dining area are from a local mill. French doors to...

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671 Buttolph Drive, Middlebury
Residential
4
3
2,177
0.2900
1982
$7,847

Listed Feb 7th, 2019

MLS# 4735866

By Elizabeth Marino of Four Seasons Sotheby\'s Int\'l Realty

Well maintained Dutch Colonial in Buttolph Acres. The current owners have done many upgrades and improvements. New bamboo flooring throughout. New tile in bathrooms and foyer. New roof, gutters, and fenced in backyard. First floor bedroom, two additional bedrooms and master bedroom with master bath on the second floor. Warm and comfortable first floor with dining room off the kitchen and two living areas. Plenty of storage in the basement and above the garage. Conveniently located,...

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1186 Halladay Road, Middlebury
Residential
4
3
2,980
4.0600
2001
$9,388

Listed Feb 1st, 2019

MLS# 4735016

By Amey Ryan of IPJ Real Estate

Sophisticated traditional cape meets private country living. Entertain a crowd or simply enjoy the quiet life in this spacious meticulously maintained 4 bedroom, 2.5 bathroom home with comfortable elegance. You will love the gourmet kitchen w/ granite counters, cherry cabinets, stainless steel appliances, maple butcher block island and walk-in pantry. The adjacent family room with a brick gas fireplace completes the space. Enjoy the convenience of the luxurious private first floor master...

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155 Butternut Ridge Drive, Middlebury
Residential
4
2
2,648
0.8000
1971
$5,126

Listed Jan 5th, 2019

MLS# 4731972

By Roxanna Emilo of Emilo Real Estate, LLC

Raised Ranch nestled in the woods with some mountain views. 4 bedrooms In law apartment in the lower level with walk out. Upstairs on the main level is three bedrooms, full bath, den, dining room and kitchen. Enjoy the fireplace on the upper level or the family room in the basement next to the in law apartment. This property has a lot to offer. Nestled in the woods, with some mountain views make this home a tranquil spot to enjoy.

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98 Court Street, Middlebury
Multi-Family
3
4
3
2,335
1.2000
1950
$7,727

Listed Dec 7th, 2018

MLS# 4729933

By Jeff Olson of Addison County Real Estate

EXTREMELY WELL KEPT 3-unit building that's been in the same hands for 26 years. Repurposed and remodeled in 2014 and fully leased, this building is a money maker. It's in a great location less than a mile from downtown, and the Middlebury rental market remains strong. New individual water heaters for each unit were installed a few years ago, and each unit sports a brand new furnace--fueled by natural gas--installed in the summer of 2018. Best, this building sits on 1.2 acres, making...

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72 Seminary Street, Middlebury
Multi-Family
4
8
4
1,440
0.6800
1969
$6,471

Listed Nov 12th, 2018

MLS# 4727792

By Tom Walsh of Coldwell Banker Bill Beck R.E. Midd

Opportunity to own profitable 4-unit apartment building(s). There are two buildings (70 Seminary and 72 Seminary) each with two, 2-BR apt. units. Long term tenants would happily stay.

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17 Twin Circle, Middlebury
Condo
2
3
2,008
1988
$5,063

Listed Oct 26th, 2018

MLS# 4725770

By Nancy Foster of Champlain Valley Properties

This very desirable one-level condo has a partially finished basement as well as other very nice upgrades. The lovely sunroom faces Battell Woods, and the large bay window has great southern exposure. It is easy to walk out your back door and go for a walk in the woods, and out your front door and have easy access to Middlebury stores and schools. The one car garage is as close as possible in these Condos. This well maintained condo is in a great location and is nicely set up for easy...

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153 Wildflower Lane, Middlebury
Residential
4
4
4,671
4.4800
1984
$12,653

Listed Oct 16th, 2018

MLS# 4723868

By John Nelson of Emilo Real Estate, LLC

This gracious, four bedroom home on four and a half a very private acres is five minutes from Middlebury, yet feels like a world apart. The spacious, art-filled interiors flow out from a three-story, light-filled atrium with a magnificent, custom-designed, circular oak staircase, providing multi-purpose living, office, and entertainment or studio spaces with functionality for every member of the household. The two-floor, "in-law" apartment includes an elevator and presents possibilities...

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TBD Case Street, Middlebury
Land
Forest District
19.0000

Listed Oct 11th, 2018

MLS# 4723187

By Bill Martin of Greentree Real Estate

Wooded, secluded, interior lot. The lot is very level and private with a stream running through it. Abutting Green Mountain National Forest, this lot is perfect for recreational purposes.

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0 Route 7, Middlebury
Land
Multiple
178.0000

Listed Sep 20th, 2018

MLS# 4719512

By Michael Tragner of Fountains Land Inc.

This forestland parcel holds gently rolling terrain situated on a hill between nearby Green Mountain National Forest lands and the Lake Champlain Valley to the west. Direct access to Route 7 offers a minute’s drive to East Middlebury Village, with downtown Middlebury just 4.5 miles to the north. This location of Vermont is one of the more desirable areas to live with its healthy jobs market and diverse outdoor recreational options. The property also offers an outstanding, managed...

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90 Ossie Road, Middlebury
Residential
4
2
2,260
0.5000
1927
$5,379

Listed Sep 5th, 2018

MLS# 4716897

By Donna Laberge of Four Seasons Sotheby\'s Int\'l Realty

Spacious home in the heart of East Middlebury village! Walking distance to store, Post Office, library, children's playground and the Waybury Inn. 10 minutes from all downtown Middlebury has to offer, 10-15 minutes to Lake Dunmore/Fern Lake areas and 20-30 minutes to cross country and downhill skiing! Spacious and comfy great room with pellet stove for the wintry days, kitchen with eating counter and opening to great room, formal dining room, living room opening to covered front porch,...

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36 Seymour Street, Middlebury
Multi-Family
2
6
2
2,048
0.3400
1875
$4,548

Listed Aug 29th, 2018

MLS# 4715584

By Ray Fortier of Coldwell Banker Bill Beck R.E. Midd

It's all about the location---walking distance to all the amenities downtown Middlebury has to offer. Excellent Investor returns----- Live in one unit and collect rent on the other to help pay your mortgage --this property qualifies for FHA financing with 3 1/2 % down payment--and 75% of the other units rent will be added to your income to help qualify-- Or collect both rents totaling $27,600 plus per year. Conventional investor financing is available with a 15% down payment. Check out the...

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918 Washington St Ext, Middlebury
Land
High Den./Forest 2/Ag
105.7000

Listed Aug 22nd, 2018

MLS# 4714601

By Curtis Trousdale of Preferred Properties

A rare opportunity to own 105.7+/- secluded acres with excellent development possibilities in Middlebury, VT. Only minutes from Middlebury College, this parcel provides the chance to build an estate level property for generations to come! Approximately 24 acres are high quality grass and wildflower pastureland, primarily used for hunting and haying. Surrounding the pasture is mostly mature softwood forestland, with hardwoods occupying the slightly elevate western portion of the land. ...

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00 Painter Road Highway, Middlebury
Land
Ag
100.0000

Listed Aug 14th, 2018

MLS# 4713068

By Nancy Foster of Champlain Valley Properties

Beautiful rolling farmland with some nice woods. Lovely mountain views. Very close to village of Middlebury, but totally private. Perfect setting for a fabulous new home, family retreat, horse farm, or whatever is perfect for a new Owner.

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290 Halladay Road, Middlebury
Multi-Family
2
4
4
2,385
1.0000
1800
$5,935

Listed Aug 10th, 2018

MLS# 4713052

By Bonnie Gridley of RE/MAX North Professionals, Middlebury

Unique Middlebury opportunity to have income from one or both houses on the 1A parcel in the country with Green Mountain views. Very versatile the contemporary farmhouse features a 1 BR in –law suite which can be just that or used as an Air BNB. It has rented for $850/mo. or between $50-$89 per night. The one level ranch house has 1 bedroom, 1 bath & rents for $1,025/mo. Current tenant is month to month. The fun & eclectic farmhouse has interesting angles, skylights, windows &...

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290 Halladay Road, Middlebury
Residential
4
4
2,385
1.0000
1800
$5,935

Listed Aug 10th, 2018

MLS# 4712831

By Bonnie Gridley of RE/MAX North Professionals, Middlebury

Fun and eclectic contemporary farmhouse with in-law suite & detached one level, one bedroom rental. This versatile home has a great country location just to the south of Middlebury with beautiful Green Mountain views and lovely views out of all the windows. Sunny & light filled with oversized windows & skylights, 2 decks & south facing porch. Enjoy the yard & wonderful garden space. The main house has 2 bedrooms, the in-law suite, 1 bedroom which rents for $850/mo. & the ranch, 1 bedroom...

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51 Seminary Street Extension, Middlebury
Residential
9
3
5,432
6.0000
1820
NA

Listed Jul 19th, 2018

MLS# 4707589

By Wade Weathers of LandVest, Inc-Burlington

Elegant home with many special features from a time gone by. Main house has many large rooms with oversized windows. Renovation needed. Private apartment has two bedrooms and separate entrance. Small two bedroom guest cottage included and also in need of renovation. Subdivision required from original 35 +/- acre parcel. Additional land available.

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888 Three Mile Bridge Rd. Road, Middlebury
Residential
4
5
3,726
11.9000
1978
$11,939

Listed Jul 6th, 2018

MLS# 4705152

By Sarah Peluso of IPJ Real Estate

This handsome colonial home is situated on 11+ acres of mostly open meadow with beautiful mountain views! The main floor includes a master suite with walk in closet and bath with gorgeous cherry cabinetry, tile shower and marble counters. The gourmet kitchen has stainless steel appliances, and is open to the dining area, with lots of natural light and a wood burning fireplace between the two! The den has another fireplace, surrounded by built in cabinetry for a warm, inviting space. The...

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3210 Case Street, Middlebury
Residential
3
3
1,900
1.0000
1976
$6,061

Listed May 30th, 2018

MLS# 4696624

By Theresa Ouellette of Adirmont Real Estate, LLC - Brandon

Exceptional opportunity - Great Location! This home has a lovely yard with nice deck overlooking the back yard. Tile entry, hard and soft wood floors and commercial grade vinyl on the first floor. Three bedrooms, three bath with large fenced in yard, AND you could have an in-home business as well! The owner operated Little Friends Day Care for many years. She was licensed by the State to care for up to 16 children. The daycare space has it's owns bath with adjoining kitchenette and...

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TBD Halladay/Route 7, Middlebury
Land
AR
4.2000

Listed Jun 9th, 2017

MLS# 4639870

By Amey Ryan of IPJ Real Estate

Four plus acres with easy access to town roads. This site could be fun to develop and landscape. Rolling hill, ledge could allow for a great house with a perched setting and/or walkout basement. Contiguous to another parcel (MLS#4639868) for sale which is 111 acres and is prime for development. Investors take note!

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TBD Route 7 South, Middlebury
Land
AR
111.3000

Listed Jun 9th, 2017

MLS# 4639868

By Amey Ryan of IPJ Real Estate

Gorgeous views of the mountains to the south from this property. Build your dream home, have a farm, estate, house & guest house, you name it! This large parcel is suitable for residential development per zoning regulations and preliminary site investigations by a Site Tech Jeff Kelley. Access will be across other lands owned by seller and is currently being permitted for curb cut. Land is divided by old Middle Road which was redirected a few years ago so older maps may not reflect actual...

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 South Ridge, Middlebury
Land
MDR
22.2400

Listed Sep 11th, 2015

MLS# 4450390

By Amey Ryan of IPJ Real Estate

This is currently a wooded parcel with a larger building envelope. Room to clear out a lovely building site and tons of privacy, yet not isolated from other people. It's the best of both worlds! South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will...

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 South Ridge, Middlebury
Land
MDR
4.9000

Listed Sep 11th, 2015

MLS# 4450389

By Amey Ryan of IPJ Real Estate

this is a wooded parcel with a larger building envelope. tons of privacy, yet not isolated from other people. It's the best of both worlds! South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape!...

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277 Meadow Glen, Middlebury
Land
MDR
1.9700

Listed Sep 11th, 2015

MLS# 4450385

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite.This lot is quite open and feels very pastoral. Views and exposure to the south! You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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239 Meadow Glen, Middlebury
Land
MDR
2.9400

Listed Sep 11th, 2015

MLS# 4450384

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite.This lot is quite open and feels very pastoral. Views and exposure to the south! You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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365 South Ridge, Middlebury
Land
MDR
1.2100

Listed Sep 11th, 2015

MLS# 4450383

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. If you appreciate privacy, but want to be close to town and still have a few neighbors, this wooded lot could be the best of both worlds! You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape!...

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411 South Ridge, Middlebury
Land
MDR
1.0100

Listed Sep 11th, 2015

MLS# 4450379

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. If you appreciate privacy, but want to be close to town and still have a few neighbors, this wooded lot could be the best of both worlds! You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape!...

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376 South Ridge, Middlebury
Land
MDR
0.6000

Listed Sep 11th, 2015

MLS# 4450375

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. The access is across the eastern edge of lot #30. This house site slopes gently east so you could have a walkout basement and some nice views to the east and south! You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and...

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52 Meadow Glen, Middlebury
Land
MDR
1.0100

Listed Sep 11th, 2015

MLS# 4450366

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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34 Meadow Glen, Middlebury
Land
MDR
1.2800

Listed Sep 11th, 2015

MLS# 4450365

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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234 South Ridge, Middlebury
Land
MDR
0.7800

Listed Sep 11th, 2015

MLS# 4450362

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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192 South Ridge, Middlebury
Land
MDR
0.8800

Listed Sep 11th, 2015

MLS# 4450361

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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92 South Ridge, Middlebury
Land
MDR
0.5200

Listed Sep 3rd, 2013

MLS# 4313244

By Amey Ryan of IPJ Real Estate

South Ridge is a growing community, conveniently located near Middlebury Union Middle School. The lot is ready to build on - town water & sewer & electrical access onsite. You can choose to purchase a lot for construction in the future, or build now. Affordable building options are available. Come and explore this neighborhood and you will be amazed by the expanse and beauty of the landscape! Please ask about other lots that are available.

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